DGT MH –CET 12th CHEMISTRY Study Material 1
12 Aldehydes, Ketones and Carboxylic Acids
SECTION-I: ALDEHYDES AND KETONES (b) CH 3 CH 2 CH(CH 3 )CHO 2-methyl butanal (c) CH CH(CH )CH CHO 3-methyl butanal Section-I: Halogen Derivatives of Alkanes 3 3 2
(d) (CH 3 ) 3 CCHO 2,2-dimethyl INTRODUCTION propanal Aldehydes and ketones are carbonyl compounds, (e) CH CH COCH CH 3-pentanone they contain carbonyl (>C=O) group. General 3 2 2 3 (f) CH COCH CH CH 2-pentanone formula of aldehydes and ketones is C H O. 3 2 2 3 n 2n (g) CH COCH(CH ) 3-methyl Definitions: 3 3 2 2-butanone Aldehydes: These are first oxidative products of primary alcohols, in which carbonyl carbon Metamerism : atom is attached to, at least one H- atom. These Metamerism is present in same class of are presented asR-CHO. compounds. It is shown by the compounds which e.g.H–CHO CH –CHO have different alkyl groups( nature or type) 3 attached to either side of polyvalent functional formaldehyde acetaldehyde group. Ketones: These are first oxidative products of e.g. pentan-2-one and pentan-3-one are secondary alcohols, in which carbonyl carbon metamers, not position isomers. atom is attached to two same or different alkyl CH CH COCH CH diethyl ketone groups. These are represented as, R–CO–R. 3 2 2 3 CH COCH CH CH methyl, n-propyl e.g. CH –CO–CH CH –CO–C H 3 2 2 3 3 3 3 2 5 ketone acetone ethyl methyl ketone pentan-2-one and 3-methyl butan-2-one are ISOMERISM IN ALIPHATIC ALDEHYDES metamers not chain isomers AND KETONES : CH 3 COCH 2 CH 2 CH 3 2 pentanone Aldehydes : They shows chain tautomerism, CH COCH(CH ) 3-methyl, Optical isomerism themselves and functional 3 3 2 2-butanone isomerism with ketones. Note: Metamers are either chain or position Ketones: They shows chain, tautomerism ,optical isomers. If metamerism is mentioned then never isomerism, metamerism themselves and write chain or position isomerism. functional isomerism with aldehydes. Tautomerism: (i) C 3 H 6 O Definition: It is one type of functional isomerism, (a) CH CH CHO propanal 3 2 in which a single compound exists in two or more (b) CH COCH propanone 3 3 readily interconvertible structures that differ in
(ii) C 4 H 8 O the relative position hydrogen.
(a) CH 3 CH 2 CH 2 CHO butanal Only -H atom involved in tautomerism
(b) CH 3 CH(CH 3 )CHO 2-methyl propanal e.g. Acetone and prop-l-en-2-ol are tautomers (c) CH COCH CH 2-butanone 3 2 3 O OH (iii) C H O || | 5 10 CH C CH CH C CH 3 3 2 3 (a) CH 3 CH 2 CH 2 CH 2 CHO pentanal
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Aldehydes, Ketones and Carboxylic Acids 15 STRUCTURE OF CARBONYL GROUP (b) Vapours of secondary alcohols are 1. Carbonyl group (> C = O) consist of one passed over Cu or Fe metal at 573 K sigma and one bond. undergo dehydrogenation gives ketones. 2. In carbonyl group carbonyl carbon atom is Cu /573 K CHOH C O H 2 in sp 2 hybridised state. Note: Tertiary alcohols are heated 2 3. The sigma bond is formed by sp hybrid with copper metal at 573 K undergoes orbital of carbon and p-orbital of oxygen i.e. dehydration to give alkenes and water. sp 2 -p overlappling. 3. From hydrocarbon 4. The bond is formed by sideways overlapping (a) Ozonolysis of alkene : of unhybridisedp-orbital of carbon and p-orbital
of oxygen i.e., p-p overlapping. CH2 CH 2 O 2 CH O CH |2 | 2 5. Carbonyl carbon atom is joined to three atoms O O 0 of sigma bond making a bond angle 120 , ethylene ozonide therefore, carbonyl group has trigonal planer Zn structure. CH2 O CH 22 H O Zn(OH) 22 Zn(OH) 2H CHO 6. In carbonyl group, oxygen is more O O electronegative than carbon hence oxygen ethylene ozonide carries partial negative charge (nucleophilic or (b) Hydration of alkyne Lewis base centre) and carbon carries partial CH CH H O 40 % H2 SO 4 positive charge (electrophilic or Lewis acid 2 10 % HgSO 4 centre). CH CHOH rearrangement CH CHO 7. The high polarity of carbonyl group is 2 3 explained on tbe basis of resonance structure. Vinyl alcohol acetaldehyde
----- 4. From dry distillation (pyrolysis or - CO CO decarboxylation) of calcium salt of acids neutral dipolar structure structure (a) Aldehydes: PREPARATION OF ALDEHYDES AND dry distilled KETONES (H COO)2 Ca H CHO CaCO 3 cal. formate formaldeyde 1. By oxidation of primary and secondary alcohols by using pyridinium chloro (b) Ketones : chromate (PCC) or pyridinium e.g.(C 2 H 5 –COO) 2 Ca+(CH 3 –COO) 2 Ca dichromate (PDC): cal.propionate Cal.acetate It oxidises only primary alcohol to aldehyde dry distilled 2C H –CO–CH + 2CaCO and secondary alcohol to ketones. PCC is 2 5 3 3 the mixture pyridine, CrO and HC1 in 1:1:1 ethyl methyl ketone ratio. This reagent does not attack >C=C< 5. From alkaline hydrolysis of geminal bond. It is also known as Collin's reagent. dihalide: The geminal dihalides are boiled with aqueous KOH or NaOH. It produces e.g. CH OH [O] PCC H CHO HO 3 2 aldehydes and ketones. 2. By dehydrogenaion of primary and secondary alcohols by using Cu or Fe | | C X 2KOH C OH 2KX or Ag metals at 573 K. | | X OH (a) Vapours of primary alcohols are passed gemin al dihalide unstable over Cu or Fe metal at 573 K undergo dehydro-genation gives aldehydes. | These are – elimination reactions. COH COHO 2 | Cu / 573 K OH CH2 CH CHO H 2
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Aldehydes, Ketones and Carboxylic Acids 16
PREPARATION OF ONLY ALDEHYDES : O 1. Rosenmund reduction ( Reduction of || CH3 (CH 29 ) C H C 25 H OH acyl chloride): Acid chloride is reduced by undecanoate Lindlar catalyst to give aldehyde. Function 5. From hydrocarbon : of BaSO 4 is to poison the catalyst at aldehyde stage. Aromatic aldehydes and its derivatives are prepared from aromatic hydrocarban by O O following methods. || || Pd BaSO 4 RCClH 2 quinoline RCHHCl Strong oxidising agent oxidies hydrocarbon into acids. It is possible to stop the oxidation e.g. Pd BaSO 4 CH3 COCI H 2 quinoline at aldehyde stage using suitable reagent, that convert methyl group into intermediate which acetyl chloride is difficult to oxidised further. CH COH + HCI 3 (i) Etard reaction (oxidation of toulene acetaldehyde by chromyl chloride (CrO 2 Cl 2 )
2. Stephen's reduction (Reduction of When toulene is oxidised by CrO 2 Cl 2 first give chrominum complex which cyanide by SnCl 2 + HCl) on acid hydrolysis gives benzaldehyde RCN2[H] SnCl2 HCl RCHNH imin e CH 3 CS H2 O 2 R CHO NH 2CrO2 Cl 2 H 3
SnCl2 HCl e.g. CH3 C N 2[H]
H2 O OCrOHCl 2 CHO CH CH NH CH CHO NH 3 H 3 3 CH H O acetaldimine acetaldeyde 2 OCrOHCl 2 3. Reduction of cyanide by di-isobutyl benzaldehyde aluminium hydride (iso-but) Al–H or 2 2CrO Cl 2H E(CH ) CHCH ] Al–H Di-iso-but- 2 2 2 3 2 2 2 (ii) Oxidation of toluene by CrO Al–H 3 (chromium oxide) in acetic anhydride RCN2[H] (iso but)2 Al H RCHNH imin e CH 3
CrO3 / 273 k H2 O 2[O] (CH3 CO) 2 O R CHO NH H2 O H 3
(iso but) Al H CHO 2 OCOCH 3 H O e.g. CH3 C N 2[H] CH 3 OCOCH 3 CH C NH H2 O CH CHO NH 3H 3 3 acetaldimine acetaldeyde benzylidene diacetate 2CH3 COOH 4. Reduction of ester by (Iso-but) Al–H 2 (iii) By side chain chlorination followed O by hydrolysis(commercial method). || (iso but)2 Al H R C OR' 2[H] dry ether CH 3 UVL Cl 2 O || R C H R' OH CHCl 2 e.g. 2KOH hydrolysis O CHO || (iso but) Al H 2 CH3 (CH) 29 C OCH 26 2[H] dry ether 2KCl 2H O ethyl undecanoate 2
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Aldehydes, Ketones and Carboxylic Acids 17 (iv) By Gatterman - koch reaction: In CHEMICAL PROPERTIES: this reaction –H in benzene ring is Mechanism in Nucleophilic addition converted into –CHO reactions:
anhy. CHO The carbonyl group has two active centre which AlCl / CuCl 2CO HCl 3 HCl can, be easily attacked. The positively changed carbon is easily attacked by nucleophile and negaively charged oxygen is easily attacked by PREPARATION OF ONLY KETONES: electrophile. 1. From acyl chloride and dialkyl cadmium: During addition reaction nucleophile attack first Recently dialkyl cadmium is used for and followed by electrophile, because anion preparation of ketones from acyl halide in produced is more stable than cation. the presence of R–MgX. Since ketone formed in reaction do not react further to During the nucleophilic addition reaction preduce 3 0 alcohol. It may be noted that hybridisation of carbonyl carbon atom changes R–MgX can not be used in place of dialkyl from sp 2 to sp 3 .
cadmium, this is because ketone formed slow H C O Nu C O C OH further react with R–MgX to give 3 0 alcohol. | fast | Dialkyl cadmium is obtained by reacting Nu Nu R–MgX with cadmium chloride carbonyl group tetrahedral addition product alkoxideanion 2R–MgX + CdCI R Cd + 2MgXCl 2 2 Note: If attacking nucleophile is weak i.e.
When acyl halide reacts with R 2 Cd in the ammonia and its derivatives the reaction is carried presence of dry ether gives ketones. in weakly acidic medium.
dry ether 2R COX R2 Cd 2R COR CdX 2 Reactivity: Aldehydes are more reactive than ketone in nucleophilic addition reaction due to e.g. dry ether 2CH3 COCl (CH 3 ) 2 Cd steric and electronic reasons (inductive effect). Aliphatic aldehydes and ketones are more reactive 2CH 3 COCH 3 + CdCl 2 2. From cyanide or nitrile and RMgX: than aromatic aldehydes and ketones. When alkyl cyanide is reacted with RMgX (i) Inductive effect: Reactivity of carbonyl in the presence of dry ether, gives addition group depends upon magnitude of positive product, which on acid hydrolysis, gives charge on carbonyl carbon atom, more the ketone positive charge On carbonyl carbon atom more will be the reactivity of carbonyl R | compounds. RCNRMgX dry ether RCNMgX alkane nitrile Mg complex Electron donating group decreases the magnitude of positive charge on carbonyl R | carbon atom, hence I reactivity decreases. H R C N MgX 2HO2 Electron withdrawing I groups increases the reactivity of carbonyl compounds by R – CO – R + NH + MgXOH 3 increasing positive charge on carbonyl Ketone carbon atom. 3. From Friedel-Craft acylation reaction: I C O I O positive charge on carbonyl carbon atom O || || C R decreases R C Cl Anhy. AlCl 3 HCl I C O alkyl phenyl ketone I
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Aldehydes, Ketones and Carboxylic Acids 18 positive charge on carbonyl carbon atom | | increases. Thus reactivity is C O NaHSO3 C OH carbonyl aq. | H–CHO > CH 3 – CHO > C 2 H 5 –CHO > compounds SO3 Na CH 3 COCH 3 > C 6 H 5 CHO > C 6 H 5 COC 6 H 5 Note: CCl 3 – CHO > CHCl 2 – CHO > CH 2 Cl (i) Some ketones like diethyl ketone, – CHO > CH 3 – CHO (ii) Steric effect: In aldehydes only one alkyl acetophenone do Hot undergo this reaction. group is attached to carbonyl carbon atom (ii) The bisulphite 'addition product of aldehyde hence attack is relatively more easy. In and ketone are crystalline solid and therefore ketones two alkyl groups are attached to this reaction is used in the separation of carbonyl carbon atom. Which hinders the aldehydes and ketones from non carbonyl approach of nucleophile, hence attack, is compounds. relatively difficult. This factor is also called (iii) As the reaction is reversible the addition as steric hinderence. In other word,more the product can be dissolved by dilute mineral steirc hinderence less the reactivity of acid or aqueous tilkalies to regenrate original carbonyl compounds. aldehydes and ketones. Hence this reaction used to purification of aldehydes and O O ketones. || || CH3 CHO CH 3 C CH 33 CH C C 25 H 3. Addition of RMgX: When carbonyl compounds are reacted with Grignards O || reagent in the presence of dry ether give addition product which on acid hydrolysis CH25 C CH 25 gives alcohols (may be 1 0 or 2 0 or 3 0 alcohols). (i) Addition reactions : 1. Addition of HCN (Prucic acid): When | | C O RMgX dry ether C O MgX aldehydes and ketones are reacted with | HCN in presence of base gives R Mg complex corresponding cyanohydrins. In this reaction oxygen atom in carbonyl group is changed | | to OH group. H C O MgX H2 O C OH MgXOH Practically, HCN need for the reaction is | | R R generated in situ from dil. HC1 and NaCN. Alcohols The amount of acid is insufficient to react (a) On formaldehyde: (In this reaction whole NaCN. Hence, solution remain > C = O group is converted into -CH2OH alkaline and which catalysed the reaction. primary alcohol) | | base H H COHCN COH dry carbonyl compounds | | | H C O RMgX ether H C O MgX cyanohydrine | R Mg complex 2. Addition of sodium bisulphite (NaHSO 3 ): When Aldehydes and ketones are reacted H with 40% aqueous saturated solution of | H NaHSO 3 , gives corresponding crystalline H C O MgX HO2 bisulphite addition compounds. The reaction | R involves the nucleophilic attack of sulphite Mg complex
ion (SO 3 --). R–CH 2 –OH + MgXOH primary alcohol
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Aldehydes, Ketones and Carboxylic Acids 19 (b) On aldehyde (RCHO): When aldehydes 4. Addition of R–OH: Aldehydes or ketones (except HCHO) are reacted with RMgX in are reacts with alcohols to form acetal or the presence of dry ether, gives Mg ketals.The acetal is used as table sugar, complex; Which on acid hydrolysis, gives wooden shop, cotton fibrics etc secondary alcohols. (a) Aldehyde: Aldehyde reacts with (In this reaction > C = O group is converted alcohol in the presence of presence of into >CH–OH sec. alcohol.) dry HC1 gas to give alkoxy alcohol (hemiacetal) or half acetal which H H | | reacts with another molecule to form HCORMgX dry ether RCOMgX | acetal. R Mg complex R dry R C O R OH HCl C OH H H H |
| OR R C O MgX H O H | 2 alkoxy alcohol (hemiacetal) or half R acetal dry R R HCl OR R CH OH MgXOH C OH R OH C H O | 2 H | OR R OR H Secondary alcohol Acetyl (ge min al) dialkoxy compound (c) On ketone: When ketones are reacted with RMgX in the presence of dry ether, (b) Ketone: Ketone reacts with alcohol gives Mg complex. Which on acid hydrolysis, in the presence of presence of dry HCI gives tertiary alcohols. (In this reaction gas to give hemiketal of half ketal, >C=O group is converted into >C—OH which reacts with another molecule to form ketal. tertiary alcohol.) R R H | | | dry HCl dry ether R C O R OH R C O RMgX R C O MgX Ketone | R Mg complex R R | | RCORdry HCl RCORHO R OH 2 R | | | H OH OR R C O MgX HO hemiketal (half ketal) Ketal | 2 R Note:
R (i) Dry hydrogen chloride protonates | the oxygen of carbonyl compound R C OH MgXOH and increase the electrophilicity | R of carbonyl carbon atom and ter. alcohol increase the rate of reaction. Note: Using RMgX carbonyl compounds are (ii) Acetal and ketal are hydrolysed convert into following. by aq. HCl to give corresponding aldehydes and ketones. (1) Formaldehyde into –CH 2 –OH (primary alcohols), 5. Addition of ammonia: Ammonia react (2) Aldehyde into > CH–OH (secondary differently with formaldehyde, acetaldehyde alcohols) and acetone forming. (3) Ketone into>C—OH (tertiary alcohols)
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Aldehydes, Ketones and Carboxylic Acids 20 e.g. II. CONDENSATION REACTIONS OR ADDITION FOLLOWED BY H | ELIMINATION OR REPLACEMENT dry ether i) CH3 C O NH 3 OF OXYGEN: acetaldehyde | acid COHNZ COH H 2 | | NHZ H2 O CH3 C O CH 3 CH NH | aldimine > C = N – Z + H 2 O NH 2 acetaldehyde a min e Where Z = R–, C 6 H 5 –, –OH, –NH 2 ,
C 6 H 5 NH–, 3CH CH NH trimerisation 3 O2 N aldimine
CH NH NO2 (2,4 DNP), NH CONH 2 | 3 CH (semicarbazide) HN NH | | 1. Reaction with R–NH : CH3 CH CH CH 3 2
N acid | CORNH 2 CNRHO 2 H substituted i min e cyclic trimer 2. Reaction with Ph–NH 2 : (ii) 6HCHO + 4NH dry ether 3 | acid methanal C O HN2 (CH )6N + 6H O 2 4 2 |
urotropine C N H2 O Note: Urotropin is condensation product of methanal and ammonia, it phenyl imine (schiffs base) is not addition product. 3. Reaction with hydroxyl amine :
CH O | | |3 || acid CONH 2 OH C NOHHO 2 (iii) NH3 / CH3 C O H 2 CH C CH 3 oxime acetone 4. Reaction with hydrazine: When aldehydes and ketones are heated with hydrazine in CH 3 O | || the presence of dilute acid undergoes CH C CH C CH H O 3 3 2 condensation, gives corresponding crystalline mesityl oxide red or orange colour hydrazone. CH O In this reaction >C = O group is converted |3 || M. R. into >C = NNH . CH3 C CH C CH 3 NH 3 2 acetone | | acid COHNNH22 CN.NH 22 HO hydrozone CH3 O | || 5. Reaction with phenyl hydrazine: When CH C CH C CH 3| 2 3 aldehydes and ketones are heated with NH 2 phenyl hydrazine in the presence of dilute diacetone a min e acid undergoes condensation, gives corresponding crystalline red or orange colour phenyl hydrazone. In this reaction
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Aldehydes, Ketones and Carboxylic Acids 21 > C = O group is converted into (a) Aldehydes on reduction gives primary alcohols. >C = NNHC 2 H 5 . | | R CHO 2[H] NaHg H2 O RCHOH acid 2 C O HN2 NHCH 65 C N.NHCH 65 aldehyde primary alcohol phenyl hydrazone (b) Ketones on reduction gives secondary 6. Reaction with H NNH – CO – NH 2 2 alcohols. (semicarbzide)
| | R R C O HNNHCONH acid C NNHCONH | | 2 2 2 NaHg H2 O semicarbazone RCO2[H] RCHOH ketones sec. alcohol 7. Reaction with 2,4-dinitrophenyl hydrazine (2,4-DNP) Note: Unsaturated aldehydes or ketones can be reduced to unsaturated alcohols
without affecting >C =C< by using LiAlH 4 or NaBH . NO 2 4 | 3. Clemmenson reduction (deoxygenation): acid C O H2 N HN NO 2 In this reaction > C = O group is converted
into >CH 2 (methylene) group. e.g. When methanal is reduced by NO 2 Zn. Hg + conc. HC1 gives methane. | C N HN NO HO ZnHg conc.H 2 2 RCHO4[H] RHHO 2 aldehyde alkane 2, 4, dinitrophenyl hydrozone (yellow) 4. Volf-Kishner reduction: In this reaction > C = O group is reduced to > CH group. III. REDUCTION 2 | | Catalytic hydrogenation or reduction by CONH NHacid CNNH HO 22 22 hydrazone using NaBH 4 or LiAlH 4 OR Na.Hg + H 2 O: 1. Catalytic hydrogenation: When aldehydes | | and ketones are reduced by passing KOH ethylene C N. NH2 glycol CH 2 N 2 hydrogen gas in the presence of Ni or Pt or Pd. at 413K to 453K, gives 1 0 or 2 0 alcohols. 5. Reduction by Mg metal only ketone (Only (a) Aldehydes on reduction gives primary for ketones): Only ketone give this reaction. alcohols. When acetone is reacted with Mg metal in the presence of benzene gives Mg-complex, which Ni 413 K RCHO H2 R CH 2 OH on acid hydrolysis produces pinacol aldehyde primary alcohols (2,3-dimethyl butane 2, 3-diol). (b) Ketones on reduction gives secondary alcohols. (CH ) CO 3 2 Mg Benzene R R (CH3 ) 2 CO | | RCOH Ni 413 K RCHOH 2 (CH3 ) 2 C O 2H O ketones sec. alcohols Mg 2 | H (CH3 ) 2 C O 2. Reduction by using NaHg + H 2 O: When aldehydes and ketones are reduced by
Na.He + H 2 O or ZnHg + CH 3 COOH or (CH3 ) 2 C OH 0 0 | Mg (OH) 2 LiAlH 4 , NaBH 4 gives 1 or 2 alcohols. Note (CH3 ) 2 C OH that NaBH 4 does not reduce ketone group. pinacol
Na.Hg H2 O NaOH Hg [H]
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Aldehydes, Ketones and Carboxylic Acids 22 When pinacol is heated with acid undergoes (iii) Reaction with Schiffs reagent: Schiffs rearrangement gives pinacolone. This is reagent (colourless) is prepared by passing
known as pinacol-pinacolone SO 2 gas in magenta or pink dye of para- rearrangement. rosaniline hydrochloride (Fuschin). When decolourised schiffs reagent is treated with CH 3 (CH3 ) 2 C OH | aldehyde in cold original pink or magenta | Acid / CH C C CH H O 3 3 2 colour is developed. (CH3 ) 2 C OH || | pinacol O CH 3 cold pinacolona R CHO Schiff 's reagent Pink IV Oxidation reactions: or magenta or bright crimson colour. 1. Oxidation by strong oxidising agent like Note : Ketones does not give these reactions because of absence of H-atom on K 2 Cr 2 O 7 + dil. H 2 SO 4 carbonyl carbon atom. Glucose, formic acid K Cr O dil.H SO CHO[O] 227 24 COOH and enolic form of fructose gives above test. aldehyde acid 3. Oxidation of methyl ketone by haloform O reaction (Haloform test): || C [O] K227 Cr O dil. H 24 SO Haloform test means preparation of haloform ketone i.e. CHC1 3 (colourless liquid), CHI 3 (yellow solid) and CHBr (brown liquid). This test is – COOH + CO + H O OR – COOH + – COOH 3 2 2 given by some alcohols, some aldehydes and acid some ketones. 2. Oxidation by mild oxidising agents like Alcohols: Alcohols that produces CH –CO Tollen's reagent, Fehling solution, 3 group (methyl ketone or 2-one group) on Schiffs reagent, or Reducing properties oxidation gives haloform test or oxidative of aldehydes or characteristic test of product of alcohols contain 3– –H atoms aldehydes or distinction test of on single carbon atom gives haloform test. aldehydes from ketones or reducing PCC reaction of aldehydes. CH3 OH [O] H CHO Aldehydes and ketones are distinguished by Negative haloform test Tollen's reagent, Fehling solution, Schiffs CH CH OH PCC CH CHO reagent. 3 2[O] 3 (i) Reaction with Tollens reagent: Positive haloform test Aldehydes and ketones: They contain R CHO 2[Ag(NH ) ] OH 3 2 CH 3 –CO group (methyl ketone or 2-one aldehyde group) or 3– –H atoms on single carbon atom.
RCOOH 2Ag 4NH3 H 2 O H – CHO Negative haloform test acid CH 3 – CHO Positive haloform test (ii) Reaction with Fehling solution: CH 3 CH 2 –CHO Negative haloform test R CHO 2Cu 4OH CH 3 –CH 2 –CO–CH 2 –CH 3 aldehyde Negative haloform test O R COOH CuO2 2HO 2 acid red ppt || NaOH X 2 R C CH3 3NaOX R – COONa + CHX + 2NaOH CHO 3 O 2Cu 4OH || e.g. H C CH 3NaOCl NaOH Cl 2 benzaldehyde No reaction 3
H – COONa + CHCl 3 + 2NaOH
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Aldehydes, Ketones and Carboxylic Acids 23 Note : The importance of this reaction is, if e.g. When acetaldehyde is warmed with dil. >C = C < present in molecule is not attacked (10%) NaOH, gives acetaldol (3-hydroxy by NaOX. butanal). Which on heating with acid loses water molecule and gives crotonaldehyde O || ( - unsaturated aldehyde).
CH3 CH CH C CH 3 3NaOCl
NaOH Cl 2 CH3 CH CH COONa
+ CHCl 3 + 2NaOH V. Reaction due to -H atom OH O 1. Acidity of -H atom in aldehydes and | || ketone: CH C CH C H 3| 2 Aldehydes and ketones undergoes number H -reactions due to acidic nature of -H acetaldol atom. The acidity of -H depends upon O HO electron withdrawing group (– I effect) of | || carbonyl group and resonance stabilisation CH C CH C H acid 3| 2 heat of conjugate base. H When -H atom is attached to only carbonyl group, then more acidic is -H O || atom CH3 CH CH C H HO2 crotonaldehyde (2 butenal) O || Cross aldol condensation reactions: CH3 C H more acidic H O O When -H atom is attached to only || || C H C H CH C H 20 % NaOH carbonyl group and alkyl group, then less 2 5 2 warm | ethanal acidic will be the -H atom. H propanal O || – less acidic -H OH O CH3 CH 2 C H || || C H C CH C H 2 5| 2 O H || – less acidic -H 3 hydroxy pen tan al CH3 C CH 3 OH O O || || 1|| 2 / H CH C CH CH C2 H 5 C CH 2 C H 3 2 3 | H 3 hydroxy pen tan al – 1 is more acidic than 2 Note: In aldol condensation reaction more C H –CH = CH – CHO + H O acidic -H atom involved in condensation 2 5 2 reaction. Mechanism of aldol condensation reaction: VI. Aldol condensation reaction or self – condensation or reaction with dilute Step-I: Base OH takes -H-atom from alkali or 10% alkali or weak alkali: aldehyde to form carbanion(enolate ion). 1. simple aldol condensation reaction: It O O || || is the reaction between two same aldehydes CH3 CHOH CH2 CHHO 2 or two same ketones. carbanion
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Aldehydes, Ketones and Carboxylic Acids 24 Step-II: The carbanion attack electrophilic (ii) When benzaldehyde (benzene carbaldehyde) carbonyl carbon of second aldehyde is heated with strong KOH, gives pot. molecule to form alkoxide ion. benzoate and benzyl alcohol.
O O O O || || || || CH C HCH C H KOH CH3 C H CH 2 C H 65 65 benzaldehyde (strong) conc.
O O C65 H COOK C 65 H CH 2 OH | || pot. benzoate benzyl alcohol CH3 C CH 2 C H | (iii) Cross Cannizzaro's reaction: When H alkoxide ion benzaldehyde and formaldehyde are heated with strong NaOH gives benzyl alcohol and Step-III: Alkoxide ion takes hydrogen ion sodium formate. In this reaction more from water to form aldol. Base OH – ion is reactive aldehydes give oxidative product in generated. crossed Cannizzaro's reaction.
O O C6 H 5 CHO HCHO NaOH | || CH C CH C H H OH 3 2 C6 H 5 CH 2 OH HCOONa | benzyl alcohol sod. formate H Note: Isobutyraldehyde gives Cannizzaro's OH O reaction eventhough presence of -H atom. | || The exception behavior of isobutyraldehyde CH C CH C H OH 3| 2 is due to +I effect of two alkyl groups. H e.g. (CH ) CH–CHO + (CH ) CH–CHO aldol 3 2 3 2 + NaOH conc. Note: Formaldehyde, benzaldehyde, (CH ) CH–COONa + (CH ) CH–CH OH. trimethyl acetaldehyde, benzoquinone, 3 2 3 2 2 sod. iso-butyrate iso-butyl alcohol chloral, iodal etc does not give this reaction VIII. ELECTROPHILIC SUBSTITUTION because of absence of -hydrogen atoms. REACTION OF AROMATIC VII. CANNIZZARO'S REACTION OR ALDEHYDES AND KETONES: SELF REDOX REACTION OR BASE CATALYSED SELF OXIDATION Note that – CHO and > C = O group are REDUCTION REACTION : meta directing Condition: It is a characteristics reaction 1. Halogenation : of aldehydes and ketones which does not CHO CHO contain -H atom. It is carried by strong | |
alkali. FeCl 3 i) Cl 2 HCl e.g. Cl (i) When formaldehyde is heated with cone. m chlorobenzaldehyde (50%) NaOH, gives sodium formate and methyl alcohol. O CHO || O O | || || C CH 3 H C H H C H NaOH FeBr 3 HBr conc. ii) Br 2 | HCOONa CH3 OH Br sod. formate methyl alcohol m bromoacetophenone
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Aldehydes, Ketones and Carboxylic Acids 25 2. Nitration SECTION-II: CARBOXYLIC ACIDS e.g. Definition: These are carboxyl derivatives of CHO alkane obtained by replacing hydrogen atom from conc. H SO alkane by carboxyl (–COOH) group. i) 2 4 HNO 3 273 K ISOMERISM CHO Carboxylic acids: They shows chain, optical | isomerism themselves and functional isomerism with esters. Total number of isomeric acids can H2 O be calculated by formula, I = 2 n–3 . NO 2 Esters : They shows chain, metamerism, optical m nitro benzaldehyde isomerism themselves and functional isomerism COCH | 3 with carboxylic acids. Total number of isomeric esters can be calculated conc. H SO 2 4 n–l –3 ii) HNO 3 273 K by formula, I = 2 = (n – 2) – 2n from C 3 onwards. 1 phenyl ethan 1 one Total number of isomeric acids and esters can be COCH n–1 | 3 calculated by formula, I = 2 – (n – 2). e.g. H2 O (i) C 2 H 4 O 2 (2-isomers) NO 2 (a) CH 3 COOH acetic acid m nitro acetophenone (b) HCOOCH 3 methyl formate
3. Sulphonation : (ii) C 3 H 6 O 2 (3-isomers. 1 acid, 2 esters)
CHO (a) CH 3 CH 2 COOH propionic acid | (b) HCOOC 2 H 5 ethyl formate Fu min g (c) CH COOCH methyl acetate i) H2 SO 4 3 3 (iii) C H O (6-isomers. 2 acids, 4 esters) CHO 4 8 2 | Acids:
(a) CH 3 CH 2 CH 2 COOH n-butyric acid H2 O (b) (CH 3 ) 2 CHCOOH isobutyric acid SO3 H m formyl benzene sulphonic acid Esters : (a) HCOOCH CH CH n-propyl formate COCH 2 2 3 | 3 (b) HCOOCH(CH 3 ) 2 isopropyl formate
Fu min g ii) (c) CH 3 COOCH 2 CH 3 ethyl acetate H2 SO 4 (d) C H COOCH methyl propionate COCH 2 5 3 | 3 12.3 STRUCTURE OF -COOH GROUP The carboxylic carbon is less electrophilic than carbonyl carbon atom in aldehydes and ketones SO3 H m oxo methyl benzene sulphonic acid because of resonance stabilisation of COOH group.
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Aldehydes, Ketones and Carboxylic Acids 26 The carbon atom is sp 2 hybridised state. The CH 3 O–C–O bond angle is 120 0 . KMnO4 KOH PREPARATION METHODS 0 1. From oxidation of 1 alcohols, aldehydes COOK COOH and ketones. H O 3 (a) From primary alcohols: Primary alcohols benzoic acid on controlled oxidation by acidified K 2 Cr 2 O 7 gives Carboxylic acid. 4. From dry ice and R–MgX : CHO 2[O] K227 CR O dil. H 24 SO O C O RMgX dry ether O C OMgX dry ice – COOH + H 2 O | R (b) From aldehydes : Aldehydes on oxidation addition product by acidified K Cr O , gives carboxylic acid. 2 2 7 O C OMgX H OH H RCOOH MgXOH CHO2[O] K227 CR O dil. H 24 SO COOH | acid R (c) From ketones: Ketones on controlled 5. From hydrolysis of acid halide and acid oxidation by acidified K Cr O gives 2 3 7 anhydride: carboxylic acid. (a) Acid halide is hydrolysed with water gives C O 2[O] K227 CR O dil. H 24 SO corresponding acids.
– COOH + H 2 O + CO 2 R COCl H OH R COOH HCl 2. From acid hydrolysis of cyanide or Note: Acid chloride are more readily hydrolysed nitrile: by aqueous base to give carboxylate ion, which
R CO N H O H R CONH H2 O on acidification gives corresponding acids. 2 2 H alkyl cyanide acid amide R COCl OH R COO HCl RCOOH NH 3 acid R COO H R COOH Note: Mild reaction conditions are used to (b) Acid anhydride is hydrolysed by water gives stop reaction at amide stage. acids OH O (R CO)O HO 2R COOH | || 2 2 CNHOH H CNH isomerise CNH imin e 6. Acid hydrolysis of esters by using dil. HC1
or dil. H 2 SO 4 : OH O conc. H2 SO 4 | || R COO R H2 O H isomerise ester CNHOH CNH CNH 2 amide R COOH R OH 3. From oxidation of alkyl benzene or acid alcohol phenyl alkene: Note: These are reverse of esterification Alkyl benzene are oxidised by strong reaction. It is auto catalysed reaction oxidising agent like chromic acid or acidic because acid formed in this reaction acts as catalyst. KMnO 4 or alkaline KMnO 4 . The entire side chain is converted into carboxyl group 7. Alkaline hydrolysis of ester (Saponification):
irrespective of length of the side chain. R COO R NaOH R COONa R OH Tertiary alkyl group donot under goes oxidation because of absence of benzylic ester aq. sod. salt of acid alcohol
hydrogen atom. R COONa H OH H R COOH NaOH
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Aldehydes, Ketones and Carboxylic Acids 27 Note : 4. Acidic strength can also be explain on the (i) Acid hydrolysis and alkaline hydrolysis of basis of Ka and Pka values. More the Ka esters are nucleophilic substitution reaction. value or less the pKa value more the acidic (ii) Hydrolysis of ester by dilute alkali is strength and vise versa. irreversible and faster reaction than acid Acidic nature: hydrolysis. 1. Electron donating groups (+1) effect
(iii) Alkaline hydrolysis of ester is preferred over i.e. NH 2 > OH > OCH 3 > CH 3 destabilize acid hydrolysis because the acid salt formed the anion, by intensify negative charge and can not force backward reaction. thus decrease the acidity of acid. -O (iv) Reactions of ester with RMgX are ------nucleophilic addition reactions. EDG C O 8. Oxidation of alkene by strong oxidising 2. Electron withdrawing groups (–I) effect, agent (vigrous oxidation): i.e. CF 3 > NO 2 > CN > F > Cl > Br > I > C 6 H 5 vigrous stabilize the anion, by dispersing negative C C C O O C oxidation charge and thus increase the acidity of acid. [O] [O] -O ---- COOH COOH EWG C ---- O e.g. Which is depends up on following
factors: KMnO 4 i) CH2 CH 2 4[O] 2H COOH H2 SO 4 (a) The number of electron attracting groups or atoms (–I effect) increases, the strength KMnO COOH ii) 4[O] 4 of acid increases. The order of acidity H2 SO 4 COOH
cyclohexene adipic acid e.g. CCl 3 COOH > CHC1 2 COOH >
CH 2 C1COOH > ACIDIC NATURE OF ALIPHATIC ACID CH 3 COOH 1. Acidic nature of carboxylic acid can be best (b) The power electron attracting groups or explained on the basis of resonance and atoms increases, the acidity increases. Lowry Bronsted theory. e.g. CH 2 FCOOH > CH 2 C1COOH 2. Carboxylic acid are weak acids and turns > CH BrCOOH blue litmus to red. In water they are , partially 2 dissociated and equilibrium is shifted in left (c) The distance of electron attracting groups or side. Thus, aqueous solution of carboxylic atoms from carboxylic group increases, acid contains, more undissociated acid acidity decreases. Therefore, decreasing molecules.Carboxylic acids are stronger acid acidity order in n-butyric acid is > > > Inductive effect is stronger at a-position than than R–OH, C 6 H 5 –OH, water and weaker than mineral acids. -position, similarly at -position it is more stronger than -position. RCOOH HO RCOO HO RCOOH 2 3 e.g.
3. Carboxylate ion is best stablised by resonance hence these are acidic in nature. CH32 CH CHClCOOH CH 32 CHClCH COOH
CH 2 ClCH 2 CH 2 COOH > CH 3 CH 2 CH 2 COOH (d) More the power of electron withdrawing group, strength of carboxylic acid increases.
CH 3 –CH 2 –COOH < H–CH 2 –COOH < C 6 H 5 CH 2 –
COOH < O–CH 2 –COOH < C1–CH 2 –COOH
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Aldehydes, Ketones and Carboxylic Acids 28 (e) Direct attachment of groups such as phenyl REACTION SHOWS THE ACIDIC NATURE OF CARBOXYLIC ACIDS (C 6 H 5 –) or vinyl (CH 2 = CH–) or acetylenic (CH = C–) to –COOH group, increases the 1. Reaction with metal: (Na, K, Ca, Zn) acidity of corresponding carboxylic acid.This (a) Reaction with Na metal: 2– is due to more electronegative sp and 2R – COOH + 2 Na 2R–COONa + H sp-hybridised carbon atom to which –COOH 2 (b) Reaction with potassium metal: group is attached. 2R–COOH + 2K 2R–COOK + H 2 (c) Reaction with calcium metal:
2R–COOH + Ca (R–COO) 2 Ca + H 2 (d) Reaction with Zn metal:
2R–COOH + Zn (R–COO) 2 Zn + H 2 2. Reaction with strong alkali (NaOH, KOH): e.g. (a) Reaction with NaOH:
(i) H–COOH > C 6 H 5 – COOH > C 6 H 5 CH 2 R–COOH + NaOH R–COONa + H2O
COOH > CH 3 COOH > C 2 H 5 COOH (b) Reaction with KOH: R–COOH + KOH R–COOK + H O (ii) CH = C–COOH > C 6 H 5 COOH > CH 2 = 2 CH – COOH pot. formate 3. Reaction with weak alkali (NaHCO , (C 6 H 5 group is more electron withdrawing 3 Na 2 CO 3 , NH 4 OH): than CH 2 = CH–). (a) Reaction with NaHCO (sodium bicarbonate ACIDIC NATURE IN AROMATIC ACID 3 or baking soda): In aromatic carboxylic acid electron donating Fast group decrease the acidic strength while electron R COOH NaHCO3 R COONa with drawing group increase the acidic strength + CO 2 + H 2 O
(b) Reaction with Na 2 CO 3 (Sodium carbonate): COOH COOH COOH Slow | | | 2R COOH Na2 CO 3 2R–COONa + CO + H O 2 2 (c) Reaction with NH 4 OH (ammonium hydroxide): EWG EDG R–COOH + NH 4 OH R–COONH 4 + H 2 O 4. Reaction involving breaking of C–O bond 1. Electron donating groups decrease the acidic (Nu-SR) length of acids by destabilizing benzoate ion. (a) Formation of anhydride (Reaction with
It follows the order, Ph – COOH > o > m > p conc. H 2 SO 4 or P 2 O 5 )
2. Electron withdrawing groups increase the 1. From P 2 O 5 acidic strength of acids by stabilizing R COOH R CO benzoate ion. P O 2 5 O H2 O It follows the order, o > p > m > Ph-COOH R COOH R CO acid
PO252 HO 2HPO 3 COOH COOH COOH COOH meta phosphoric | | | | acid NO 2 Note: Formic acid does not form formic unhydride (H–CO) 2 O, When it NO 2 is heated with P 2 O 5 , undergoes NO 2 dehydration forming CO. PKa Values 2.16 3.41 3.47 4.19 P2 O 5 H COOH CO H2 O
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Aldehydes, Ketones and Carboxylic Acids 29 2. From acyl chloride and sodium salt of O carboxylic acids: || R C OH R O H conc. Pyridine H SO R COCl R COONa 2 4 8 R – COOOC – R + NaCl O (b) Esterification (Fischer esterification) OR || Alcoholy sis of acids OR Acy lation of R C O R HO2 alcohols. 18
conc. H SO R COOH R ' OH 2 4 (c) Reaction with PCl , PCl and SOCl acid alcohol 3 5 2 3RCOOH + PCl 3RCOCl + H PO R – COO – R' + H O 3 3 3 2 RCOOH + PCl RCOCl + POCl + HCl ester 5 3 RCOOH + SOCl Pyridine RCOCl + Note: 2 SO + HCl (i) These reactions are reversible in nature. 2 (ii) The yield of ester may increased by using When acid chloride is heated with ammonia excess of alcohol or removal of water by gives acid amide.
distillation or excess of acid. Water may be RCOC1 + NH 3 RCONH 2 + HC1
removed by using concentrated H 2 SO 4 or (d) Reaction with ammonia :
dry HC1 or anhydrous ZnCl 2 . When carboxylic acid is reacted with ammonia,
(iii) The concentrated H 2 SO 4 or dry HC1 or gives ammonium salt of acid. Which on heating
anhydrous ZnCl 2 acts as mainly dehydrating loses water molecule and gives amide. agent and it also act as catalyst in the R–COOH + NH 3 R–COONH 4 esterification reaction. R COONH R CONH H O (iv) These are nucleophilic substitution reaction. 4 2 2 (v) The reaction is shifted to the right by using excess 3. Reaction involving – COOH group
of alcohol or removal of water by distillation. Reduction by using LiAlH 4 or diborane
(vi) The greater the bulk of the substituents near (B 2 H 6 ) as reducing agent or hydrogen in the the OH group of alcohol and –COOH group presence of copper chromite
of acid, the slower is the rate of esterification (CuO, CuCr 2 O 4 ) as catalyst: Carboxylic acid
due to stearic hindrance. are reduced by using LiAlH 4 as catalyst gives primary alcohols.The > C = O group Thus, the reactivity of alcohol towards is reduced to > CH group. esterification is: 2
(i) LiAlH4 / ether CH OH > C H OH > C H OH > C H OH R COOH 4[H] 3 2 5 3 7 4 9 (ii) H3 O Similarly the reactivity of carboxylic acid R – CH OH + H O increase as: 2 2
(i) LiAlH4 / ether HCOOH > CH COOH > C H COOH > CH3 COOH 4[H] 3 2 5 (ii) H3 O
(CH 3 ) 2 CHCOOH CH 3 – CH 2 OH + H 2 O (vii) The reverse of esterification is known as Note: Sodium boronhydride (NaBH4) does hydrolysis which may effected by acids or not reduces carboxyl group. alkalies. (ii) Decarboxylation: (viii) The mechanism of esterification is detected (a) Decarboxylation by using soda lime: by tracer technique by taking isotopic oxygen in alcohol. After esterification isotopic oxygen Sodium salt of carboxylic acid is heated with become in ester. This indicate that during soda lime (NaOH+ CaO 3:1 ratio) gives alkane esterification the cleavage of C–O bond of CaO R COONa NaOH R H NaCO 3 carboxylic acid and O–H bond of alcohol.
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Aldehydes, Ketones and Carboxylic Acids 30 4. Halogenation (Hell-Vohlard-Zelinsky 12.8ELECTROPHILIC SUBSTITUTION reaction) or HVZ reaction: REACTION OF CARBOXYLIC ACIDS Carboxylic acids having -H atom Aromatic carboxylic acid undergoes electrophilic undergoes halogenation at only -position substitution reaction. Carboxyl group is meta in the presence of red phosphorus to give directing. -halo carboxylic acids. Note: Aromatic carboxylic acid never undergoes (i) Red. P -Friedel Craft reaction because only, A1CL3, R CH2 COOH H 2 X Cl, Br (ii) H2 O (Lewis acid) get bonded to carboxyl group. Other R CH COOH HCl Lewis acid does not bonded to carboxyl group. | (i) Halogenation e.g. X -halo carboxylic acid COOH COOH | | e.g. FeX 3 HX (i) Red. P X 2 i) CH3 COOH Cl 2 (ii) H2 O X X Cl, B m halobenzoic acid CH 2 Cl–COOH + HCl chloroacetic acid COOH COOH CH2 COOH | | (i) Red. P ii) FeX Br 2 (ii) H O (ii) 3 2 X 2 NO Br 2 X NO 2 | CH COOH HBr Nitration e.g. COOH COOH 1 bromo 1 phenyl ethanoic acid | |
conc. H2 SO 4 H O The importance of this reaction is that only HNO 3 2 -H is substituted. NO 2
Br2 / Red P m nitro benzoic acid i) CH3 COOH
Br2 / Red P BrCH2 COOH
Br2 / Red P Br2 CH COOH Br3 C COOH
Br2 / Red P ii) CH3 CH 2 COOH
Br2 / Red P CH3 CHBr COOH
Br2 / Red P CH3 CBr 2 COOH No reaction
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Aldehydes, Ketones and Carboxylic Acids 31
MULTIPLE CHOICE QUESTIONS SECTION-I: ALDEHYDES AND KETONES 10. The IUPAC name of crotonaldehyde is Introduction, Classification, Nomenclature, a) pentenal b) but-2-en-l-al Isomerism, Structure Of > C = O Group c) but-2-an-l-al d) but-2-en-l-ol 1. Aldehydes are characterised by the general 11. IUPAC name of the following compound is formula CHO
a) C n H 2n O b) C n H 2n
c) C n H 2n+ OH d) C n H 2n+2 O 2. Hybridisation of carbon in – CHO group is a) sp b) sp 2 COCH 3 3 c) sp d) none of these a) 4-formyl acetophenone 3. Formalin is a b) 4-ketomethyl benzaldehyde a) 100% solution of HCHO c) 1-formyl 4-ketomethyl benzene b) 40% solution of HCHO d) 4-formyl 1-ketomethyl benzene c) 60% solution of HCHO 12. IUPAC name of ketone is d) 40% solution of CH COOH 3 a) alkanol b) alkanal 4. An aldehyde group can be present c) alkanone d) alkyl alkanoate a) in between carbon chain 13. Tautomerism is possible in b) at any position in carbon atom 1. CH 3 –CHO 2. CH 3 –CO–CH 3 c) only at the end of carbon chain 3. H–CHO 4. (CH 3 ) 3 C–CHO d) at the second carbon atom of the carbon chain a) 1, 2 b) 2 3 5. Butanal is an example of c) 3, 4 d) 1, 2, 4 a) primary alcohol b) secondary alcohol 14. IUPAC name of following compound will be c) aliphatic aldehyde d) aliphatic ketone CHO 6. In IUPAC system aldehydes are called CH a) alkanes b) alkenes 3 c) alkanals d) alkanols 7. IUPAC name of mesityl oxide is OH a) 4-methyl penta-3-none a) 4-formyl 3-methyl 1-hydroxy benzene b) 4-methyl pente-3-none b) 4-formyl 3-methyl phenol c) 4-methyl pent-3-en 2-one c) 4-hydroxy 2-methyl benzaldehyde d) 4-methyl pent-3-en 1-one d) 4-hydroxy 2-methyl carbaldehyde 8. IUPAC name of pinacol is 15. IUPAC name following compound is a) 2,3-dimethyl butan 2,3-diol b) 2,3-dimethyl butane 2,3-diol || O c) 2,3-dimethyl 2-butanol a) 4-oxo pent-2-ene b) pent-2-en-4-one d) 2,3-dimethyl 3-butanol c) 2-oxo-pent-3-ene d) pent-3-en-2-one 9. IUPAC name of diacetone amine is 16. Which of the followingis 3-phenylprop-2-en-l-al? a) 2-methyl 4-keto 2-pentanamine a) C 6 H 5 –CH = CH–CH 2 –CHO b) 4-amino 4-methyl 2-pentanone b) C 6 H 5 –CH = CH – CHO c) 4-amino 2-pentanone c) C 6 H 5 –CH 2 –CHO d) 4-amino 3-pentanone d) C 6 H 5 –CH = CH–CH 2 –CH 2 –CHO
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Aldehydes, Ketones and Carboxylic Acids 32 17. IUPAC name of benzophenone is 24. IUPAC name of isobutyraldehyde is a) 2-phenyl propenal a) 2-methyl propanone b) 3-phenyl butenal b) 2-methyl propanal c) diphenyl methanone c) 2-methyl propanone d) diphenyl ethanone d) methyl ethanoate 18. IUPAC name of the following compound is 25. Which of the following is trimethyl acetaldehyde? a) (CH ) C–CH –CHO O 3 3 2 || b) (CH 3 ) 3 C–CH 2 –CH 2 –CHO c) (CH ) C–CHO H 3 3
d) (CH 3 ) 2 CH–CH(CH 3 )CHO a) 2-(2-propenyl)butanal 26. IUPAC name of the following compound is b) 2-(l-propenyl)butanal c) 4-formyl 4-ethyl but-2-ene OHC d) 2-ethyl pent-3-en-1-al 19. Aldehyde group can occur : a) any where in carbon chain a) 2-methIyl nona 2,6-dine-l-al b) in the middle of carbon chain b) 3-methlyl nona 2,6-dine-l-al c) at only second carbon atom of carbon chain c) 4,6-dimethyl hepta 3,5-dien-l-al d) only at end of the carbon chain d) 3,7-dimethylocta2,6-dien-l-al 20. The carbon atom of carbonyl group is 27. Aldehyde shows functional isomerism with a) sp 3 -hybridise b) sp 2 -hybridised a) aliphatic ether c) sp-hybridised d) sp 3 -d-hybridised b) ketones
21. C n H 2n O is general formula for c) dimer of ethanoic acid a) aldehydes d) thio cyclic ether b) ketones c) all carbonyl compounds 28. Pentan-2-one and 3-methyl butan-2-one are d) aldehyde and ketones a) chain isomers b) position isomers 22. IUPAC name of p-methyl butyraldehyde c) metamers d) tautomers a) 2-methyl butanal b) 3-methyl butanal 29. Tautomer of ethyl methyl ketone is c) 2-methyl propanal d) 3-methyl pentanal a) but-2-en-2-ol b) but-2-en-l-ol 23. Given : c) but-2-en-l-oicacid d) prop-l-en-2-ol 30. Which of the following is acrolein?
CH 3 CH 3 a) CH 3 –CH = CH–CHO CH 3 b) CH = CH–CHO CH 3 2 CH 3 c) CH = CH–CH – CHO CH 3 2 2 || || || d) CH = CH – CH – CH – CHO O O O 2 2 2 (I) (II) (III) 31. What is the IUPAC name of compound when - CHO group is attached to neoamyl group ? Which of the given compunds can exhibit a) 2-methyl propanal tautomerism ? b) 3-methyl propanal a) I and II b) I and III c) 2, 2-dimethyl butanal c) II and III d) I, II and III d) 3,3-dimethyl butanal
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Aldehydes, Ketones and Carboxylic Acids 33 32. Which of the following is isophthaldehyde ? 38. Following compound is named as CHO CHO CHO
CHO a) b) CH 3 a) 4-methyl cyclohexane carbaldehyde CHO b) 5-methyl cyclohexane carbaldehyde CHO CHO c) -methyl cyclohexane carbaldehyde CHO d) both a and b c) d) 39. keto-enol tautomeric with CHO a) CH OH b) CH COCH CHO 3 3 3
c) CH 3 COOH d)CH 3 COOCH 3 33. What is the IUPAC name of compound when 40. Ketones are isomeric with carbonyl carbon atom is attached to phenyl group a) alcohols b) aldehydes and ethyl group c) ester d) acetic acid a) propanone bertzene 41. The structural formula of the compound isomeric b) 1-phenylpropan-l-one with acetone is c) 2-phenylpropan-l-one a) CH 3 CH 2 CHO b) CH 3 CHO d) propiophenone c) CH 3 CH 2 OH d) none of these 34. What is IUPAC name of compound when ketone 42. CH –CO–CH and CH = COH–CH are group is attached to one isopropyl group and one 3 3 2 3 a) metamers t-butyl group ? b) tautomers a) 2, 4, 4-trimethyl 3-pentanone c) geometrical isomers b) 2, 2, 4-trimethyl 3-pentanone d) optical isomers c) 2, 4-dimethyl 3-pentanone 43. Aldehyeds and ketone are d) 2, 2-dimethyl 3-pentanone a) tautomers 35. IUPAC name of ethyl isopropyl ketone is b) chian isomers a) 4-methyl pent-3-one c) funcational isomers b) 2-methyl pent-3-one d) position isomers c) 4-methyl pent-2-one 44. Total number of isomeric aldehydes can d) 2-methyl pent-2-one calculated by formula 36. IUPAC name of acrolein is a) I = 2 n–2 b) I = 2 n–3 a) but-2-enal b) prop-2-enal c) I = 2 n–2–1 d) 1 = 2 –n c) pentanal d) 2-methyl propanal 45. Total number of isomeric ketones can calculated 37. IUPAC name of the following compound is by formula a) I = 2 n–3 – l b)I = 2 n–2 CH2 CHO c) I = 2 n–2 – l d) I = 2 n
46. Molecular formula C 3 H 6 O represents a) aldehydes b) ketones a) Phenyl acetaldehyde c) both 'a' and 'b' d) aldehydes and alcohols b) 1- Phenyl formyl methane 47. C 3 H 6 O shows c) 2- Phenyl ethanal a) chain isomerism b) position isomerism d) 1- Phenyl methanal c) metamerism d) functional isomerism
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Aldehydes, Ketones and Carboxylic Acids 34 48. How many aldehydes are possible for molecular 58. Calcium formate, on dry heating, produces
formula C 4 H S O ? a) acetone b) acetic acid a) 2 b) 3 c) acetaldehyde d) formaldehyde c) 4 d) 5 59. The reaction of RON with RMgX followed by 49. How many ketones are possible for molecular hydrolysis gives
formula C 4 H 8 O? a) an aldehydes b) an ketones a) 1 b) 2 c) 2 0 alcohols d) 3 0 alcohols c) 3 d) 4 60. An isomer of C 3 H 6 Cl 2 on boiling with aq. KOH 50. 2-pentanone and 3-pentanone are give acetone. Hence, the isomer is, a) chain isomers b) position isomers a) 2, 2-dichloro propane c) metamers d) functional isomerism b) 1, 2-dichloro propane 51. Ketone never show c) 1, 1-dichloro propane a) chain isomerism b) position isomerism d) 1, 3-dichloro propane c) both a and b d) optical isomerism 61. 2, 2-dichloro butane on boiling with aq. potash 52. In > C = O group sigma bond is formed by gives a) sp 2 -p-overlapping b) sp 3 -p-overlapping a) butanal b) 2-butanone c) sp-p-overlapping d) s-p-overlapping c) 2-butanol d) butanoic acid 53. The -bond in carbonyl group is formed by 62. Propanone can be obtained from oxidation of what? a) s-s-overlapping b) p-p-overlapping a) 2-propanol b) 1-propanol c) s-p-overlapping d) p-d-overlapping c) 2-butanol d) 2methyl,l-butanol 54. IUPAC name of following compound is 63. The reaction O O O || Pd. BaSO 4 CH3 COCl H 2 auinoline CH 3 C H HCl a) heptane 2,6-dione b) octan-6-one is called c) octane 2,7-dione d) hexane-2,5-dione a) Cannizzaro's reaction 55. Butanone and butanal are b) Stephen's reduction a) chain isomers b) position isomers c) Haloform reaction c) functional isomers d) tautomers d) Rosenmund's reduction 56. Metamerism is present in 64. Rosenmund's reduction is used to prepare a) CH –O–CH b) CH–CO–CH 3 3 a) alcohol b) carboxylic acid c) CH –CO–C H d) CH –CO–C H 3 2 5 3 3 7 c) aldehyde d) Ketones Preparation Methods 65. Benzaldehyde is obtained from Rosenmund's reducation of 57. Product of folio wing reaction is O O || || alkaline Hydrolysis ? Cl Cl a)CH 3 b) X O || a) b) O | || OH Cl Cl OH | c) d) Cl Cl c)| d) | OH | OH
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Aldehydes, Ketones and Carboxylic Acids 35 66. 1,1-dichlorocyclohexane on alkaline hydrolysis 71. 2-methyl propanal is formed from isopropyl gives magnesium halide and what ?
a) cyclohexane carbaldehyde a) CH 3 CN b)HCHO
b) cyclohexanone c)HCN d)CH 3 COCH 3 c) benzophenone 72. Calcium acetate on heating gives d) cyclohexane carboxylic acid a) acetone b) formic acid 67. Product of the following reaction is c) acetal dehyde d) methane X 73. Which of the following is Collin's reagent ?
Pd BaSO 4 || H2 Quinoline ? a) pyridine O b) chromium oxide a) propanone b) propanal c) pyridinium chlorochromate
c) propionic acid d) propane d) KOH + KMnO 4 68. Rosenmund's reduction convert 74. Dry distillation of a mixture of calcium acetate a) carboxylic acid to aldehyde and calcium formate can form b) ketone to 2.-alcohol a) formaldehyde b) acetaldehyde c) acyl halide to ketone c) acetone d) all of these d) acyl halide to aldehyde 75. Which of the following is not used in the preparation of ketone ? 69. An optical active alcohol of formula C 4 H 10 O on oxidation gives which of the following compound? a) Oxidation of secondary alcohols b) Dehydrogenation of 2 0 alcohol a) (CH 3 ) 2 CHCHO b) (CH 3 ) 2 C = CH 2 c) Pyrolysis of calcium acetate c) CH 3 COC 2 H 5 d) CH 3 CH 2 CH 2 CHO 70. A single compound of the structure is obtainable d) Acid hydrolysis of alkyl cyanide 76. Which of the following compounds is oxidised to CH CH |3 | 3 prepare ethyl methyl ketone ? OHC CH2 CH CH 2 C O a) 1-butanol b) t-butyl alcohol from ozonolysis of which of the following cyclic c) 2-butanol d) 2-propanol compounds? 77. Product formed when but-1-yne is reacted with
dil.H 2 SO 4 and HgSO 4 a) H3 C a) b)
CH 3
b) OH H3 C | c) d) CH 3 || OH H3 C 78. Isopropyl alcohol On oxidation forms c) H C a)acetone b)ether 3 CH 3 c) acetaldehyde d) ester 79. Ethylidence chloride on hydrolysis with aq.NaOH gives
a) CH 3 CHO b)CH 3 COC 2 H 5
d) c) C 2 H 5 OH d) CH 3 CH(OH) 2 CH 3
CH 3
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Aldehydes, Ketones and Carboxylic Acids 36 80. Acetone is prepared by 88. Ethylidene chloride on treatment with aqueous a) oxidation of acetic acid KOH gives? b) pyrolysis of acetic acid a) Acetaldehyde b) Ethylene glycol c) pyrolysis of calcium acetate c) Formaldehyde d) None d) oxidation of n-propyl alcohol 89. Find out reducing agent in following conversion. 81. Formation of acetaldehyde from ethanol is known as X H a) oxidation b) substitution c) addition d) reduction
82. Ketones can be obtained in one step by a) Na.Hg + H 2 O
a) hydrolysis of esters b) H 2 + Ni
b) oxidation of primary alcohols c) Pd.BaSO 4 + quirioline
c) oxidation of secondary alcohols d) SnCl 2 + HC1 d) reaction of acid unhydride and alcohol. 90. Which poison the catalyst (Pd) at aldehyde stage 83. 2-butanone can be obtained by heating a mixture in the reduction of acyl halide
of calcium salt of a)PCC b)BaSG 4
a) formic acid and butyric acid c) SnCl 2 d) CuSO 4 b) propionic acid and formic acid 91. Cyclohexanoyl chloride on reduction by poisoned c) propionic acid and acetic acid catalyst gives d) acetic acid and formic acid a) benzaldehyde b) cyclohexanol 84. Ozonolysis following compound in the presence c) cyclohexanone d) cyclohexyl methanal of Zn gives 92. Stephen's reduction convert a) acyl chloride to aldehyde b) cyanide to aldehyde c) cyanide to carboxylic acid d) cyanide to ketones a) b) 93. The reaction H H SnCl2 HCl R C N R CHO NH 3 H2 O O c) d) a) Rosenumund's reduction O b) Stephen's reducation 85. On heating calcium acetate and calcium formate, c) Clemmenson's reducation the product formed is d) Cannizzaro's reaction 94. Formonitrile is reduced by SnCl + HC1 and a) CH 3 COCH 3 b) CH 3 CHO 2 product on acid hydrolysis gives c) HCHO + CaCO 3 d) CH 3 CHO + CaCO 3 86. Which of the following compound gives a ketone a) formic acid b) methanal with Grignard reagent ? c) acetic acid d) acetone a) Formaldehyde b) Ethyl alcohol 95. Product of the following reaction is c) Methyl cyanide d) Methyl iodide 87. Which one is not synthesized by Grignard CN reagent? (iso but)2 Al H ? a) Primary alcohol b) Secondary alcohol c) A ketone d) An ester CN
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Aldehydes, Ketones and Carboxylic Acids 37 101. Acetaldehyde is COOH NH 2 a) oxidising agent a) b) b) reducing agent c) both oxidising and reducing agent COOH NH 2 d) none of these CHO CHO 102. Ethyl cyanide is reduced by di-isobutyl aluminium c) d) hydride gives a) propanal b) propanoic acid CN CHO c) propan-1-amine d) propane 96. Rosenmund's reduction carried out by using 103. Methyl benzoate is reduced by di-isobut aluminium hydride gives a) H 2 /Ni b) Na.Hg + H 2 O c) LiAlH d) Pd-BaSO + quinoline O O 4 4 || || 97. Product of the following reaction is a) b) CN
SnCl2 HCl 2(H) ? H3 O O O || || COOH CHO c)H d) H a) b)
O 104. Pent-3-ene-l-nitrile on reduction by di-isobutyl || aluminium hydride gives NH 2 C CH 3 c) d) NH a) 2 98. Conversion of ester to aldehyde which of the O || following reagent is used ? b) H a) SnCl + HC1 O 2 || b) Pd.BaSO + quinoline c) 4 H c) Cr O O 2 3 || d) (isobut) Al–H d) 2 OH 99. The product of following reaction is
(iso but)2 AI H 105. Etard oxidation convert toluene to C2 H 5 COOCH 3 ? a) benzoic acid b) acetophenone a) CH –CHO b)C H CHO 3 2 6 c) benzaldehyde d) benzoyl chloride O 106. Oxidising agent in Etard oxidation is || c) d) C H –COOH a) K Cr O + dil.H SO CH3 C C 2 H 5 2 5 2 2 2 2 4 b) KOH + KMNO 100. Compound A is reacted with KCN and followed 4
c) dil.HNO 3 by reduction using SnCl 2 + HC1 and successive
hydrolysis gives propanal. The compound A is d) CrO 2 Cl 2 in CS 2 107. Oxidation of toluene by chromium oxide in acetic a) C 2 H 5 –X anhydride gives b) C 2 H 5 –OH a) benzaldehyde b) benzoic acid c) CH 3 –CH 2 –CH 2 –X c) benzophenone d) acetophenone d) C 2 H 5 –CN
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Aldehydes, Ketones and Carboxylic Acids 38 108. p-nitro toluene convert p-nitro benzaldehyde by c) H using
a) KOH + KMnO 4 b) CrO 3 in (CH 3 CO) 2 O d) NH 2 c) SnCl + HC1 d) Pd-BaSO + guinoline 2 4 114. Ethyl acetate is reduced by di-isobutyl aluminium 109. Find out B in the reaction hydride gives
AlCl3 CrO 332 /(CH CO) O a)H b) CHX3 A B H3 O
a) Acetophenone O OH || || b) benzaldehyde c) d) OH c) cyclohexyl carbaldehyde d) benzoic acid 115. Compound A is reacted with C 2 H 5 –X gives B. 110. Find out C in the following reaction The compound B is reduced by di-isobutyl aluminium hydride gives butanal. The compound A is AlCl CHCl 3 A Cl2 / U.V.L. B Aq. KOH C 2 5 a)OH b) OAg
a) benzaldehyde b) l-phenyl ethanal c)H d) ONa c) Acetophenone d) benzophenone || 111. The reaction OH 116. Benzal chloride on hydrolysis gives CHO CO HCl CuCl a) benzole acid b) benzaldehyde c) benzo chlorid d) benzyl cholride a) Rosenmund's reaction 117. Toluene on side chain chlorination and following by hydrolysis gives b) Stephen's reaction a) Tolyl chloride b) benzaldehyde c) Cannizzaro's reaction c) p-chloro toluene d) acetophenone d) Gatterman-koch reaction 118. Side chain chlorination of ajkyl benzene followed 112. Tbluene is subjected to Gatterman-Koch reaction by hydrolysis gives produces a) aromatic aldehyde a) benzaldehyde b) aromatic ketones b) benzoic acid c) aromatic carboxylic acid c) 2-methyl benzaldehyde d) both a and b d) acetophenone 113. Following compound on reducation by using Properties and Uses 119. A reagent which reacts differently with (iso-but) 2 Al-H gives CH 2 O,C 2 H 4 O, C 3 H 6 O is CN a) NH 2 OH b) C 6 H 5 NHNH 2 c)HCN d)NH a) H 3 120. Which of the following has maximum reactivity towards HCN ? a) HCHO b) OH b) CH 3 CHO
c) CH 3 COCH 3
d) CH 3 COC 2 H 5
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Aldehydes, Ketones and Carboxylic Acids 39
121. Consider the following substances 129. Acetone on treatment with CH 3 MgI on further hydrolysis gives 1. HCHO 2. CH 3 CHO a) (CH ) CHCH OH 3. CH 3 COCH 3 4. CH 3 COC 2 H 5 3 2 2
The correct order of reactivity towards b) (CH 3 ) 3 COH
nucleophilic addition reaction is c) CH 3 CH(OH)CH 2 CH 3
a) l > 2 > 3 > 4 b) 1 > 3 > 2 > 4 d) CH 3 CH 2 CH(OH)CH 2 CH 3 c) l > 2 > 4 > 3 d) 1 > 4 > 2 > 3 130. Base catalysed aldol condensation occurs with 122. The reagent with which both acetaldehyde and a) propanal b) butanal ketone react easily is c) ethanal d) all of these a) Fehling solution 131. Treatment of propanal with dilute NaOH solution b) Grignard's reagent gives
c) Schiffs reagent a) CH 3 CH 2 COOCH 2 CH 2 CH 3
d) Tollen's reagent b) CH 3 CH 2 CHOHCH(CH 3 )CHO
123. Inpresence of conc. alkali formaldehyde c) CH 3 CH 2 CHOHCH 2 GH 2 CHO undergoes d) CH 3 CH 2 COCH 2 CH 2 CHO a) Aldol condensation b) Cannizzaro's reaction 132. Ethanal and propanone undergoes aldol c) Esterification d) Wurtz reaction condensation reaction inpresence of dilute alkali 124. The Cannizzare's reaction is not given by to form
a) benzaldehyde b) chloral a) CH 3 C(OH)(CH 3 )CH 2 CHO
c) methanal d) ethanal b) CH 3 CH(OH)CH 2 COCH 3
125. Treatment of butanal with dilute NaOH solution c) CH 3 COC(OH)(CH 3 ) 2
gives d) CH 3 COCH(CH 3 )CH 2 OH
a) CH 3 CH 2 CH 2 COOCH 2 CH 2 CH 2 CH 3 133. Iodoform test is not given by
b) CH 3 CH 2 CH 2 CHOHCH 2 CH 2 CH 2 CHO a) ethanol b) ethanal
c) CH 3 CH 2 CH 2 CHOHCH(C 2 H 5 )CHO c) acetone d) 3-pentanone
d) CH 3 CH 2 CH 2 COCH 2 CH 2 CH 2 CHO 134. Methyl ketones are usually characterised through 126. The products of the reaction of two molecules of a) the Tollen's reagent HCHO with strong potash is b) the Schiffs reagent
a) CH 3 OH and HCOOH c) the iodoform test
b) CH 3 OH and HCOONa d) Cannizzaro's reaction
c) CH 3 OH and HCOOK 135. Grignards reagent adds to
d) C 2 H 5 OH a) >C = 0 b) >C = S
127. In the reaction of NaHSO 3 with carbonyl c) –C = N d) all of the above compounds to form bisulphite product, the 136. An organic compound of formula, C H O forms nucleophile is 3 6 phenyl hydrazone, but gives negative Tollen's test. – a) HSO 3 b) SO 3 Na The compound is c) SO – d) none of the above 3 a) CH 2 = CHOCH 3 128. The formation of cyanohydrin from a ketone is b) CH 3 CH 2 CHO an example of c) CH 3 COCH 3 a) electrophilic addition d) CH 2 = CHCH 2 OH b) nucleophilic addition 137. Which does not react with Fehling solution ? c) electrophilic substitution a) Ethanal b) Glucose d) nucleophilic substitution c) Formic acid d) Benzaldehyde
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Aldehydes, Ketones and Carboxylic Acids 40 138. The reaction of RMgX with a ketone, followed 147. Cyanohydrine of the following compound on + by treatment with H 3 O forms hydrolysis give optically active compound. a) 1 0 alcohol b) 2 0 alcohol a) CH 3 –COCH 3 b) H–CHO c) 3 0 alcohol d) alkane. c) CH 3 – CHO d) All of these 139. When acetone is heated with ammonia gives 148. When ethanal is heated with Fehling's solution, it diacetone amine, the intermediate compound gives a precipitate of formed in this reaction is, a) Cu b) CuO
a) (CH 3 ) 2 C = CHCOCH 3 c) Cu 2 O d) Cu 2 O + CuO b) CH CH CH = CH COCH 3 2 2 3 149. Benzene is reacted with carbon monoxide in HC1
c) (CH 3 ) 2 C = CHCH 2 CHO in the presence of catalyst, cupric chloride gives d) (CH ) C = CH CH COCH 3 2 2 2 3 COOH CHO 140. > C = O is converted into – CH 2 – by a) b) a) Clemmenson reduction b) H /Ni 2 CHO Cl c) Mendius reduction c) d) d) NaHg + H O reaction. 2 150. Which of the following is used to prepare ketone 141. Which of the following give self redox reaction? from acyl chloride a) Methanal b) Ethanal a) R–MgX b) R Cd c) Butanal d) Methanol 2 c) CO + HC1 d) CrO 142. Which of the following reagent react with CH O 3 2 151. Dimethyl cadmium and acetyl chloride produces forming urotropine ? a) acetone a) NH 2 OH b) NH 3 b) t-butyl alcohol c) HCN d) RMgX c) 2 0 -propyl alcohol 143. Propanal and propanone undergoes condensation reaction in presence of dil.KOH to form, d) n-propyl alcohol 152. Product of the following reaction is a) CH 3 CH 2 CH(OH)CH 2 COCH 3 b) CH C(OH)(CH )CH(CH )CHO dry ether 3 3 3 CH3 COCl CH 3 MgX H3 O c) CH 3 CH(OH)(CH 3 )CH 2 CH 2 CHO a) b) d) none of these OH 144. Which one of the following reaction yield diace- tone alcohol from carbonyl compound? O O a) Cannizzaro's reaction || c) d) || b) Catalytic hydrogenation H OH c) Aldol condensation 153. Benzonitrile and phenyl magnesium bromide d) Oxidation produces 145. When H-CHO reacts with NHj, urotropin is O formed. In this molecule how many C–C bonds || are present? a) a) 4 b) 2 c) 0 d) 6 O 146. Acetone shows similarity with acetaldehyde in || reacting to b) a) Tollen's reagent b) Schiffs reagent c) Fehling solution d) Grignard reagent
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Aldehydes, Ketones and Carboxylic Acids 41 O 157. Product of the following reaction is || O c) Unhy. AlCl 3
O O d) || || a)OH b) 154. Product of the following reaction is CN MgX O O dry ether || || H3 O c) d)
a) 158. In the following sequence of reaction end product is. O || HO2 Hg/HSO 2 4 [O] CaC2 A B C
b) Ca dry distillation OH D E a) acetaldehyde b) propanone c) c) methanal d) ethanoic acid 159. In the following sequence of reaction end product is O || Hg /H2 SO 4 A CH3 MgX B d) a) b) | 155. Friedel Craft acetylation of benzene gives O a) benzophenone b) acetophenone c) alkyl benzene d) di phenyl c) d) OH H 156. Diphenyl methanone is obtained from 160. The product 'B' in the following reaction. O || H HCN A H3 O a) Cl Unhy. AlCl 3 O a)|| b) H | b) U.V.L. H2 O Cl2 A OH O O || || CH c) d) 3 | H c) CO HCl OH CuCl 2 161. The correct order of solubility of following O compound is || CH 3 1.H–CHO 2. CH –CHO O 3 (isobutyl)2 Al H 3. CH –CH –CHO 4. CH –COCH d) 3 2 3 3 a) 4 > 3 > 2 > 1 b) 1 > 2 > 4 > 3 c) 1 > 2 > 3 > 4 d) 1 > 4 > 2 > 3
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Aldehydes, Ketones and Carboxylic Acids 42 162. Acetylene on hydration gives compound A, which c) This reaction proceeds in presence of strong on Clemmenson's reduction gives ? alkali a) Ethane b) Ethyl alcohol d) Ketones, in which -hydrogen atom is present, c) Acetaldehyde d) Ethene give this reaction 170. If formaldehyde and KOH are heated then we get 163. Compound 'A' has molecular formula C 5 H 10 O reduce Tollen's reagent on oxidation gives a) methane b) acetylene monocarboxylic acid with same number of carbon c) ethyl formate d) methyl alcohol atoms. The compound A' is 171. Benzaldehyde is converted to benzyl alcohol by a) CH COCH(CH ) b) CH (CH ) –CHO 3 3 2 3 2 3 a) Wurtz reaction c) C H COC H d) CH COCH CH CH 2 5 2 5 3 2 2 3 b) Fitting reaction 164. Wolf-Kishner reduction is c) Wurtz fittings reaction a) reduction of carbonyl compound in to alcohol d) Cannizzaro's reaction b) reduction of carbonyl compound in to alkene 172. Aldehydes are oxidised to acids by c) reduction of carboxyl compound in to alkane a) potassium dichromate d) reduction of nitro compound into aniline b) Tollen's reagent 165. Among the following compound the reactivity order is c) Fehling's solution d) all of these 1. H–CHO 2. CH 3 –CHO 173. Formaldehyde + ammoniac Y the product Y is O || a) methanol 3. 4. C H –COCH CH3 C CH 3 2 5 3 b) formamide a) l > 2 > 4 > 3 b) 4 > 3 > 2 > 1 c) para-formaldehyde c) l > 2 > 3 > 4 d) 1 > 3 > 4 > 2 d) hexamethylene tetraamine 166. Less reactivity of ketone is due to 174. Acetaldehyde and acetone can be identified by a) +1 inductive effect decrease positive charge a) Schiff s test b) Lucas test on carbonyl carbon atom c) Iodoform test d) Bromoform test b) steric effect of two bulky alkyl groups 175. Ethanal reacts with alkali to give 3-hydroxy c) sp 2 hybridised carbon atom of carbonyl carbon butanal. The reaction is atom a) Aldol condensation d) both a and b b) Claisen condensation 167. To distinguish between acetone and iso-propyl c) Cannizzaro's reaction alcohol, which of the following reagent can help d) Clemmenson reduction a)NaCl b)NaOH 176. Which of the following undergoes haloform
c) Na 2 CO 3 d) NaHSO 3 reaction ? 168. Which of the following statement is wrong? a)HCHO b)(CH 3 ) 2 CO a) aldehyde and ketones are reducing agents c) C 2 H 5 C1 d) CH 3 –O–CH 3 b) aldehyde and ketones are nonpolar compounds 177. Which of the following cation is involved in c) aldehydes are more reactive than ketones Tollens reagent ? + – d) aldehydes and ketones are reduced to alcohol a) [Ag(NH 3 ) 2 ] b) 2OH + 169. Which of the following statement is correct c) [Ag(NH 3 ) 3 ] d) AgNO 3 regarding the aldol condensation? 178. Diethyl ketone and a dimethyl ketone can be a) All aldehydes give this reaction distinguished with b) Ketones do not give this reaction a) Tollen's reagent b) Fehling's solution c) Schiffs reagent d) Haloform test
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Aldehydes, Ketones and Carboxylic Acids 43
179. Tollen's reagent is 188. A neutral compound C 4 H 8 O 2 , reduce Fehling's solution, and liberate H gas when treated with a) ammonical CuSO 4 2 b) ammonical AgNO sodium metal and give positive iodoform test. The 3 compound is c) alkaline solution containing complex of copper a) CH –CHOHCH –CHO nitrate. 3 2 b) HO–CH –CH –CHO d) none of these 2 2 c) CH –CO–CH –CHO 180. Reduction of a keto group to a methylene group 3 2
is converted by using d) CH 3 COCH 2 –CH 2 –OH a) ZnHg + conc. HC1 R OR b) NaHg + water 189. Compound of general formula C c) Sn + conc. HC1 are called H OR a) diester b) acidlinhydride d) Zn + CH 3 COOH 181. Which statement is false regarding acetaldehyde c) hemiacetal d) acetal and acetone ? 190. In the reaction a) Both reduce ammonical silver nitrate to silver CH CH O A dry HCl mirror 3
b) Both react with hydroxylamine to form oximes CH 3 CH(OC 2 H 5 ) 2 +H 2 O c) Both react with hydrazine to form hydrazone The compound A is d) Both react with sodium bisulphite to form a) propan-1-ol b) ethanol addition product c) methanol d) C 2 H 5 –O–C 2 H 5 182. Which of following give haloform test? 191. During reduction of aldehyde with hydrazine and KOH, the first is the formation of a) CH 3 –CHO b)C 2 H 5 –CHO a) R – CH = NH b) R – CH = N – NH c)H–CHO d)C 2 H 5 –CO–C 2 H 5 2
183. Which of the following compounds does not c) RCONH 2 d) R – C = N contain an – OH group? 192. Product of following reaction will be a) Alcohol b) Phenol H OH dry HCl c) Aldehyde d) Carboxylic acid
184. HCHO and CH 3 CHO differ from each other towards a) Schiffs reagent b) Fehling solution a)O b) O O c) ammonia d) ammonical AgNO 3 185. The most active carbonyl compound is c)O d) O a)HCHO b)CH CHO 3 O | O c) CH 3 COCH 3 d) C 2 H 5 CHO 186. Out of 193. Compound of general formula are called 1. butane 2. butan-1-ol a) acetal b) hemiketal 3. butanal 4. butanone c) ketal d) hemiacetal The decreasing order of their B.P is 194. Acetals are a) 1 > 2 > 3 > 4 b) 2 > 4 > 3 > 1 a) aldehyde b) ketones c) 2 > 3 > 4 > 1 d) 4 > 2 > 3 > 1 c) ethers d) diether 187. Acetone is converted into propane by Wolff- Kishner reduction by using reagent 195. Pentan-3-en-2-one is reduced by LiAlH4 gives a) pent-4-en-2-ol b) pent-3-en-l-ol a) LiAlH 4 b) Zn.Hg + conc. HCl c) pent-2-ol d) pent-3-en-2-ol c) H 2 + pd-BaSO 4 d) NH 2 –NH 2 and KOH
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Aldehydes, Ketones and Carboxylic Acids 44 196. Which is best solvent? c) disinfectant
a)H–CHO b)CH 3 COCH 3 d) disinfectant and preservative
c) CH 3 – CHO d) CH 3 COOH 201. Carbonyl group in aromatic aldehyde and ketone 197. What is the structure of carbonyl compounds that is will give following compound ? a) o-directing b) p-directing O c) o-and p-directing d) m-directing CH || 3 202. Benzaldehyde on nitration gives a) o-nitrobenzaldehyde b) p-nitrobtiizaldehyde O O c) mixture of 'a' and 'b' || || CH 3 d) m-nitrobenzaldehyde a) and 203. Product of the following reaction will be
(i) O 3 O O (ii) H2 O / Zn || || CH 3 H and b) a) cyclohexanal b) cyclohexanone O c) cyclohexane carbaldehyde || CH 3 d) cyclohexane carboxylic acid c) and 204. But-2-en-l-ol on oxidation by using PCC gives a) Butan-1-ol b) butanal O O || c) but-2-en-al d) butan-2-one || CH 3 205. Following compound on oxidation by dil.H SO and 2 4 d) gives
O2 N OH 198. Prop 1,3-diphenyl 2-en-l-one is crossed condensation product. Which is obtained from a) benzophenone a) H2 N COOH b) Acetophenone c) benzaldehyde COOH d) Acetophenone and benzaldehyde b) H2 N 199. In mechanism of aldol condensation reaction the second step is c) O2 N COOH a) abstraction of -H atom carbon of aldehyde by base to form carbanion d) O N O b) The attack of carbanion on carbonyl carbon 2 atom of another molecule to form alkoxide ion 206. Product of the following reaction is c) The attack of carbanion on carbonyl carbon O atom of another molecule to form oxocation || d) Alkoxide ion take proton from water to form Cl Unhy. AlCl -hydroxy aldehyde 3 200. Formaldehyde is used as a) solvent a) acetophenone b) antiseptic b) diphenyl methanone
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Aldehydes, Ketones and Carboxylic Acids 45 c) 2-diphenyl cthanone O || d) 1-phenyl ethanone 207. Methyl ketone group is identified by 211. NH2 NH 2A Br 2 B KOH AlBr 3 a) Lucas test b) Haloform test The product A and B are c) Hinsberg test d) Millon's test COH 208. Match the list-I and II and select the correct a) and answer List-I List-II OH Br | | 1. Cannizzaro's reaction a) SnCl 2 + HCl 2. Stephen's reaction b) 50%NaOH b) and
3. Clemmenson reduction c) Pd-BaSO 4 + Br quinoline | 4. Rosenmund's reduction d) Zn. Hg c) and + Conc. HC1 NH Br a) 1-b, 2-d, 3-a, 4-c b) 1-b, 2-c, 3-d, 4-a | 2 | c) 1-b, 2-a, 3-d, 4-c d) 1-d, 2-a, 3-c, 4-b d) and 209. Which of the following is not correct reaction? a) 6H CHO 4NH3 (CH 264 ) N 6H 2 O 212. A carbonyl compound 'A' react with hydrogen OH O cyanide to give cyanohydrin 'B' which on acid O | || hydrolysis gives, optically active -hydroxy propanoic acid 'C' Compounds A, B, C b) dil. NaOH respectively are OH O H H | | c) dil. NaOH a) HCHO,H C OH,H C OH | | CN COOH O || d) NH2 NH 2 H H C2 H 5 ONa | |
b) CH3 CHO, CH 3 C OH, CH 3 C OH 210. What is product formed when cyclohexane | | CN COOH carbaldehyde undergoes aldol condensation followed by heating. H H CHO | | c) CH CHO,CH C OH,CH C OH a) 25 25| 25 | CN COOH CHO CH CH CH |3 | 3 | 3 d) CH C O, CH C OH, CH C OH b) 3 3| 3 | CN COOH 213. Which of the following alkane cannot be prepared c) by Clemmenson's reduction of ketones? CHO CHO Acetone + A Oxime of acetone Acetone + B propane Acetone + C Pinacol d) A, B and C are
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Aldehydes, Ketones and Carboxylic Acids 46
a) NH 2 –OH, Mg, Zn.Hg + conc. HC1 218. Which of the following alkane cannot be prepared by clemmenson's reducation of ketones? b) NH 2 –OH, Zn.Hg + conc. HCL, Mg
c) Mg, NH 2 –OH, Zn.Hg + conc. HC a) b) d) NH 2 –OH, Na.Hg + H 2 O, Mg 214. CHO NaOH 50 % product (s), | c) d) COOH 219. Reaction of aldehyde with NH 2 –OH will be fastest
Identify the products at which of the following P H a) 1 b) 6 COONa CH2 OH a) | b) | c) 7 d) 8 COONa COONa 220. In the reaction. CHO Zn Hg HCl c) both a and b d) | A COONa NH NH KOH C O 2 2 B 215. Structure C H Cl an alkaline hydrolysis gives a Na.Hg H O 8 8 2 2 C product which does not give iodoform test but give silver mirror test, is a) A = aldehyde, B = ketone, C = alcohol
CCl2 C 2 H 5 b) A, B, C are alkene. a) c) A, B are alkane and C = alcohol d) A, B are alkane, C = alkene Cl2 CH 3 221. In Cannizzaro's reaction of formaldehyde involves b) an a) Intramolecular shift of proton CH2 Cl b) Intramolecular shift of hydride c) Intermolecular shift of proton c) Cl d) Intermolecular shift of hydride 222. Consider two aldehydes CH 3 CH2 CHCl 2 1. CH 3 -CHO 2. H–CHO d) The correct statement is/are a) both undergoes aldol condensation 216. Which of the following reagent to get b) both do not undergoes aldol condensation 3 2 sp -hybridised carbon atom from sp -hybridised c) only (1) undergoes aldol condensation carbon atorri? d) only (2) undergoes aldol condensation a) NH –NH b) NH –CO–NH–NH 2 2 2 2 223. Final product B in the following sequence of c) NH –NH /KOH d) NH OH 2 2 2 reaction 217. An alkene (A) on ozonolysis gives (B) as one of Cu NaOH the product, (B) can gives Cannizzaro's reaction. C6 H 5 CH 2 OH 573 k A strong B The compound (A) is + C 6 H 5 CH 2 –OH a) benzaldehyde b) acetophenone a) b) c) sodium phenoxide d) sodium benzoate 224. The final product 'C' in the following reaction...... H CHO CH CH CHO OH A c) d) 3 2
/ H B NaBH 4 C
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Aldehydes, Ketones and Carboxylic Acids 47 229. Which of the following isomeric compound is most a) CH2 C CHO | reactive? O O || CH 3 a)|| b) c) d) all are equally reactive b) CH CH CH OH 3| 2 CH 3 230. The reagent which oxidise aldehyde and ketone c) CH C CH OH is 2| 2 a) Tollen's reagent b) Fehling's solution CH 3 c) Schiffs reagent d) K Cr O + H SO d) CH = CH–CH – CH – OH 2 2 7 2 4 2 2 2 231. The product of given reaction is 225. Which of the following four hydrogens is most acidic ? O alkaline ? O KMnO 4 2 || 3 4 CH2 C CH 2 CH 3 a) CH 2 = CH(CH 2 ) 3 –COOH b) CH –(CH ) –COOH H 3 2 4 1 CHO
a) 1 b) 2 c) (CH2 ) 4 COOH c) 3 d) 4 CHO
226. Find out A, B, C, D in following reaction d) (CH2 ) 4 CHO 1. CH3 CH CH CHO CH3 CH CH 232. 3-methyl cylohexene on oxidation will give – COOH O || OH 2. CH CH CH CHO B CH CH CH a) 3 3 O || CH 2 – OH OH C b) HO 3. R COOH R CH OH 2 O || 4. R COCl D R CHO H c) H a) 1 = H .pd.BaSO , 2 = Ammonical AgNO O 2 4 3 || 3 = LiAlH , 4 = LiAlH OH 4 4 d) HO b) 1 = LiAlH 4 , 2 = LiAlH 4 , 3 = H 2 .Pd.BaSO 4 , 4 = Ammoniacal AgNO 233. Cyclohexanone is treated with Ba(OH) gives c) 1 = Ammonical AgNO , 2 = LiAlH , 2 3 4 OH O 3 = LiAlH , 4 = H Pd + BaSO OH O 4 2 4 | || | || d) 1 = LiAlH4, 2 = LiAlH , 3 = Ammoniacal 4 a) b) AgNO 3 , 4 = H 2 Pd + BaSO 4 227. Which among the following is most reactive in OH O O nucleophilic addition ? | || || a) FCH – CHO b) C1–CH CHO 2 2 c) d) c) Br–CH 2 –CHO d) I–CH 2 –CHO 228. Which of the following carbonyl compound is most 234. Mixture of ethanal and propanal is subjected to polar? aldol condensation, the product formed are a) CH COC H b) CH COCH 3 2 5 3 3 a) 1 b) 2 c) CH CHO d)H – CHO 3 c) 3 d) 4
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Aldehydes, Ketones and Carboxylic Acids 48
235. Aldehyde which shows Cannizzaro's reaction is 242. (CH 3 ) 2 C = CHCOCH 3 can be oxidised to (CH ) C = CH–COONa by a)H–CHO b)C 6 H 5 –CHO 3 2 a) NaOH + KOH b) NaOH c) CCl 3 – CHO d) all of these KMnO + 236. The aldehyde having -H atom gives c)NaOI d) 4 /H Cannizzaro's reaction is 243. For the following conversion which can be used
a) CH 3 –CH 2 –CHO R2 C O R 2 CH 2 CH | 3 a) Clammenson's reaction b) CH3 CH CHO b) Wolff Kishner reaction c) Zn + conc. HC1 c) CH 3 –CH 2 –CH 2 –CHO d) both 'a' and 'b' d) CH3 CH CHO | 244. Benzaldehyde can be prepared by hydrolysis of Cl a) Benzyl chloride b) Benzal chloride 237. Mixture cf H–CHO and C H –CHO is treated 6 5 c) Benzotrichloride d) benzonitrile with cone. NaOH then self redox reaction involves 245. 1-phenyl ethan-1-ol is prepared by reaction of benzaldehyde with 1. oxidation of H–CHO a) methyl bromide 2. oxidation of C H –CHO 6 5 b) ethyl magnesium iodide 3. reduction of H–CHO c) methyl magnesium bromide 4. reduction of C 6 H 5 –CHO a) 1, 3 b) 1, 2 d) methyl iodide and zinc metal c) 1, 4 d) 2, 3 246. Oxidation of toluene to benzaldehyde by chromyl chloride is called 238. When ethanoyl chloride is reduced with hydrogen a) Rosenmund reaction using Pd deposited over BaSO 4 catalyst it forms a) ethane b) chloroethane b) Wurtz reaction c) ethanal d) ethanol c) Etard reaction 239. Crotonaldehyde is easily oxidised to crotonic acid d) Fitting reaction using 247. Which of the following reagent convert
a) alkaline KMnO 4 b) Tollen's reagent C65 H CHO C 65 H COOH c) acidic KMnO d) CrO 4 3 a) Fehling's solution b) PCC 240. Which of the following aldehyde forms stable c) Tollen's reagent d) H + Ni hydrate? 2 a) Trichloroacetaldehyde 248. The product of following reaction will be b) acetaldehyde c) fomaldehyde CHO | d) propanal R.T. 241. An unknown alkyl halide 'A' reacts with alcoholic Conc. KOH
KOH to produce C 4 H 8 . Ozonolysis of the Cl hydrocarbon gives one mole of propanal and one mole of methanal the correct structure of 'A' is Br a) m-hydroxy benzaldehyde a)Br b) | b) potassium m-chlorobenzoate and benzyl | alcohol Br c) potassium m-chlorobenzoate and m- Br | chlorobenzyl alcohol c) d) Br d) m-cresol
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Aldehydes, Ketones and Carboxylic Acids 49 249. Hydrogenation of benzyol chloride in the presence b) Pentan-2-one and 3-methyl butan-2-one
of Pd on BaSO 4 gives c) Pentanal a) benzyl alcohol b) benzoic acid d) pent-3-one c) benzaldehyde d) phenol 257. CH 3 –CH = CH – CHO is oxidised to
250. An organic compound does not give a precipitate CH 3 – CH = CH – COOH using oxidising agent with 2, 4-DNP and does not react with sodium a) alkaline KMnO 4 metal. It could be b) K 2 Cr 2 O 7 + conc. H 2 SO 4 a) CH 3 –CH 2 –CHO b) CH 3 COCH 3 c) dil. HNO 3 c) CH 3 –CHO d)CH 3 OC 2 H 5 d) ammonical AgNO 3 251. What is 'B' in the following reaction? O (i)SnCl2 HCl Na2 CO 3 || CH3 CN A B (ii) H3 O 258. Ketones R C R' where R Rc alkyl group can be obtained in one step by a) CH3 CH CH 2 CH 3 | a) oxidation of 1 0 alcohol OH b) hydrolysis of ester
b) CH3 CH CH 2 CHO c) hydrolysis of acid anhydride | 0 OH d) oxidation of 3 alcohol 259. Among the given compound the most susceptible c) CH –CH –COONa 3 2 to nucleophilic attack at carbonyl group is d) CH –CH –ONa 3 2 a)HCHO b)MeCOOMe 252. Under Wolff-Kishner reduction the conversion c) MeCHO d) MeCOO COme may be brought about are 260. The reaction given below is a) benzophenone to diphenyl methane OH b) benzaldehyde to benzyl alcohol 2H CHO H COONa CHOH3 c) cyclohexanone to cyclohexene The slowest step is d) cyclohexanone to cyclohexanol a) Wurtz's reaction b) Cannizzaro's reaction 253. When formaldehyde react with ethyl amine, it c) Fittig's reaction d) Etard oxidation gives 261. Which of the following does not used to convert a) formaldehyde imine ketone to secondary alcohol? b) formaldehyde ethyl amine a) LiAlH 4 b) NaBH 4 c) dimethyl amine c) H 2 /Pd-BaSO 4 d) Na + C 2 H 5 OH d) diethylamine 262. The appropriate reagent for following 254. Imine derivatives of aldehyde and ketone is called transformation. as O || a) Schiff s reagent b) Fehling's reagent c) Schiffs base d) Schiffs acid
255. Acetone on condensation gives CH3 O CH3 O a) Zn.Hg + HC1 b) NH NH , KOH a) mesitylene b) mesityl oxide 2 2 c) H + Ni d) both a and b c) propanal d) di-isopropyl ether 2 263. In the following sequence of reaction, 256. A carbonyl compound with molecular weight 86, does not reduce Fehling's solution, but form TolueneKMnO4 A SOCl 2 B H 2 Pd C. BaSO 4 crystalline bisulphite derivatives and gives The produce C is iodoform test. The possible compound can be a) C H –COOH b) C H –CH a) Pentan-2-one and pentan-3-one 6 5 6 5 3 c) C 6 H 5 –CHO d)C 6 H 5 –CH 2 –OH
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Aldehydes, Ketones and Carboxylic Acids 50
264. Which of the following is correct? 270. Compound A of formula C 3 H 8 O is treated with 0 a) reduction of any aldehyde gives 2 alcohol acidic KMnO 3 to form product B of formula C H O, which form shining silver mirror on b) reduction of any ketone gives tertiary alcohols 3 6 warming with ammoniacal AgNO 3 , when B is c) Wolff-Kisher reduction convert > C = O to treated with NH COHNH in HC1 and sodium –CH –OH group 2 2 2 acetate gives the product C. Identity the structure d) Ozonolysis of alkene in the presence of zinc of C. gives aldehydes or keones/mixture of aldehyde and ketones O || 265. Ozonolysis of C H give methanal and 2-methyl 7 14 a) CH3 C N NH C NH 2 pentan-3-one. The C H is | 7 14 CH a) 2-ethyl 3-methyl but-1-ene 3 b) 3-ethyl-2-methyl but-3-ene O c) hept-1-ene || b) CH C N C NH NH d) hept-2-ene 3 | 2 266. In the reaction CH 3
C2 H 5 C2 H 5 O | | H O || CH C O HCN A 3 CH C OH 3 3 c) | CH3 CH 2 CH N.NH C NH 2 COOH O The acid obtained will be || a) L-isomer d) CH3 CH 2 CH N C NH NH 2 b) D-isomer 271. The correct order of reactivity of Ph-MgCl with c) 20% D + 80% L-isomer O || O d) 50% D + 50% L-isomer || 1. 2. CH3 C H 267. A substance C 4 H 10 O yield on oxidation C 4 H 8 O which gives oxime and positive iodoform test. The O original substance on treatment with cone. H SO || 2 4 3. CH3 C CH 3 gives C 4 H 8 . The structure of compound is a) 1 > 2 > 3 b) 3 > 2 > 1 a)OH b) | OH c) 2 > 3 > 1 d) 2 > 1 > 3 OHBr Br 272. Which one of the following oxidised to c)| d) OH corresponding carbonyl compound?
a) b) 268. Which of the following react with NaOH produces | | OH acid and alcohol? Br O a) C H CHO b)CH –CHO || 6 5 3 c)OH d)
c) CH 3 COOH d)C 6 H 5 COOH 269. Which of the following is not correctly matched? 273. 2, 2-diethoxy butane is obtained from ethanol and what? Clemmenson 's a) C0 reduction CH 2 a) CH 3 –CH 2 –CH 2 –CHO Wolff Kishner b) CH 3 –COCH 2 –CH 3 b) C 0 reduction CH OH c) Rosenmund's CH3 CH CH 2 CH 3 c) COCl reduction CHO | OH Stephen 's d) N reduction CHO d) CH 3 –CH 2 –CH 2 –CH 1 –I
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Aldehydes, Ketones and Carboxylic Acids 51 274. Which reagent is used to convert butan-2-one to 279. On reaction with ketone with hydroxyl amine give propionic acid? ketoxime which on reduction produces a) Tollen's reagent b) Fehling's solution a) carboxylic acid b) 1 0 amine 0 c) acidic KMnO 4 d) PCC c) 2 -amine d) amide
275. The compounds HCHO and CH 3 CHO on 280. Aldehyde with NH 2 –NH 2 forms intermolecular aldol condensation gives. a) aniline b) nitrobenzene
a) HO–CH 2 –CH 2 –CHO c) hydrazine d) hydrazone b) CH –CHOH–CH OH 3 2 281. OH C3 H 6 O Mesityl oxide c) CH 3 –CHOH–CH 3 The C H O is d) CH 2 –CHOH–CH 2 –CH 2 OH 3 6
276. Nucleophilic addition reaction is most favored in a) CH 3 –CH 2 –CHO O b) CH COCH || 3 3 a) b) c) CH = CH–CH –OH H 2 2 d) CH C CH c) d) H 3| 2 OH 282. 3-hydroxy 2-methyl pentanal is formed when X 277. The smallest ketone and it's functional isomer are react with Y in dilute Z solution. What are X,Y,Z? treated with NH –OH to form oxime 2 X Y Z a) two different oxime are formed a) CH 3 –CHO CH 3 –CHO NaOH b) three different oxime are formed b) C 2 H 5 –CHO CH 3 –CHO NaOH c) two oximes are optically active c) C 2 H 5 –CHO C 2 H 5 –CHO NaOH d) all oximes are optically active d) C 2 H 5 –CHO C 2 H 5 –CHO NaCl OH 283. A base can absract an -H atom from | HCN B a) CH = CH b) CH = CH 278. RCOR' A RCR' 2 2 | c) CH – CHO d) C H – CHO CH NH 3 6 5 2 2 284. Which of the following pathways produces A and B are 2-pentanone ? 1. pent-1-yne is treated with H SO + HgSO OH 2 4 4 | and water a) A R C R'B Na CHOH2 5 2. 3-methyl hex-2- ene is treated with O | 3 CN followed by hydrolysis 3. n-butylmagnesium halide is reacted with OH formaldehyde | 4. hydroboration oxidation of pent-1-ene b) A R C R' B HO3 | a) 1, 3 b) 1, 2 COOH c) 2, 4 d) 1, 3, 4 OH 285. Which of the following reagent react with same | manner with c) A R C R' B NH | 3 CN CHO
H CHO, CH3 CHO,CH 3 COCH 3 R ' | a) Fehling's solution b) NH d) A R CH CN B NaOH 3 c)HCN d)NaOH
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Aldehydes, Ketones and Carboxylic Acids 52 286. Which statement is correct with ethanal and 294. Aldehydes with Tollen's reagent are propanone a) reducing agent b) oxidising agents
1. Both react with NaHSO 3 c) hydrating agents d) bleaching agents 2. Both gives iodoform test 295. Low reactivity of ketones with respect to 3. Both can be reduced into alcohols aldehydes is due to 4. Both undergoes aldol condensation a) greater + I effect of alkyl group a) 1, 3 b) 2, 3 b) greater steric hindrance of alkyl group c) 2, 4 d) all of these c) both 'a' and 'b' 287. Which of the following react same manner with d) less steric hindrance of alkyl group
H–CHO and C 6 H 5 –CHO ? 296. Aldehydes can be distinguished from ketones by
a) Fehling's solution b) CH 3 –MgX using
c) NH 3 d) dil. NaOH a) dil. NaOH b) R–MgX
288. Acetone gives addition elimination reaction with c) Na 2 CO 3 d) Schiff's reagent
1. NH 2 –OH 2. NH 2 –CONH–NH 2 297. Which of the following are generally used for preparing derivatives of aldehydes and ketones? 3. NaHSO 3 4. CH 3 –NH 2 a) 2, 4 b) 3, 4 a) Hydrocyanic acid c) 1, 2, 4 d) 1, 2, 3 b) Hydroxylamine 289. An carbonyl compounds gives nucleophilic c) Phenyl hydrazine addition reaction with d) All of these
1. HCN 2. NaSHO 3 298. Which of the following is an example of aldol condensation ? 3. R–MgX 4. NH 2 –NH 2 a) 1, 2 b) 2, 3 OH a) 2CH3 CHO CH 3 CH(OH) CH 2 CHO c) 1, 2, 4 d) 1, 2, 3 b) OH 290. Product of the following reaction is CHCHO65 CHCHOH 652
O OH c) HCHO HCH2 OH (H) LiAlH4 in ether OH OH OH d) CHCHO6 5 HCHO CHCHOH6 6 2 a) b) 299. Which of the following can be used to differentiate between acetaldehyde and propanal?
c) d) a) Ammonical AgNO 3
b) CuSO 4 + Na-K tartarate in NaOH
291. The product formed when HCHO is heated with c) I 2 in the presence of base conc. KOH d) Decolourised Fuchin a) CH CHO b)CH OH 3 3 300. Molecular formula 'A' (C 4 H 8 O) reacts with CH MgI gives 3-methyl 2-butanol. The structure c) C 2 H 2 d) CH 4 3 of A is 292. Formaldehyde reacts with NH 3 tourotropine which has the composition a) CH 3 CH 2 CH 2 CHO b) C H COCH a) (CH 2 ) 5 N 5 b) (CH 2 ) 5 N 5 2 5 3 c) (CH ) CHCHO c) (CH 2 ) 4 N 6 d) (CH 2 ) 6 N 4 3 2
293. Pinacol is converted in to pinacolone by d) C 2 H 5 OCH 3
a) rearrangment b) oxidation 301. When acetone reacts with Ba(OH) 2 it gives c) reduction d) hydrolysis a) acetoxime b) urotropine c) t-butyl alcohol d) diacetone alcohol
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Aldehydes, Ketones and Carboxylic Acids 53 302. Which of the following aldehydes does not reduce 311. When two molecules of HCHO react in presence
Fehling solution readily ? of base to produce CH 3 OH and HCOONa, the a) Acetaldehyde b) Formaldehyde reaction is called c) Propanal d) Benzaldehyde a) Wurtz reaction b) Cannizzaro reaction c) Aldol condensation d) Hoffman reaction 303. 1-propanol is obtained from C 2 H 5 Mgl and what? a)CH3CHO b) HCHO 312. Aldol condensation of acetaldehyde results in the formation of c)HCN d)C H CHO 5 5 a) CH COCHOHCH 304. Treatment of propionaldehyde with dil. NaOH 3 3 b) CH CHOHCH CHO solution gives 3 2
c) CH 3 CH 2 CHOHCHO a) CH 3 CH 2 COOCH 2 C 2 H 5 d) CH 3 CH 2 OH + CH 3 COOH b) CH 3 CH 2 CHOHCH 2 CH 2 CHO c) CH CH CH(OH)CH(CH )CHO 313. Which of the following reagents can not be used 3 2 3 to distinguish between pentanal and 2-pentanone? d) CH CH COCH CH CHO 3 2 2 2 a) I in NaOH b) Fehling solution 305. Oxidation number of carbon in HCHO is 2 c) Na metal d) Tollen's reagent a) 0 b) 2 314. Acetaldehyde reacts with NH OH to give c) 3 d) 4 2 a) acetal amine b) acetal oxide 306. Which of the following compound does not c) acetaldoxime d) amino acetal undergo aldol condensation? 315. Which of the following statement is true? a) Acetaldehyde a) Aldehydes are less susceptible to oxidation than b) Propanal ketones c) Ethyl methyl ketone b) All aldehydes undergo Cannizzaro reaction d) Benzaldehyde c) Aldehydes are more susceptible to oxidation 307. Which of the following compound undergoes aldol than ketones condensation? d) Formaldehyde does not react with ammonia a) CH CHO b) C H CHO 3 2 5 316. Silver mirror test is given by c) CH COCH d) All 3 3 a) aldehyde b) ketones 308. The reaction, c) amines d) ethers alkali CH3 CHO CH 3 CHO 317. Which of the following reagent is used to convert > C = O to > CH ? CH CH(OH)CH CHO 2 3 2 a) ZnHg + H O b) ZnHg + conc.HCl represents 2 c) NaHg + H O d) Sn + conc.HCl a) Cannizzaro reaction 2 318. The formation of acetone sodium bisulphite from b) Aldol condensation a acetone is an example of c) Wurtz reaction a) electrophilic addition d) Mendius reaction b) nucleophilic addition 309. Mesityl oxide is formed by the condensation of c) nucleophilic substitution a) acetaldehyde b) acetone d) electrophilic substitution c) propanal d) formaldehyde 319. In which reaction new C–C bond does not form 310. The most probable compound whose molecular a) Aldol b) Cannizzaro's formula is C 3 H 6 O and which can give Tollen's reagent test c) Wurtz d) HCN + RMgX 320. Mesityl oxide is a) CH 3 CH 2 CHO b) CH 3 COCH 3 a) ketone b) aldehyde c) CH 3 OCH 2 CH 3 d) CH 2 = CHCH 2 OH c)ester d)ethers
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Aldehydes, Ketones and Carboxylic Acids 54
321. Schiffs reagent is obtained by passing a) H 2 /Pd b)NH 2 NH 2 c) LiAlH in ether d) Zn(Hg)/HCl a) SO 2 gas in aq. solution of rosaniline 4 331. Aldehydes having no cc-hydrogen atom undergo b) NO 2 gas in aq. solution of rosaniline a) Hoffman reaction c) O 2 gas in aq. solution of rosaniline b) Aldol condensation d) CO 2 gas in aq. sol. of rosaniline 322. Which of the following can reduce Tollen's c) Cannizzaro reaction reagent but not Fehling solution? d) Wurtz reaction
a) C 6 H 5 CHO b)CH 3 CHO 332. Which of the following does not react with phenyl hydrazine? c) C 3 H 7 CHO d)CH 3 COCH 3 323. An aldehyde on oxidation gives a) Ethanol b) Ethanal a) an alcohol b) an acid c) Acetone d) 2-pentanone c) an ether d) a ketone 333. Which of the following compound does not undergo Cannizzaro reaction? 324. Magenta is a) Ethanol a) alc. phenolphthalein b) Methanal b) p-rosaniline hydrochloride c) Benzaldehyde c) methyl red d) 2, 2, 4, 4-tetra methyl 3-pentanone d) red litmus 334. Reduction in presence of amalgamated zinc and 325. Aldehyde on reaction with Grignard reagent and cone. HC1 is known as subsequent hydrolysis yields a) Mendius reduction a) primary alcohol b) tertiary alcohol b) Wurtz reaction c) secondary alcohol d) dihydroxy alcohol c) Hoffmanns reaction 326. Which of the following does not have alpha d) Clemmenson's reduction hydrogen? 335. Aldehyde having no -hydrogen undergo a) Formaldehyde disproportionation in presence of strong potash b) Acetaldehyde to give a corresponding salt of acid and alcohol. c) Dimethyl acetaldehyde The reaction is known as, d) Acetone a) Wurtz reaction 327. Rochelle salt is b) Aldol condensation a) ammonium tartarate c) Cannizzaro's reaction b) sodium potassium tartarate d) Esterification
c) potassium ammonium tartarate 336. An organic compound contains H 2 O and single d) sodium tartarate carbon. It responds positive to Tollen's reagent. The compound is 328. Fuschin is, a)HCHO b)CH OH a) pink dye of para-rosa-aniline hydrochloride 3 c) CH CHO d) none of these b) Schiff s reagent 3 337. Formaldehyde gives an addition product with c) Tollen's reagent methyl magnesium iodide which oh acid hydrolysis d) Fehling solution gives 329. Which of the following is a gas at room a) CH 3 OH b) C 2 H 5 OH temperature? c) (CH 3 ) 2 CHOH d) CH 3 CHOHCH 5 a) CH 3 CHO b)HCHO 338. Formaldehyde and formic acid are distinguished
c) CH 3 COCH 3 d) C 2 H 5 OC 2 H 5 by treating with
330. Clemmenson reduction is carried out with a) Tollen's reagent b) NaHCO 3 followed by treatment with glycolic KOH c) Fehling solution d) Schiff s reagent
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Aldehydes, Ketones and Carboxylic Acids 55 339. Pick up the correct statements from the following b) Reaction with phenyl hydrazine a) both aldehydes and ketones use sp 2 -hybrid c) Reaction with hydrazine carbon atoms for their addition reaction d) All of these b) acetic acid neither reacts with Fehling's 348. Which of the following reagent form oxime with solution nor with Tollen's reagent carbonyl compound ? c) chloral is aldehyde a) NH 3 OH b) NH 2 OH d) all are correct c)NaOH d)CH 2 N 2 340. Canal is heated with ammonical silver nitrate. The 349. Ketonic form of acetone contains product formed is, a) 8- bonds and 2- bonds a) CH CH CH COOH 3 2 2 b) 9- bonds and 1- bond b) (CH ) CHCOOH 3 2 c) 7- bonds and 3- bonds c) CH COOH + CH OH 3 3 d) 4- bonds and 5- bonds d) HCOOH + C H COOH 2 5 350. -hydroxy butyraldehyde is an example of 341. Fehling solution is a) aldol b) ketol a) acidified CuSO solution 4 c) ester d) alcohol b) ammonical AgNO3 solution 351. Which is most difficult to oxidise ? c) copper sulphate, sodium hydroxide and a)HCHO b)CH COCH Rochelle salt 3 3 c) CH CHO d) C H CHO d) none of these 3 2 5 352. Aldehydes or ketones having atleast one 342. Union of two or more molecules of the same or -hydrogen undergo condensation reaction in different compound with elimination of water to presence of dilute base. This reaction is called form a new substance is known as a) Aldol condensation a) synthesis b) polymerisation b) Cannizzaro's reaction c) condensation d) none of these c) Hoffmann's reaction 343. Which of the following compound will undergo self aldol condensation in presence of dilute alkali? a) Mendius reaction a) C H CHO b)(CH ) CCHO 353. The reagent with which both aldehyde and 6 5 3 3 acetone react easily is c) C H CHO d)CC1 CHO 2 5 3 a) Fehling's reagent b) Grignard reagent 344. When a ketone is condensed into an ketol, the reagent used is c) Schiff s reagent d) Tollen's reagent a) Na CO b) NaHCO 354. When, acetaldehyde is heated with Tollen's 2 3 3 reagent, following is obtained c) Br water d)C1 2 2 a) Methyl alcohol b) Silver acetate 345. Benzaldehyde undergoes auto-oxidation and reduction in presence of c) Silver mirror d) Formaldehyde a) conc. NaOH b) Na2CO 355. Which of the following compounds would undergo 3 Cannizzaro's reaction c) NaHCO d) dil. NaOH 3 a) Propionaldehyde b) Benzaldehyde 346. Nucleophilic attack on carbonyl carbon changed its hydridisation from c) Bromobenzene d) Acetaldehyde a) sp to sp 2 b) sp 2 to sp 3 356. Schiff s reagent gives pink colour with c) sp 3 to sp 2 d) sp to sp 3 a) Aldehydes b) Ethers 347. Which of the following reaction is used for c) Ketones d) Carboxylic acid detecting the presence of carbonyl group in 357. An aldehyde on oxidation gives aldehydes and ketones ? a) An alcohol b) An acid a) Reaction with hydroxylamine c) A ketone d) An ether
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Aldehydes, Ketones and Carboxylic Acids 56 358. Schiff s reagent is 369. An aldehyde can undergo the aldol condensation having a) Magneta solution decolourised with SO 2 b) Ammonical cobalt chloride solution a) an aromatic ring c) Ammonical manganese sulphate solution b) no alpha H atom d) Magneta solution decolourised with chlorine c) atleast one -H atom 359. Acetone and acetaldehyde are differentiated by d) at least one -H atom + 370. An organic compund 'X' having molecular a) NaOH + I 2 b) Ag(NH 3 ) 2 formula C H O yields phenyl hydrazone and c) HNO d) I 5 10 2 2 gives negative response to the iodoform test and 360. Hexamethylene tetramine is used as Tollen's test. It produces n-pentane on reduction a) analgesic b) antipyretic 'X' could be : c) urinary antiseptic d) all the above a) pentanal b) 2-pentanone 361. Benzyl alcohol is obtained from benzaldehyde by c) 3-pentanone d) n-amyl alcohol a) Fitting's reaction b) Cannizaro's reaction 371. Aldol condensation will not take place in c) Kolbe's reaction d) Wurtz's reaction a)HCHO b)CH 3 CHO 362. Which of the following gives difference between c) CH COCH d) CH CH CHO aldehyde and ketone? 3 3 3 2 372. CH 3 COCH 3 can be converted to CH 3 CH 2 CH 3 a) Fehling's solution b) Tollen's reagent the action of c) Schiff's reagent d) All of the above a) HIO 3 b) ZnHg + HCl 363. Formaldehyde gives an additive product with ethyl c) HNO d) H PO magnesium iodide which on aqueous hydrolysis 3 3 3 373. The compound most suitable for the preparation gives of cyanohydrin is a) isopropyl alcohol b) ethyl alcohol a) C H COOH b)C H COC H c) methyl alcohol d) n-propyl alcohol 2 5 2 5 2 5 c) C H NH d) C H –C H 364. The reagent which easily reacts with ethanal and 6 5 2 2 5 2 5 374. Baking powder is propanalis a) NaHCO b) NaHCO .6H O a) Fehling's solution b) Grignardreagent 3 3 2 c) Na CO d) Na CO .10H O c) Schiffs reagent d) Tollen's reagent 2 3 2 3 2 375. Which one of the following undergoes reaction 365. Magnetais with 50% sodium hydroxide solution to give the a) alkaline phenolphthalein corresponding alcohol and acid ? b) methyl red a) Butanal b) Formaldehyde c) p-rosanilinehydrochloride c) Phenol d) Benzoic acid d) red litmus 376. Which of the following compounds can be 366. Grignard reagent on reaction with ketones for regenerated to carbonyl compounds? a) tertiary alcohol b) secondary alcohol a) Urotropin b) Bisulphite complex c) acetic acid d) acetaldehyde c) Cynohydrine d) Diacetone amine 367. The compound which reacts with Fehling 377. What is 'C' in the following reaction? solutionis C H CN C H MgI (i) dry ether 65 65 (ii) H O a) C 6 H 5 COOH b) HCOOH 3 c) C H CHO d) CH ClCH 6 5 2 3 ANH2 OH B LiAlH 4 368. Acetone gives test with a) diphenyl methane a) Phenyl hydrazine b) Fehling solution b) diphenyl methanamine c) Schiffs reagent d) All the above c) nitrodiphenyl methane d) diphenyl
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Aldehydes, Ketones and Carboxylic Acids 57 SECTION-II: CARBOXYLIC ACIDS 13. IUPAC name of isobutyric acid is. Introduction, Nomenclature, Isomerism a) 3-methyl propionic acid 1. General formula for carboxylic acid is b) 2-methyl propanoic acid
a) C n H n O 2 b) C n H 2n O 2 c) 3-methyl butanoic acid
c) C n H 2n O d) C n H 2n+2 O 2 d) isobutanoic acid 2. The general formula of an ester, where R 14. IUPAC name of following compound is represents an alkyl group, is (CH 3 ) 2 CHCOOC 2 H 5 a)ROH b)RCOOH a) ethyl isobutanoate c)RCOOR d)ROR b) ethyl isobutyrate 3. Vinegar contains acetic acid nearly c) ethyl 2-methyl propanoate a) 6-10% b) 30% d) ethyl 1-methyl ethanoate c) 12-15% d) 20% 15. IUPAC name of following compound is 4. The bite of honey-bee inject into our body (CH 3 ) 3 C–CH 2 –COOH a) acetic acid b) formic acid a) 2,2-dimethyl butanoic acid c) butyric acid d) carbolic acid b) 3, 3-dimethyl butanoic acid 5. Glacial acetic acid at low temperature is a c) 2,3-dimethyl propanoic acid a) thin liquid b) viscous liquid d) 2,3-dimethyl butanoic acid c) ice like solid d) semi solid 16. IUPAC name of following compound is 6. The suffix used in carboxylic acid is C H –COOCH(CH ) a) -oic b) -ane 2 5 3 2 a) isopropyl propanoate c) ene d) -al b) isopropyl propionate 7. Formic acid owes its origin to c) 2-propyl propanoate a) milk b) butter d) 2-propyl ethanoate c) red ants d) vinegar 17. Structure of ethyl ethanoate is 8. Vinegar obtained from canesugar contains a) CH COOC H b) C H COOCH a) Citric acid b) Lactic acid 3 2 5 2 5 3 c) H–COOC H d) H–COOCH c) Acetic acid d) Palmitic acid 2 5 3 9. Write the IUPAC name of CH CH COOH. 18. An organic compound having the molecular 3 2 formula C H O is a) ethyl formic acid 2 4 2 a) formic acid b) acetic acid b) ethyl carboxylic acid c) ethyl acetate d) propionic acid c) ethane methanoic acid 19. Aliphatic carboxylic acids shows isomer of type d) propanoic acid 10. IUPAC name m-toluic acid is a) position b) chain a) 3-methyl benzoic acid c) functional d) all of these b) 2-methyl benzoic acid 20. Carboxylic acid is isomeric with c) 4-methyl benzoic acid a) aldehydes b) alcohols d) 2,4-dimethyl benzoic acid c) easter d) saturated ketones 11. IUPAC name of carboxylic acid is 21. Acids and esters are a) alkinoic acid b) alkanoic acid a) chain isomers b) position isomers c) alkenoic acid d) alkyl alkanoate c) functional isomers d) metamers
12. IUPAC name of ester is 22. Molecular formula C 2 H 4 O 2 represents a) alkoxy alkane b) alkoxy alkene a)acids b)esters c) alkane alkanoate d) alkyl alkanoate c) aldehydes d) both 'a' and 'b'
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Aldehydes, Ketones and Carboxylic Acids 58
23. Molecular formula C 2 H 4 O 2 shows 32. Monocarboxylic acid shows functional isomerism a) chain isomerism with b) position isomerism 1) Ester 2) aldehydes c) functional isomerism 3) ketones 4) ether d) metamerism a) 1, 2 b) 1 24. IUPAC name of following compound is c) 2, 3 d) 3, 4 COOH 33. IUPAC name of malic acid is a) 3-hydroxy butanoic acid OH b) 2-hydroxy butanedioic acid c) 2-hydroxy butanoic acid a) 2-carboxy phenol d) 2-hydroxy pentanedioic acid b) 2-carboxy benzyl alcohol 34. IUPAC name of p-methyl butyric acid is c) 2-hydroxy benzoic acid a) 3-methyl butanoic acid d) 2-hydroxy benzene carboxylic acid b) 4-methyl pentanoic acid 25. How many carboxylic acids are possible for c) 2-methyl butanoic acid C H O ? 4 8 2 d) 2-methyl propanoic acid a) 2 b) 3 35. IUPAC name of following compound is c) 4 d) 5 26. Total number of isomeric acids can be calculated CH 3 by formula | a) I = 2 n–1 b) I = 2 n–3 c) I = 2 n d) I = 2 n–2 – 1 | 27. Citric acid is COOH a) monocarboxylic acid b) dicarboxylic acid a) 4-methyl cyclohexane 1-carboxylic acid c) tricarboxylic acid b) 4-carboxyl 1-methyl cyclohexane d) fatty acid c) m-Tbluic acid 28. The following structure is d) o-Toluic acid O 36. IUPAC name of following compound is, || OH HO O O || || a) oxalic acid b) phthalic acid HO OH c) fumaric acid d) succinic acid 29. The acid which is obtained from plant a) 2-oxo butane dioic acid a) Propionic acid b) valeric acid b) 2-oxo propane 1, 3-dicarboxylic acid c) fumaric d) malic acid c) 2-oxo 1, 5-pentane dioic acid 30. Lemon is sour due to d) Hexane dioic acid a) Oxalic acid b) tartaric acid 37. The IUPAC name of caproic acid is c) citric acid d) malic acid a) pentanoic acid 31. Saturated monocarboxylic acid is second oxidative product of b) 2-phenyl ethanoic acid a) 1 0 alcohol b) 2 0 alcohol c) 2-phenyl propanoic acid c) both a & b d) ketones d) hexanoic acid
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Aldehydes, Ketones and Carboxylic Acids 59 38. Which of the following is isobutyric acid ? 45. Common name of the following compound is O || COOH a) | HO CH 3 b) OH
a) o-Toluic acid b) m-Toluic acid c) c) p-Toluic acid d) Phthalic acid OH 46. IUPAC name of malonic acid is a) propane dioic acid b) ethane dioic acid d) c) butane dioic acid d) pentane dioic acid OH 47. Carbon atom in carboxyl group is 39. Which of the following is 2-phenyl pentanoic acid? a) sp-hybridised state b) sp 2 hybridised state H c) sp 3 hybridised state H H d) sp 3 d hybridised state a) b) 48. Which of the following is 3-oxo cyclohex-4-ene- 1-carboxylic acid? OH COOH O | || OH O a) b) OH c) d) O || O 40. n-valeric acid is functional isomer of || OH a) methyl propionate b) n-butyl formate c)OH d) c) propyl isobutyrate d) ethyl isobutyrate 41. Butyric acid and isobutyric acid are O O a) chain isomers b) position isomers 49. Which of the following is not fatty acid? c) metamers d) tautomers a) propionic acid b) butyric acid
42. Which isomers of C 5 H 10 O 2 shows optical c) iso-butyric acid d) iso-phthalic acid isomerism? 50. IUPAC name of following acid is a) 2-methyl butanoic acid O b) valeric acid || c) neo-valeric acid OH d) 3-methyl butanoic acid OH 43. How many carboxylic acids are possible for molecular formula C H O ? 5 10 2 a) isophthalic acid a) 3 b) 4 b) benzene 1, 3-dicarboxylic acid c) 5 d) 6 c) phenyl 1, 3-dicarboxylic acid 44. Molecular formula C H O shows 4 8 2 d) terephthalic acid 1) chain 2) metamerism 51. Carboxylic acid do not give characteristic 3) functional 4) optical property of a) 1, 2, 3 b) 3, 4 a) R-group b) –COOH group c) 2, 3, 4 d) all of these c) >C = O group d) –O–H group
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Aldehydes, Ketones and Carboxylic Acids 60
Preparation Methods I2 NaOH 1. CH3 COCH 3
52. Consider the following sequence of reactions and 2. K2 CrO 2 7 H identify the final product (Y) CH3 COCH 3
Ag ( NH ) Mg CO2 /H 3 O 3. CH COCH 3 2 CHCHCHBr3 2 2 dry ether X dry ether Y 3 3 a) only 2 b) 1 and 2 a) CH 3 CH 2 COOH c) 2 and 3 d) 1 and 3 b) (CH 3 ) 2 CHCOOH c) CH CH CH CH COOH 59. Which is leaving group in the hydrolysis of 3 2 2 2 CH COOC H ? d) CH CH CH COOH 3 2 5 3 2 2 a) C H + b) C H O – 53. Solid carbondioxide and RMgX produces 2 5 2 5 c) CH COO – d) CH – a) alkanoic acid b) alkanal 3 3 60. For the preparation of isopropyl acetate from c) alkanone d) alkyl alkanoate esterification. The compounds used as, 54. Carbonation of CH MgI gives an organic 3 a) CH COOH and CH CH OH compound. This compound is also obtained by 3 3 2 b) (CH ) CHCOOH and CH OH a) hydrolysis of acetonitrile by a mineral acid 3 2 3 c) CH COOH and (CH ) CHOH b) oxidation of methyl alcohol 3 3 2 d) C H COOH and CH OH c) hydrolysis of isoacetonitrile by a mineral acid 2 3 3 61. Find out X in the following reaction d) hydrolysis of methyl formate with dilute mineral conc. H2 SO 4 acid X CH3 OH C 25 H COOCH 32 H O 55. Propyl propionate is prepared from which of the a) C 2 H 5 –X b)(CH 3 CO) 2 O following c) CH 3 COOH d)C 2 H 5 COOH a) CH CH CH OH,CH CH COOH 3 2 2 3 2 62. Ethyl propionate is formed from ethyl iodide and
b) CH 3 COOH,CH 3 (CH 2 ) 3 COOH what? c) CH CHOHCH ,CH CH COOH 3 3 3 2 a) C 2 H 5 COOH b)C 2 H 5 COOAg d) CH CH CH OH,(CH ) CHCOOH 3 2 2 3 2 c) (C 2 H 5 CO) 2 O d) All of these 56. A mixture of carboxylic acid (A) and alcohol (B) 63. Propanoic acid is the oxidative product of on heating give and ester (C) having molecular a) ethanol b) 3-pentanone mass 74. What is (C)? c) 1-butanol d) 2-propanol a) HCOOC H b) CH COOCHg 2 5 3 64. Reaction c) Both 'a' and 'b' d) None of these
CH3 COOH C 25 H OH CH 3 COOC 252 H H O 57. CH 3 –CH 2 –COOH can be obtained in following synthesis is an illustration of
a) dehydration b) esterification a) CH CH CN OH 3 2 c) neutralization d) dehydrogenation H3 O 65. R–CH –CH OH can be converted into b) CH3 CH 2 CN 2 2
RCH 2 COOH. The reaction is c) N2 Ni CH3 CH 2 CN a) reduction b) hydrolysis
CH3 MgX c) oxidation d) decarboxylation d) CH3 CH 2 CN 66. If hydrolysis of ester is carried out in presence of O an acid, using water containing radioactive oxygen || atom, the product most likely to be radioactive is 58. CH3 C CH 3 can be converted to a) alcohol b) ester CH –COOH by following method. 3 c) acid d) both 'a' and 'c'
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Aldehydes, Ketones and Carboxylic Acids 61 67. If acetic acid reacts with methyl alcohol 75. 2-methyl propane nitrile on acid hydrolysis give containing labelled oxygen atom. In presence of a) butyric acid b) isobutyric acid dry HC1, the labelled oxygen atom, at the c) propionic acid d) pentanoic complete reaction will be found in 76. In esterification reaction the correct order of a) methyl acetate reactivity of alcohol is b) water a) 1 0 > 2 0 > 3 0 b) 3 0 > 2 0 > 1 0 c) may be 'a' and 'b' c) 1 0 > 3 0 > 2 0 d) 3 0 > 1 0 > 2 0 d) not predictable 77. Monocarboxylic acid are regarded as _____ 68. Propionic acid is obtained from dry ice and what? oxidation product of aldehyde
a) CHgMgI b) C 2 H 5 MgBr a) first b) second
c) C 3 H 7 MgBr d) None of these c) third d) fourth 69. Carbonation of Grignard reagent followed by 78. Formic acid is obtained when hydrolysis gives a) Acetaldehyde is oxidised by acidic KMnO 4 a) aldehyde b) acid b) Calcium formate is heated with calcium c) ketone d) primary alcohol acetate 70. Which of one the esters is formed by esterification c) Methanol is oxidised by PCC of propan-2-ol with acetic acid? d) Methanol is oxidised by acidic dichromate a) (CH ) CHCOOCH 3 2 3 79. Which of the following acid containing aldehyde
b) CH 3 COOCH(CH 3 ) 2 group? c) CH CH CH COOCH 3 2 2 3 a) CH 3 –COOH b) H–COOH d) (CH ) CHCOOCH CH 3 2 2 3 c) HOOC–COOH d) (CH 3 ) 2 CH–COOH
71. CH 3 COCH 3 can be converted into CH 3 COOH 80. Formic acid is not representative member of by carboxylic acid because a) reduction b) hydrolysis a) it is first member of the series c) decarboxylation d) oxidation b) it does not contain alkyl group 72. Which reaction does not have the correct oxidising c) it is a gas agent? d) it reduced Tollen's reagent a) PCC CH3 COCH 3 CH 3 COOH 81. Molecular formula C 4 H 8 O on oxidation gives acetic acid. The structure of C H O will be 4 8 9 b) Ag( NH3 ) CH3 CHO CHCOOH3 O || 2 a)OH b) Cr2 O 7 /H c) CH3 CHO CHCOOH3
2 d) CHCOCHCr2 O 7 /H CHCOOH 3 3 3 c)H d) 73. For the following reaction H
H O 82. Mixture of acetic acid and propionic acid is R CN 2 R COOH obtained by oxidation of a) there is protonation of electronegative nitrogen O b) an amide is formed as an intermediate || a)OH b) c) nitrogen atom is expelled as ammonia d) all are correct 74. Acetylation is the introduction of
a) CH 3 COOH group b) R–CO group c) d) – H c) CH 3 CH 2 O d) CH 3 –CO
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Aldehydes, Ketones and Carboxylic Acids 62 83. Isobutyric acid is obtained by oxidation of 91. Benzoic acid is obtained by acid hydrolysis of a) butanal a) benzonitrile b) 2-methyl propanal b) 2-phenyl ethane nitrile c) 2-methyl propan-1-ol c) phenylisocyanide d) both b and c d) 2-phenyl ethane isonitrile 84. 1-phenyl ethanone on oxidation gives 92. Find out final product in following reaction
a) salicylic acid b) benzoic acid CH2 X
c) succinic acid d) phthalic acid KCN A H3 O B 85. Cyclohexane carboxylic acid is obtained by oxidation of COOH O a) || C CH 3 a) b) CH2 X b)
CH2 OH COOH c) d) both b and c
CH2 COOH c) 86. Following compound on oxidation by acidic KMnO gives 4 CHO d)
a) Adipic acid b) succinic acid 93. Compound A an hydrohalogentation gives B, c) fumaric acid d) maleic acid which is treated with alc.KCN and followed by 87. Benzoic acid is obtained by oxidation of acid hydrolysis give 2-methyl butanoic acid. The 1. benzaldehyde 2. benzyl alcohol compound A will be 3. Acetophenone OH OH | | a) only 1 b) 2, 3 a) b) c) 1, 3 d) 1, 2, 3 c) d) 88. Find out A in the following reaction 94. Hexane dioic acid is obtained by oxidation of Aaq. KOH B PCC propanal a) benzene a) n-propyl alcohol b) n-propyl halide b) cyclohexane c) n-propyl amine d) diethyl ether c) cyclohexene 89. Acid hydrolysis of cyanide may produces d) cyclohexane carbaldehyde a) carboxylic acid b) mineral acid 95. Find out missing compound in following reaction
c) aldehyde d) amine dry ether CO2 ? R COOH H3 O 90. Molecular formula C 4 H 7 N on acid hydrolysis gives 2-methyl propanoic acid. The possible a) R–X b) R–Li c)R–MgX d)R–ONa structure of C 4 H 7 N will be 96. Dry ice and benzyl magnesium halide produces a) b) a) benzoic acid C N NC b) phthalic acid c)CN d) NC c) 2-phenyl ethanoic acid d) 2-phenyl propanoic acid
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Aldehydes, Ketones and Carboxylic Acids 63 97. Product of the following reaction is 101. Following compound on hydrolysis give Cl MgX dry ether H. OH ? CO 2 H3 O a) b) H NO 2
COOH CH2 COOH a) b) c)OH d)
COOH COOH 102. Benzoic acid is obtained by hydrolysis of CH COOH 3 O c) d) || a)X b)
NO 2 NO 2 98. 2-methyl propanoic acid is obtained from dry ice O || and what CH 3 a)X b) X c) d)
103. 1-phenyl ethanoyl chloride on hydrolysis gives c)MgX d) MgX a) ethanoic acid b) 1-phenyl ethanoic acid 99. Find out final product 'E' in the following reaction c) 2-phenyl ethanoic acid series d) benzoic acid OH 104. Hydrolysis of acid anhydride gives | a) aldehydes b) ketones Zn A CH3 CI B Cl2 /U.V.L. C unhy AlCI 3 c) acid amides d) carboxylic acids
Mg / Ether CO2 / Ether D E 105. Hydrolysis of ethanoic anhydride gives H3 O CH COOH a) methanoic acid b) propanoic acid a) 2 c) ethanoic acid d) oxalic acid O 106. product compound on hydrolysis give || O O b) OH || || O O O || a) || c) OH OH O b) || OH OH O d) O 100. Hydrolysis of acyl halide give c) || a) aldehydes OH b) ketones d) O OH c) carboxylic acids d) ester
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Aldehydes, Ketones and Carboxylic Acids 64 107. Product of the following reaction is c) carboxylic acid and alcohol O O d) aldehyde and ketone || || 112. Molecular formula C H O on acid hydrolysis give O 4 8 2 H OH ? acetic acid and ethanol. The structures of
C 4 H 8 O 9 will be
a) a) b) O OH
O O || b) c) d) OH O O || ||
H c) OH CH3 OH 113. A H.OH O || The compound A is OH O O d) || || a) b) H 108. Which of the following compound does not gives benzoic acid on oxidation? O || O CH CH OH 3 2 c)O d) a) b)
O 114. Molecular formula C H O on acid hydrolysis || 3 6 2 gives A and B. The compound 'A' reduce Tollens c) d) CO O reagent. The possible structure of C H O will 3 6 2 2 be 109. Benzoic acetic anhydride on hydrolysis gives a) CH 3 –CH 2 –COOH b) CH 3 –COOCH 3 a) benzoic acid c) H–COOC 2 H 5 d) CH 3 –C–CH 3 b) acetic acid 115. Which of the following method cannot be used in c) mixture of benzoic acid and acetic acid the preparation of acid ? d) benzylalcohol and acetic acid a) R COCI H2 O 110. Product 'B' in the following reaction
b) R COOOC R H2 O CH 3 –CH 2 –COX
Pd.BaSO4 quinoline [O] H A B c) R COOR HO2
a) CH –CH –COOH Na ethanol 3 2 d) R C N b) CH –COOH 3 116. Vigorous oxidation by acidic permagnet solution c) CH 3 –CH 2 –CHO of (CH 3 )C = CH–CH 2 CH 3 gives O OH || | a) d) CH3 C CH 3 OH 111. Acid hydrolysis of ester produces O || O a) carboxylic acid b) || b) alcohol OH and
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Aldehydes, Ketones and Carboxylic Acids 65 COCH c) 3 COOH and a) b) OH OH COOH CH 3 d) || and COOH COOH O OH c) d) 117. A set of reaction yielded a product D.
SOCl 2 C6 H 6 COOH CHO CHCOOH2 5 A unhy. AlCl 3 121. o-xylene on oxidation gives
BHCN C H3 O D a) phthalic acid b) isophthalic acid c) terephthalic acid d) citric acid COOH | 122. Following compound is obtained by oxidation is CH2 C CH 3 a) | COOH H OH | C C2 H 5 | COOH b) COOH C2 H 5 OH | 1) C CH | 3 c) COOH CH 3 OH | COCH CH C C H 3 2| 2 5 d) COOH 2) 118. Product of the following reaction C2 H 5
HBr Mg / ether CO 2 A B CH H2 O 2 H3 O 3
COOH COOH 3) a) b)
CH 3 OH H || c)|| d) 4) CH CH CH O O 3 3
119. Alkyl benzene on oxidation by alkaline KMnO 4 gives a) aldehyde b) ketone CH CH CH c) carboxylic acid d) esters 2 2 3 120. Product of the reaction a) 1, 3 b) 2, 3 c) 2, 4 d) 1, 2, 3, 4 COCH 3 123. Phenyl ethene on oxidation produces KOH KMnO 4 a) phthalic acid b) p-ethenyl benzoic acid c) benzoic acid d) salicylic acid CH 3
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Aldehydes, Ketones and Carboxylic Acids 66
124. Find out final product of the reaction 132. In esterification reaction concentrated H 2 SO 4 act as unhy. AlCl 3 CH3 COCl A a) dehydrating agent b) catalyst KOH KMnO 4 c) reducing agent d) oxidising agent CHO 133. After completion of esterification, excess of a) b) alcohol is removed by using
a) CaCl 2 b) CaOCl 2 COCH 3 COOH c) Na CO d) NaOH c) d) 2 3 134. Synthesis of ester involves the reaction of alcohol with 125. Potassium salt of isophthalic acid on acid a) a ketone b) an amide hydrolysis gives c) CH MgBr d)RCOOH a) phthalic acid b) isophthalic acid 3 135. Which of the following reagent produces 2-methyl c) terephthalic acid d) benzoic acid propanoic acid with dry ice ? 126. Carbonation of organometallic reagent a) CHgMgI b) C 2 H 5 MgI a) is a one carbon homologation c) (CH 3 ) 2 CHMgI d) C 3 H 7 MgI b) involves its carbanionic attacks on electron 136. 1-propanol on oxidation give deficient carbonyl carbon a) propanal b) propionic acid c) both are correct c) propanone d) ethanal d) none is correct 137. –CN group is converted into –COOH group by 127. Hydrolysis of nitrites with alkaline solution gives a) hydrolysis b) oxidation a) salt of acid b) amides c) reduction d) esterification c)acid d)esters 138. Esters are formed from acid by the replacement of 128. The mechanism of carbonation of organometallic a) non-ionisable H atom by alkyl group compound is analogous to that of addition to b) ionisable H atom by alkyl group a) aldehyde and ketones c) OH group by RO group b) nitriles c) alcohols d) both 'b' and 'c' d) amines 139. Which one of the following correctly represents 129. Dry ice reacts with n-propyl magnesium iodide esterification reaction to give
a) propyl acetic acid b) propionic acid a) RCO OH H O R' R COOR' HO2 c) butanoic acid d) none of these b) RCOO H HO R' R COOR' HO 130. Esterification reaction is 2 a) nucleophilic substitution c) RCO OH H O R' R' COOR HO2 b) electrophilic substitution
c) electrophilic addition d) RCOO H HO R' R' COOR HO2 d) dehydration 140. The compound formed when propyl magnesium 131. In which case R–COOH is not product ? bromide is treated with carbon dioxide is a) C H COOH b)C H COOH a) R CN RMgX 3 7 2 5 c) C 3 H 7 CHO d) C 3 H 7 OCH 3 b) R CN H3 O 141. The alkyl cyanides when hydrolysed to the corresponding acid, the gas evolved is c) R MgX CO 2 a) N 2 b) O 2 Oxidation d) RCOR c) NH 3 d) CO 2
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Aldehydes, Ketones and Carboxylic Acids 67 142. In esteriflcation of an acid, the other reagent is 151. Which of the following acid is strongest?
a) Alcohol b) An aldehyde a) CH 3 –COOH b)Cl 2 –CH 2 –COOH
c) Amine d) Water c) C1 2 CH–COOH d) CCl 3 –COOH 143. When methyl cyanide is hydrolysed in presence 152. Which of the following is weak acid ? of alkali and followed by treatment with HC1. COOH COOH The product is NO a) Acetamide b) Methane a) b) 2 c) Formic acid d) Acetic acid 144. Which product is formed, when acetonitrile is OCH 3 hydrolysed partially with dil. HC1 ? COOH COOH a) Acetic acid b) Acetamide c) Methyl cyanide d) Acetic anhydrides c) d) 145. Carboxylic acid is formed by the hydrolysis of an NO addition compound formed by reaction of 2 NO Grignard's reagent with 2 a) ethanal b) methanal 153. Which is the following is strongest acid ? a) CH CH CH COOH c) carbon dioxide d) methyl cyanide 3 2 2 b) CH CH CHBrCOOH 146. Which is formed, when benzonitrile is hydrolysed 3 2
by dil. HC1 ? c) CH 3 CHBrCH 2 COOH
a) Benzoic acid b) Benzaldehyde d) CH 2 BrCH 2 CH 2 COOH c) Benzamide d) Benzoic unhydride 154. Which of the following has highest Pka value ? a) C H –COOH b) CH–OH Acidic Nature 6 5 c) C 6 H 5 –OH d)CH 3 –COOH 147. The acidic nature of carboxylic acid is due to 155. Which of the following is strong acid? a) high degree of ionisation of acid a) CF 3 COOH b)CC1 3 COOH b) greater resonance stabilization of the acid c) CBr 3 COOH d)Cl 3 COOH c) greater resonance stabilization of its anion 156. Which of the following is strongest acid ? d) all of the above a)H–COOH b)C 6 H 5 –COOH 148. Acidic character of carboxylic acid ____ with c) CH –COOH d) CH CH –COOH an molecular mass increases 3 3 2 157. Weakest acid among the following is a) sometime increases some time decreases a) H–COOH b) decreases b) C H –COOH c) increases 6 5 c) o–NO –C H –COOH d) none of the above 2 6 4 d) CH – COOH 149. Among the acid 3 158. Benzole acid is more stronger than all aliphatic
1) HC C COOH 2) H2 C CH COOH carboxylic acid except H–COOH, why ? a) C H –COOH is aromatic acid 3) CH 3 –CH 2 –COOH 6 5
The acidic strength follows the order b) In C 6 H 5 –COOH, the –COOH group is 2 a) 3 < 2 < 1 b) 3 = 2 < 1 attached to sp -hydridised carbon atom c) 1 < 2 < 3 d) 1 < 2 = 3 c) resonance stabilization of benzene ring 150. Which of the following is the most stable acid ? d) resonance stabilization of benzoate ion.
a) CH 2 (F)COOH b) CH 2 (Br)COOH
c) CH 2 (C1)COOH d) CH 2 (I)COOH
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Aldehydes, Ketones and Carboxylic Acids 68 159. The aqueous solution of RCOOH contains, COOH a) RCOO – + H + c)H – COOH d) b) RCO + + OH – 167. Which of the following acid has smallest c) RCOO – + H O + 3 dissociation constant ? d) RCOOH + RCOO – + H O + 3 a) CH –CHFCOOH 160. Which one of the following would be expected to 3 b) BrCH CH –COOH be most highly ionised in water 2 2 c) F–CH –CH –COOH a) C1–CH –CH –CH –COOH 2 2 2 2 2 d) CH –CHBr–COOH b) CH CHC1CH –COOH 3 3 2 168. Which among the following is strongest acid ? c) CH 3 –CH 2 –CHC1–COOH COOH COOH d) CH 3 –CH 2 –CH 2 –COOH 161. Between CH COOH and H–COOH, the 3 a) b) HCOOH will be a) less acidic b) more acidic NH 2 CN c) equally acidic d) non-acidic COOH COOH 162. Formic acid and acetic acid may be distinguished by the reaction with c) d) a) sodium metal b) Tollen's reagent c) sodium ethoxide d) NaOH OCH 3 NO 2 163. Which is tribasic acid 169. Among the acid which have lowest PKa value, a) adipic acid b) succinic acid a) CH 3 COOH
c) citric acid d) tartaric acid b) CH 3 –CH 2 –COOH 164. Consider the following acids c) CH CH COOH 3 | 1) CH 3 COOH 2)C1 2 CHCOOH NO 2 3) C1CH COOH 4) C1 CCOOH 2 3 d) CH CH COOH The correct sequence of acidity is 3 | a) l > 4 > 3 > 2 b) 1 > 3 > 2 > 4 COOH 170. The correct order of increasing strength of c) 1 > 2 > 3 > 4 d) 4 > 2 > 3 > 1 compounds 165. Which of the following order of relative strength 1) CH COOH 2)NO CH COOH of acid is correct ? 3 2 2 3) CF COOH 4)C H –COOH a) F–CH –COOH > Cl CH COOH > Br– 3 2 5 2 2 a) 4 > 3 > 2 > 1 b) 3 > 2 > 1 > 4 CH –COOH > CH COOH 2 3 c) 3 > l > 2 > 4 d) 3 > 4 > 2 > 1 b) CH COOH > F–CH –COOH > C1CH – 3 2 2 171. Among the following acidic strength is COOH > CH 3 Br–CH 2 COOH 1) CH 3 –CH 2 –COOH c) BrCH 2 COOH > C1–CH 2 COOH > F–CH 2 – 2) CH3 CH COOH COOH > CH 3 COOH | CN d) C1CH 3 COOH > FCH 9 –COOH > BrCH 2 – COOH 3) CH CH COOH 3 | 166. Which of the following is weakest acid Cl 4) CH CH COOH OH 3 | a) b) OH CO 2 a) 4 > 1 > 2 > 3 b) 3 > 4 > 2 > 1 c) 4 > 2 > 3 > 1 d) 4 > 3 > 2 > 1
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Aldehydes, Ketones and Carboxylic Acids 69 Properties and Uses a) optical isomers b) tautomerism c) cis-trans isomers d) metamerism CH COOH CH HH A(ester) B (water) 172. 3 3 179. Product 'B' following reaction is Alcohol contain isotopic oxygen (•). The isotopic CN oxygen will be in HO3A BrRedP 2 B
a) CH 3 CO•CH 3 + H 2 O Br b) CH 3 COOCH 3 + H 2 • COOH c) both are correct a)COOH b) d) none is correct Br 173. Select incorrect statement COOH COOH a) NaOH is strong enough to remove the proton c) d) from phenols and carboxylic acids Br
b) NaHCO 3 is only strong enough to remove the Br proton of carboxylic acids 180. Which has maximum value of equilibrium c) Mixture of phenol and carboxylic acid can be constant? – + separated using NaHCO 3 a) CF 3 COOH + H 2 O CF 3 COO + H 3 O d) Mixture of phenol and carboxylic acid can be b) HCOOH + H O HCOO – + H O + separated using NaOH 2 3 c) CH COOH + H O CH –CHOO – + H O + 174. What is the main reason for the fact that 3 2 3 3 + carboxylic acid can undergo ionization ? d) C 6 H 5 COOH + H 2 O C 6 H 5 – COO– + H 3 O a) Absence of alpha-hydrogen 181. When propionic acid is heated with ammonia give, b) Resonance stabilization of the carboxylate ion a) CH 3 CONH 2 b) C 2 H 5 COONH 4 c) High reactivity of alpha-hydrogen c) C 2 H 5 CONH 2 d) CH 3 COONH 4 d) Less reactivity of a-H atom 182. Product 'A' and 'B' in the following reaction is
175. Tollen's reagent is reduced by K222 Cr O dil. H 24 SO CH3 CH CH 2 A B a)HCOOH b)CH COOH 3 a) acetone c) CH C1COOH d) CC1 COOH 2 3 b) acetaldehyde and formaldehyde 176. The end product of following sequence of reaction is c) propanoic acid d) acetic acid and formic acid CH CHO [O] A NH 3 B C 3 183. Sodium acetate reacts with acetyl chloride to give
a) CH 3 COONH 4 b) CH 3 CONH 2 a) acetic acid b) acetic anhydride
c) CH 3 COOH d) CH 3 –OH + N 2 c) methyl acetate d) ethyl acetate
KOH KMnO 4 PCl 5 177. Toluene A 184. Acetic acid react with PC1 5 gives
a) CH 3 COC1 b)C1CH 2 CH 2 C1 BCH3 COONa C c) CH 3 COOCl d)CH 3 Cl Product 'C' is 185. Which of the following compound reacts with
a) benzoic ethanoic unhydride NaHCO 3 solution to give sodium salt and carbon b) benzophenone dioxide ? c) acetophenohe a) Phenol b) 1-propanol d) benzoquinone c) Acetic acid d) Nitric acid
178. Propionic acid on bromination in the presence of 186. An optically active compound 'X' evolve CO 2 red phosphorus gives 2-bromo propionic acids it with NaHCO 3 . The 'X' react with LiAlH 4 gives shows chiral compound. The compound 'X' is
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Aldehydes, Ketones and Carboxylic Acids 70
a) CH 3 –CH 2 –CH 2 –CH 2 –COOH C) CH 3 –CH–COOH d) (CH ) C–COOH b) CH CH CH CH 3 3 3| 2 3 193. During formation of unhydride from P 2 O 5 and COOH acid. The acid molecule undergoes a) intermolecular dehydration c) CH32 CH CH CH 23 CH | b) interamolecular dehydration COOH c) oxidation
d) CH3 CH CH 2 CH 3 d) hydration | 194. Acetic anhydride is obtained by the reaction of CH2 OH a) sodium and acetic acid 187. An propanoyl chloride is formed when PC1 5 reacts with an b) ammonia and acetic acid a) prop anoic acid b) alcohol c) ethanol and acetic acid
c) acetic acid d) ester d) P 2 O 5 and acetic acid. 188. Which of the following substance will give amide, 195. An ester is subjected to hydrolyse. Product of hydrolysis will be tested for when it reacts with NH 3 ? a) carboxylic acid and alcoholic group a) CH 3 X b) CH 3 NH 2 b) carboxylic acid and ketonic group c) CH 3 COCl d)(CH 3 CO) 2 O 189. Formic acid is a stronger acid than acetic acid. c) carboxylic acid and aldehyde group This is due to the fact that d) aldehyde and ketonic group a) formic acid is reducing agent 196. Carboxylic acid reacts with potassium metal. The b) formic acid molecule is of smaller size amount of potassium used up and hydrogen liberated are in the molar ratio of c) there is no alkyl group on -carbon in formic acid a) 2 : 1 b) 1 : 1 d) formic acid does not undergo association c) 3 : 2 d) 2 : 3 190. What are the product in the following reaction 197. HVZ reaction is characteristic reaction of a) -H atom b) -H atom CH | 3 c) -H atom d) -H atom CH C CH K2 Cr 2 O z 3 2 dil. H2 SO 4 198. Carboxylic acid reacts with calcium metal. The amount of calcium used up and hydrogen liberated a) CH –COCH and H–COOH 3 3 are in the molar ratio of b) CH –CH CHO and CO 3 2 2 a) 2 : 1 b) 1 : 1 c) CH –COOH and H–COOH 3 c) 3 : 2 d) 2 : 3 d) CH –CHO and H–COOH 3 199. Two molecules of acetic acid are heated with 191. Product of the following reaction is P 2 O 5 . The product formed is [O] PCl3 CH 3 COONa a) two moles of ethanol CH3 COCH 3 A B C a) acetic unhydride b) two moles of methyl cyanide b) propanoic unhydride c) acetic anhydride b) propanoic unhydride d) formic acid d) isopropyl alcohol 200. Carboxylic acid can a) decompose carbonate and evolve CO 192. Which of the following does not under go HVZ 2
reaction ? b) reacts with metal forming H 2 gas c) neutralise ammonium hydroxide form salt a) CH 3 –COOH d) all of the above b) CH 3 –CH 2 –COOH
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Aldehydes, Ketones and Carboxylic Acids 71 201. Which of the following group will increase more a) l > 3 > 2 > 1 b) 2 > 3 > 1 > 4 acidity of acetic acid ? c) 3 > l > 2 > 4 d) 3 > 1 > 4 > 2
a) –NO 2 b) –CH 3 209. The compounds formed by the acid hydrolysis of – c) CH 3 O d) – NH 2 ethyl acetate are
202. P 2 O 5 is anhydride of a) formic acid and propanol
a) H 3 PO 3 b) HPO 3 b) acetic acid and ethanol
c) H 3 PO 4 d) HC1O c) acetone and ethanol 203. The solvent that can dissolve all the carboxylic d) acetone and methanol acids is 210. – COOH group of a compound does not react
a) water b) dil. HC1 with NaHSO 3 even though it has > C = O group because of c) dil. NaOH d) conc. H 2 SO 4 204. Acetyl chloride can be prepared a) cyclic structure b) acidic character c) linear structure d) resonance a) by the action of CH 3 COOH with chloroform 211. Final product of following reaction is b) by the action of PC1 3 on acetic acid
(i) dry ether Br 2 c) by the action of C1 2 on acetic acid CO2 (CH 3 ) 3 C MgBr A B (ii) H3 O Red P
d) by the action of CC1 4 on acetic acid
205. Of the following four reactions, formic and acetic CH 3 | acid differ in which respect ? a) CH3 C COOH a) Formation of ester with alcohol | Br b) Replacement of hydrogen by sodium c) Reduction of Fehling solution CH 3 d) Blue litmus reaction | b) CH3 C CH COOH 206. Arrange the following carboxylic acid in their | | CH Br decreasing acidity 3
COOH c) CH CH CH COOH 1. | Oxalic acid 3 2 | COOH Br
2. HOOC–CH 2 –COOH Malonic acid d) No product will be formed. 212. Acids having higher B.P. than alcohols because CH2 COOH 3. | Succinic acid of CH COOH 2 a) intra molecular HB a) 3 > 2 > 1 b) 1 > 2 > 3 b) dimerisation of acid c) 2 > 3 > 1 d) 2 > 1 > 3 c) dipole-dipole attraction 207. Among the following which compound will react d) Vander Waals force of attraction
with Na 2 CO 3 solution to give sodium salt and 213. Product of the following reaction is CO ? 2 CH ClCH COOAg A H3 O B a) Phenol b) 1-hexanol 3 2 5
c) Formic acid d) Ethanal a) CH 3 –COOH + C 2 H 5 –OH
208. Identify the correct order of boiling point of b) CH 3 –CHO + C 2 H 5 –OH
following compound ? c) C 2 H 5 –COOH + CH 3 –OH d) C H –COOH + C H –OH 1.OH 2. OH 2 5 2 5 || 214. Adipic acid is formed by oxidation of OH O 3. 4. a) cyclohexane b) cyclohexene || O O c) hex-1-ene d) hex-2-ene
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Aldehydes, Ketones and Carboxylic Acids 72 215. Product 'B'of the following 217. Product 'B' of the following
Red P Red P CH3 CH 2 COOH Cl 2 A CH3 CH 2 COOH Br 2
KOH alc. B Aq. KOH B
a) CH 3 –CHC1–COOH a) CH 3 –CH 2 –CHOH–COOH
b) CH 3 –CHOH–COOH b) CH 3 –CHOH–CH 2 –COOH
c) CH 2 = CH–COOH c) HO–CH 2 –CH 2 –CH 2 –COOH
d) CH C–COOH d) CH 3 –CH = CH–COOH 216. Which of the following does not give HVZ 218. Terepnthalic acid is heated with ammonia gives reaction? a) phthalamide b) phthalimide a) Acetic acid b) Propionic acid c) isophthalic d) ammoniumphthalate c) Isobutyric acid d) Neovaleric acid
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Aldehydes, Ketones and Carboxylic Acids 73 Answer Key
SECTION-I: ALDEHYDES AND KETONES 1.(a) 2.(b) 3.(b) 4.(c) 5.(c) 6.(c) 7.(c) 8.(b) 9.(b) 10.(b) 11.(b) 12.(c) 13.(a) 14.(c) 15.(d) 16.(b) 17.(c) 18.(d) 19.(d) 20.(b) 21.(d) 22.(b) 23.(d) 24.(b) 25.(c) 26.(d) 27.(b) 28.(c) 29.(a) 30.(b) 31.(d) 32.(c) 33.(b) 34.(b) 35.(b) 36.(b) 37.(c) 38.(d) 39.(b) 40.(b) 41.(a) 42.(b) 43.(c) 44.(b) 45.(a) 46.(c) 47.(d) 48.(a) 49.(a) 50.(c) 51.(c) 52.(a) 53. (b) 54.(c) 55.(c) 56.(d) 57.(a) 58.(d) 59.(b) 60.(a) 61.(b) 62.(a) 63.(d) 64.(c) 65.(b) 66.(b) 67.(b) 68.(d) 69.(c) 70.(a) 71.(c) 72.(a) 73.(c) 74.(b) 75.(d) 76.(c) 77.(b) 78.(a) 79.(a) 80.(c) 81.(a) 82.(c) 83.(c) 84.(a) 85.(d) 86.(c) 87.(d) 88.(a) 89.(a) 90.(b) 91.(d) 92.(b) 93.(b) 94.(b) 95.(d) 96.(d) 97.(b) 98.(d) 99.(b) 100.(a) 101.(c) 102.(a) 103.(c) 104.(b) 105.(c) 106.(d) 107.(a) 108.(b) 109.(d) 110.(c) 111.(d) 112.(c) 113.(c) 114.(a) 115.(b) 116.(b) 117.(b) 118.(d) 119.(d) 120.(a) 121.(a) 122.(b) 123.(b) 124.(d) 125.(c) 126.(c) 127.(c) 128.(b) 129.(b) 130.(d) 131.(b) 132.(b) 133.(d) 134.(c) 135.(d) 136.(c) 137.(d) 138.(c) 139.(a) 140.(a) 141.(a) 142.(b) 143.(a) 144.(c) 145.(c) 146.(d) 147.(c) 148.(c) 149.(c) 150.(b) 151.(a) 152.(b) 153. (a) 154.(d) 155.(b) 156.(a) 157.(b) 158.(b) 159.(c) 160.(d) 161.(c) 162.(a) 163.(b) 164.(c) 165.(c) 166.(d) 167.(d) 168.(b) 169.(d) 170.(d) 171.(d) 172.(d) 173.(d) 174.(a) 175.(a) 176.(b) 177.(a) 178.(d) 179.(b) 180.(a) 181.(a) 182.(a) 183.(c) 184.(c) 185.(a) 186.(c) 187.(d) 188.(a) 189.(d) 190.(b) 191.(b) 192.(c) 193.(b) 194.(d) 195.(d) 196.(b) 197.(b) 198.(d) 199.(b) 200.(d) 201.(c) 202.(b) 203.(b) 204.(b) 205.(d) 206.(b) 207.(b) 208.(c) 209.(b) 210.(b) 211.(c) 212.(b) 213.(b) 214.(b) 215.(d) 216.(c) 217.(b) 218.(a) 219.(b) 220.(c) 221.(b) 222.(c) 223.(d) 224.(c) 225.(b) 226.(c) 227.(a) 228.(d) 229.(a) 230.(d) 231.(a) 232.(d) 233.(c) 234.(d) 235.(d) 236.(b) 237.(c) 238.(c) 239.(b) 240.(a) 241.(a) 242.(c) 243.(d) 244.(b) 245.(c) 246.(c) 247.(c) 248.(c) 249.(c) 250.(d) 251.(b) 252.(a) 253. (b) 254.(c) 255.(c) 256.(b) 257.(d) 258.(d) 259.(a) 260.(b) 261.(c) 262.(d) 263.(c) 264.(d) 265.(a) 266.(d) 267.(c) 268.(a) 269.(b) 270.(c) 271.(c) 272.(a) 273.(b) 274.(c) 275.(a) 276.(d) 277.(a) 278.(a) 279.(b) 280.(d) 281.(b) 282.(c) 283.(c) 284.(b) 285.(c) 286.(d) 287.(b) 288.(c) 289.(d) 290.(b) 291.(b) 292.(d) 293.(a) 294.(a) 295.(c) 296.(d) 297.(d) 298.(a) 299.(c) 300.(c)
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Aldehydes, Ketones and Carboxylic Acids 74 Answer Key SECTION-I: ALDEHYDES AND KETONES 301.(d) 302.(d) 303.(b) 304.(c) 305.(a) 306.(d) 307.(d) 308.(b) 309.(b) 310.(a) 311.(b) 312.(b) 313.(c) 314.(c) 315.(c) 316.(a) 317.(b) 318.(b) 319.(b) 320.(a) 321.(a) 322.(a) 323.(b) 324.(b) 325.(c) 326.(a) 327.(b) 328.(a) 329.(b) 330.(d) 331.(c) 332.(a) 333.(a) 334.(d) 335.(c) 336.(a) 337.(b) 338.(b) 339.(d) 340.(a) 341.(c) 342.(c) 343.(c) 344.(a) 345.(a) 346.(b) 347.(d) 348.(b) 349.(b) 350.(a) 351.(b) 352.(a) 353. (b) 354.(c) 355.(b) 356.(a) 357.(b) 358.(a) 359.(b) 360.(c) 361.(b) 362.(d) 363.(d) 364.(b) 365.(c) 366.(a) 367.(b) 368.(a) 369.(c) 370.(c) 371.(a) 372.(b) 373.(b) 374.(a) 375.(b) 376.(b) 377.(b) SECTION-II: CARBOXYLIC ACIDS 1.(b) 2.(c) 3.(a) 4.(b) 5.(c) 6.(a) 7.(c) 8.(c) 9.(d) 10.(a) 11.(b) 12.(d) 13.(b) 14.(c) 15.(b) 16.(c) 17.(a) 18.(b) 19.(b) 20.(c) 21.(c) 22.(d) 23.(c) 24.(c) 25.(a) 26.(b) 27.(c) 28.(d) 29.(b) 30.(c) 31.(c) 32.(b) 33.(b) 34.(a) 35.(a) 36.(c) 37.(d) 38.(c) 39.(d) 40.(b) 41.(a) 42.(a) 43.(b) 44.(a) 45.(a) 46.(a) 47.(b) 48.(b) 49.(d) 50.(b) 51.(c) 52.(d) 53. (a) 54.(a) 55.(a) 56.(c) 57.(b) 58.(b) 59.(b) 60.(c) 61.(d) 62.(b) 63.(b) 64.(b) 65.(c) 66.(c) 67.(a) 68.(b) 69.(b) 70.(b) 71.(d) 72.(a) 73.(d) 74.(d) 75.(b) 76.(a) 77.(a) 78.(d) 79.(b) 80.(b) 81.(b) 82.(b) 83.(d) 84.(b) 85.(d) 86.(a) 87.(d) 88.(b) 89.(a) 90.(c) 91.(a) 92.(c) 93.(c) 94.(c) 95.(c) 96.(c) 97.(c) 98.(c) 99.(d) 100.(c) 101.(c) 102.(a) 103.(c) 104.(d) 105.(c) 106.(a) 107.(d) 108.(d) 109.(c) 110.(a) 111.(c) 112.(b) 113.(c) 114.(c) 115.(d) 116.(d) 117.(b) 118.(c) 119.(c) 120.(c) 121.(a) 122.(d) 123.(c) 124.(d) 125.(b) 126.(c) 127.(a) 128.(a) 129.(c) 130.(a) 131.(a) 132.(a) 133.(a) 134.(d) 135.(c) 136.(b) 137.(a) 138.(c) 139.(a) 140.(a) 141.(c) 142.(a) 143.(d) 144.(b) 145.(c) 146.(a) 147.(c) 148.(b) 149.(a) 150.(d) 151.(d) 152.(a) 153. (b) 154.(b) 155.(a) 156.(a) 157.(d) 158.(b) 159.(d) 160.(c) 161.(b) 162.(b) 163.(d) 164.(d) 165.(a) 166.(a) 167.(b) 168.(d) 169.(c) 170.(b) 171.(c) 172.(a) 173.(d) 174.(b) 175.(a) 176.(b) 177.(a) 178.(a) 179.(a) 180.(a) 181.(c) 182.(d) 183.(b) 184.(a) 185.(c) 186.(b) 187.(a) 188.(c) 189.(c) 190.(a) 191.(a) 192.(d) 193.(a) 194.(d) 195.(a) 196.(a) 197.(a) 198.(b) 199.(c) 200.(d) 201.(a) 202.(b) 203.(c) 204.(b) 205.(c) 206.(b) 207.(c) 208.(c) 209.(b) 210.(d) 211.(d) 212.(b) 213.(c) 214.(b) 215.(c) 216.(d) 217.(a) 218.(b)
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