IUPAC Nomenclature & Structural Isomerism Contents Topic Page No.
Theory 01 - 07
Exercise - 1 08 - 23
Exercise - 2 24 - 26
Exercise - 3 26 - 28
Exercise - 4 29 - 31
Answer Key 32 - 33 Syllabus
Hybridisation of carbon; Sigma and pi-bonds; Shapes of simple organic molecules & structural isomerism, IUPAC nomenclature of simple organic compounds (only hydrocarbons, mono-functional and bi-functional compounds);
Name : ______Contact No. ______IUPAC NOMENCLATURE & STRUCTURAL ISOMERISM
KEY CONCEPTS
Classification of organic compounds
IUPAC Nomenclature : Groups : Atom or a group of atoms which possess any 'charge' on it or any 'free valency' are called as Groups. Alkyl group : When a hydrogen is removed from saturated hydrocarbon then alkyl group is formed. It is
represented by R & its general formula is CnH2n + 1. A bond is vacant on alkyl group on which any functional group may come. CH4 H CH3 – Methyl
CH3 – CH3 H CH3 – CH2 – Ethyl
(a) C3H7 has following two isomers
(i) Normal propyl CH3–CH2–CH2–
(ii) Isopropyl (1-methyl ethyl) CH 3–CH–
CH3
(b) C4H9 has following four structures :
(i) n-butyl H3C–CH2–CH2–CH2–
(ii) Iso butyl (2-methyl propyl) CH 3–CH–CH2–
CH3
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 1 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU (iii) Secondary butyl (1-methyl propyl) CH 3–CH2–CH–
CH3
CH3
(iv) Tertiary butyl (1,1-dimethyl ethyl) CH3–C–
CH3 Alkenyl group :
CH2 = CH – Ethenyl
CH2 = CH – CH2 – Propenyal
CH3 – CH = CH – Propenyl(1-propenyl)
CH 3–C=CH2 Isopropenyl (1-methyl-1-ethenyl) C
Alkynyl group : CH C– Ethynyl
Retained Name : Normal group :
(a) It is represented by 'n'.
(b) Straight chain of carbon atom is known as normal group.
(c) Free bond will come either on 1st carbon atom or on last carbon atom.
n-butyl C–C–C–C–
n-propyl C–C–C–
Iso group : It is represented by following structure C –C– C Neo group : (a) When two methyl group are attached to second last carbon atom group is named as neo group. (b) It is represented by following structure -
For eg. Neo pentyl
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 2 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU ALLOTMENT OF IUPAC NOMENCLATURE Table : The Word Root of Unbranched Alkanes
Number of Name Carbon Atoms 1 Methane 2 Ethane 3 Propane 4 Butane 5 Pentane
6 Hexane 7 Heptane 8 Octane 9 Nonane 10 Decane
11 Undecane 12 Dodecane 13 Tridecane 14 Tetradecane 15 Pentadecane
16 Hexadecane 17 Heptadecane 18 Octadecane 19 Nonadecane
20 Eicosane 21 Heneicosane 22 Docosane 23 Tricosane 30 Triacontane
31 Hentriacontane 40 Tetracontane 50 Pentacontane 60 Hexacontane 70 Heptacontane
80 Octacontane 90 Nonacontane 100 Centane or Hectane
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 3 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU Rules for Naming the compound having poly functional groups : - If any organic compound possess more than one functional group, then functional group of highest priority is taken in longest chain along with maximum number of substituents. The priority order of the final groups is as under
Table : Functional Groups in decreasing order of seniority
Class Name Suffix Prefix + ammonio – – ammonium (R4N ) 1. Cations ------+ phosphonio – – phosphonium (R4P ) + sulphonio – – sulphonium (R3S )
2. R – COOH Alkanoic Acid – oic Acid (carboxylic acid) Carboxy
3. Alkane sulphonic Acid – sulphonic Acid sulpho R – SO3H
4. R – C – O – C – R Alkanoic Anhydride – anhydride ------|| || O O
5. R – COOR Alkyl Alkanoate – alkanoate (carboxylate) Alkoxy carbonyl
6. R – C – X – oyl halide (carbonyl halide) || Alkanoyl halide halo carbonyl O
7. R – C – NH 2 – amide (carboxamide) || Alkanamide Carbamoyl O – nitrile (carbonitrile) cyano 8. R – C N Alkanenitrile
9. R – C – H Alkanal – al (carbaldehyde) formyl || O
10. R – C – R Alkanone – one Oxo / Keto || O
11. Alkanol R – OH – ol hydroxy
12. R – SH Alkanethiol – thiol mercapto
Alkanamine – amine amino 13. R – NH2
Isomerism Organic compounds having same molecular formula but differing from each other at least in some physical or chemical properties or both are known as isomers (Berzelius) and the phenomenon is known as isomerism. The difference in properties of isomers is due to the difference in the relative arrangements of various atoms or groups present in their molecules. Isomerism can be classified as follows:
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 4 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU Constitutional or structural isomerism
(1) Chain, nuclear or skeleton isomerism : This type of isomerism arises due to the difference in the nature of the carbon chain (i.e., straight or branched) which forms the nucleus of the molecule. Examples :
(i) C4H10 : CH3 CH 2 CH 2 CH 3 , CH3 CH CH 3 n Butane | CH3 Isobutane
CH3 | (ii) C5H12 : (Three) CH CH CH CH CH , CH CH CH CH , CH C CH 3 2 2 2 3 3| 2 3 3 3 n Pentane | CH3 CH Isopentane 3 Neopentane
Except alkynes chain isomerism is observed when the number of carbon atoms is four or more than four. Chain isomers differ in the nature of carbon chain, i.e., in the length of carbon chain. The isomers showing chain isomerism belong to the same homologous series, i.e., functional group, class of the compound (Cyclic or open) remains unchanged. Chain and position isomerism cannot be possible together between two isomeric compounds. If two compounds are chain isomers then these two will not be positional isomers.
(2) Position isomerism : It is due to the difference in the position of the substituent atom or group or an unsaturated linkage in the same carbon chain.
C3 H6 Cl2 : CH3 CCl 2 CH 3 ,CH3 CH 2 CHCl 2 , CH3 CH CH 2 , CH2 CH 2 CH 2 2,2 Dichloro propane, 1,1 Dichloro propane | | | | (gemdihalide) (gemdihalide) Cl Cl Cl Cl 1,2 Dichloro propane 1,3 Dichloro propane ( , -dihali de) (Vicdihalide) Aldehydes, carboxylic acids (and their derivatives) and cyanides do not show position isomerism. Monosubstituted alicylic compounds and aromatic compounds do not show position isomerism. Structural isomers which differ in the position of the functional group are called regiomers.
For example, (i) CH3 CH 2 CH 2 OH (ii) CH3 CH CH 3 | OH
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 5 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU (3) Functional isomerism : This type of isomerism is due to difference in the nature of functional group present in the isomers. The following pairs of compounds always form functional isomers with each other. Examples :
(i) Alcohols and ethers (Cn H2n+2O)
C2H6O : CH3 CH 2 OH ; H3 C O CH 3 Ethyl alcohol Dimethyl ether
C3H8O : CH3 CH 2 CH 2 OH ; C2 H 5 O CH 3 n propyl alcohol Ethyl methyl ether
C4H10O : CH3 CH 2 CH 2 CH 2 OH ; CHOCH2 5 2 5 n Butyl alcohol Diethyl ether
(ii) Aldehydes, ketones and unsaturated alcohols …etc. (Cn H2nO) O ||
C3H6O : CH3 CH 2 CHO ; CH3 C CH 3 ; CH2 CH CH 3 ; CH2 CH CH 2 OH Propionaldehyde Acetone Allyl alcohol O 1,2 Epoxy propane
(iii) Acids, esters and hydroxy carbonyl compounds …etc. (Cn H2nO2)
C2H4O2 : CH3 COOH ; HCOOCH3 Acetic acid Methyl formate
O ||
C3H6O2 : CH3 CH 2 COOH ; CH3 COOCH 3 ; H3C CH CHO ; CH3 C CH 2 OH Propionic acid Methyl acetate 1 Hydroxy propan-2-one OH 2-Hydroxypropanal
(iv) Alkynes and alkadienes (C n H2n-2)
C4H6 : CH3 CH 2 C CH ; H2 C CH CH CH 2 ; CH3 C C CH 3 ; H2 C C CH CH 3 1 Butyne 1,3 Butadiene 2 Butyne 1,2 Butadiene
(v) Nitro alkanes and alkyl nitrites ( NO2 and ONO ) O
C2H5NO2 : CHN2 5 ; CHONO2 5 Ethyl nitrite O Nitro ethane (vi) Amines (Primary, secondary and tertiary)
H CH3
C3H9N : CH3 CH 2 CH 2 NH 2 ; CH3 CH 2 N ; CH3 CH CH 3 ; CH3 CH 2 N Propan -1- amine | CH3 NH2 CH3 N Methyl ethanamine Propan -2- amine N,N Dimethyl methanamine (vii) Alcohols and phenols
CH2OH OH
CH3
C7H8O :
Benzyl alcohol o-Cresol
(viii) Oximes and amides O ||
C2H5NO : CH3 CH NOH ; CH3 C NH 2 Acetaldoxime Acetamide
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 6 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU (4) Ring-chain isomerism : This type of isomerism is due to different modes of linking of carbon atoms, i.e., the isomers possess either open chain or closed chain sturctures. C H2 H2C CH2 H2C CH2 C6H12 : ; CHCH3 ; CH CH CH CH CH CH CH2 3 2 2 2 2 H2C 1 Hexene H2C CH2 C Methylcyclopentane
H2 Cyclohexane
Ring – chain isomers are always functional isomers. (5) Metamerism : This type of isomerism is due to the difference in the nature of alkyl groups attached to the polyvalent atoms or functional group. Metamers always belong to the same homologous series. Compounds like ethers, thio-ethers ketones, secondary amines, etc. show metamerism.
CH3 CH2 5 (i) C5H13N : CHN3 7 ; CHN2 5 CH3 CH3 Dimethyl propyl amine Diethyl methyl amine
(ii) C6H15N : C3 H 7 NH C 3 H 7 ; C2 H 5 NH C 4 H 9 Dipropyl amine Butyl ethyl amine
If same polyvalent functional group is there in two or more organic compounds, then chain or position isomerism is not possible, there will be metamerism e.g.,
(a) CH3 C CH 2 CH 2 CH 3 ; CH3 CH 2 C CH 2 CH 3 are metamers and not position isomers. | | | | O O (Pentan 2 one) (Pentan 3 one)
(b) CH3 C CH 2 CH 2 CH 3 ; CH3 C CH CH 3 are metamers and not chain isomers. || | | | O O CH3 (Pentan 2 one) (3-Methylbutan-2-one)
Note : Alkenes donot show metamerism.
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 7 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU PART - I : OBJECTIVE QUESTIONS
* Marked Questions are having more than one correct option. Section (A) : Fundamental of Organic Chemistry
A-1. In homologous series : (A) Molecular formula is same (B) Structural formula is same (C) Physical properties are same (D) General formula is same
A-2. How many secondary carbon atoms does methyl cyclopropane have? (A) None (B) One (C) Two (D) Three
A-3. Which of the following is the first member of ester homologous series ? (A) Ethyl ethanoate (B) Methyl ethanoate (C) Methyl methanoate (D)Ethyl methanoate
A-4. How many carbons are in simplest alkyne having two side chains ? (A) 5 (B) 6 (C) 7 (D) 8
A-5. How many 1º carbon atom will be present in a simplest hydrocarbon having two 3º & one 2º carbon atom? (A) 3 (B) 4 (C) 5 (D) 6
A-6.* The pair of compounds having the same general formula :
(A) and (B) and
(C) and (D) and H–CC–CC–H
A-7. (a) and (b)
True statement for the above compounds is: (A) (A) is phenol while (B) is alcohol (B) Both (A) and (B) are primary alcohol (C) (A) is primary and (B) is secondary alcohol (D) (A) is secondary and (B) is primary alcohol
A-8. The total number of secondary H-atoms in the structure given below are :
(CH3)2CHCH2C2H5 (A) 1 (B) 4 (C) 3 (D) 2
A-9. Which of the following is the triad of a homologous series -
(A) CH3NH2, (CH3)2NH, (CH3)3 N (B) C2H5OH, (CH3)2CHOH, (CH3)3COH (C) Both the above (D) CH2 = CH2, CH3 – CH = CH2, C2H5 – CH = CH2 A-10. The homologue of phenol is -
CH2 OH OH OH OH
CH3 OH (A) (B) (C) (D)
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 8 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU A-11. What is not true about homologous series ? (A) All the members have similar chemical properties (B) They have identical physical properties (C) They can be represented by a general formula (D) Adjacent members differ in molecular mass by 14
A-12. An organic compound has molecular formula C9H18. It is a saturated hydrocarbon and its all hydrogen atoms are identical. Its structural formula can be :
(A) (B)
(C) (D)
Section (B) : Classification and General Rules of IUPAC Nomenclature
B-1. C4H6O2 does not represent: (A) A diketone (B) A compound with two aldehyde (C) An alkenoic acid (D) An alkanoic acid
B-2. As per IUPAC rules, which one of the following groups, will be regarded as the principal functional group? (A) –CC– (B) –OH (C) C (D) C H || || O O B-3. The group of hetrocylic compounds is: (A) Phenol, Furane (B) Furane, Thiophene (C) Thiophene, Phenol (D) Furane, Aniline
B-4. Which of the following is a heterocyclic compound HC CH HC COOH HC CH HC CH (A) | (B) | (C) | (D) | HC CH HC COOH HC CH HC CH
B-5. The number of sigma and pi-bonds in 1-butene 3-yne are: (A) 5 sigma and 5 pi (B) 7 sigma and 3 pi (C) 8 sigma and 2 pi (D) 6 sigma and 4 pi
B-6. Which is an acyclic compound : (A) Methane (B) Benzene (C) Pyrrole (D) Cyclobutane
B-7. Which of the following is not an alicyclic compound ?
(A) (B) (C) (D)
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 9 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU B-8. Which of the following has not bridgehead carbon :
(A) (B) (C) (D)
B-9. Which of the following compounds is unsaturated hydrocarbon.
(A) (B) CH3–CN (C) (D)
Section (C) : IUPAC-Nomenclature of Alkane
C-1. The compound which has one isopropyl group is: (A) 2,2,3,3-tetramethyl pentane (B) 2,2-dimethyl pentane (C) 2,2,3-trimethyl pentane (D) 2-methyl pentane
C-2. The IUPAC name of the compound Br(Cl) IC. CF3 is: (A) 2-bromo-2-chloro-2-iodo1,1,1-trifluoroethane (B) 1,1,1-trifluoro-2-bromo-2-chloro-2-iodo ethane (C) 2-bromo-2-chloro-1,1,1-trifluoro-2-iodo ethane (D) 1-bromo-1-chloro-1-iodo-2,2,2-trifloro ethane
C-3. The IUPAC name of the following structure is [CH3CH(CH3)]2 C(CH2CH3)C(CH3) C(CH2CH3)2 (A) 3,5-diethyl-4,6-dimethyl-5-[1-methylethyl]-3-heptene (B) 3,5-diethyl-5-isopropyl-4,6-dimethyl-2-heptene (C) 3,5-diethyl-5-propyl-4,6-dimethyl-3-heptene (D) None of these F Cl C-4. The IUPAC name of this compound is : | | CH C CH C CH (A) 2-fluoro-4-chloro-2,4-diethyl pentane 3 2 3 | | (B) 3-fluoro-5-chloro-3-methyl-5-ethyl hexane CH2CH3 CH2CH3 (C) 3-chloro-5-fluoro-3,5-dimethyl heptane (D) 3,5-dimethyl-5-fluoro-3-chloro heptane
C-5. The IUPAC name of is -
(A) 2-bromo-4-isopropylpentane (B) 2, 3-dimethyl-5-bromohexane (C) 2-bromo-4, 5-dimethylhexane (D) 5-bromo-2, 3-dimethylhexane C-6. Give the IUPAC name of CH3 | H3C C CH3 | CH3 CH2 CH2 CH CH CH2 CH2 CH3 | H3C CH | CH3 (A) 4-isopropyl-5-ter. butyl octane (B) 4-ter. butyl-5-isopropyl octane (C) 2-methyl-3-propyl-4-ter. butyl heptane (D) 2, 2-dimethyl-3-propyl-4-isopropyl heptane C-7. Which alkane would have only the primary and tertiary carbon ? (A) Pentane (B) 2-Methylbutane (C) 2, 2-Dimethylpropane (D) 2, 3-Dimethylbutane
C-8. In the structure of 4-Isopropyl-2, 4, 5-trimethylheptane, number of 1°, 2° & 3° H's are respectively : (A) 18, 5, 4 (B) 21, 4, 3 (C) 18, 4, 3 (D) 21, 5, 4
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 10 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU Section (D) : IUPAC-Nomenclature of Alkene & Alkyne
D-1. The IUPAC name of the compound having the formula is: CH | 3 H C C CH CH 3 | 2 CH3 (A) 3,3,3-trimethyl-1-propene (B) 1,1,1-trimethyl-2-propene (C) 3,3-dimethyl-1-butene (D) 2,2-dimethyl-3-butene
D-2. The IUPAC name of the compound CH2=CH–CH(CH3)2 is: (A) 1,1-dimethyl-2-propene (B) 3-methyl-1-butene (C) 2-vinyl propane (D) None of the above
D-3. The correct IUPAC name of the compound :
(A) 5-ethyl-3, 6-dimethyl non-3-ene (B) 5-ethyl-4, 7-dimethyl non-3-ene (C) 4-methyl-5, 7-diethyl oct-2-ene (D) 2,4-ethyl-5-methyl oct-2-ene
D-4. The correct IUPAC name of :
CH3 – C C – CH 3 | |
CHCH2 5 2 5
(A) 1, 2-diethyl butane (B) 2-ethyl 3-methylpentane (C) 3, 4-dimethyl-3-hexene (D) none is correct
D-5. The IUPAC name of the compound CH3CH = CHCH=CHCCCH3 is: (A) 4,6-octadiene-2-yne (B) 2,4-octadiene-6-yne (C) 2-octyn-4,6-diene (D) 6-octyn-2,4-diene
D-6. The correct IUPAC name of 2-ethyl-3-pentyne is: (A) 3-methyl hexyne-4 (B) 4-ethyl pentyne-2 (C) 4-methyl hexyne-2 (D) None of these
D-7. The molecular formula of the first member of the family of alkenynes and its name is given by the set
(A) C3H2, alkene (B) C5H6, 1-penten-3-yne (C) C6H8, 1-hexen-5-yne (D) C4H4, butenyne
D-8. The IUPAC name of is -
(A) 2-ethyl-3-methyl-1-penten-4-yne (B) 2-ethyl-3-methyl-4-pentyn-1-ene (C) 4-ethyl-3-methyl-1-pentyn-4-ene (D) 4-ethyl-3-ethyl-4-penten-1-yne
D-9. The IUPAC name of
CH CH3 || is : HC C C C C CH2 CH3 (A) 5-ethyl- 5-heptene-1, 3- diyne (B) 3-ethyl- 2-heptene-4, 6- diyne (C) 5-ethenyl-1, 3- heptatriyne (D) 3-ethenyl-4, 6-heptatriyne
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 11 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU D-10.
The IUPAC name of the above structure is : (A) 2, 4, 5 - Triethyl-3-nonene (B) 5, 6 - Diethyl -3- methyl -4-decene (C) 2, 4, 5 - Triethyl -3- octene (D) 3 - Heptyl - 5- methyl-3- heptene
D-11. IUPAC name of the compound is :
(A) 3-Ethyl-4-chloropenta-1, 4-diene (B) 2-Chloro-3-ethylpenta-1, 4-diene (C) 4-Chloroethenylpent-1-ene (D) 3-Ethenyl-4-chloropent-4-ene
Section (E) : IUPAC-Nomenclature of Cyclic Compounds
E-1. The IUPAC name of the compound is -
(A) 1-chloro-2-bromocylohexane (B) 1, 2-bromochlorocyclohexane (C) 4-bromo-3-chlorocyclohexane (D) 1-bromo-2-chlorocyclohexane
E-2. The IUPAC name of the given compound
is -
(A) Octylcyclopentane (B) 3-cyclopentyloctane (C) cyclopentaneoctane (D) 6-cyclopentyloctane
E-3. The IUPAC name of is: CH CH CHCH2CH3 | CH3 (A) 1-cyclohexyl-3-methyl-1-pentene (B) 3-methyl-5-cyclohexyl-pent-ene (C) 1-cyclohexyl-3-ethyl-but-1-ene (D) 1-cyclohexyl-3,4-dimethyl-but-1-ene
E-4. The correct IUPAC name for the compound
C2H5 CH3 is -
(A) 6-Ethyl-1-methylcyclohex-1-ene (B) 3-Ethyl-2-methylcyclohex-1-ene (C) 1-Ethyl-2-methylcyclohex-2-ene (D) 2-Ethyl-1-methylcyclohex-1-ene
E-5. The name of the compound is -
(A) bicyclo [2.2.1] octane (B) bicyclo [1.1.1] octane (C) 1, 4-bismethylenecyclohexane (D) bicyclo [2.2.2] octane
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 12 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU E-6. Which of the following structures represents bicyclo [3.2.0] heptane -
(A) (B) (C) (D)
E-7. The IUPAC name of compound is -
(A) Bicyclo [2.2.1] hept-2-ene (B) Bicyclo [2.2.1] hept-5-ene (C) Bicyclo [2.1.2] hept-2-ene (D) Bicyclo [1.2.2] hept-2-ene
E-8. The IUPAC name of compound is -
(A) Spiro [5.3] nonane (B) Spiro [3.5] nonane (C) Spiro [5.4] nonane (D) Spiro [4.5] nonane
E-9. The IUPAC name of is -
(A) 3-cyclopropyl-3-ethyl-2-propene (B) 1-cyclopropyl-1-ethylpropene (C) 3-cyclopropyl-2-pentene (D) (1-ethyl-1-propenyl) cyclopropane
E-10. The IUPAC name of is -
(A) 3-cyclobutylcyclopropane (B) 1-cyclopropyl-3-methylcyclobutane (C) 1, 3-cyclopropylmethylcyclobutane (D) 2-methylbicyclo [4.3.0] heptane
E-11. IUPAC name for is :
(A) Sec-butyl cyclobutane (B) 2-(n-butyl)cyclobutane (C) 2-Cyclobutylbutane (D) 1-Cyclobutylbutane
E-12. The correct IUPAC name of is :
(A) 1, 4-Diethyl-2-methyl-5-propylcyclohexane (B) 1, 4-Diethyl-5-methyl-2-propylcyclohexane (C) 2, 5-Diethyl-1-methyl-4-propylcyclohexane (D) 2, 5-Diethyl-4-methyl-1-propylcyclohexane
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 13 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU E-13. The correct IUPAC name of the compound
(A) 1-Ethenylcyclohexa (B) 5-Ethenylcyclohexa-1, 3-diene (C) 6-Ethenylcyclohexa-1, 3-diene (D) Cyclohexa-2, 4-dienylethene
Section (F) : IUPAC-Nomenclature of Functional I groups
F-1. The IUPAC name of the compound CH2 CH CH2 is: | | | OH OH OH (A) 1,2,3-tri hydroxy propane (B) 3-hydroxy pentane-1,5-diol (C) 1,2,3-hydroxy propane (D) Propane-1,2,3-triol
Ph | F-2. The IUPAC name of the compound is CH3 CH CH NH2 | CH3
(A) 1-amino-1-phenyl-2-methyl propane (B) 2-methyl-1-phenyl propane-1-amine (C) 2-methyl-1-amino-1-phenyl propane (D) 1-isopropyl-1-phenyl methyl amine
F-3. The IUPAC name of the given compound is:
(A) 1,1-dimethyl-3-hydroxy cyclohexane (B) 3,3-dimethyl-1-hydroxy cyclohexane (C) 3,3-dimethyl-1-cyclohexanol (D) 1,1-dimethyl-3-cyclohexanol
F-4. The IUPAC name of acetyl acetone is: (A) 2,5-Pentane dione (B) 2,4-Pentane dione (C) 2,4-Hexane dione (D) 2,4-butane dione
F-5. IUPAC name of is:
(A) 5-methyl hexanol (B) 2-methyl hexanol (C) 2-methyl hex-3-enol (D) 4-methyl pent-2-en-1-ol
F-6. The IUPAC name of is: CH3 CH2 N CH2CH3 | CH3 (A) N-methyl-N-ethylethylamine (B) diethyl methylamine (C) N-ethyl-N-methyl ethanamine (D) methyl diethylamine
F-7. The IUPAC name of the compound:
(A) Propylene Oxide (B) 1,2-Oxo propane (C) 1,2-Epoxy propane (D) 1,2-Propoxide
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 14 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU F-8. The IUPAC name of is
(A) 3-Methyl cyclobut-1-en-2-ol (B) 4-Methyl cyclobut-2-en-1-ol (C) 4-Methyl cyclobut-1-en-3-ol (D) 2-Methyl cyclobut-3-en-1-ol
F-9. Ethyl methyl vinyl amine has the structure -
(A) CH3CH2 N CH2CH CH2 (B) CH3CH2 N CH CH2 | | CH3 CH3
(C) CH2 CH N CH CH2 (D) CH3 N CH CH2 | | CH3 CH3
F-10. The IUPAC name of is - (A) 4-oxopentan-2-ol (B) 4-hydroxypentan-2-one (C) pentane-4-ol-2-one (D) pentane-2-one-4-ol
F-11. All the following IUPAC names are correct except: (A) 1-chloro-1-ethoxy propane (B) 1-amino-1-ethoxypropane (C) 1-ethoxy-2-propanol (D) 1-ethoxy-1-propanamine
F-12. The IUPAC name of is -
(A) bicyclo [3.2.0] hexan-2-ol (B) spiro [3.2] hexan-1-ol (C) spiro [3.2] hexan-4-ol (D) spiro [2.3] hexan-4-ol
F-13. The IUPAC name of camphor is -
(A) 6-oxo-1,2,2- trimethyl bicyclo [2,2,1] heptane (B) 1,7,7-trimethyl bicyclo [2,2,1] heptan-2-one (C) 1,5,5-trimethyl bicyclo [2,1,1] hexan-2-one (D) 1,7,7-trimethyl bicyclo [2,1,2] heptan-2-one
Section (G) : IUPAC-Nomenclature of Functional groups
G-1. The correct IUPAC name of compound :
CH 3 CH 2 C CH CHO || | O CN (A) 2-cyano-3-oxopentanal (B) 2-formyl-3-oxopentanenitrile (C) 2-cyano-1,3-pentanedione (D) 1,3-dioxo-2-cyanopentane
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 15 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU O CH || | 3 G-2. The IUPAC name of compound is: CH3 C CH CH CH CH3 | | CH3 CHO
(A) 3,5-Dimethyl-4-Formyl pentanone (B) 1-Isopropyl-2-methyl-4-oxo butanal (C) 2-Isopropyl-3-methyl-4-oxo pentanal (D) None of the above
HO C O CH3 | | G-3. The IUPAC name of compound is: CH3 C C — C H | | NH2 Cl
(A) 2-amino-3-chloro-2-methyl-2-pentenoic acid (B) 3-amino-4-chloro-2-methyl-2-pentenoic acid (C) 4-amino-3-chloro-2-methyl-2-pentenoic acid (D) All of the above
G-4. The IUPAC name of the structure is:
H2N CH CH CHO | | HOOC COOH (A) 3-amino-2-formyl butane-1, 4-dioic acid (B) 3-amino-2, 3-dicarboxy propanal (C) 2-amino-3-formyl butane-1, 4-dioic acid (D) 1-amino-2-formyl succinic acid
G-5. Which of the following compound is wrongly named? (A) ; 2-Chloro pentanoic acid CH3CH2CH2CHCOOH | Cl
(B) CH3C CCHCOOH ; 2-Methyl hex-3-enoic acid | CH3
(C) CH3CH2CH=CHCOCH3 ; Hex-3-en-2-one
(D) CH3 CHCH 2CH2CHO ; 4-Methyl pentanal | CH3
G-6. The IUPAC name of (C2H5)2 NCH2CH.COOH is: | Cl (A) 2-chloro-4-N-ethylpentanoic acid (B) 2-chloro-3-(N,N-diethyl amino)-propanoic acid (C) 2-chloro-2-oxo diethylamine (D) 2-chloro-2-carboxy-N-ethyl ethane
G-7. The correct IUPAC name of is: CH3 CH2 C COOH || CH2 (A) 2-methyl butanoic acid (B) 2-ethylprop-2-enoic acid (C) 2-carboxybut-1-ene (D) None of the above
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 16 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU G-8. IUPAC name will be CH2 CH CH2 | | | CN CN CN (A) 1,2,3-Tricyano propane (B) Propane trinitrile-1,2,3 (C) 1,2,3-cyano propane (D) Propane-1,2,3-tricarbonitrile
G-9. The IUPAC name of compound
(A) 1,2,3-tricarboxy-2-propanol (B) 2-hydroxy propane-1,2,3 tricarboxylic acid (C) 3-hydroxy-3-Carboxy-1,5-pentane dioic acid (D) None
G-10. Which of the following is crotonic acid:
(A) CH2= CH–COOH (B) C6H5–CH=CH–COOH
(C) CH3–CH=CH–COOH (D) CH COOH || CH COOH
G-11. The IUPAC name of
CH2 CHO | OHC CH2 CH2 CH CH2 CHO is : (A) 4, 4-di(formylmethyl) butanal (B) 2-(formylmethyl) butane-1, 4-dicarbaldehyde (C) hexane-3-acetal-1, 6-dial (D) 3-(formylmethyl) hexane-1, 6-dial
G-12. is named as :
(A) 2, 3-Dimethylenebutanal (B) 2, 3-Dimethylbutanal (C) 3-Methyl-2-methylenebut-3-enal (D) 2, 3-Dimethylenebutanone
Section (H) : IUPAC-Nomenclature of Functional groups
H-1. The IUPAC name of BrCH2 CH CO CH2 CH2CH3 is: | CONH2 (A) 2-bromomethyl-3-oxo hexanamide (B) 1-bromo-2-amino-3-oxo hexane (C) 1-bromo-2-amino-n-propyl ketone (D) 3-bromo-2-propyl propanamide
H-2. One among the following is the correct IUPAC name of the compound H | CH3CH2 N CHO (A) N-Formyl aminoethane (B) N-Ethyl formyl amine (C) N-Ethyl methanamide (D) Ethylamino methanal
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 17 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU H-3. The IUPAC name of compound
H3COOC CH COOCH3 | CH2OH (A) methyl 2-hydroxymethylpropandioate (B) Methyl methyl-2-hydroxypropandioate (C) dimethyl-2-hydroxy methyl propandioate (D) 2-hydroxy methyl-dimethyl propandioate
H-4. The IUPAC name of is:
(A) 2-chlorocarbonyl ethylbenzoate (B) 2-carboxyethyl benzoyl chloride (C) ethyl 2-(chlorocarbonyl) benzoate (D) ethyl 1-(chlorocarbonyl) benzoate
H-5. Structural formula of isopropyl methanoate is:
(A) (B) CH3 C O CH CH3 || | O CH3 (C) (D) H C O CH CH CH3 C O CH2 CH2 3 || | || | O CH3 O CH3
H-6. The IUPAC name of CH C O CH2 C OH is: || || O O (A) 1-acetoxy acetic acid (B) 2-acetoxy ethanoic acid (C) 2-ethanoyl oxyacetic acid (D) 2-ethanoyloxyethanoic acid
H-7. The correct systematic name of the above compound is:
CH3 O C CH2 COOH || O (A) 2-acetoxy ethanoic acid (B) 2-methoxy carbonyl ethanoic acid (C) 3-methoxy formyl ethanoic acid (D) 2-methoxy formyl acetic acid
H-8. The IUPAC name of the compound is : (A) Propanoic anhydride (B) Dipropanoic anhydride (C) Ethoxy propanoic acid (D) 1-Oxopropyl propanoate
H-9. The IUPAC name of the compound is :
(A) Cyclobutanedioic anhydride (B) Butanedicarboxylic anhydride
(C) Cyclobutanedicarboxylic anhydride (D) Butanedioic anhydride
H-10. Ethyl ethanoyloxyethanoate is :
(A) (B) (C) (D)
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 18 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU H-11. The correct IUPAC name of the compound is : (A) 1, 2, 3-Triaminobutane-1, 3-dione (B) 2, 4-Diamino-3-oxobutanamide (C) 1, 3-Dioxobutane-1, 2, 4-triamine (D) 1, 3, 4-Triaminobutane-2, 4-dione
Section (I) : IUPAC-Nomenclature of Aromatic Compounds
I-1. The IUPAC name of is:
(A) 2-methoxy-4-nitro benzaldehyde (B) 4-nitro anisaldehyde (C) 3-methoxy-4-formyl nitro benzene (D) 2-formyl-4-nitro anisole
I-2. The IUPAC name of C6H5 CH CH2 CCl3 is ; | C6H5 (A) 1,1,1-trichloro-3,3-diphenyl propane (B) 1,1-diphenyl-3,3,3-trichloro propane (C) both (A) and (B) (D) none of these
I-3. The IUPAC name of is -
(A) 1-amino-2-carboxybenzene (B) 2-amino-1-carboxybenzene (C) 1-amino-2-benzenecaroxylic acid (D) 2-aminobenzenecarboxylic acid
I-4. IUPAC name of
(A) 4-Chlorophenyl benzoate (B) Phenyl 4-chlorobenzenecarboxylate (C) Benzyl 4-chlorobenzenecarboxylate (D) 4-Chloro diphenylcarboxylate
I-5. The correct IUPAC name of the compound.
(A) N–Formyl-4-chlorobenzenamine (B) N–Formyl-4-chloroaniline (C) N–(4-chlorophenyl)methanamide (D) N–(Parachlorophenyl)–N–formylaniline
Section (J) : Structural Isomerism
J-1. Esters are fiunctional isomers of: (A) Hydroxy aldehyde (B) Ketone (C) Diketone (D) Diols
J-2. Which of the following is the first member of ester homologous series? (A) Ethyl ethanoate (B) Methyl ethanoate (C) Methyl methanoate (D) Ethyl methanoate
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 19 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU J-3. & are called as –
(A) Position isomers (B) Chain isomers (C) Function isomers (D) Ring chain isomers
J-4. Possible number of dichlorobenzene isomers is – (A) 1 (B) 2 (C) 3 (D) 4
J-5. Functional isomer of CH3COOCH3 is – (A) CH3CH2COOH (B) HOCH2—CH2CHO (C) Both of the above (D) None of the above
J-6. Propene and cyclopropane are – (A) Chain isomers (B) Position isomers (C) Geometrical isomers (D) None of the above
J-7. Metamerism is shown by - (A) Diethyl ether and n-propyl methyl ether (B) Ethyl alcohol and diethyl ether (C) Acetone and propionaldehyde (D) Propionic acid and acetic acid
J-8. Which of the following pairs of compounds are not metamers ?
(A) CH3OCH2CH2CH3 and CH3CH2OCH2CH3 (B) CH3CH2OCH2CH3 and CH3OCH(CH3)2 (C) CH3NHCH2CH2CH3 and CH3CH2NHCH2CH3 (D) CH3NHCH2CH2CH3 and CH3NHCH(CH3)2
J-9. Which compound is not the isomer of 3-Ethyl-2-methylpentane ?
(A) (B) (C) (D)
J-10. What is the correct relationship between the following compounds ?
(A) Chain isomers (B) Position isomers (C) Functional isomers (D) Identical
J-11. Which one of the compound is not isomer of others ?
(A) (B) (C) (D)
J-12. Which of the given set of molecules have similar molecular formula : (A) Nonane, 2-methylheptane (B) 3-Isopropylcyclopent-1-ene, 3-methylhexane (C) 3-Methylcyclopent-1-ene, penta-1, 3-diene (D) Ethylcyclohexane, oct-2-ene
J-13. Molecular formula C4H10O represent : (A) Two primary alcohol (B) One secondary alcohol (C) One tertiary alcohol (D) All of these
J-14. Aldehydes show with each other : (A) Chain isomers (B) Position isomers (C) Functional isomers (D) Both (A) and (B)
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 20 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU J-15. Which of the following is not an isomer of 1-butyne ? (A) but-2-yne (B) buta-1, 3-diene (C) but-2-ene (D) methyl cyclopropene
COOH OCOH J-16. & functional isomer
OMe OEt Et & metamers Me
CH2 – CH 2 – OH CH2 – O – CH 3
& metamers
Me – N – Me CH2 – NH – CH 3
& Functional isomers
(A) TFTF (B) FTTF (C) TTFT (D) TFFT
J-17. Which of the following is not the correct relationship
Me Me Me Me Me
Me Me O–Me OH O – Me OH I II III IV
(A) II & IV are metamer (B) I & II are functional isomer (C) I & III are chain isomer (D) I and IV are positional isomer
J-18. Which of the following is not an isomer of compound CH3 – CH2CHO ?
(A) (B) (C) (D) CH2=CH–CH2–OH
Section (K) : Number of Structural Isomers
K-1. How many positional isoemrs are possible for dimethylcyclohexane : (A) 3 (B) 4 (C) 5 (D) 6
K-2. How many positional isoemrs are possible for 3-ethylpentane (including it self) (A) 1 (B) 2 (C) 3 (D) 4
K-3. The total number of unsaturated cyclic structure possible for a compound with the molecular formula C4H6 is: (A) 3 (B) 4 (C) 5 (D) 6
K-4. Total number of 2° amine isomers of C4H11N would be (only structural) : (A) 4 (B) 3 (C) 5 (D) 2
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 21 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU K-5. How many structural isomers of all the tertiary alcohols with molecular formula C6H14O. (A) 2 (B) 3 (C) 4 (D) 5
K-6. The number of structural isomers for C5H10 is : (A) 8 (B) 6 (C) 9 (D) 10
K-7. The number of primary, secondary and tertiary amines possible with the molecular formula C3H9N respectively: (A) 1, 2, 2 (B) 1, 2, 1 (C) 2, 1, 1 (D) 3, 0, 1 PART - II : MISCELLANEOUS QUESTIONS
Comprehensions Type : Comprehension The international group IUPAC has developed a detailed. system of nomenclature that we call the IUPAC rule. Which are accepted throughout the world as the standard method for naming organic compounds. In this system Alkyl groups are named by replacing the ‘-ane’ suffix of alkane name with ‘-yl’ like methyl ethyl etc. complex alkyl groups are named. by a systematic method using the longest alkyl chain as the base alkyl group. The base alkyl group is numbered beginning with the carbon atom bonded to the main chain. The substitutes on the base alkyl group are listed with appropriate number and parentheses are used to set off the name of the complex alkyl group.
1. Give the IUPAC name of following alkyl group
CH3
CH3 CH CH CH2
CH3 (A) (Di-isohexyl) (B) (2,3-dimethyl butyl) (C) (2,2-dimethyl butyl) (D) (2,-methyl-3-ethylbutyl)
CH2 CH CH2 2. Choose the correct IUPAC name of following alkyl group OH CH3 (A) (2-methyl-3-Propanoyl) (B) (3-hydroxy-2-methyl propyl) (C) (2-methyl-3-hydroxy propyl) (D) (1-hydroxy-2-methyl propyl
3. The structure of (2,2-dimethyl-3-ethylpentyl) group is -
CH3 CH3
(A) CH3 C CH CH2 CH2 (B) CH3 CH C CH2 CH2
CH3 C2H5 C2H5 CH3
CH3
(C) CH3 CH2 CH C CH2 (D) None of these
C2H5 CH3
4. (2-propenyl) group is -
(A) CH2=CH–CH2– (B) CH3–CH=CH– (C) Both (A) and (B) (D) None of these
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 22 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU Assertion / Reasoning Type DIRECTIONS :
Each question has 5 choices (A), (B), (C), (D) and (E) out of which ONLY ONE is correct. (A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1. (B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1. (C) Statement-1 is True, Statement-2 is False. (D) Statement-1 is False, Statement-2 is True. (E) Statement-1 and Statement-2 both are False.
H 5. Statement-1 : is called cyclohexanenitrile. CN
Statement-2 : : It contains six carbon atoms in the ring and CN as the functional group.
6. Statement-1 : The locant (2,8,7) is preferred over the locant (3,4,9). Statement-2 : The first term, i.e., 2 in the first set is lower than the first term, i.e, 3 in the second set.
7. Statement-1 : The IUPAC name of CH3CH=CH–CCH is pent-3-en-1-yne and not pent-2-en-4-yne. Statement-2 : While deciding the locants for double bond and triple bonds. lowest locant rule for multiple bonds is followed.
8. Statement-1 : The IUPAC name for the compound C 2H5 C CH2OH is -
CH2
2-ethylprop-2-en-1-ol.
Statement-2 : Ethyl (C2H5) rather than methylene (=CH2) is considered as the substituent group because ‘e’ of ethyl comes first in alphabetically order than ‘m’ of methylene.
9. Statement-1 : The IUPAC name for O is 7-oxabicyclo [4. 1. 0] heptane.
Statement-2 : The prefix oxo is used for the C=O group.
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 23 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU PART - I : MIXED OBJECTIVE
* Marked Questions are having more than one correct option.
Br | 1. The IUPAC name of CH3 CH CH2 CH2 CH2 C CH3 is | | OH Br (A) 6, 6-Dibromo heptan-2-ol (B) 2, 2-Dibromo heptan-6-ol (C) 6, 6-Dibromo heptan-2-al (D) None of these
2. IUPAC name of 4-Isopropyl m-xylene is : (A) 1-Isopropyl 2, 4-dimethyl benzene (B) 4-Isopropyl-m-xylene (C) 1-Isopropyl-3, 5-dimethyl benzene (D) 4-Isopropyl-3, 5-dimethyl benzene
3. The structure of 2-(3-oxobutyl)cyclohexanone is :
(A) (B)
(C) (D)
4. The compounds with molecular formula C100H202 can show (A) Metamerism (B) Position and chain isomerism (C) Functional isomerism (D) Ring-chain isomerism
5. How many primary amines are possible for the formula C8H11N (only Aromatic structural isomers) (A) 4 (B) 6 (C) 7 (D) 14
6. The total number of aromatic isomeric ethers of molecular formula C8H10O is (A) Six (B) Seven (C) Four (D) Five
7. How many structural isomers could be obtained from molecular formula C2FCl BrI (A) Four (B) Five (C) Six (D) Three
8. Which type of isomerism is observed between I and II.
and
(A) Functional isomerism (B) Metamerism (C) Optical isomerism (D) Geometrical isomerism
9. Which of the following compound does not have molecular formula C6H6 (A) Hexa-1, 3-dien-5-yne (B) 3-(2-cyclopropenyl)cycloprop-1-ene(or Bicyclopropenyl) (C) Cyclohexa-1, 3-diene-5-yne (D) Cyclohexa-1, 3, 5-triene
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 24 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU 10. IUPAC name of is
(A) 3, 5-Dimethylcyclohex-1-ene (B) 4, 6-Dimethylcyclohex-1-ene (C) 1, 5-Dimethylcyclohex-2-ene (D) none of these
11. Which of the following are isomers
(A) I, II only (B) III, IV only (C) I, II, III (D) All
12. Total number of structurally different dichloropropanes is (A) 2 (B) 3 (C) 4 (D) 5
13.* Consider the following structures :
CH3 Cl CH – CH – CH – CH – Cl 3 2 2 2 CH3 – C – CH 3 – CH2 – Cl Cl I III IV II (A) I & II are chain isomers (B) I & III are functional isomers (C) II & IV are functional isomers (D) III & IV are chain isomers
PART - II : SUBJECTIVE QUESTIONS
Allot the IUPAC name to the following compounds :
1. 2. 3.
4. 5. 6.
CH2CH2 || || CH C C C C CH 7. 8. CH2=CH– C=CH–CH=CH2 9. 3 3 | Br
10. 11. 12. CH2 = CH – CH2 – N C
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 25 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU 13. 14. 15.
16. CH3OCH2OCH2CH2OCH3 17. 18. CH3 – CH2 – O – C(CH3)3
19. 20. 21. CH3 O CH2 CH2 N CH3 | H
22.
23. Identify the molecular weight of the compound ‘X’ containing carbon and hydrogen atoms only with 3 and 2 bonds in one molecule.
24. Find the hybridization state of each carbon atoms in following compound.
CH2 = C = CH – CH2 – C C – CH2 – NH2 25. Calculate the molecular weight of the lowest hydrocarbon which contains sp & sp2 hybridised carbon atoms only.
26. Which isomerism is shown by and
27. The ring chain functional isomer of compound But-2-ene are.
PART - I : IIT-JEE PROBLEMS (PREVIOUS YEARS)
* Marked Questions are having more than one correct option.
1. Write IUPAC name of the following : [JEE-2002]
2. Which of the following represents the given mode of hybridisation, sp2 – sp2 – sp – sp, from left to right? [JEE-2003]
(A) H2C = CH – C CH (B) CH C – C – C CH
(C) H2C = C = C = CH2 (D)
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 26 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU 3. Write IUPAC name of the following : [JEE-2004]
O || 4. IUPAC name of C6H5 C Cl [JEE-2006] (A) Benzoylchloride (B) Benzenecarbonylchloride (C ) Chlorophenyl ketone (D) phenylchloroketone
5. The number of structural isomers for C6H14 is : [JEE-2007] (A) 3 (B) 4 (C) 5 (D) 6
6. What is the IUPAC name of the following compound? [JEE-2008]
(A) 4-bromo-3-cyanopheol (B) 2-bromo-5-hydroxbenzonitrile (C) 2-cyano-4-hydroxybromobenzene (D) 6-bromo-3-hydroxybenzonitrile
7. The total number of cyclic possible for a hydrocarbon with the molecular C4H6 is /are : [JEE-2010] PART - II : AIEEE PROBLEMS (PREVIOUS YEARS)
1. Of the following compounds which has a wrong IUPAC name - [AIEEE-2002]
CH3 – CH2 – CH2 – C – O – CH2 – CH3 || O ethyl butanoate
CH3 – CH – C – CH – CH3 | || | CH3 O CH3 2,4 dimethyl -3- pentanone
CH3 | H3C – CH – CH – CH3 | OH 2-methyl -3- butanol
IV CH3 – CH2 – CH2 – CHO butanal (1) (2) (3) (4) IV
2. The general formula CnH2nO2 could be for open chain : [AIEEE-2003] (1) diketones (2) carboxylic acids (3) diols (4) dialdhydes.
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 27 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU 3. The IUPAC name of CH3COCH(CH3)2 is – [AIEEE-2003] (1) 4-methylisopropyl ketone (2) 3-methyl-2-butanone (3) Isopropylmethyl ketone (4) 2-methyl-3-butanone
4. The IUPAC name of the compound [AIEEE-2004]
is -
(1) 3,3 -dimethyl-1-hydroxy cyclohexane (2) 1, 1 – dimethyl–3– hydroxy cyclohexane (3) 3,3-dimethyl-1-cyclohexanol (4) 1,1 - dimethyl - 3- cyclohexanol
5. Write IUPAC name of the following : [AIEEE-2005]
6. The IUPAC name of the compound shown below is - [AIEEE 2006]
(1) 6-bromo-2-chlorocyclohexene (2) 3-bromo-1-chlorocyclohexene (3) 1-bromo-3-chlorocylohexene (4) 2-bromo-6-chlorocycohex-1-ene
7. The IUPAC name of [AIEEE 2007]
is –
(1) 1, 1-diethyl-2-dimethylpentane (2) 4, 4-dimethyl-5, 5-diethylpentane (3) 5, 5-diethyl-4, 4-dimethylpentane (4) 3-ethyl-4, 4 dimethylheptane
8. The correct decreasing order of priority for the functional groups of organic compounds in the IUPAC system of nomenclature is [AIEEE 2008]
(1) –SO3H, –COOH, –CONH2, –CHO (2) –CHO, –COOH, –SO3H, –CONH2
(3) –CONH2, –CHO, –SO3H, –COOH (4) –COOH, –SO3H, –CONH2, –CHO
9. The IUPAC name of the following compound is : [AIEEE-2009, 3/160]
(1) 4-Bromo-3-cyanophenol (2) 2-Bromo-5-hydroxybenzonitrile (3) 2-Cyano-4-hydroxybromobenzene (4) 6-Bromo-3-hydroxybenzonitrile
10. The IUPAC name of neopentane is : [AIEEE-2009] (1) 2, 2-dimethylpropane (2) 2-methylpropane (3) 2, 2-dimethylbutane (4) 2-methylbutane
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 28 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU NCERT QUESTIONS
1. Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary , tertiary), vinyl or aryl halides :
(i) (CH3)2CHCH(Cl)CH3 (ii) CH3CH2CH(CH3)CH(C2H5)Cl
(iii) CH3CH2C(CH3)2CH2I (iv) (CH3)3CCH2CH(Br)C6H5
(v) CH3CH(CH3)CH(Br)CH3 (vi) CH3C(C2H5)2CH2Br
(vii) CH3C(Cl)(C2H5)CH2CH3 (viii) CH3CH=C(Cl)CH2CH(CH3)2
(ix) CH3CH=CHC(Br)(CH3)2 (x) p-CIC6H4CH2CH(CH3)2
(xi) m-CICH2C6H4CH2C(CH3)3 (xii) O-BR-C6H4CH(CH3)CH2CH3
2. Give the IUPAC names of the following compounds :
(i) CH3CH(Cl)CH(Br)CH3 (ii) CHF2CBrClF (iii) ClCH2C CCH2Br (iv) (CCl3)3CCl
(v) CH3C(p-ClC6H4)2CH(Br)CH3 (vi) (CH3)3CCH=ClC6H4I-p
3. Write IUPAC names of the following compounds :
(i) (ii) (iii)
(iv) (v) (vi)
(vii) (viii) (ix)
(x) C6H5–O–C2C2H5 (xi) C6H5–O–C7H15(n–) (xii)
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 29 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU 4. Write structures of the compounds whose IUPAC names are as follows : (i) 2-Methylbutan-2-ol (ii) 1-Phenylpropan-2-ol (iii) 3, 5-Dimethylhexane-1, 3, 5-triol (iv) 2, 3-Diethylphenol (v) 1-Ethoxypropane (vi) 2-Ethoxy-3-methylpentane (vii) Cyclohexylmethanol (viii) 3-Cyclohexylpentan-3-ol (ix) Cyclopent-3-en-1-ol (x) 4-Chloro-3-ethylbutan-1-ol.
5. Draw the structures of all isomeric alcohols of molecular formula C5H12O and give their IUPAC names.
6. Name of the following compounds according to IUPAC system of nomenclature :
(i) CH3CH(CH3)CH2CH2CHO (ii) CH3CH2COCH(C2H5)CH2CH2Cl
(iii) CH3CH=CHCHO (iv) CH3COCH2COCH3
(v) CH3CH(CH3)CH2C(CH3)2COCH3 (vi) (CH3)3CCH2COOH (vii) OHCC6H4CHO-p
7. Draw the structures of the following compounds : (i) 3-Methylbutanal (ii) p-Nitropropiophenone (iii) p-Methylbenzaldehyde (iv) 4-Methylpent-3-ene-2-one (v) 4-Chloropentan-2-one (vi) 3-Bromo-4-phenylpentanoic acid (vii) p, p’-Dihydroxybenzophenone (viii) Hex-2-en-4-ynoic acid
8. Write the IUPAC names of the following ketones and aldehydes. Wherever possible, give also common names:
(i) CH3CO(CH2)4CH3 (ii) CH3CH2CHBrCH2(CH3)CHO
(iii) CH3(CH2)5CHO (iv) Ph–CH=CH–CHO
(v) (vi) PhCOPh
9. Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines.
(i) (CH3)2CHNH2 (ii) CH3(CH2)2NH2 (iii) CH3NHCH(CH3)2
(iv) (CH3)3CNH2 (v) C6H5NHCH3 (vi) (CH3CH2)2NCH3
(vii) m-BrC6H4NH2
10. Write structures of different chain isomers of alkanes corresponding to the molecular formula C6H14. Also write their IUPAC names.
11. Write IUPAC names of the following compounds :
(i) (CH3)3CCH2C(CH3)3 (ii) (CH3)2C(C2H5)2 (iii) tetra – tert – butylmethane
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 30 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU 12. Write IUPAC names of the following compounds :
(i) (ii)
(iii) CH2=C(CH2CH2CH3)2 (iv)
13. Write structures and IUPAC names of different structural isomers of alkenes corresponding to C5H10.
14. Draw cis and trans isomers of the following compounds. Also write their IUPAC names :
(i) CHCl=CHCl (ii) C2H5CCH3=CCH3C2H5
15. Write structures of different isomers corresponding to the 5th member of alkyne series. Also write IUPAC names of all the isomers. What type of isomerism is exhibited by different pairs of isomers ?
16. Write IUPAC names of the following compounds :
(a) CH3CH=C(CH3)2 (b) CH2=CH–C C–CH3 (c)
(d) (e) (f)
(g)
17. For the following compounds, write structural formulas and IUPAC names for all possible isomers having the number of double or triple bond as indicated :
(a) C4H8 (one double bond) (b) C5H8 (one triple bond)
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 31 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU EXERCISE # 1 PART # I A-1. (D) A-2. (C) A-3. (C) A-4. (B) A-5. (B) A-6.* (ABD) A-7. (D)
A-8. (B) A-9. (D) A-10. (B) A-11. (B) A-12. (B) B-1. (D) B-2. (D) B-3. (B) B-4. (A) B-5. (B) B-6. (A) B-7. (D) B-8. (D) B-9. (D) C-1. (D) C-2. (C) C-3. (A) C-4. (C) C-5. (B) C-6. (B) C-7. (D) C-8. (B) D-1. (C) D-2. (B) D-3. (A) D-4. (C) D-5. (B) D-6. (C) D-7. (D) D-8. (A) D-9. (A) D-10. (A) D-11. (B) E-1. (D) E-2. (B) E-3. (A) E-4. (A) E-5. (D) E-6. (C) E-7. (A) E-8. (B) E-9. (C) E-10. (B) E-11. (A) E-12. (A) E-13. (B) F-1. (D) F-2. (B) F-3. (C) F-4. (B) F-5. (D) F-6. (C) F-7. (C) F-8. (B) F-9. (B) F-10. (B) F-11. (B) F-12. (D) F-13. (B) G-1. (B) G-2. (C) G-3. (B) G-4. (C)
G-5. (B) G-6. (B) G-7. (B) G-8. (D) G-9. (B) G-10. (C) G-11. (D) G-12. (C) H-1. (A) H-2. (C) H-3. (A) H-4. (C) H-5. (D) H-6. (D) H-7. (B) H-8. (A) H-9. (D) H-10. (D) H-11. (B) I-1. (A) I-2. (A) I-3. (D) I-4. (B) I-5. (C) J-1. (A) J-2. (C) J-3. (A) J-4. (C) J-5. (C) J-6. (D) J-7. (A) J-8. (D) J-9. (B) J-10. (A) J-11. (D) J-12. (D) J-13. (D) J-14. (A) J-15. (C) J-16. (C) J-17. (D) J-18. (A) K-1. (B) K-2. (A) K-3. (B) K-4. (B) K-5. (B) K-6. (D) K-7. (C)
PART # II
1. (B) 2. (B) 3. (C) 4. (A) 5. (D) 6. (A) 7. (A)
8. (C) 9. (B)
EXERCISE # 2 PART # I
1. (A) 2. (A) 3. (B) 4. (B) 5. (D) 6. (D) 7. (D)
8. (B) 9. (C) 10. (A) 11. (C) 12. (C) 13.* (AD)
PART # II
1. 3-(1-Chloroethyl)-4-methyl-4-phenylpentan-2-one 2. 2-Cyclopropyl-4-ethylhex-1-ene 3. 6-isopropylcyclodec-1-yne 4. 1-Chloro-2, 3-epoxypropane 5. 3-Mercaptobenzoic acid 6. N, N-Diethyl cyclohexanecarboxamide 7. 3–Cyclopropyl-3-methylbutanal 8. 3–Bromohexa–1, 3, 5–triene 9. 2–Methyl–3–methylenehex–1–en–4–yne 10. 3–Methoxy–5, 5–dimethylcyclohex–2–en–1–ol 11. 2–Bromo–1–chloro–3–iodocyclohexane 12. Carbylamineprop-2-ene 13. 1, 1, 1–Trichloro-2, 2-bis(4–chlorophenyl)ethane 14. 1–(3–bromophenyl)–6–phenylhexa–1,3,5–triyne 15. 3–Methyl–2–(3–oxobutyl)cyclohexan-1-one 16. 2, 4, 7-Trioxaoctane 17. 1, 3, 5, 7-Tetraoxacyclooctane 18. 2-Ethoxy-2-methylpropane
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 32 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU 19. N-Methylbenzamide 20. 3-Ethylphenyl ethanoate 21. N-Methyl-2-methoxy-1-ethanamine 22. Pentano-5-lactone 23. H – C º C – H, Mol wt. = 26 24.
25. H2C = C = CH2 ;M.W. = 40. 26. Metamerism 27. ,
EXERCISE # 3 PART # I
1. (4-Hydroxyphenyl) ethanal 2. (A) 3. 3-Aminobenzoic acid 4. (B)
5. (C) 6. (B) 7. 5
PART # II
1. (3) 2. (2) 3. (2) 4. (3) 5. 4-Methylbenzenesulphonic acid
6. (2) 7. (4) 8. (4) 9. (2) 10. (1) EXERCISE # 4 NCERT QUESTIONS
10. (i) CH3–CH2–CH2–CH2–CH2–CH3 n-Hexane (ii) CH3– CH –CH2–CH2–CH3 2-Methylpentane |
CH3
(iii) CH3–CH2– CH –CH2–CH3 3-Methylpentane (iv) CH3– CH – CH –CH3 2, 3-Dimethylbutane | | |
CH3 CH3 CH3
CH3 | (v) CH – C –CH –CH 2, 2-Dimethylbutane 3 | 2 3
CH3 11. (i) 2, 2, 4, 4-Tetramethylpentane (ii) 3, 3-Dimethylpentane (iii) 3, 3-Di-tert-butayl-2, 2, 4, 4-tetramethylpentane 12. (i) 2, 8-Dimethyl-3, 6-decadiene ; (ii) 1, 3, 5, 7 Octatetraene ; (iii) 2-n-Propylpent-1-ene ; (iv) 4-Ethyl-2, 6-dimethyl-dec-4-ene ;
13. (a) CH2=CH–CH2–CH2–CH3 Pent-1-ene (b) CH3–CH=CH–CH2–CH3 Pent-2-ene
(c) CH3– C =CH–CH3 2-Methylbut-2-ene (d) CH3– CH –CH=CH2 3-Methylbut-1-ene | |
CH3 CH3
(e) CH2= C –CH2–CH3 2-Methylbut-1-ene |
CH3
14. (i) (ii)
th 15. 5 member of alkyne has the molecular formula C6H10. The possible isomers are :
Physical & Inorganic By Organic Chemistry By A-479 Indra vihar, kota IUPAC NOMENCLATURE AND NV Sir VKP Sir # 33 Ph. - 9982433693 (NV Sir) 9462729791(VKP Sir) STRUCTURAL ISOMERISM B.Tech. IIT Delhi M.Sc. IT-BHU