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Organic Notes OSBINCBSE.COM OSBINCBSE.COM osbincbse.com Chapter 10 : HALOALKANES AND HALOARENES CLASSIFICATION On the Basis of Number of Halogen Atoms Monohalocompounds may further be classified according to the hybridisation of the carbon atom to which the halogen is bonded. Compounds Containing sp3 C—X Bond (X= F,Cl, Br, I) : (a) Alkyl halides or haloalkanes (R—X) : (b) Allylic halides (c) Benzylic halides Compounds Containing sp2 C—X Bond: (a) Vinylic halides (b) Aryl halides Nomenclature : Nature of C-X Bond : The carbon atom bears a partial positive charge whereas the halogen atom bears a partial negative charge. Methods of Preparation : The hydroxyl group of an alcohol is replaced by halogen on reaction with concentrated halogen acids, phosphorus halides or thionyl chloride. Thionyl chloride is preferred because the other two products are escapable gases. Hence the reaction gives pure alkyl halides. OSBINCBSE.COM The order of reactivity of alcohols with a given haloacid is 3° >2° >1°. From Hydrocarbons : HSSLIVE.IN Page 1 OSBINCBSE.COM OSBINCBSE.COM osbincbse.com (a) By free radical halogenations : (b) By electrophilic substitution Physical Properties Due to greater polarity as well as higher molecular mass as compared to the parent hydrocarbon, the intermolecular forces of attraction (dipole-dipole and van der Waals) are stronger in the halogen derivatives. That is why the boiling points of chlorides, (c) Sandmeyer’s reaction : Mixing the solution of bromides and iodides are considerably higher than freshly prepared diazonium salt with cuprous chloride those of the hydrocarbons of comparable molecular or cuprous bromide results in the replacement of the mass. diazonium group by –Cl or –Br. For the same alkyl group, the boiling points of alkyl halides decrease in the order: RI> RBr> RCl> RF . The boiling points of isomeric haloalkanes decrease with increase in branching. Boiling points of isomeric dihalobenzenes are very nearly the same. Whereas melting Point is of the order Para > Ortho = meta . Preperation of Iodo benzene (d) From alkenes (i) Addition of hydrogen halides: An alkene is converted to corresponding alkyl halide by reaction with hydrogen chloride, hydrogen bromide or hydrogen iodide. Chemical Reactions Reactions of Haloalkanes (i) Nucleophilic substitution (ii) Addition of halogens: an important method for (ii) Elimination reactions the detection of double bond in a molecule. Colourless (iii) Reaction with metals. vic -dibromide is the product. OSBINCBSE.COM(i) Nucleophilic substitution reactions - Halogen Exchange Nucleophile Substrate Product Leaving Nu Finkelstein reaction : --KOH ROH + KX HSSLIVE.IN Page 2 OSBINCBSE.COM OSBINCBSE.COM osbincbse.com When alkyl chlorides/bromides are treated with NaI in dry acetone Alkyl iodides are prepared. This -- H2O ROH + HX reaction is known as Finkelstein reaction . --NaOR’ ROR’+NaX (Williamson’s synthesis) RX --NaI RI + NaX (Finkelstein Reaction) Swarts reaction. --NH 3 RNH 2 + HX When an alkyl chloride/bromide in the presence of AgF or Hg 2F2 or CoF 2 or SbF 3. Alkyl Fluorides are --R’NH 2 RNHR’ +HX obtained.The reaction is termed as Swarts reaction. --R NH R N + HX 2 3 2-bromopentane gives pent -2-ene as the major --KCN RCN + KX product. Alkane nitrile CH 3CHBrCH 2CH 2CH 3 ----- alc.KOH -- -- AgCN RNC + AgX CH 3-CH=CH-CH 2-CH 3 (major) Alkyl isocyanide 3.Reaction with metals --AgNO R NO + AgX 2 2 RX + Mg ----dry ether - RMgX Nitro alkane Grignard reagents are highly reactive and react with any RX -- KNO 2 RONO + KX source of proton to give hydrocarbons. Even water, Alkyl nitrites alcohols, amines are sufficiently acidic to convert them to --R’COOAg R’COOR + AgX corresponding hydrocarbons. Ester --LIAlH 4 RH + AlX 3 + LiX It is therefore necessary to avoid even traces of moisture from a Grignard reagent. On the other hand, this could be --R’M RR’ + MX considered as one of the methods for converting halides to hydrocarbons. Wurtz reaction Mechanism: Alkyl halides react with sodium in dry ether to give 2 (a) Substitution nucleophilic bimolecular (SN ) hydrocarbons containing double the number of carbon i) The rate depends upon the concentration of both the atoms present in the halide. This reaction is known as - reactants. Rate = k [RX] [Nu ] ; Order = 2 Wurtz reaction. ii) Inversion of Configuration takes place. iii) Order of Reactivity Primary Halide > Sec.Halide > Tertiary Halide REACTIONS OF HALOARENES 1.Nucleophilic substitution (b) Substitution nucleophilic unimolecular (SN 1) Aryl halides are extremely less reactive towards i) The rate of reaction depends upon the concentration nucleophilic substitution reactions due to the of only one reactant, Rate = k [RX] ; Order = 1. following reasons: ii) Carbocation Intermediate (i) Resonance effect : iii) Order of Reactivity OSBINCBSE.COM Tertiary Halide > Sec.Halide > Primary Halide For a given alkyl group, the reactivity of the halide, R-X, follows the same order in both the (ii) Difference in hybridisation of carbon atom in mechanisms R–I> R–Br>R–Cl>>R–F. C—X bond: HSSLIVE.IN Page 3 OSBINCBSE.COM OSBINCBSE.COM osbincbse.com 2.Elimination reactions When a haloalkane with β-hydrogen atom is heated with alcoholic solution of potassium hydroxide, there Thus, C—Cl bond length in haloalkane is 177pm while in is elimination of hydrogen atom from β-carbon and haloarene is 169 pm . Since it is difficult to break a a halogen atom from the α-carbon atom.As a result, shorter bond than a longer bond , therefore, haloarenes an alkene is formed as a product. are less reactive than haloalkanes towards nucleophilic CH 3-CH 2Br ----- alc.KOH -- CH 2=CH 2 +KBr + H 2O substitution reaction. 1 Saytzeff Rule : “in dehydrohalogenation reactions, (iii) Instability of phenyl cation: SN mechanism is ruled the preferred product is that alkene which has the out. (iv)Because of the possible repulsion , it is less likely for greater number of alkyl groups attached to the doubly the electron rich nucleophile to approach electron rich bonded carbon atoms.” arenes . Replacement by hydroxyl group (iv) Friedel-Crafts reaction DOW’S PROCESS The presence of an electron withdrawing group (-NO 2) at ortho- and para-positions increases the reactivity of haloarenes. Fittig reaction Wurtz-Fittig reaction POLYHALOGEN COMPOUNDS Trichloro methane (Chloroform) The major use of chloroform today is in the production of the freon refrigerant R-22. It was once used as a general anaesthetic in surgery but has been replaced by less toxic, safer anaesthetics, such as ether. OSBINCBSE.COMChloroform is slowly oxidised by air in the presence of 2. Electrophilic substitution reactions light to an extremely poisonous gas, carbonyl chloride , HALOGENATION (Phosgene). It is therefore stored in closed dark coloured bottles completely filled so that air is kept out. HSSLIVE.IN Page 4 OSBINCBSE.COM OSBINCBSE.COM osbincbse.com Triiodo methane (Iodoform) : It was used earlier as an antiseptic but the antiseptic properties are due to the NITRATION liberation of free iodine and not due to iodoform itself. Freons : The chlorofluorocarbon compounds of methane and ethane are collectively known as freons. Freon 12 (CCl 2F2) is one of the most common freons in industrial use. It is manufactured from tetrachloromethane by Swarts reaction . SULPHONATION p,p’-Dichloro diphenyl trichloro ethane(DDT) ========== Chapter 11: ALCHOLS , PHENOLS & ETHERS Classification Mono, Di,Tri or Polyhydric Compounds Monohydric alcohols may be further classified according to the hybridisation of the carbon atom to which the hydroxyl group is attached. (i) Compounds containing bond: Primary, secondary and tertiary alcohols: Allylic alcohols: Benzylic alcohols (i) Compounds containing bond: OSBINCBSE.COM Ethers HSSLIVE.IN Page 5 OSBINCBSE.COM OSBINCBSE.COM osbincbse.com Ethers are classified as simple or symmetrical ( C2H5OC 2H5), if the alkyl or aryl groups attached to the oxygen atom are the same, and mixed or unsymmetrical , (C 2H5OCH 3 and C 2H5OC 6H5 ) . Structures of Functional Groups The carbon– oxygen bond length (136 pm) in phenol is slightly less than that in methanol. This is due to (i) partial double bond character on account of the conjugation of unshared electron pair of oxygen with the aromatic ring and (ii) sp 2 hybridised state of carbon to which oxygen is The bond angle in alcohols is slightly less than the attached. tetrahedral angle. It is due to the repulsion between In ethers the bond angle is slightly greater than the unshared electron pairs of oxygen. In phenols, the 2 the –OH group is attached to sp hybridised carbon tetrahedral angle due to the repulsive interaction of an aromatic ring. between the two bulky (–R) groups. The C–O bond length (141 pm) is almost the same as in alcohols. Alcohols and Phenols Preparation of Alcohols 1. From alkenes : (i) By acid catalysed hydration : Alkenes react with water in the presence of acid as catalyst to form alcohols. (ii) By hydroboration–oxidation : Diborane (BH3)2 reacts with alkenes to give trialkyl boranes as addition product. This is oxidised to alcohol by hydrogen peroxide in the presence of aqueous sodium hydroxide. 3CH 3CH=CH 2 -------B2H6 --- (CH 3CH 2CH 2)3B -----H2O2 -- 3CH 3CH 2CH 2OH Propene Tripropyl borane n-Propanol 2. From carbonyl compounds (i) By reduction of aldehydes and ketones : Aldehydes yield primary alcohols whereas ketones give secondary alcohols. (ii) By reduction of carboxylic acids and esters : Carboxylic acids are reduced to primary alcohols in excellent yields by lithium aluminium hydride, a strong reducing agent. RCOOH ---- LiAlH 4 / H 2O - RCH 2OH However, LiAlH4 is an expensiveOSBINCBSE.COM reagent, and therefore, used for preparing special chemicals only. Commercially, acids are reduced to alcohols by converting them to the esters followed by their reduction using hydrogen in the presence of catalyst . HSSLIVE.IN Page 6 OSBINCBSE.COM OSBINCBSE.COM osbincbse.com 3. From Grignard reagents Alcohols are produced by the reaction of Grignard reagents with aldehydes and ketones.
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