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J"'? ) ^^"ff" C^Hs-CN+KCl C6H5OH -f NaCl The preferred large-scale procedure for the preparation of phenol from chlorobenzene employs superheated steam at 475" in the presence of suitable catalysts. Example (b) represents a commercial route to aniline but the yield of benzonitrile in example (c) is poor. g. —NO2) are situated ortho or para (but not meta) to the displaced g r o u p ; for example, the hydrolysis of /7-chloronitrobenzene with aqueous alkali proceeds relatively readily. The effect of such groups is to allow for a more extensive delocalisation of the charge in the reaction intermediate (IV) and thus to lower the activation energy for its formation.

Amines, phenols) which contain activating ortho-para directing functional groups proceeds very readily, and polyhalogenated compounds are frequently obtained unless the extent of substitution is care­ fully controlled (p. 89). On the other hand, deactivating {meta directing) groups do not prevent reaction; for example, nitro­ benzene may be successfully chlorinated to w-chloronitrobenzene. NO, NO, 48 ORGANIC CHEMISTRY FOR GENERAL DEGREE STUDENTS The catalysed chlorination of toluene gives a mixture of o- and /7-chlorotoluenes which may be separated by taking advantage of the more ready sulphonation of the ortho isomer which occurs when the mixture is heated with concentrated sulphuric acid.

CH, CH2C1 Benzyl chloride CHCl 2 Benzylidene chloride CCl, Benzotrichloride (benzal chloride) This side-chain halogenation is reminiscent of, but proceeds more AROMATIC HALOGEN 49 COMPOUNDS readily than, substitution in alkanes and involves a radical process. Reaction is induced by the formation of chlorine atoms which are capable of removing hydrogen atoms from the methyl group. The benzyl radical I thus formed, which is stabilised by virtue of its mesomeric nature, is capable of abstracting a chlorine atom from a further molecule of chlorine, leaving a chlorine atom to propagate the reaction sequence.

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