By P. W. G. Smith
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G. —NO2, —CO-R) are already present in the nucleus, reaction is essentially prevented. PREPARATION FROM AMINES Whereas nuclear halogenation affords the most direct method for the synthesis of aryl chlorides and bromides, halogen com pounds are often best prepared indirectly from the corresponding amino compounds. Reaction of a primary amine with nitrous acid in the presence of hydrochloric acid yields the corresponding diazonium chloride (pp. ). When this is heated with a solution of cuprous chloride in concentrated hydrochloric acid the aryl chloride is formed with displacement of the diazo group as nitrogen (the Sandmeyer reaction, p.
2CI- CH2 CH2 + CI- CH2CI CH, + CI2 Benzyl chloride is also prepared by the reaction of sulphury 1 chloride with toluene in the presence of peroxides, which also proceeds by a radical process. Mono-substitution by a radical process in homologues of benzene possessing longer side-chains occurs predominantly in the α-position; further substitution can then occur in other positions in the chain to give ultimately a complex mixture of polyhalo genated products. CHLOROMETHYLATION The direct introduction of a chloromethyl group (—CH2CI) into an aromatic nucleus is conveniently effected using a mixture of formaldehyde (introduced as paraformaldehyde) and gaseous 50 ORGANIC CHEMISTRY FOR GENERAL DEGREE STUDENTS hydrogen chloride in the presence of anhydrous zinc or aluminium chlorides.
CI '^ci N02 NO, xvni xvn ALKYL GROUPS (—R) Toluene is more readily nitrated than benzene, and in common with other activating groups, the methyl group is found to be ortho-para directing. In this case the activation of the nucleus is in accord with the established electron-releasing ( + / ) effect of the methyl group, which is supported by the fact that toluene has a finite dipole moment with the methyl group at the positive end of the dipole. -CH3 0 4 D The additional stabilisation of the reaction intermediates formed as the result of attack at an ortho or para position, which is provided by the inductive electron release, is illustrated in the canonical forms XIX and XX.