(g)Hydrolysis of benzyl cyanide yields phenylacetic acid.Alternatively, the Grignard reagent derived from benzyl bromide may be carboxylated.(h)The first goal is to synthesize p-nitrobenzoic acid because this may be readily converted to thedesired acyl chloride. First convert toluene to p-nitrotoluene; then oxidize. Nitration must pre-cede oxidation of the side chain in order to achieve the desired para orientation.Treatment of p-nitrobenzoic acid with thionyl chloride yields p-nitrobenzoyl chloride.(i)In order to achieve the correct orientation in m-nitrobenzoyl chloride, oxidation of the methylgroup must precede nitration.Once m-nitrobenzoic acid has been prepared, it may be converted to the corresponding acylchloride.SOCl2m-Nitrobenzoic acid
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