Compound (A), , C_8H_9Br, gives a white preci | vedclass

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Question

(A) $1$. Compound $(A)$ has the formula $C_8H_9Br.$ The formation of a white precipitate with alcoholic $AgNO_3$ indicates the presence of a reactive

Vedclass · Accepted Answer

o-Methylbenzyl bromide

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(A) $1$. Compound $(A)$ has the formula $C_8H_9Br.$ The formation of a white precipitate with alcoholic $AgNO_3$ indicates the presence of a reactive bromine atom,likely a benzylic bromide $(-CH_2Br)$.$2$. Oxidation of $(A)$ gives an acid $(B)$ with formula $C_8H_6O_4.$ This acid readily forms an anhydride upon heating,which is a characteristic property of phthalic acid (benzene$-1,2-$dicarboxylic acid).$3$. For $(A)$ to yield phthalic acid upon oxidation,it must have two substituents at the ortho positions on the benzene ring that can be oxidized to carboxylic acid groups. One is the $-CH_2Br$ group (which oxidizes to $-COOH$) and the other must be a methyl group $(-CH_3)$ at the ortho position.$4$. Therefore,$(A)$ is $o$-methylbenzyl bromide ($1$-bromo$-2-$methylbenzene derivative). The reaction sequence is: $o$-methylbenzyl bromide $\xrightarrow{Oxidation}$ phthalic acid $\xrightarrow{\Delta}$ phthalic anhydride.

Compound $(A), \, C_8H_9Br,$ gives a white precipitate when warmed with alcoholic $AgNO_3.$ Oxidation of $(A)$ gives an acid $(B), \, C_8H_6O_4.$ $(B)$ easily forms anhydride on heating. Identify the compound $(A).$

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