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Question

(A) $1$. The starting material is $p$-nitrotoluene. Bromination in the presence of $FeBr_3$ occurs at the ortho position relative to the methyl group

Vedclass · Accepted Answer

$2-$bromotoluene

Vedclass · Answer

(A) $1$. The starting material is $p$-nitrotoluene. Bromination in the presence of $FeBr_3$ occurs at the ortho position relative to the methyl group (since $-CH_3$ is ortho/para directing and $-NO_2$ is meta directing),yielding $2$-bromo-$4$-nitrotoluene $(A)$.$2$. Reduction of the nitro group using $Sn/HCl$ converts the $-NO_2$ group to an $-NH_2$ group,yielding $2$-bromo-$4$-aminotoluene $(B)$.$3$. Treatment with $NaNO_2/HCl$ at $0-5^{\circ}C$ performs diazotization of the $-NH_2$ group,forming the diazonium salt,$2$-bromo-$4$-methylbenzenediazonium chloride $(C)$.$4$. Finally,treatment with $H_3PO_2$ and $H_2O$ reduces the diazonium group to a hydrogen atom,resulting in $2$-bromotoluene $(D)$.

Column $I$	Column $II$
$A$. $CH_3CH_2CH_2CN$	$p$. Reduction with $Pd-C/H_2$
$B$. $CH_3CH_2OCOCH_3$	$q$. Reduction with $SnCl_2/HCl$
$C$. $CH_3-CH=CH-CH_2OH$	$r$. Development of foul smell on treatment with chloroform and alcoholic $KOH$
$D$. $CH_3CH_2CH_2CH_2NH_2$	$s$. Reduction with diisobutylaluminium hydride $(DIBAL-H)$
	$t$. Alkaline hydrolysis

Product $D$ is:-

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The product $(A)$ is:

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