m-Bromotoluene is prepared by : | vedclass

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(D) The preparation of $m$-bromotoluene cannot be done by direct bromination of toluene because the $-CH_3$ group is ortho/para directing.To obtain th

Vedclass · Accepted Answer

Bromination of aceto-$p$-toluidine followed by hydrolysis and deamination

Vedclass · Answer

(D) The preparation of $m$-bromotoluene cannot be done by direct bromination of toluene because the $-CH_3$ group is ortho/para directing.To obtain the meta-isomer,we use the following sequence:$1$. Acetylation of $p$-toluidine to form aceto-$p$-toluidine.$2$. Bromination of aceto-$p$-toluidine,where the $-NHCOCH_3$ group is ortho/para directing,directing the bromine to the position meta to the methyl group.$3$. Hydrolysis of the amide to remove the acetyl group.$4$. Deamination (diazotization followed by reduction) to remove the $-NH_2$ group,leaving the bromine at the meta position relative to the methyl group.

$m$-Bromotoluene is prepared by :

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