Question

m-bromotoluene is prepared by:

• A. bromination of toluene
• B. Friedel Craft's reaction of bromobenzene with $C{H}_{3}Cl$
• C. bromination of nitrobenzene and subsequent replacement of $-N{O}_2$ group with methyl group
• D. bromination of aceto-p-toluidine followed by hydrolysis and deamination

Answer 1

Answer: (C), (D)

The correct options are
C bromination of nitrobenzene and subsequent replacement of $-N{O}_2$ group with methyl group
D bromination of aceto-p-toluidine followed by hydrolysis and deamination

A) Bromination of toluene will give ortho and para bromo toluene as methyl group is an ortho para directing group. Hence, option $A$ is incorrect.
B) Friedel Craft's reaction of bromobenzene with methyl chloride will give polyalkylation products. Hence, option $B$ is incorrect.
C) m-Bromotoluene is prepared by bromination of nitrobenzene and subsequent replacement of nitro group with methyl group (reaction is given below). Hence, option $C$ is correct.
D) Bromination of aceto-p-toluidine followed by hydrolysis and deamination can also be used to prepare m-bromotoluene as both acetamide and methyl groups are ortho para directing groups but acetamido group has higher influence (reaction is given below). Hence, option $D$ is also correct.