Predict the major product of the following re | vedclass

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(D) The starting material is $4$-methylacetanilide. The acetamido group $(-NHCOCH_3)$ is a strong activating group due to the $+M$ effect of the nitro

Vedclass · Accepted Answer

$2-$bromo$-4-$methylacetanilide.

Vedclass · Answer

(D) The starting material is $4$-methylacetanilide. The acetamido group $(-NHCOCH_3)$ is a strong activating group due to the $+M$ effect of the nitrogen lone pair,making it ortho/para directing. The methyl group $(-CH_3)$ is also activating and ortho/para directing. In $4$-methylacetanilide,the para position relative to the acetamido group is occupied by the methyl group. Therefore,electrophilic aromatic substitution (bromination) occurs at the ortho position relative to the acetamido group. Since the methyl group is at the para position,the ortho position relative to the acetamido group is also the meta position relative to the methyl group. The acetamido group is a stronger activator than the methyl group,so it directs the incoming electrophile $(Br^+)$. The product is $2$-bromo-$4$-methylacetanilide.

Predict the major product of the following reaction:

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