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Question

What would be the major product of the following reaction?


A

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B

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C


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D
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Solution

The correct option is A

The carbonyl is deactivating in nature. It will drastically reduce the rates of any electrophilic aromatic substitutions. But the acid helps in the enol formation. No matter however small the percentage of the enol, bromination at the alpha position is more conducive which converts the enol into the bromoketone. This conversion causes more enol to be formed and more of it is converted into the alpha brominated carbonyl. So there are no electrophilic aromatic substitution products in appreciable quantities. The major product is:

The product shown here will further deactivate the benzene ring against any electrophilic aromatic substitution.


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