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Question

Predict the structure of ‘B’ in the given 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

Anisole on reacting with acetic anhydride in presence of AlCl3 is a Friedel craft acylation reaction. It is an aromatic electrophilic substitution reaction. Here, the carbonyl group in acetic anhydride will act as the electrophile. Since, OCH3 is an activating group the product will be ortho or para. Here, the major product will be para due to the less steric hindrance between OCH3 and electrophilic group.
Product 'A' formed reacts with ZnHg, HCl which is a clemmensen reagent.
In Clemmensen reaction, the aldehyde and keto group will get reduced to hydrocarbons.
Hence, the keto group in 'A' is reduced to CH2 to give product 'B'
Product 'B' on reacting with H3PO4 undergo dehydration to form the respective product.


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