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Question

Which one of the following will be reactive for Perkin condensation ?

A
C6H5CHO
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B
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C
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D
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Solution

The correct option is D
Aromatic aldehyde on reacting with carboxylic acid anhydride in presence of salt of carboxylic acid to form α,β-unsaturated acids. This reaction is called Perkin reaction.

In this reaction, the enolate formed from the anhydride will attack the electrophilic carbonyl carbon of aromatic aldehyde.

Thus, electron withdrawing groups attached to the ring increases the electrophilicity of carbonyl carbon which result in increase in efficiency of Perkin condensation while electron releasing groups ( electron donating group) decreases the efficiency of Perkin's reaction.


Hence, option (d) be the most reactive towards Perkin's condensation due to withdrawing nature of NO2 group.

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