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Question

Of the following, which is the product formed when cyclohexanone undergoes aldol condensation followed by heating?


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


This is the typical aldol condensation followed by E1CB elimination. You should look for αβ unsaturated ketone. Because of the hydroxide base, there will be a small amount of enolate in the reaction flash. The enolate behaves as a carbon nucleophile and then attacks the electrophilic carbonyl carbon to give he aldol condensation product, which (because there is heat), further undergoes E1CB elimination to give the following product:



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