Q57E - Organic Chemistry (Mcmurry)

Question

The bicyclic ketone shown below does not undergo aldol self-condensation even though it has two hydrogen atoms. Explain.

Step-by-Step Solution

Answer

The given bicyclic ketone does not undergo aldol self-condensation even though it has two hydrogen atoms because the formation of enolate does not occur due to the double bond present at the bridgehead of the bicyclic ring.

The first step for aldol self-condensation is the formation of enolate.

Explanation

In the case of bicyclic ketone, the double bond is formed at the bridgehead of the bicyclic ring which causes too much strain in the ring, and hence the reaction is not possible in bicyclic ketone.