Question

Treatment of 1-phenyl-2-propenone with a strong base such as LDA does not yield an anion, even though it contains a hydrogen on the carbon atom next to the carbonyl group. Explain.

Short answer

LDA does not yield an anion due to steric hindrance.

Step-by-step solution

Given compound

The given compound is 1-Phenyl-2-propenone.

1-Phenyl-2-propenone

LDA does not yield an anion

LDA is a highly steric hindrance base. So, it will not deprotonate the highly crowded side proton of the compound.

Steric hinderance

Thus, LDA does not yield an anion with the compound.