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Chapter 23: Q70. (page 924)

Question: Explain why Ha is much less acidic than Hb . Then draw a mechanism for the following reaction.

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Answer

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01

Acidity of protons

The protons are more acidic when the adjacent group is more electron-withdrawing.The ester is an electron-withdrawing group that stabilizes the carbanion due to the presence of the carbonyl group.

Hence, the ester attracts its electron from the adjacent proton making it more acidic.

02

Explanation

The Ha is much less acidic because the delocalization of the carbanion can't occur by the removal of Ha .

Removal of Ha with base does not generate an anion that can delocalize onto the carbonyl O atom, whereas removal of Hb generates an enolate that is delocalized on O.

Abstraction of the acidic proton

Abstraction of the acidic proton

The mechanism of the given reaction is shown as:

Reaction mechanism

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