Which of the following carbanions is the most stable?

A4-methylbenzyl anion
B4-nitrobenzyl anion
C4-methoxybenzyl anion
Dbenzyl anion

Answer: B

In the benzyl anion the negative charge appears at ortho and para carbons. A para nitro group accepts the charge (-M and -I), putting it on oxygen. Methyl and methoxy donate electrons and destabilise the anion, so 4-nitrobenzyl anion is the most stable.

Practice General Organic Chemistry I: Electronic Effects More on Applications: stability of carbocations, carbanions, free radicals

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