please do not guess! i know LDA deprotonates from the adjacent carbon with more

Question

please do not guess! i know LDA deprotonates from the adjacent carbon with more hydrogens, but what if neither side has any hydrogens. this is a multiple choice question. please give me the answer and explanation for 5 stars. also only answer if you're confident

Predict the product of the following reaction between benzoic acid and lithium diisopropylamide (LDA). please do not guess! i know LDA deprotonates from the adjacent carbon with more hydrogens, but what if neither side has any hydrogens. this is a multiple choice question. please give me the answer and explanation for 5 stars. also only answer if you're confident

Explanation / Answer

the product will be (b)
this is because lDA is a strong base whose nucleophilicity is relatively low, due to steric reasons.

If a carboxylic acid is treated with LDA, a lithium carboxylate is initially formed. The second equivalent of LDA abstracts the hydrogen, thus yielding a dianion.

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