11. Account for the chemoselectivity of these reductions. 11. Account for the chemoselectivity of these reductions.
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$NaBH_4$ is a mild reducing agent that selectively reduces ketones and aldehydes, but not esters. The ketone is reduced to a secondary alcohol, while the ester remains unaffected. This is because the carbonyl carbon in the ketone is more electrophilic than the Show more…
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More specifically, the reduction of methyl 4-formylbenzoate by sodium borohydride will be studied. There are three possible products of this reaction (2-4). If the reaction is chemoselective, the majority of product formed in the reaction should be either 2 or 3. So, we have two questions: is the reaction chemoselective? If so, which functional group is selectively reduced?
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Offer a mechanistic explanation for each step of the following transformation, commenting on the stereoselectivity observed in the borohydride reduction step.
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