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Which of the following reagents can reduce a carboxylic acid to an alcohol in the presence of a ketone (without also reducing the ketone)?Select answer from the options belowNaBH4LiAlH4BH3 . THFDIBAH

Question

Which of the following reagents can reduce a carboxylic acid to an alcohol in the presence of a ketone (without also reducing the ketone)?Select answer from the options belowNaBH4LiAlH4BH3 . THFDIBAH

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Solution

The reagent that can selectively reduce a carboxylic acid to an alcohol in the presence of a ketone, without also reducing the ketone, is DIBAL-H (Diisobutylaluminium hydride).

Here's why:

  1. NaBH4 (Sodium borohydride) is a mild reducing agent and it does not have the ability to reduce carboxylic acids or esters.

  2. LiAlH4 (Lithium aluminium hydride) is a strong reducing agent and it will reduce both carboxylic acids and ketones, so it's not selective.

  3. BH3 . THF (Borane-tetrahydrofuran) is also a strong reducing agent and it will reduce both carboxylic acids and ketones, so it's not selective.

  4. DIBAL-H (Diisobutylaluminium hydride) is a selective reducing agent. It can reduce carboxylic acids and esters to alcohols without reducing ketones when used at low temperatures (-78 degrees Celsius). Therefore, DIBAL-H is the correct answer.

This problem has been solved

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