A molecule possesses both a carboxylic acid () group and an ester () group. Which specialized reducing agent will selectively reduce the carboxylic acid to a primary alcohol while leaving the ester fu

Question

A molecule possesses both a carboxylic acid ($-COOH$) group and an ester ($-COOR$) group. Which specialized reducing agent will selectively reduce the carboxylic acid to a primary alcohol while leaving the ester functional group completely untouched?

Prashant Kotian · Accepted Answer

Correct answer: C. is too mild to reduce either group. is too harsh and reduces both acids and esters. DIBAL-H primarily reduces esters/nitriles to aldehydes at low temps. However, Diborane () uniquely and selectively reduces carboxylic acids to primary alcohols even in the presence of sensitive groups like esters.

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