A molecule possesses both a carboxylic acid () group and an ester () group. Which specialized reduci — Aldehydes Ketones and Carboxylic Acids Chemistry Question
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?
Answer: C
💡 Solution & Explanation
$NaBH_4$ is too mild to reduce either group. $LiAlH_4$ is too harsh and reduces both acids and esters. DIBAL-H primarily reduces esters/nitriles to aldehydes at low temps. However, Diborane ($B_2H_6$) uniquely and selectively reduces carboxylic acids to primary alcohols even in the presence of sensitive groups like esters.
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