Ester hydrolysis followed by carboxylic acid reduction Steps:

• CH3COOCH3 (methyl acetate) undergoes hydrolysis with aqueous NaOH to yield CH3COONa and CH3OH.
• Acidification of the mixture gives CH3COOH and CH3OH.
• LiAlH4 reduces CH3COOH to CH3CH2OH via hydride addition to the carbonyl, followed by workup.
• CH3OH remains unaffected as LiAlH4 does not reduce alcohols. Why D is correct:
• Ester hydrolysis produces methanol and acetic acid; LiAlH4 selectively reduces the carboxylic acid to ethanol per standard carbonyl reduction mechanism. Why the others are wrong:
• A: Direct LiAlH4 reduction of acetone would yield only isopropanol, bypassing the aqueous reaction.
• B: Identical to D but not the selected answer.
• C: Identical to D but not the selected answer. Final answer: D