See image — Alcohols Phenols and Ethers Chemistry Question
Question
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💡 Solution & Explanation
Concept: Fischer esterification is an acid-catalyzed reaction between a carboxylic acid and an alcohol to form an ester and water. The reaction selectively converts the carboxylic acid (-COOH) group to an ester (-COOEt), leaving other functional groups (such as -OH) intact under normal conditions. Step 1: Identify the functional groups in mandelic acid. Mandelic acid is Ph-CH(OH)-COOH. It contains two oxygen-bearing functional groups: a secondary alcohol (-OH on the alpha carbon) and a carboxylic acid (-COOH). Step 2: Determine which group reacts in Fischer esterification. Fischer esterification specifically involves the carboxylic acid group reacting with EtOH under acid (HCl) catalysis to form an ester. The alcohol group on the alpha carbon does not undergo esterification under these conditions. Step 3: Write the product. The -COOH reacts with EtOH to give -CO2Et, while the -OH on the alpha carbon remains unchanged. Product: Ph-CH(OH)-CO2Et. Step 4: Evaluate options. - Option (a): Ph-CH(O-Et)-CO2H — this shows etherification of the alpha-OH and retention of COOH, which is not what Fischer esterification does. - Option (b): Shows an epoxide/lactone structure — not the product of simple Fischer esterification with EtOH. - Option (c): Ph-CH(OH)-CO2Et — carboxylic acid esterified to ethyl ester, alpha-OH retained. This is correct. - Option (d): Ph-CH(OH)-C(=O)-Et — this is a ketone (ethyl ketone), not an ester; incorrect. Therefore, the correct answer is C.