See image — Alcohols Phenols and Ethers Chemistry Question

💡 Solution & Explanation

Concept: In esterification reactions under acid catalysis (Fischer esterification), the more nucleophilic and less sterically hindered alcohol reacts preferentially with the carboxylic acid. Step 1 - Identify the two hydroxyl groups in the substrate: The starting material is 4-(hydroxymethyl)cyclohexan-1-ol, which contains (i) a primary alcohol (-CH2OH) attached to C1 of the cyclohexane ring, and (ii) a secondary alcohol (-OH) directly on C4 of the cyclohexane ring. Step 2 - Assess reactivity: Primary alcohols are less sterically hindered than secondary alcohols. In Fischer esterification, steric hindrance plays a key role in determining which -OH group reacts. The primary -CH2OH group is more accessible and less sterically crowded than the secondary ring -OH, making it more reactive toward the carboxylic acid under these conditions. Step 3 - Determine the product: The primary -CH2OH reacts with PhCOOH (benzoic acid) under HCl catalysis to form the ester Ph-C(=O)-O-CH2- (benzyl benzoate type linkage), while the secondary -OH on the ring remains unreacted. This corresponds to option (b): a cyclohexane ring with HO- at C4 (secondary, unreacted) and -CH2-O-C(=O)-Ph at C1 (primary alcohol esterified). Step 4 - Eliminate other options: - Option (a): Shows esterification at the secondary (ring) alcohol and the primary -CH2OH left free. This is the less favored product due to greater steric hindrance at the secondary position. - Option (c): Shows an ether linkage (CH2-O-Ph), not an ester; this is not the product of esterification with a carboxylic acid. - Option (d): Shows esterification at the secondary ring carbon directly, which is sterically disfavored compared to the primary alcohol. Therefore, the correct answer is B.