See image — Alcohols Phenols and Ethers Chemistry Question

💡 Solution & Explanation

Step 1 - Identify the functional groups in compound (A): Compound (A) is a 1,3,5-trisubstituted cyclohexane bearing: a aldehyde (CHO) at C1, a methyl ester (COOCH3) at C3, and a ketone (C=O, i.e., the ring carbonyl at C5). Step 2 - Reactivity of LiAlH4 toward different functional groups: LiAlH4 (LAH) is a powerful, non-selective hydride reducing agent. It reduces all common carbonyl-containing groups: - Aldehydes (CHO) → primary alcohols (CH2OH) - Ketones (C=O) → secondary alcohols (CHOH) - Esters (COOR) → two alcohols: the acid portion gives a primary alcohol, and the alkoxy portion (here CH3OH, methanol) is released Step 3 - Apply reductions: - The aldehyde (CHO) at C1 is reduced to CH2OH (primary alcohol). - The methyl ester (COOCH3) at C3 is reduced to CH2OH (primary alcohol) plus methanol (which leaves). - The ketone (C=O) at C5 on the ring is reduced to CHOH (secondary alcohol). Step 4 - Product structure: All three carbonyl groups are reduced. The product is a cyclohexane ring with: a -CH2OH group at C1, a -CH2OH group at C3, and a -OH (secondary alcohol) at C5. This matches option (c): three alcohol groups on the cyclohexane ring. Step 5 - Why other options fail: (a) Only the aldehyde is reduced to OH; ester and ketone remain — LAH reduces all three, so this is incomplete. (b) Only aldehyde and ketone are reduced; ester remains — LAH also reduces esters, so this is incomplete. (d) The aldehyde is NOT reduced (still CHO) while ketone and ester are reduced — LAH readily reduces aldehydes, so this is incorrect. Therefore, the correct answer is C.