See image — Aldehydes Ketones and Carboxylic Acids Chemistry Question

💡 Solution & Explanation

Step 1 - Identify the starting material structure: The starting material is a spiro compound where a quaternary carbon is shared between two rings: (1) a 1,3-dioxolane ring (5-membered cyclic acetal, -O-CH2-CH2-O- connected to the spiro carbon) and (2) a 6-membered delta-lactone ring (-C(=O)-O- with two CH2 groups connecting back to the spiro carbon). The spiro carbon also bears two additional CH2 groups that form part of both rings. Step 2 - Identify the functional groups that undergo hydrolysis under H3O+/H2O: Under acidic aqueous conditions, two types of bonds are hydrolyzed: - Cyclic acetal (1,3-dioxolane): hydrolyzes to reveal a ketone (or aldehyde). In this case, the spiro acetal carbon bears two carbon substituents, so hydrolysis of the acetal gives a ketone (C=O) at that position. - Lactone (cyclic ester): hydrolyzes under acid/water to give a hydroxy acid (the ring opens to give -OH and -COOH). Step 3 - Determine the product of acetal hydrolysis: The 1,3-dioxolane acetal hydrolyzes to give a ketone at the spiro carbon, releasing ethylene glycol (HOCH2CH2OH). Step 4 - Determine the product of lactone hydrolysis: The delta-lactone ring opens under acidic aqueous conditions to give a carboxylic acid (-COOH) at one end and a free hydroxyl (-OH) at the other end of the chain. Step 5 - Combine both hydrolyses: After both the acetal and the lactone are hydrolyzed, the product has: a carboxylic acid group (-COOH) from the lactone ring opening, a ketone group (C=O) from the acetal hydrolysis, and a hydroxyl group (-OH) from the lactone ring opening. The chain connectivity gives: HO-C(=O)-CH2-CH2-C(=O)-CH2-CH2-OH, i.e., a compound with a terminal carboxylic acid, two methylene groups, a ketone, two more methylene groups, and a terminal hydroxyl. This matches option (c). Step 6 - Why other options fail: (a) Glutaric acid would result only if there were two ester/lactone groups hydrolyzed with no acetal present - incorrect connectivity. (b) Option (b) retains the dioxolane ring intact, meaning the acetal was not hydrolyzed - under H3O+/H2O both groups hydrolyze. (d) Option (d) also retains the dioxolane ring and has wrong substitution. Therefore, the correct answer is C.