See image — Aldehydes Ketones and Carboxylic Acids Chemistry Question

💡 Solution & Explanation

Step 1 - Identify the starting material: The starting material is a norbornane (bicyclo[2.2.1]heptane) framework that contains a cyclic anhydride (the O-C(=O)-O five-membered ring fused to the skeleton) and an additional ester/anhydride carbonyl group (C=O with O). This is a dianhydride or a compound with two anhydride-type functional groups incorporated into the bicyclic framework. Step 2 - Reaction with water (hydrolysis): The reaction uses 2H2O, meaning two equivalents of water are added. Each anhydride linkage (R-CO-O-CO-R') hydrolyzes with one equivalent of water to open the anhydride ring and produce two carboxylic acid groups (-CO2H). Simultaneously, ether (C-O-C) linkages or additional ester bonds hydrolyze to produce hydroxyl groups (-OH). Step 3 - Determine products from each functional group: - The cyclic anhydride (O-C(=O)-O portion) hydrolyzes with one H2O to give two -CO2H groups. - The second ester/anhydride C-O linkage (the O on the norbornane ring connecting to the carbonyl) hydrolyzes with the second H2O to give an -OH group and release the carboxylic acid already formed, OR the ether oxygen bridges on the ring open to give two -OH groups while the carbonyl becomes -CO2H. Step 4 - Analyze the options: - Option (a) has CH3 group which is not present in the starting material - eliminated. - Option (b) has a ketone (C=O) remaining after hydrolysis, but full hydrolysis of anhydrides should give carboxylic acids, not ketones - eliminated. - Option (c) has two -OH groups (from hydrolysis of the two C-O ether/ester bonds on the norbornane ring) and two -CO2H groups (from hydrolysis of the anhydride carbonyls). This is consistent with adding 2H2O to open both the cyclic anhydride (giving 2 CO2H) and the ether linkages (giving 2 OH). This matches complete hydrolysis of the dianhydride/diester structure. - Option (d) has aldehyde groups (CHO) which cannot result from hydrolysis of anhydrides or esters - eliminated. Step 5 - Confirm answer (c): The norbornane dianhydride compound upon reaction with 2H2O undergoes hydrolysis of both anhydride/ester linkages: the cyclic anhydride opens to give two -CO2H groups, and the ether-type C-O bonds on the ring open to give two -OH groups, producing the diol-diacid norbornane product shown in option (c). Therefore, the correct answer is C.