See image — Aldehydes Ketones and Carboxylic Acids Chemistry Question

💡 Solution & Explanation

Step 1 - Reaction concept: 1-methyl-1-cyclohexyl hydroperoxide undergoes acid-catalyzed (H3O+) Hock rearrangement (similar to the cumene hydroperoxide process). The O-O bond cleaves heterolytically with migration of a carbon substituent, ultimately opening the ring and giving a cleavage product. Step 2 - Hock rearrangement mechanism: In acid, the -OOH is protonated and water leaves, forming a carbocation/oxocarbenium species. A 1,2-carbon shift (ring carbon migrates) occurs from the tertiary carbon to the electrophilic oxygen, causing ring opening. The cyclohexane ring opens to give a linear chain containing both a ketone and an alcohol functionality. Step 3 - Product identification from molecular formula C7H14O2: The starting hydroperoxide has the formula C7H14O2 (1-methylcyclohexyl = C7H13, plus OOH adds O2H, total C7H14O2). The product P retains C7H14O2 - no atoms are lost, consistent with a rearrangement rather than fragmentation. Step 4 - Functional group analysis from tests: - Positive iodoform test: requires CH3-C(=O)- (methyl ketone) or CH3-CH(OH)- group. A methyl ketone (CH3CO-) satisfies this. - Positive 2,4-DNP test: indicates a carbonyl group (ketone or aldehyde). - Positive CrO3 test: indicates an oxidizable group, i.e., a secondary alcohol (or primary alcohol or aldehyde). Since 2,4-DNP is also positive, there is both a carbonyl AND an alcohol. Step 5 - Ring opening of 1-methylcyclohexyl hydroperoxide: The ring has 6 carbons; with the methyl at C1, opening gives a 7-carbon chain. The Hock rearrangement of 1-methylcyclohexyl hydroperoxide opens the ring such that the methyl ketone end (CH3-CO-) forms at one end and a primary alcohol (-CH2-OH) forms at the other end of the chain. Step 6 - Checking option (c): CH3-C(=O)-CH2-CH2-CH2-CH2-CH2-OH - Molecular formula: C7H14O2 ✓ - Positive iodoform test: CH3-CO- group present ✓ - Positive 2,4-DNP: ketone present ✓ - Positive CrO3: primary alcohol present ✓ All three tests are satisfied. Step 7 - Why other options fail: - Option (a): CH3-CO-CH2-CH2-CH2-CH(OH)-CH3 has a secondary alcohol; iodoform would also be positive from CH3CHOH but the structure doesn't arise cleanly from ring opening. - Option (b): Similar issue; secondary alcohol at C4 position. - Option (d): The branched structure with gem-dimethyl doesn't arise from a simple ring-opening Hock rearrangement of this substrate. Option (c) is the straight-chain 7-oxoheptan-1-ol (7-hydroxy-2-heptanone) which is the correct Hock rearrangement product of 1-methyl-1-cyclohexyl hydroperoxide, satisfying all three chemical tests. Therefore, the correct answer is C.