See image — Alcohols Phenols and Ethers Chemistry Question

💡 Solution & Explanation

The starting material is cyclohexene, a six-membered ring with one double bond. The target product is hexane-1,6-diol, HO-(CH2)6-OH, a linear diol with hydroxyl groups at both ends. Concept: Cyclohexene has one C=C double bond. Cleavage of this double bond opens the ring and, if both carbons of the double bond are converted to aldehyde or carboxylic acid groups, subsequent reduction gives the terminal diol HO-(CH2)6-OH. Option (a): O3, Zn (reductive workup) performs ozonolysis giving a dialdehyde: OHC-(CH2)4-CHO (hexanedial). LiAlH4 then reduces both aldehyde groups to primary alcohols, giving HO-(CH2)6-OH. This works. Option (b): O3/H2O2 (oxidative workup) performs ozonolysis giving a dicarboxylic acid: HOOC-(CH2)4-COOH (hexanedioic acid / adipic acid). LiAlH4 then reduces both carboxylic acid groups to primary alcohols, giving HO-(CH2)6-OH. This works. Option (c): Cold dilute KMnO4 performs syn-dihydroxylation of the double bond, giving cyclohexane-1,2-diol (a vicinal diol). HIO4 (periodic acid) then cleaves the vicinal diol oxidatively, breaking the C-C bond and giving OHC-(CH2)4-CHO (hexanedial), the same dialdehyde as in option (a). LiAlH4 then reduces both aldehydes to give HO-(CH2)6-OH. This works. Since all three methods independently achieve the conversion of cyclohexene to HO-(CH2)6-OH, the answer is (d) All of these. Therefore, the correct answer is D.