Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Identify the major product (C) in the following reaction sequence:
Correct answer
3
Step-by-step solution
The starting material, cyclohexane-1,2-diol, undergoes oxidative cleavage by periodic acid ( HIO ₄ 2 H ₂ O ) to break the C - C bond between the hydroxyl-bearing carbons, forming hexanedial. A = OHC - CH ₂- CH ₂- CH ₂- CH ₂- CHO Hexanedial undergoes an intramolecular aldol condensation in the presence of a base ( NaOH ) and heat ( ). Deprotonation at an -carbon forms an enolate that attacks the other carbonyl group, forming a stable 5-membered ring. Heating causes dehydration to yield the , -unsaturated aldehyde, c