Identify the starting material (?) in the following reaction sequence: ? [ 2. O ₃ , then Zn / CH ₃ COOH ] 1. H ₂ SO ₄ , heat OHC

Step-by-step solution

The given reaction sequence consists of two steps: dehydration of an alcohol using H ₂ SO ₄ and heat to form an alkene, followed by reductive ozonolysis of the alkene using O ₃ and Zn / CH ₃ COOH to form carbonyl compounds. The final product is hexanedial, OHC - CH ₂- CH ₂- CH ₂- CH ₂- CHO , which is a six-carbon dialdehyde. Working backwards, the alkene that yields hexanedial upon reductive ozonolysis must be a six-membered cyclic alkene, which is cyclohexene. The starting material that undergoes dehydration to fo