Question

Cyclohexene can be converted to 1 -cyclopentenecarbaldehyde by the following series of reactions. Propose a structural formula for each intermediate compound.

Short answer

Answer: The intermediate compound in the reaction is the ozonide compound with the structure: C3-C4-(O)-C5-C6-(O)-O.

Step-by-step solution

Identify the starting compound

Cyclohexene is a six-membered ring with one double bond: C1=C2-C3-C4-C5-C6

Oxidation of cyclohexene

Performing an oxidation reaction of cyclohexene with an appropriate oxidizing agent (e.g., ozone) will form an unstable ozonide compound as an intermediate, which can further decompose to give the desired product.

Propose the structure of the ozonide intermediate

After adding ozone to cyclohexene, the resulting ozonide intermediate compound will have the following structure: C3-C4-(O)-C5-C6-(O)-O

Decomposition of the ozonide intermediate

The ozonide intermediate then decomposes to form 1-cyclopentenecarbaldehyde. This step involves breaking of the C3-C4 bond and the reformation of the double bond between C1 and C2.

Propose the structure of 1-cyclopentenecarbaldehyde

After decomposition of the ozonide intermediate, the final product, 1-cyclopentenecarbaldehyde, will have the following structure: C1=C2-C3-C4-C5-C6=O So, the intermediate compound in the reaction is the ozonide compound with the structure: C3-C4-(O)-C5-C6-(O)-O