Question

Assume common laboratory reagents and chemicals are available. Starting with cyclopentanol and any other alcohol(s) each having not more than 4 carbons, synthesize:

• A. One of steps will involve the formation of Carbon-Carbon sigma bond
• B. One of steps must involve the formation of Carbon-Carbon pi bond
• C. One of the steps involve addition across the carbonyl pi bond
• D. Organometallics and alkyl halides will likely be used

Answer 1

Answer: (A), (C), (D)

Organometallics and alkyl halides will likely be used

Start with cyclopentanol and arrive at cyclopentyl magnesium bromide via cyclopentyl bromide.

Separately, start with butan-2-ol and use PCC to get butan-2-one.

Get the ketone to react with the synthesized Grignard reagent
and then effect a work up:

The above is first treated with metallic sodium in ether, and then subsequently
made to react with methyliodide to give the final product: