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. Organometalics and alkyl halides will likely be used.

Answer 1

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

The correct options are
A One of steps will involve the formation of Carbon-Carbon sigma bond
C One of the steps involve addition across the carbonyl pi bond
D Organometalics and alkyl halides will likely be used.

start with cyclopropylmethanol, cyclopentanol and butan-1-ol respectively. We start with the first one:

The primary alcohol is converted into a Grignard reagent:


When we get the above two to react with each other followed by a separate workup,

Convert cyclopentanol to cyclopentanone:

Now, we convert the secondary alcohol from the Grignard addition step into a fresh
Grignard reagent:

When this reacts Grignard reagent reacts with cyclopentanone, we get:

This alcohol, when deprotonated by Na in ether and the subsequently made to react with $C{H}_{3}I$,