Q11P - Organic Chemistry (Mcmurry)

Question

Use the reaction of a Grignard reagent with a carbonyl compound to synthesize the following compound:

Step-by-Step Solution

Answer

The reaction of cyclohexanone with Grignard reagent is shown as,

Step 1: Grignard reaction to synthesize an alcohol

First, to synthesize alcohol from the Grignard reaction, identify the three groups bonded to the carbon-containing OH group. If all the three groups are different, the starting compound should be ketone.

Step 2: The alcohol needed to produce the product

The structure of alcohol can be interpreted first. 1-ethylcyclohexanol is tertiary alcohol and can be synthesized only from ketone. The only combination of ketone and Grignard reagent possible is,

Grignard reaction