Q66E - Organic Chemistry (Mcmurry)

Question

Identify the reagents a-e in the following scheme:

Step-by-Step Solution

Answer

The answer is 

Step 1: Grignard reagent

Grignard reagents are alkyl magnesium halides. One of their uses is to convert carbonyl compounds into alcohols.

Step 2: Explanation

The sequence of reagents is shown below.

The Grignard reagent,  Methyl magnesium halide, converts the cyclohexanone into methyl cyclohexanol. It can be converted into methyl hexane on reaction with Sodium hydroxide and to methoxy methylcyclohexane on reaction with Sodium hydroxide with methanol. The methyl cyclohexene reacts with hydrogen peroxide and water to give the epoxide compound. The epoxide is then converted into dihydroxy compound in reaction with Sodium hydroxide and water.