Q45E - Organic Chemistry (Mcmurry)

Question

The Meerwein–Ponndorf–Verley reaction involves the reduction of a ketone by treatment with an excess of aluminum triisopropoxide,${\left[{\left({\mathbf{CH}}_3\right)}_2\mathbf{CHO}\right]}_3\mathbf{Al}$ . The mechanism of the process is closely related to the Cannizzaro reaction in that a hydride ion acts as a leaving group. Propose a mechanism.

 

Step-by-Step Solution

Answer

Formation of Complex

Formation of Alcohol

Step-by-Step Solution Step 1: Meerwein–Ponndorf–Verley reaction

In this method, carbonyl compounds aldehydes or ketones to the respective alcohol by treatment with a catalyst aluminum isopropoxide in isopropanol as a solvent.

The mechanism of the first step is as follows;

The reaction proceeds via a six-member transition state

Step 2: Formation of the final product

In this step, the acidic hydrolysis of the intermediate takes place and we get a desire product as follows;

Formation of Complex

Formation of Alcohol