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Chapter 19: Q45E (page 648)

The Meerwein鈥揚onndorf鈥揤erley reaction involves the reduction of a ketone by treatment with an excess of aluminum triisopropoxide,[(CH3)2CHO]3Al.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.

Short Answer

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Formation of Complex

Formation of Alcohol

Step by step solution

01

Step-by-Step SolutionStep 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

02

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

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Most popular questions from this chapter

Name the following aldehydes and ketones:

Treatment of 2-cyclohexenone with HCN/KCN yields a saturated keto nitrile rather than an unsaturated cyanohydrin. Show the structure of the product,

and propose a mechanism for the reaction.

How might you use IR spectroscopy to determine whether reaction between2-cyclohexenoneand lithium dimethylcopper gives the direct addition productor the conjugate addition product?

At what position would you expect to observe IR absorptions for the following molecules?

a.

b.

c.

d.

Choose the structure that best fits the IR spectrum shown.
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