Lipases are chiral enzymes that catalyze the reaction of esters with water (hydr

Question

Lipases are chiral enzymes that catalyze the reaction of esters with water (hydrolysis) to yield alcohols and carboxylic acids. The same reaction can be performed using strong acid as a catalyst.

Consider the diester 1. Which statement is true regarding the hydrolysis of this substrate? Assume that only one of the ester groups reacts.

a. Hydrolysis can result in the formation of two diastereomers.

b. Hydrolysis with lipase gives an unequal mixture of enantiomers.

c. Use of a chiral phosphoric acid catalyst results in the formation of a racemic mixture of products.

d. Hydrolysis results in the formation of an achiral product.

e. When sulfuric acid is used as catalyst, the ester groups react at unequal rates.

Explanation / Answer

Hydrolysis of ester as shown above.

The true statements reagrding the hydrolysis of this substrate would be,

b. Hydrolysis with lipase gives an unequal mixture of enantiomers.

This is when only one of the ester group reacts under the given condition.

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