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Chapter 21: Q12P (page 1106)

When ethyl 4-hydroxybutyrate is heated in the presence of a trace of a basic catalyst (sodium acetate), one of the products is a lactone. Propose a mechanism for the formation of this lactone.

Short Answer

Expert verified

Mechanism of the reaction:

Step by step solution

01

About ethyl 4-hydroxybutyrate:

The ethyl group and hydroxyl butane attached by the COO group is called ethyl 4-hydroxybutyrate.

This has the following structure.

Ethyl 4-hydroxybutyrate

02

About lactone:

The cyclic esters of carboxylic acid derivatives are called lactones. These compounds have unsaturation in the ring in which one or more carbon atoms of the rings get replaced by heteroatoms.

03

Mechanism of the reaction:

The negative charge on the oxygen atom of acetate ion attacks the hydrogen of ethyl 4-hydroxybutyrate. This will result in the formation of a negative charge on the oxygen of ethyl 4-hydroxybutyrate.

Several rearrangements lead to the formation of the desired product. The mechanism is given below.

Mechanism of the reaction

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