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Chapter 22: 54P (page 868)

Draw a stepwise mechanism for the following reduction.

Short Answer

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Answer

Reduction follows multiple steps:

Step 1

Step 2

Step 3

Step 4

Step by step solution

01

Step-by-Step Solution Step 1: Reducing agents

Esters give alcohol on reduction with strong reducing agents like LiAlH4 .

Cyclic ketones are known as lactones. When treated with strong reducing agents, lactones give alcohol.

02

Reduction of lactone mechanism

In the mechanism, the reagent LiAlH4 reduces the first cyclic ring of lactone to give aldehyde, followed by complete reduction to give alcohol.

Reduction of first lactone ring

Reagent LiAlH4 provides nucleophile H- , which attacks the carbonyl carbon and forms tetrahedral intermediate giving aldehyde.

Formation of aldehyde

The formed aldehyde undergoes complete reduction with LiAlH4 to give alcohol.

Reduction of aldehyde

The second lactone ring is also reduced similarly, giving alcohol.

Reduction of second lactone ring

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