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Chapter 22: 54P (page 868)

Draw a stepwise mechanism for the following reduction.

Short Answer

Expert verified

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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Most popular questions from this chapter

Question: Draw the structure corresponding to each name.

  1. 5-methylheptanoyl chloride
  2. isopropyl propanoate
  3. acetic formic anhydride
  4. N-isobutyl-N-methylbutanamide
  5. 3-methylpentanenitrile
  6. o-cyanobenzoic acid
  7. sec-butyl 2-methylhexanoate
  8. N-ethylhexanamide

Question: Draw the organic products formed in each reaction.

a.

b.

c.

d.

e.

f.

g.

h.

Question: What product is formed when acetic acid is treated with each reagent: (a)CH3NH2 ; (b) CH3NH2, then heat; (c) CH3NH2 + DCC?

What Grignard reagent and aldehyde (or ketone) are needed to prepare each alcohol? Show all possible routes

(a)

(b)

(c)

Draw the products formed from LiAlH4 reduction of each compound.
See all solutions

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