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The Wittig reaction is useful for placing double bonds in

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 59SP Chapter 18

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 59SP

Problem 59SP

The Wittig reaction is useful for placing double bonds in less stable positions. For example, the following transformation is easily accomplished using a Wittig reaction.

(a) Show how you would use a Wittig reaction to do this.

(b) Show how you might do this without using a Wittig reaction, and explain why the Wittig reaction is a much

better synthesis.

Step-by-Step Solution:

Solution:

Here we have to explain the synthesis of the given chemical reaction by wittig reaction and the synthesis of the same chemical reaction  by without using wittig method..

Step 1

Wittig reaction:-

The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide (often called a Wittig reagent) to give an alkene and triphenylphosphine oxide.

alkene synthesis using the Wittig reaction

        ylide                         aldehyde or ketone                                  alkene

General Mechanism:-

       

The nucleophilic C of the ylide Wittig reagent adds to the electrophilic C in the polar carbonyl group, electrons from the C=O π bond are used to form a σ bond to the +ve P atom. This creates a cyclic intermediate called an oxaphosphetane.

Decomposition of the intermediate by breaking the C-P and C-O σ bonds leads to the formation of the C=C π bond of the alkene and triphenylphosphine oxide.

Step 2 of 2

Chapter 18, Problem 59SP is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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The Wittig reaction is useful for placing double bonds in