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Chapter 21: 20P (page 817)

What starting materials are needed to prepare each alkene by a Wittig reaction? When there are two possible routes, indicate which route, if any, is preferred.

a.

b

c.

Short Answer

Expert verified

a.

b.

c.

Step by step solution

01

Wittig reaction

It involves the formation of an alkene by the treatment of a ketone or an aldehyde with ylide. The ylide is termed Wittig reagent.

02

Formation of product

a.

The reaction is shown below.

Synthesis in a

b.

The reaction is shown below.

Synthesis in b

c.

The reaction is shown below.

Synthesis in c

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Most popular questions from this chapter

What two enamines are formed when 2-methylcyclohexanone is treated with (CH3)2NH?

Draw the products of each reaction.

a.


b.

c.

d.

e.

f.

g.

h.

Brevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acid-catalyzed cyclization of 6,7-dihydroxynonan-2-one.

a. Suggest a structure for brevicomin.

b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2-one. You may also use three-carbon alcohols and any required organic or inorganic reagents.

Outline a synthesis of each Wittig reagent from Ph3P and an alkyl halide.

a.

b.

c.

Draw a stepwise mechanism for the following reaction
See all solutions

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