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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

Draw the products (including stereoisomers) formed when benzaldehyde (C6H5CHO) is treated with each Wittig reagent

a.

b.

Draw the products formed in each reaction sequence.

a.

b.

Give the structure corresponding to each name.

a. 2-methyl-3-phenylbutanal

b. 3,3-dimethylcyclohexanecarbaldehyde

c. 3-benzoylcyclopentanone

d. 2-formylcyclopentanone

e. (R)-3-methylheptan-2-one

f. m-acetylbenzaldehyde

g. 2-sec-butylcyclopent-3-enone

h. 5,6-dimethylcyclohex-1-enecarbaldehyde

Consider the para-substituted aromatic ketones, NO2C6H4COCH2 (p-nitroacetophenone) and CH3OC6H4COCH3 (p-methoxyacetophenone).

a. Which carbonyl compound is more stable?

b. Which compound forms the higher percentage of hydrate at equilibrium?

c. Which compound exhibits a carbonyl absorption at a higher wavenumber in its IR spectrum?

Explain your reasoning in each part.

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

a.

b.

c.
See all solutions

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