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Chapter 21: 17P (page 817)

Draw the products of the following Wittig reactions

a.

b.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Wittig reaction 

The treatment of a carbonyl compound with triphenylphosphonium ylide forms an alkene. Tiphenylphosphonium ylide is known as the Wittig reagent.

02

Product formation

a.

The reaction of propan-2-one with Ph3P=CH2 is shown below:

Product formation in a

b.

The reaction of cyclopentanone with Ph3P=CHCH2 CH2 CH2 CH3is shown below:

Product formation in b

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Most popular questions from this chapter

Explain why benzaldehyde is less reactive than cyclohexanecarbaldehyde towards nucleophilic attack.

Devise a synthesis of each alkene using a Wittig reaction to form the double bond. You may use benzene and organic alcohols having four or fewer carbons as starting materials and any required reagents

a.

b.

Draw the products of each reaction.

a.

b.

Which compound forms the higher concentration of hydrate at equilibrium, PhCOCHO or PhCH2CHO ? Explain your reasoning.

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.
See all solutions

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