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Chapter 16: Q79P (page 796)

Draw structures for A-D for each of the following:

Short Answer

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An aldehyde or a ketone reacts with a phosphonium ylide in a Wittig reaction to form an alkene. A Wittig reaction is a concerted [2 + 2] cycloaddition reaction.

Step by step solution

01

Wittig reaction

An aldehyde or a ketone reacts with a phosphonium ylide in a Wittig reaction to form an alkene. A Wittig reaction is a concerted [2 + 2] cycloaddition reaction.

02

Formation of the products

5-methyl cyclopente-2-ene-1-one reacts with dialkyl copper lithium to form the compound which reacts with CF3COO- to form the compound which then reacts with DIBAL-H to form the desired compound as follows:

b)

In the presence of NaBH4, carbonyl compound (ketone) is converted to secondary alcohol followed by reaction with PBr3 and nBuLi to form the desired compound as follows:

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Most popular questions from this chapter

Identify compounds A and B:

In the mechanism of cyanohydrin formation, why isHCN the only acid that protonates the alkoxide ion instead of HCI?

Give two names for each of the following:

a.

b.

c.

d.

e.

f.

What alcohols are obtained from the Reduction of the following compounds with sodium borohydride?

a. 2-methylpropanal b. cyclohexanone c. 4-tert-butylcyclohexanone d. acetophenone

Why are numbers not used to designate the position of the functional group in propanone and butanedione?
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