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Chapter 21: 19P (page 817)

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

a.

b.

Short Answer

Expert verified

a.

b.

c.

Step by step solution

01

Wittig reaction 

The reaction of the carbonyl compound with the Wittig reagent leads to the formation of substituted alkene.

02

Product formation 

a.

The reaction of benzaldehyde with the given reagent results in the formation of (Z)-but-1-enylbenzene and (E)-but-1-enylbenzene.

The reaction is shown below:

Product formation in a

b.

The reaction of benzaldehyde with the given reagent results in the formation of (E)-1,2-diphenylethene and (Z)-1,2-diphenylethene.

The reaction is shown below:

Product formation in b

c.

The reaction of benzaldehyde with the given reagent results in the formation of (Z)-methyl 3-phenylacrylate and methyl cinnamate.

The reaction is shown below:

Product formation in c

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Most popular questions from this chapter

An unknown compound D exhibits a strong absorption in its IR spectrum at 1692 cm-1 . The mass spectrum of D shows a molecular ion at m/z = 150 and a base peak at 121. The 1H- NMR spectrum of D is shown below. What is the structure of D?

Show two different methods to carry out the following transformation: a one-step method using a Wittig reagent, and a two-step method using a Grignard reagent. Which route, if any, is preferred?

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a.

b.

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a.

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