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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

Two naturally occurring compounds that contain stable cyclic hemiacetals and acetals are monensin and digoxin, the chapter-opening molecule. Monensin, a polyether antibiotic produced by Streptomyces cinamonensis,is used as an additive in cattle feed. Digoxin is a widely prescribedcardiac drug used to increase the force of heart contractions. Label each acetal, hemiacetal, and ether in both compounds.

β-d-Glucose, a hemiacetal, can be converted to a mixture of acetals on treatment with in the presence of acid. Draw a stepwise mechanism for this reaction. Explain why two acetals are formed from a single starting material.

Draw a stepwise mechanism for the following reaction

Draw the products of each reaction.

a.

b.

What carbonyl compound and diol are needed to prepare each compound?

a.

b.
See all solutions

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