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Chapter 8: Q.49 (page 328)

What alkyl chloride affords the following alkene exclusively under E2 reaction conditions?

Short Answer

Expert verified

The alkyl chloride forms the mentioned alkene is shown below:

Step by step solution

01

Identification of the substrate

The primary halides always favor E2 reactions, whereas the secondary and tertiary halides favor E1 and E2, both depending on the bases used.

So to make the product exclusively an E2 product, a bulky base like potassium-tert-butoxide is used, which takes up a β proton from the less hindered carbon.

02

Different types of β hydrogens

Different types of βhydrogens give different types of elimination products. Here only one type of βhydrogen is present, so it gives only one product.

So, taking into account all the steps and the types of βhydrogens present, the possible alkyl halide which undergoes E2 reaction is as follows:

Representation of E2 reaction

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Most popular questions from this chapter

Label each pair of alkenes as constitutional isomers, stereoisomers, or identical.

a.

b.

c.

d.

Label each pair of alkenes as constitutional isomers, stereoisomers, or identical.

a.

b.

c.

d.

How does each of the following changes affect the rate of an E1 reaction?

a. doubling [RX]

b. doubling [B:]

c. changing the halide from (CH3)3CBrto CH3CH2CH2Br

d. changing the leaving group from Cl–toBr–

e. changing the solvent from DMSO to CH3OH

Rank the following alkenes in order of increasing stability:

Name each compound and decide which stereoisomer will react faster in an E2 elimination reaction. Explain your choice.
See all solutions

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