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Chapter 9: Q88P (page 453)

Which reactant in each of the following pairs undergoes an elimination reaction more rapidly? Explain your choice.

Short Answer

Expert verified
  1. (CH3)3CBr

Step by step solution

01

Definition of elimination reaction

Elimination reaction often competes with substitution reactions. In this reaction, a substrate (typically an alkyl halide) eliminates one equivalent (unit) of acid to form an alkene. Two possible mechanisms are available for this elimination reaction 鈥�E1 and E2 mechanisms.

02

 

a) (CH3)3CBr undergoes an elimination reaction more rapidly because Br-is a better leaving group than Cl-.

03

Step 3:

This compound is the only one that undergoes E2 elimination reaction because the other compound does not have an axial hydrogen bonded to beta-carbon.

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Most popular questions from this chapter

How will the rate of the reaction between bromomethane and hydroxide ion be affected if the following changes in concentration are made?

a. The concentration of the alkyl halide is not changed and the concentration of the nucleophile is tripled.

b. The concentration of the alkyl halide is cut in half and the concentration of the nucleophile is not changed.

c. The concentration of the alkyl halide is cut in half and the concentration of the nucleophile is doubled.

Why is a cumulated diene not formed in the reaction shown below?

If 2-fluoropentane were to undergo an E1 reaction, would you expect the major product to be the more stable alkene or the less stable alkene? Explain your answer.

For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.

a. (R)-2-bromohexane + high concentration of CH3O-

b. (R)-3-bromo-3-methylhexane + CH3OH

c. trans-1-chloro-2-methylcyclohexane + high concentration of CH3O-

d. trans-1-chloro-3-methylcyclohexane + high concentration of CH3O-

e. 3-bromo-3-methylpentane + high concentration of CH3CH2O-

f. 3-bromo-3-methylpentane + CH3CH2OH

a. Explain why the reaction of an alkyl halide with ammonia gives a low yield of primary amine.

b. Explain why a much better yield of primary amine is obtained from the reaction of an alkyl halide with an azide ion (-N3), followed by catalytic hydrogenation. (Hint: An alkyl azide is not nucleophilic.)
See all solutions

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