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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

Which species in each pair is more stable?

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.)

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