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Chapter 9: Q94P (page 391)

Rank the following from most reactive to least reactive in an E2reaction:

Short Answer

Expert verified

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.

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

Step 2:

The first compound has two axial hydrogens attached to beta carbon, the second compound has one axial hydrogen attached to the beta carbon, but it cannot form the more substituted product alkene that can be formed by the first compound. The last compound does not have axial hydrogens attached to beta carbon so it cannot undergo E2 reaction.

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Most popular questions from this chapter

Which alkyl halide in each pair is more reactive in an E2 reaction with hydroxide ion?

Amines are good nucleophiles, even though they are neutral. How would the rate of an SN2 reaction between an amine and an alkyl halide be affected if the polarity of the solvent is increased?

Two bromoethers are obtained from the reaction of the following alkyl dihalide with methanol. Draw the structures of the ethers.

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.)

a. Propose a mechanism for the following reaction.

b. Explain why two products are formed.

c. Explain why methanol substitutes for only one of the bromines.
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