8. Elimination Reactions

Predict the product

Predict the product

Propose mechanisms for the following reactions.

(a)

HINT: Alcohol dehydrations usually go through E1 elimination of the protonated alcohol, with a carbocation intermediate. Rearrangements are common.

a. Which reacts faster in an E2 reaction: 3-bromocyclohexene or bromocyclohexane?

b. Which reacts faster in an E1 reaction?

Draw the major product obtained when an alkyl halide in [PROBLEM 9-83] undergoes an E1 reaction.

c.

What products will be obtained from the E1 reaction of the alkyl halides in [PROBLEM 9-45]?

b.

What products will be obtained from the E1 reaction of the alkyl halides in [PROBLEM 9-45]?

a.

Propose a mechanism for the following reaction:

What products will be obtained from the E1 reaction of the alkyl halides in [PROBLEM 9-45]?

c.

Although 2-methyl-1,2-propanediol is an unsymmetrical vicinal diol, only one product is obtained when it is dehydrated in an acidic solution.

b. Why is only one product obtained?

Identify the bonds that break and form in the following elimination reactions.

(a)

Practice your electron-pushing skills by drawing a mechanism for the following E1 reactions.

(a)