Predict the major and minor elimination products of the following proposed reactions (ignoring any possible substitutions for now). In each case, explain whether you expect the mechanism of the elimination to be E1 or E2.
(a)

Propose mechanisms for the following reactions. Additional products may be formed, but your mechanism only needs to explain the products shown.

(a)

Write a balanced equation for each reaction, showing the major product you expect.

(d)

Predict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.

h. 1-bromo-1-methylcyclopentane heated in methanol

Predict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.

g. 1−bromo−1−methylcyclopentane + NaOEt in ethanol

For each reaction, decide whether substitution or elimination (or both) is possible, and predict the products you expect. Label the major products.

a. 1−bromo−1−methylcyclohexane + NaOH in acetone

Under second-order conditions (strong base/nucleophile), S_N2 and E2 reactions may occur simultaneously and compete with each other. Show what products might be expected from the reaction of 2-bromo-3-methylbutane (a moderately hindered 2° alkyl halide) with sodium ethoxide.

When (1-bromoethyl)cyclohexane is heated in methanol for an extended period of time, five products result: two ethers and three alkenes. Predict the products of this reaction, and propose mechanisms for their formation.

Give the substitution and elimination products you would expect from the following reactions.

a. 3-bromo-3-ethylpentane heated in methanol