Give the substitution and elimination products you would expect from the following reactions.
a. 3-bromo-3-ethylpentane heated in methanol

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)

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.

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

(b)

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

Four alkenes are formed from the E1 reaction of 3-bromo-2,3-dimethylpentane and methanol. Draw the structures of the alkenes and rank them according to the amount that would be formed.

Draw the major elimination product that would be obtained from each of the following reactants with a strong base and with a weak base:

a.