8. Elimination Reactions

Predict the product(s) of the following substitution or elimination reactions, paying close attention to the stereochemical outcome of the reactions.

(g)

Which of the following S_N2 and E2 reactions, respectively, is faster? Justify your choice.

(a)

For which of the following reactions would you expect elimination to be more favored than substitution?

(a)

For each of the following reactions, (1) decide whether an E2 or an E1 occurs, and (2) draw the major elimination product:

a.

b.

What are the products of the following reactions?

a.

b.

The following chlorocyclohexane undergoes neither Sₙ2 nor E2 under the conditions shown. Why?

Predict the product of the following reactions.

(f)

Draw the elimination products that are formed when 3-bromo-3-methyl-1-butene reacts with

a. CH₃O⁻.

Silver-assisted solvolysis of bromomethylcyclopentane in methanol gives a complex product mixture of the following five compounds. Propose mechanisms to account for these products.

(c)

Predict the product for the following reaction and write a mechanism to explain how it is formed.

For which of the following reactions would you expect elimination to be more favored than substitution?

(d)

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.

(b)

Which of these reactions are likely to produce both elimination and substitution products?

a. 2-bromopentane + NaOCH₃

b. 3-bromo-3-methylpentane + NaOMe. (Me = methyl, CH₃)

c. 2-bromo-3-ethylpentane + NaOH

Make models of the following compounds, and predict the products formed when they react with the strong bases shown.

(d)

Predict the major product(s) of the following elimination reactions, paying close attention to the stereochemical outcome of the reactions.

(d)