8. Elimination Reactions

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

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.

a. Draw the structures of the products obtained from the reaction of each enantiomer of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol.

b. Are all the products optically active?

What are the products of the following reactions?

f.

What are the products of the following reactions?

e.

For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.

d. trans-1-chloro-3-methylcyclohexane + high concentration of CH₃O⁻

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

Draw the structures of the products obtained from the following reaction:

Draw the products of each of the following S_N2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

a. (3S,4S)-3-bromo-4-methylhexane + CH₃O⁻

For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.

c. trans-1-chloro-2-methylcyclohexane + high concentration of CH₃O⁻

What product is formed when 1-bromopropane reacts with each of the following nucleophiles?

d. HS⁻

What product is formed when 1-bromopropane reacts with each of the following nucleophiles?

c. CH₃S⁻