7. Substitution Reactions

Predict the product of the following substitution reactions, paying close attention to the stereochemical outcome of the reactions.

(f)

Predict the product of the reaction

Predict the product of the reaction

For each reaction, give the expected substitution product, and predict whether the ­mechanism will be predominantly first order (SN1) or second order (SN2).

d. cyclohexylbromide + methanol

e. cyclohexylbromide + sodium ethoxide

Explain why the following alkyl halide does not undergo a substitution reaction, regardless of the base that is used.

Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:

c. benzyl chloride + CH₃CH₂OH

d. allyl chloride + CH₃OH

Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:

a. (R)-2-bromopentane+CH₃O⁻

b. (R)-3-bromo-3-methylheptane+CH₃OH

Propose a mechanism for the following reaction:

What stereoisomers do the following reactions form?

b.

What stereoisomers do the following reactions form?

c.

What stereoisomers do the following reactions form?

a.

What is the major product of each of the following reactions?

d.

What is the major product of each of the following reactions?

c.

What is the major product of each of the following reactions?

b.

What is the major product of each of the following reactions?

a.