Predict the products of the following S_N2 reactions.
(c)


(d)

Often, compounds can be synthesized by more than one method. Show how this 3° alcohol can be made from the following:

(d) a 3° alkyl bromide

Give the substitution products expected from solvolysis of each compound by heating in ethanol.

(c)

(d)

Propose a mechanism for the reaction of benzyl bromide with ethanol to give benzyl ethyl ether.

Propose a mechanism involving a hydride shift or an alkyl shift for each solvolysis reaction. Explain how each rearrangement forms a more stable intermediate.

Hint: Most rearrangements convert 2° (or incipient 1°) carbocations to 3° or resonance-stabilized carbocations.

(d)

Choose the member of each pair that will react faster by the SN1 mechanism.

e. 2-iodo-2-methylbutane or tert-butyl chloride

f. 2-bromo-2-methylbutane or ethyl iodide

When tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether.

b. What happens to the rate if the concentration of tert-butyl bromide is tripled and the concentration of ethanol is doubled?

c. What happens to the rate if the temperature is raised?

tert-Butyl chloride undergoes solvolysis in both acetic acid and formic acid. Solvolysis occurs 5000 times faster in one of these two solvents than in the other. In which solvent is solvolysis faster? Explain your answer. (Hint: Formic acid is more polar than acetic acid.)

Rank the following alkyl halides from most reactive to least reactive in an S_N1 reaction:

2-bromo-2-methylpentane, 2-chloro-2-methylpentane, 3-chloropentane, and 2-iodo-2-methylpentane.