Give the substitution products expected from solvolysis of each compound by heating in ethanol.
(c)
(d)

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

c. n-propyl bromide or allyl bromide

d. 1-bromo-2,2-dimethylpropane or 2-bromopropane

Predict the compound in each pair that will undergo solvolysis (in aqueous ethanol) more rapidly.

(c)

(d)

Allylic halides have the structure

a. Show how the first-order ionization of an allylic halide leads to a resonance-stabilized cation.

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

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)

Predict the products of the following S_N2 reactions.

(c)

(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