Draw the stereoisomers that are formed from the following S_N1 reactions:
a. 3-bromo-3-methylpentane and methanol
b. 3-chloro-3-methylhexane and methanol

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

(a) (CH₃CH₂)₂CH—Cl or (CH₃)₃C—Cl

(b)

Choose the member of each pair that will react faster by the S_N1 mechanism.

a. 1-bromopropane or 2-bromopropane

b. 2-bromo-2-methylbutane or 2-bromo-3-methylbutane

Furfuryl chloride can undergo substitution by both S_N2 and S_N1 mechanisms. Because it is a 1° alkyl halide, we expect S_N2 but not S_N1 reactions. Draw a mechanism for the S_N1 reaction shown below, paying careful attention to the structure of the intermediate. How can this primary halide undergo S_N1 reactions?

Optically active butan-2-ol racemizes in dilute acid. Propose a mechanism for this racemization.

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

Which reacts faster in an S_N1 reaction?

The bromoalkanes shown below participate in S_N1 reactions with the relative rates shown. Explain this trend. relative rate:

Practice your electron-pushing skills by drawing a mechanism for the following S_N1 reactions.

(b)