1. (3 points) Write the structure of (S)-1-bromo-2-methylbutane and give the name and structure for the product that would be expected from its reaction with sodium iodide in acetone. What mechanism is involved?

This is an SN2 mechanism, but inversion is not observed because the reaction does not involve the stereocenter.

2. (4 points) Write a complete mechanism for the solvolysis reaction of
1-bromo-1-methylcyclopentane in methanol solvent. Both a substitution and an elimination product are formed - show pathways to both products.

3. (3 points) Show a mechanism for the reaction shown below.
The cis isomer of the compound shown below does not do the same reaction. Explain why not.

The cis isomer would not have the nucleophile and the leaving group properly placed for the backside attack of an SN2 mechanism.