1. (2 points) Write a complete IUPAC name for the following:

4-bromo-1-cyclopentyl-3-methylbutan-1-ol

2. (3 points) Write a complete mechanism for the SN1 reaction of cyclopentanol to form chlorocyclopentane. Show all steps and use electron-pushing arrows in each step.

3. (3 points) Write a complete mechanism for the substitution reaction forming chlorocyclopentane from cyclopentane. Show initiation and propagation steps.
Electron-pushing arrows are not required.

4. (2 points) Clearly identify the bonds that are broken and made in the reaction shown below. Find appropriate BDE values from the table and calculate ΔH for the reaction (use kJ/mol).