Organic Chemistry I Chem 334 - Fall 2011

Quiz 4

Professor Carl C. Wamser

1. (2 points)  Give a complete name for the compound below:

5-bromo-2-cyclohexyl-4-methylhexan-3-ol

2. (2 points)  Calculate ?H for the reaction below. Use units of kcal/mol.

3. (3 points)  Write a complete mechanism for the SN1 reaction of cyclobutanol with HI. 
Show all steps and use electron-pushing arrows.

4. (3 points)  Chlorination of 2,2-dimethylbutane gives three products of formula  C6H13Cl.
Write the structures of the three products expected and predict their relative ratios,
assuming free radical chlorination prefers  3° > 2° > 1°  in the ratio  5 : 4 : 1 .