Organic Chemistry I Chem 334 - Fall 2010

Quiz 4

Professor Carl C. Wamser

1.  (2 points)  Give complete names for each of the following:

a)

3,3-dimethylcyclohexanol

b)

2-ethyl-1,4-hexanediol

2-ethylhexane-1,4-diol

2.  (2 points)  Complete each of the following reactions by adding the missing part: 
either the starting compounds, the necessary reagents and conditions, or the final major product. 
Include stereochemistry if it is specific.

a)

b)

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

4.  (3 points)  Use the attached table of bond dissociation energies to calculate delta H for the reaction shown below. 
Clearly indicate which BDE values you use for the calculation, and which bonds they correspond to in the reaction.
Use kcal/mol units.