Chemistry Department

 

University of Alberta

           

CHEM 263 B2

 

Exam II

 

Thursday, March 12, 2009

 

1.    Name the following compounds:

 

1. (3 points)

 

 

trans-4-tert-butylcyclohexanecarbaldehyde

 

2. (5-points)

 

 

(E,3R)-3-ethoxy-6-hydroxy-3-methyl-4-hexen-2-one

 

 

3. (2 points)

 

 

Oxacyclopropane or ethylene oxide

 

2.    Using the following partial structure, draw the structure of (R)-4-methoxy-4-methylheptanal. (4 points)

 

 

 

3.    What reagents would you use to effect the following conversions?

 

1.  

 

2.  

 

 

 

3.  

 

 

4.  

 

5.  

4.    Give the structure(s) of the principle organic products of the following reactions:

 

1.  

 

2.  

3.  

           

           

4.  

5.  

           

 

5.    Provide a synthetic pathway for the following transformations using the starting material provided and any other reagents:

 

1.  

 

 

2.  

6.    Propose a mechanism for the following reaction (don’t forget the curved arrows!):

 

 

 

7.    Propose a mechanism for the following reaction:

 

Don’t forget that you are permitted to use a partial structure such as follows: