Chemistry Department

 

University of Alberta

           

CHEM 263 B2

 

Exam II

 

Tuesday, March 9, 2010

 

1.    Name the following compounds:

 

1. (2 points)

 

 

oxacyclopentane or tetrahydrofuran

 

2. (4-points)

 

 

(R)-4-methoxy-4,5-dimethyl-2-hexanone

 

3. (4 points)

 

 

cis-3-hydroxycyclohexanecarbaldehyde

 

2.    Using the following partial structure, draw the structure of (E,3R)-3-ethoxy-6-hydroxy-3-methyl-4-hexen-2-one. (7 points)

 

 

 

3.    What reagents would you use to effect the following conversions?  (21 points)

 

1.  

 

 

2.  

 

 

3.  

 

 

4.  

 

5.  

 

6.  

 

7.  

 

 

4.    Dutch elm disease is caused by a fungus transmitted to elm trees by the elm bark beetle.  The female beetle, when she has located an attractive elm tree, releases several pheromones, including multistriatin.  These pheromones attract male beetles, which bring with them the deadly fungus.  Treating multistriatin with dilute aqueous acid at room temperature leads to the formation of a product, C₁₀H₂₀O₃, which shows a strong IR peak near 1715 cm^-1.  Propose a structure for this product.  (3 points)

 

 

 

5.    Give the structure(s) of the principle organic products of the following reactions:  (15 points)

 

1.  

 

 

2.  

           

           

3.  

 

           

4.  

 

           

 

5.  

           

 

 

6.    Provide a synthetic pathway for the following transformations using the starting material provided and any other reagents:  (27 points)

 

1.  

 

 

 

2.  

 

 

 

 

3.  

 

 

7.    Propose a mechanism for the following reaction (don’t forget the curved arrows!):  (I12 points)