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1. (10 pts) Give a plausible mechanism for this transformation.
(J. Org. Chem., 1996, 61, 5916)


2. (10 pts) Explain why ozonolysis of the acetate of 
cyclohex-2-en-1-ol leads to the product shown upon methanolysis. 
(J. Org. Chem., 1996, 61, 5953)


3.  (10 pts)   Give a mechanistic explanation for the following 
transformation. (J. Org. Chem., 1996, 61, 7976)


4. (8 pts) Give a mechanism for the first step.  (4 pts) Predict 
the product for step 2.  (2 pts) What is the structure of 9-BBN? 
(3 pts) What is Swern oxidation?
(J. Org. Chem., 1996, 61, 8456)


5.  (6 pts for each ?; 48 pts total) 
In each of the following give the major product for the 
indicated reaction.

(a)   
(J. Org. Chem., 1996, 61, 8338)

(b)  
(J. Org. Chem., 1996, 61, 8604)

(c)  
(J. Org. Chem., 1996, 61, 8362)

(d) 
(J. Org. Chem., 1996, 61, 8439)

(e)  
(J. Org. Chem., 1996, 61, 5736)

6. (10 pts)   Give the mechanism of the following transformation.
(J. Org. Chem., 1996, 61, 8366)


7. Two rotamers are shown (A and B).  The syn-rotamer (A) shows 
a signal in the 1H NMR for the methyl groups of the t-butyl unit 
at 1.23 ppm.  The other rotamer (B) shows the same signal at 
1.45 ppm.  (8 pts) Explain.  Rotamer A is present in a larger 
concentration than rotamer B.  (8 pts) Offer a brief explanation 
that accounts for this observation.
(J. Org. Chem., 1996, 61, 8402)


8. (10 pts) Give a reasonable mechanism for the following transformation.
(J. Org. Chem., 1996, 61, 8148)


9. (10 pts) Give a reasonable mechanism for the following transformation.
(J. Org. Chem., 1996, 61, 8636)

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