Organic Chemistry 354 Quiz - November 14, 1997

Dr. Sundin

1. Give the mechanism of the following transformation:

2. a. Which aldehyde gives the following aldol when treated with sodium hydroxide?

b. On work-up, the above product often dehydrates. Give a one word answer describing the product which best explains why the above aldol easily dehydrates.

3. Outline a synthesis of one of the following compounds using either the malonic ester synthesis or the acetoacetic ester synthesis.

4. Give the structure of a compound with a formula, C₄H₉Cl, and the following low resolution proton nmr:

1.00 d, 3H

1.46 d, 3H

1.60 d, 2H

3.95 d, 1H