CHE 31: Organic Chemistry
Test 2
April 24, 1998

1. Multiple choice (2 points each)
Which of the following compounds would be the least reactive with nitric acid in the presence of sulfuric acid?

Which of the following compounds is the most acidic?

Which of the following compounds would be the most reactive towards water?

Which of the following is the best method for accomplishing the transformation shown?


Which of the following best describes the problems involved in using the reaction shown in a synthesis?


2. Provide the major products for the following reactions, indicating stereochemistry where relevant. (4 points each)

3. Predict the major product(s) formed in the bromination of anisole, showing the important resonance structures. Show a mechanism for this reaction, using arrows to show the flow of electrons. Why do you think this reaction can be carried out without a catalyst? (20 points)

4. Propose syntheses to accomplish the following transformations, using any needed reagents. (8 points each)

(a)

(b)

(c)

5. A student carried out solubility tests on her unknown compound and found that it was soluble in water and turned blue litmus paper red. She determined that making her derivative would involve two separate steps. (10 points)
(a) What kind of functional group does she have?
(b) What reagent is needed for the first step in her derivative preparation?
(c) Show an example of this type of reaction.

6. Purine (shown below) is a heterocyclic aromatic compound whose derivatives are constituents of DNA and RNA. Why is purine aromatic? Which, if any, of the nitrogens contribute lone pair electrons to the p system? (8 points)