150 points total, one hour duration.  Fill in the answers directly on to the question sheet.

1.  (12 points) Give a systematic name for each of the following, including stereochemistry where appropriate.

4,4-dichlorocyclohexanecarbaldehyde

(2R)-amino-4-octanone

2. (16 points) Explain (using resonance forms) why p-nitrophenylacetone (A) is more acidic than phenylacetone (B) at the benzylic position (acidic Hs are shown).

3. (42 points) What would be the product(s) of each of the following reactions?

4. (10 points) Rank the following compounds A-D in order of increasing acidity:

D is an ether, so it is an extremely weak base. A is a simple sec. alcohol, pK_a ~18, C and D are phenols. D has an NO₂ group that can stabilize the anion (see Q2 above), giving

D < A < B < C

5. (28 points) How might you accomplish the following conversions?

6.  (14 points) Glucose can be hydrolyzed as shown to give an aldehyde.  Give a mechanism for the reaction:

7.  (28 points)  How might you accomplish either one of the following syntheses?  You must use the starting material shown at least once; other than this, you may use any legitimate reagent which adds two carbons or fewer.   If you have time to answer both parts, I will grade the better of the two.  You may use the back page.  Do not worry about the stereochemistry in these products, this lies beyond the scope of this class.

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