CHEMISTRY 3302 June 4, 1998
1) Neither calculators nor notes of any kind are allowed while
taking the exam. The periodic table is, of course, freely available.
2) Sign the first exam page at the top with your name (please
also print your name to ensure legibility). To be considered
for regrading, the exam must be taken in ink.
3) If a problem is giving you particular difficulty, go on with
other questions and return to it as time allows. The questions
are approximately in order of difficulty.
4) Concise explanations which expand upon your answers are encouraged.
Partial credit will be liberally awarded if it is clear that you
had the right idea, but simply made a small mistake at a later
point in the answer. Don't get carried away, however, as this
will waste your time.
I. Molecular Properties (25 points)
Circle the one choice that fits the described property.
Least reactive to nucleophilic substitution by MeO-
Best acceptor for Michael (1,4) addition
Highest boiling point
II. Chemical Transformations (28 points)
Fill in the boxes with the appropriate educts, reagents, or products.
A normal workup is assumed. Be sure to show stereochemistry if
necessary to distinguish isomers.
III. Organic Logic and Analysis (20 points)
Consider the following transformation of a g-aminoester
to a lactam:
a. Write a step-by-step mechanism for the formation of the lactam.
b. On the previous page, circle the most basic atom (i.e., the
site that is most readily protonated by an acid) in the starting
material and in the product. If it is a different atom
in the product than in the starting material, explain why a change
c. This reaction is, in fact, a reversible equilibrium. What drives this reaction to the right?
IV. Multistep Synthesis (27 points possible)
On the next page is a list of 8 reagents (feel free to tear it
off). You will need 6 of these reagents to complete the total
synthesis outlined below (2 are not used). Fill in the reagents
by letter in the boxes over the reaction arrows. The structures
of the starting material, final product, and one intermediate
are provided, as is one set of reagents. Draw the correct structures
for all other intermediates in the boxes provided. Certain
spectral clues are listed under some of the structure boxes. A
normal workup is assumed for all reactions.
REAGENTS FOR PROBLEM 4: