Exam 3
Name __________________________
CHEM 212
1. (27 pts) Complete the following chemical reactions showing all major organic products; illustrate proper
stereochemistry where appropriate. If no reaction occurs, indicate “NR”:
a.
b.
c.
d.
e.
f.
g.
h.
i.
2. (9 pts) Indicate the starting materials and reagents necessary to make the following.
a.
b.
c.
3. (8 pts) Using mechanisms, illustrate the process for the conversion of diethyl malonate to the alkylated acetic acid
shown.
4. (8 pts) Propose a mechanism for the following Fischer Esterification:
O
OH
+
OH
H2SO4 cat.
O
O
+
H2O
5. (7 pts) Give the pKA for the ionization of the -hydrogens of the following carbonyl compounds. For -dicarbonyls,
indicate the pKA for the central methylene protons as shown.
6. (6 pts) trans-Peptidase is the active enzyme that bacteria
use to build their cell walls. Penicillins are potent antibacterial compounds that inhibit this process by binding to
the hydroxyl group of trans-peptidase and rendering it
inert. Shown below are the active end of trans-peptidase
and the structure of penicillin. Propose a process/reaction
by which penicillin binds to the enzyme. Hint: look for the
most reactive carbonyl in the molecule.
7. (12 pts) We studied the NAS reactions of the carboxylic acid derivatives. There are many other families of
compounds that also undergo NAS reactions (at least from a reagent/product standpoint). Suggest the probable
course of the NAS reactions of the following compounds:
8. (15 pts) Short syntheses. Show how the following starting materials can be converted to the indicated products using
a multi-step method:
a.
b.
c.
9. (8 pts) DEET, sold under the trade name “Off” is a powerful repellant for mosquitoes. Propose a
synthesis from m-bromotoluene and any reagents you require.
Approx. Course Grade: A
A-
B+
B
B-
C+
C
D
F
O
N
SCORE _______ /100 pts