CHEM 2324
April 23, 2009
Version A
Exam 3
Name:
UTEP ID #:
1.-5. Match each drawing to a step in the synthesis of trimethylamine from methanal (formaldehyde), dimethylamine, and
NaBH
3
CN (not shown). The initial reactants are show but not the charges.
O N O N
H H
1.
2. a. 1 st b. 2 nd
Space provided for your own drawings:
3. c. 3
O rd
N
H
4. d. 4
H th
O N
5. e. 5
H th
O N
6.-9. Match each superscripted atom 1.-4. to which atom it will eventually be bonded to (ionic or covalent) in the following overall reaction.
Ph
3
1
P
+
H
2
C
3
H
I
4 followed by
H
C
5
Li
6
H followed by
O
7
C 8
6. atom 1. a.
atom 5.
7. atom 2. b. atom 6.
8. atom 3. c. atom 7.
9. atom 4. d. atom 8. e. not a.-d.
N
10. is a(n): a.
enamine b. hydrazone c. imine d. iminium e. not a.-d.

11.-15. Match each set of reagents to its major organic product to the right. Do the reactions in order of parentheses.
Assume any necessary workup between steps. Answers may be repeated.
11. excess (CH
3
I + Mg) + ethyl ethanoate a.
OH
12. ((CH
3
I + Mg) + propanenitrile) + NaBH
4 b.
OH
OH
13. ((CH
3
CH
2
CH
2
Cl + Mg) + CO
2
) + LiAlH
4 c.
OH
14. ((2 (CH
3
I + 2 Li) + CuI) + ethanoyl chloride) + (CH
3
I + Mg)
15. (ethyl 2-methylpropanoate + [(CH
3
)
2
CHCH
2
]
2
AlH) + NaBH
4 d. e. not a.-d.
16.-20. Match each compound on the left with the type of catalysis that can be used or is required to make it from propanal. Assume each oxygen has a complete octet and appropriate charge. Answers must be repeated.
OH
16.
OH
OCH
3 a. acid
17.
OH
OCH
3 b. base
18. c. acid or base
19.
OH d. not a.-c.
20.
O
21-25. Match each set of reagents with a final product below. Answers may be repeated. Assume any necessary workup between steps. Do the reactions in order of parentheses.
21. ((propanoic acid + SOCl
2
+ pyridine catalyst) + excess NH
3
) then take the main product and treat with SOCl
2
+ heat
22. ((propanoic acid + heat) + 2 NH
3
) then take the organic byproduct and heat it
23. (((propyl propanoate + sodium hydroxide + heat) + HCl workup) + SOCl
2
+ pyridine catalyst) + sodium propanoate
24. (propanoic acid + propan-1-ol + sulfuric acid + heat) + Na +OCH
2
CH
3
+ heat
25. (propanoyl chloride + H
2
O) + CH
2
N
2
O
O O O O a.
NH
2 b.
O
c.
O d.
Cl e. not a.-d.
The Exam 3 retake homework will be due Monday, April 27, by 1:00 p.m., through http://organic.utep.edu/quiz , no excuses! These exam sheets will be available for you to pickup by 1:00 p.m. today or during normal business hours, thereafter, from PSCI 202.