CHEM 2324
Exam 3
November 16, 2015
Version A
Name:
UTEP ID:
1.-5. Match each compound to a functional group type on the right. Answers may be repeated.
O
1.
a. acetal
OH
O H
2.
3.
O
b. aldehyde
O
c. enol ether
O
4.
d. hemiacetal
OH
O
5.
e. hydrate
6.-10. Starting from an aldehyde, give the most direct neutral precursor to each of the following compounds. Answers
may be repeated.
6. The precursor of an acetal
a. the structure in question 1.
7. The precursor of a hemiacetal
b. the structure in question 2.
8. The precursor of an enol
c. the structure in question 3.
9. The precursor of an enol ether
d. the structure in question 4.
10. The precursor of a hydrate
e. the structure in question 5.
11. Which is the Wittig reagent (ylide) in the synthesis of (E)-but-2-ene from iodoethane and ethanal? Not all counter
ions or charges are shown.
H
a.
PPh3
O
PPh3
b.
c.
PPh3
O PPh3
d.
e.
O PPh3
12.-16. Match each compound to a functional group type. Answers may be repeated. R = hydrogen or methyl.
N
12.
a. cyanohydrin
O
13.
b. enamine
HO
C N
14.
15.
HO R
N
c. hemiaminal
d. imine
N
16.
e. not a.-d.
17.-21. Starting from an aldehyde, give the most direct neutral precursor to each of the following compounds. Answer
may be repeated.
17. The precursor of an aminal
a. the structure in question 12.
18. The precursor of a cyanohydrin
b. the structure in question 13.
19. The precursor of an enamine
c. the structure in question 14.
20. The precursor of a hemiaminal
d. the structure in question 15.
21. The precursor of an imine
e. the structure in question 16.
22-26. What is the suffix of the name each of the following compounds? Answers may be repeated.
O
-
22. R
O
a. oyl halide
O
23.
R
NH2
b. oic anhydride
O
24. R
OR'
O
25. R
c. oate
O
O
R
d. amide
O
26. R
X
e. not a.-d.
27.-31. Match each reaction sequence to a major product below. Answers may be repeated. Assume any necessary
workup.
27. ethanoic acid + thionyl chloride (pyridine catalysis), followed by lithium dimethylcuprate ((CH3)2Cu- Li+), followed
by ammonia, sodium cyanoborohydride and acid
28. ethanoic acid + ammonia + heat followed by thionyl chloride and heat, followed by diisobutylaluminum hydride,
followed by methylamine, sodium cyanoborohydride and acid
29. propanoic acid + heat (acid catalysis) followed by ammonia, remove the salt byproduct, followed by lithium
aluminum hydride
30. methanoic acid + methanol + heat (acid catalysis) followed by dimethylamine, followed by lithium aluminum hydride
31. ethanoic acid + ammonia, followed by lithium aluminum hydride
NH2
a.
NH2
b.
c.
H
N
d.
N
e. not a.-d.
If required, the Exam 3 retake homework will be due Thursday, November 19, before 5 pm through
http://organic.utep.edu/quiz, no exceptions or excuses. These sheets will be available in CCSB 2.0702 after 1 pm today.
Put your name on these sheets so that you can recover your class answers. An exam file will also be available from
http://organic.utep.edu/courses/2324/exams. Expect an email from me this evening.