CHEM 2324
April 21, 2015
Exam 3 Version A
Name:
UTEP ID:
1.-5. Match each functional group centered on a given numbered carbon in the structure below to a best functional group name on the
right. Answers may be repeated.
O
C1
O
O
C4
O C
2
O
1.
2.
3.
4.
5.
C5 H
O
C3
H
O
C1
C2
C3
C4
C5
a. aldehyde
b. enol ether
c. ester
d. ketal
e. ketone
6.-10. Match each functional group centered on a given numbered carbon in the structure below to a best functional group name on the
right. Answers may be repeated. Interestingly, this compounds looks a lot like a common sedative.
OH
O H
C8
C7
C9
N
N
H C6
C10
H
6.
7.
8.
9.
10.
N
C6
C7
C8
C9
C10
a. nitrile
b. imine
c. enamine
d. cyanohydrin
e. amide
Assume any necessary workup for the following reactions:
11.-15. Order the reactants, intermediates, and final product of the reaction of methyl ethanoate and excess Grignard reagent of
iodomethane. Counter ions, byproducts, non-bonding electrons, and charges are not shown.
11.
12.
13.
CH3
CH3
a.
O
CH3
O
b.
CH3
O CH3
CH3
14.
CH3
c.
CH3
O
CH3
15.
O
d.
OH
CH3
CH3
CH3
CH3 O
e.
CH3
CH3
16. The product of 1-chloropropane and magnesium reacts with butanone to make mostly?
a. 2-propylbutan-2-ol
b. 2-ethylpentan-2-ol
c. 3-methylhexan-3-ol
d. heptan-4-ol
e. not a.-d.
17. The product of 2-chloro-2-methylpropane and magnesium reacts with carbon dioxide to make mostly?
a. 3-methylbutan-2-one
b. 2,2-dimethylpropanoic acid
c. 2-methylbutanoic acid d. 2,2-dimethylpropanal
e. not a.-d.
18. Ignoring E or Z isomers, the product 1-chloropropane, triphenylphospine, and base reacts with butanone to make mostly?
a. 2-propylbut-2-ene
b. 2-ethylpent-2-ene
c. 3-methylhex-3-ene
d. 4-methylhex-3-ene
e. not a.-d.
19. The reaction of 2-methylpropanal, ammonia, sodium cyanoborohydride, and acid catalysis makes mostly?
a.
NH2
NH2
NH2
b.
c.
NH2
d.
e. not a.-d.
20. The reaction of propanone and dimethylamine ((CH3)2NH) makes mostly?
N
a.
N
b.
c.
N
d.
N
e. not a.-d.
21. The reaction of propanal, ethane-1,2-diol, and acid catalysis makes mostly?
O
O
b. O
a.
O
O
O
c.
O
d.
O
e. not a.-d.
22.-26. Match each set of reagents to a major product on the right. Answers may be repeated. Assume any necessary workup between
steps.
22. butanoic acid + thionyl chloride + pyridine catalysis followed by methanol
a. butanamide
23. sodium butanoate + hydrochloric acid followed by methanol + acid catalysis
b. butanenitrile
24. methyl butanoate + ammonia followed by thionyl chloride + heat
c. butanoyl chloride
25. butanamide + water + acid catalysis followed by thionyl chloride + pyridine catalysis
d. methyl butanoate
26. butanoic acid + heat followed by excess ammonia
e. not a.-d.
27.-33. Match each set of reagents to a major product below. Answers are repeated. Assume any necessary workup between steps.
Extra space is provided so that you can draw your intermediates.
27. ethanoic acid + diazomethane followed by excess methyl magnesium chloride
28. butanoic acid + dimethylamine + dicyclohexylcarbodiimide followed by diisobutylaluminum hydride followed by sodium
borohydride
29. propanoic acid + sodium hydroxide followed by methyllithium followed by sodium borohydride
30. ethanoic acid + thionyl chloride + pyridine catalysis followed by tri-tert-butoxyaluminum hydride followed by ethyl magnesium
bromide
31. 2-methylpropanoic + thionyl chloride + pyridine catalysis followed by sodium 2-methylpropanoate followed by lithium aluminum
hydride
32. propanoic acid + ammonia + heat followed by thionyl chloride + heat followed by methyl magnesium chloride followed by water
+ acid catalysis followed by sodium borohydride
33. butanoic acid + ammonia followed by heat followed by lithium aluminum hydride
a.
OH
OH
OH
b.
c.
d.
OH
e. not a.-d.
If required, the Exam 3 retake homework will be due Friday, April 24, 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.