CHEM 2322
February 20, 2012
Exam 1
Name:
UTEP ID #:
1. The major organic product of (R)-1-bromo-3-methylpentane and sodium hydroxide should be?
a. (S)-3-methylpent-1-ene
b. (S)-3-methylpentan-1-ol
c. (R)-3-methylpent-1-ene
d. (R)-3-methylpentan-1-ol
2. The major organic product of 3-bromo-3-methylpentane and water should be?
e. not a.-d.
a. 2-ethylbut-1-ene
b. 3-methylpentan-3-ol
c. (E)-3-methylpent-2-ene
d. (Z)-3-methylpent-2-ene
e. not a.-d.
3. Which mechanism is most like the reverse of the mechanism of the addition of an electrophilic to an alkene?
a. SN2
b. SN1
c. E2
d. E1
e. not a.-d.
4. Which part of the Gibbs free energy equation (ΔG=ΔH-TΔS) is positive at high temperatures for the
following reaction as written? Remember that Palladium is only a catalyst for this reaction.
Pd
+ H2
a. ΔG
b. ΔH
c. ΔS
d. not a.-c.
e. all a.-c.
5.-9. Match each reaction on the left to a major product on the right. Answers may be repeated. Assume any
necessary workup.
Br
+-
Na OCH3
5.
a.
Br
+-
K O
6.
b.
Br
+-
Na OCH3
7.
c.
+-
K O
Br
8.
d.
+-
Br
Na OCH3
9.
e. not a.-d.
10. Which reagent does not form a cyclic intermediate or product with an alkene?
a. carbenes
b. peracids
c. OsO4
d. Cl2 in H2O followed by NaOH
e. not a.-d.
+
H ,rearrangement, elimination
OH O3,Zn
11. What is the major product of
? Ignore smaller byproducts.
O
O
O
O
a.
b.
c.
d.
e. not a.-d.
12.-16. Match an alkene on the right that could be reacted with borane followed by sodium hydroperoxide and
appropriate workup to make each of the alcohol products on the left. Answers may be repeated.
OH
12.
13.
a.
OH
b.
OH
14.
15.
c.
OH
d.
OH
16.
e. not a.-d.
17.-21. Match each reaction sequence (steps separated by lines) on the left to a major product on the right.
Assume any necessary workup between steps. Answers may be repeated.
H2,Lindlar
BH3
NaO2H
PCC,CH2Cl2
17.
O
a.
OH
HgSO4,H2SO4,H2O
18.
OH
b.
Dicyclohexylborane
NaO2H
19.
c.
O
Na,NH3
peracid
+
H3O
O
20.
d.
H2,Lindlar
OsO4,H2S
21.
e. not a.-d.