CHEM 2325 Exam 2 Version A
July 22, 2015
Name:
UTEP ID:
1. How many ones are in the adjacency matrix of cyclopentadiene,
a. 2
b. 4
?
c. 6
d. 8
e. not a.-d.
2. Given that when no other priorities can be decided, R has higher alphabetical priority than S, the 2,3,4-triene bond of
5-(buta-1,2-dienyl)nona-2,3,4,6,7-pentaene is? Hint: Decide the configuration of the other cumulated bonds first.
C
C C
C
a. E
b. R
c. S
d. Z
e. not a.-d.
d.
e.
3. Which diene will give off the least heat of hydrogenation?
a.
b.
c.
Br2
?
warm
4. What is the major product of the following reaction?
Br
a.
Br
Br
Br
Br
Br
Br
Br
Br
b.
c.
Br
d.
D
e.
N
NO2 pressure?
H+
H
H
H
5. What is the major product of the following reaction?
Assume chiral
products are racemic. Hint: Do not star the deuterium because it is as electronegative as a hydrogen.
N
N
NO2
N
NO2
N
NO2
a.
D
D
b.
D
c.
NO2
d.
D
hv
e. not a.-d.
?
6. What is the major product of the following reaction?
a.
b.
c.
7.-11. Classify each compound as:
O
a. aromatic
d.
b. anti-aromatic
e. not a.-d.
c. non-aromatic
d. not a.-c.
OH
O
O
O
7.
8.
O
OH
9.
10.
N
11.
a
b
d
c
12. What is the longest bond of the following compound? e
13. Which compound reacts the slowest with Cl2/FeCl3?
O
OCH3
a.
O
b.
OH
O
c.
OH
d.
e.
c
b
a
d
O
e
14. Which position will be substituted in the major product of the reaction of H2SO4 and
?
15.-19. Match each reaction sequence to a major product on the right. Answers may be repeated. Assume any
necessary workup between steps.
Cl
HNO3
Zn
NaNO2
O
H2SO4
15.
HCl
CuBr
HCl, cold
AlCl3
Br
a.
Cl
N2H4
Br2
KOH, heat
FeBr3
Br
O
16.
AlCl3
b.
Cl
HNO3
Br2
Zn
NaNO2
HCl
HCl, cold
O
H2SO4
17.
c.
AlCl3
Cl
AlCl3
HNO3
H2
NaNO2
H2SO4
Pd
HCl, cold
HNO3
Br2
H2
NaNO2
Pd
HCl, cold
H2SO4
FeBr3
19.
20. Which reaction above uses a Wolff-Kishner reduction?
a. question 15
Br
AlCl3
Cl
18.
FeBr3
H3PO2
b. question 16
CuBr
Br
d.
c. question 17
H3PO2
Br
e.
d. question 18
e. question 19
The Exam 2 retake homework is due Friday, July 24, before 5:00 p.m. via http://organic.utep.edu/quiz. You may work
together on this homework but everyone is responsible for submitting his or her own answers via the online form and
you should not consult with anyone outside of class. Turn in your homework as long before the due date and time as
possible. No excuses for late entries!