CHEM 2325
July 23, 2014
Exam 2
Name:
UTEP ID:
N H
1. How many ones are in the adjacency matrix of pyrrole,
a. 2
b. 4
?
c. 6
d. 8
e. not a.-d.
2. Which structure is possible for hepta-1,2,3,5,6-pentaene? Except for the hydrogens with wedges or slashes, all
other atoms are supposed to be in the plane of the paper.
H
H
H
C C
a.
H
C
H
H
H
H
H
C C
b.
H
C
H
H
H
H
H
H
H
H
H
C
H
C C
c.
H
C
C C
d.
H
H
H
e. not a.-d.
3. Which compound has the largest HOMO-LUMO gap?
a.
b.
c.
d.
e.
Br2
heat
4. Ignoring stereochemistry, what is the major product of the following reaction?
Br
Br
Br
Br
a.
Br
b.
Br
Br
c.
e. not a.-d.
pressure
NO2 +
5. What is the major product of the following reaction?
racemic.
O2N
O2N
a.
? Assume chiral products are
O2N
b.
Br
d.
O2N
c.
d.
heat
e. not a.-d.
?
6. What is the major product of the following reaction?
a.
b.
c.
7.-11. Classify each compound as:
N
7.
8.
d.
a. aromatic
c. non-aromatic
N
N
9.
b
a
12. What is the longest bond of styrene?
b. anti-aromatic
10.
e
c
d
e. not a.-d.
N
d. not a.-c.
N
11.
13. Which compound reacts the fastest with Br2/FeBr3?
N
N
NO2
C
N
N
O
a.
b.
c.
d.
e.
c
O
Br
b
a
14. Which position will be substituted in the major product of the reaction of HNO3/H2SO4 and
e
d
15.-19. Exactly match each reaction on the left to its major intermediate on the right. Y represents the group that is
being introduced. The nitro group is not shown in its intermediate.
Br
Br
y
+ Na+-NH2
15.
H
a.
N2
anion
+
+ Na+-BF4
16.
b.
N2
+
C
+ CuBr
17.
+
c.
cation
H
+ Br2/FeBr3
+
18.
d.
y
H
arenium
Br
C
+ -OH
19.
O2N
e.
radical
20.-23. Match each reaction sequence to its major product on the right. Answers may be repeated.
Br
Br2/FeBr3
20.
a.
Br
H2SO4
Br2/FeBr3
H2O
21.
b.
HNO3/H2SO4
[H]
Br2/FeBr3
22.
HNO3/H2SO4
23.
Br2/FeBr3
[H]
NaNO2
HCl
cold
NaNO2
HCl
cold
H3PO2
Br
c.
H3PO2
d. not a.-c.
The Exam 2 retake homework is due Friday, July 25, 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!
?