CHEM 2325
Exam 2
October 20, 2015
Version A
Name:
UTEP ID#:
O
N
1. How many ones are in the adjacency matrix of the following compound?
a. 4
b. 6
c. 8
d. 10
2. Which structure is has S and Z stereochemistry?
C
e. not a.-d.
C
C C
a.
b.
e. not a.-d.
C
C C
C
C C
c.
C C
d.
3. Which picture best represents the Pi-energy diagram of the arenium ion intermediate of electrophilic aromatic
substitution of benzene? Hint: The arenium ion is populated with 4 Pi electrons which are not shown.
a.
b.
c.
d.
e. not a.-d.
HBr
warm
4. What is the major product of the following reaction?
Br
Br
Br
a.
b.
Br
c.
d.
e. not a.-d.
O
OCH3
5. What is the major product of the following reaction?
products are racemic?
O
CH3O
presure
+
OCH3
Assume chiral
e. not a.-d.
O
CH3O
CH3O
OCH3
CH3O
OCH3
OCH3
a.
b.
O
c.
heat
A
light
6. What is B in the following sequence?
S
+
C H
O
7.
8.
N
O
d.
B
Assume chiral products are racemic.
a.
b.
c.
7.-10. Classify each of the following: a. aromatic
Answers may be repeated.
O
OCH3
d.
b. antiaromatic
e. not a.-d.
c. nonaromatic
d. not a.-c.
O
S
9.
10.
11. What is the length in angstroms (Å, 10-10 m) of the bond between the carbanion and carbonyl carbons of the
O
H
following compound?
C
-
H
a. 1.2
b. 1.3
c. 1.4
d. 1.5
e. not a.-d.
12. Knowing that sulfur is just below oxygen in the Periodic Table, which compound would react third fastest with tertbutyl chloride and AlCl3?
O
S
O
S
S
S
O
a.
b.
c.
O
S OH
O
O
d.
O
S
b
a
e.
d
O
c
13. Which position would be most substituted if reacted with CH3Cl/AlCl3?
e
14.-16. Starting with benzene, match each reaction sequence to a major product below. Assume any necessary workup
between steps, which are separated by commas. Answers may be repeated.
14. Cl2/AlCl3, NaNH2, cold NaNO2/HCl, CuOH, HNO3/H2SO4, use the minor product from previous step, H2/Pd, NaNO2/HCl,
CuCN, H3O+
15. Cl2/AlCl3, H2SO4, HNO3/H2SO4, H3O+, NaOH, H2/Pd, cold NaNO2/HCl, H3PO2, NaOH, CO2, H3O+
16. HNO3/H2SO4, H2/Pd, cold NaNO2/HCl, CuCN, H3O+, 1-chloropropane/AlCl3, O2, H+ catalysis
CO2H
a.
OH
b.
HO
CO2H
HO
CO2H
c.
d. not a.-c.
17. Which reaction sequence from the above questions involves a nucleophilic aromatic substitution mechanism?
a. question 14
b. question 15
c. question 16
d. not a.-c.
18. Which reaction sequence from the above questions involves a benzyne intermediate?
a. question 14
b. question 15
c. question 16
d. not a.-c.
19. Which reaction sequence from the above questions involves aromatic substitution with electrophilic oxygen?
a. question 14
b. question 15
c. question 16
d. not a.-c.
20. Which reaction sequence from the above questions involves the Kolbe synthesis?
a. question 14
b. question 15
c. question 16
d. not a.-c.
If required, the Exam 2 retake homework will be due Friday, October 23, 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/2325/exams. Expect an email from me this evening.