CHM 202F- Organic Chemistry II
Exam 3
Nov. 21, 2005
Name (Please Print):_____________KEY__________________
Test Form 1.
To be properly graded, you must indicate your correct Test Form number on your
Scantron!!
100 pts. 24 questions. 8 pages total.
For your convenience, the structures of some compounds/reagents referred to by name
in some of the problems are provided in the upper right hand corner of the given
problem.
You’re welcome to rip out the last page (blank) to use as a scratch sheet. Please write
your name at the top of it, and you must turn it in with your exam at the end of the
period.
All questions are to be filled in on your Scantron.
1
1. Which pair of compounds is best suited to making the following product:
O
NaOH
?

a.
O
Ph
b.
O
c.
O
O
+
O
O
+
Ph
H
Ph
d. O
+
H
H
O
e.
O
Ph
H
O
+
+
Ph
Ph
H
H
H
2. Which activated ylide could be used to synthesize A?
A.
(trans and cis)
a. 1
b. 2
c. 3
d. 4
e. either 1 or 2 could be used
2.
1.
P(Ph)3
P(Ph)3
3.
P(Ph)3
4.
P(Ph)3
3. Which would NOT form essentially one Claisen condensation product when one
compound is added slowly to the mixture of the other in NaOEt?
O
a.
O
H
OEt
O
EtO
O
O
OEt
+ Ph
O
O
+
OEt
2
+
OEt
OEt
O
O
OEt
OEt
d.
O
OEt
Ph
OEt
+
OEt
e.
O
+
Ph
c.
b.
O
A.
4. Which reaction yields compound A?
O
O
b.
O
1. CH3MgBr
a.
1. NaOEt
+
2. H3O
O
O
2. H3O+
O
O
c.
O
d.
KMnO4, OH-, 
1. NaOEt
O
2. H3O+
O
e. None of the above
5. Identify the reaction product.
NaOH
Compound A +
(from question above)
?

O
O
O
a.
O
b.
O
c.
O
O
O
d.
e. None of the above
O
O
6. Identify compound Z in the following synthesis.
1. KMnO4, KOH, 
2. H3O+
X
SOCl2
Y
1. LiAl(OtBu)3H, -78 C
2. H2O
O
H c.
b.
a.
O
O
O
d.
e.
H
3
OLi
Z
OEt
O
O
Compound Q
7. Identify the reaction product.
1. H+ / Br2
2. KOtBu
?
3. NaOEt, Compound Q
4. HCl, H2O, 
O
a.
O
b.
O
O
O
O
c.
O
d.
O
e.
O
O
O
8. Identify the proper reaction conditions
O
?
O
O
a. 1. LAH; 2. H2O
b. 1. LAH; 2. H2O; 3. H2CrO4
c. 1. NaOEt; 2. HCl, H2O, 
d. 1. CH3CH2MgBr; 2. H3O+
e. 1. MCPBA; 2. H3O+
9. The product, B, of the following reaction is,
a.
b.
d.
c.
4
e.
Questions 10-12 pertain to the following synthesis:
EtO2C
CO2Et
Ph
1. HCl/H2O
1. NaOEt / EtOH
1. NaOEt / EtOH
+ X
CO2H
CO2Et
Z
Ph
2. H3O+
Ph
2. 
2. Y
Ph
10. What is compound X?
O
a.
b.
O
O
O
c.
O
d.
e.
OEt
EtO
OEt
H
OEt
EtO
OEt
OEt
Br
O
11. What is compound Y?
O
a.
c.
b.
d.
e.
Ph
Br
Ph
Ph
OEt
Br
Ph
Br
Br
Br
12. What is compound Z?
a.
b.
Ph
CO2Et
CO2Et
c.
Ph
CO2Et
O
CO2Et
Ph
Ph
Ph
Ph
13. Identify the reaction conditions.
O
O
?
H
HO
Br
CO2Et
CO2Et
Ph
H
e.
Ph
CO2Et
CO2Et
Ph
d.
Ph
O
a. KMnO4, OH , 
b. 1. Mg / Et2O; 2. CO2; 3. H3O+
c. 1. NaBH4; 2. H2O; 3. NaOCH3; 4. CO2; 5. H3O+
d. 1. HO(CH2)2OH / H+; 2. Mg / Et2O; 3. CO2; 4. H3O+
e. none of the above
-
5
14. Identify the reaction product.
b.
a.
c.
d.
e.
15. Identify the reaction product.
O
OOH
?
O
a. O
O
b.
O
c.
O
e.
O
O
O
d.
O
O
16. Identify the reaction product.
O
H
NaOH
O
a.
O
O
b.
O
?

d.
c.
O
H
O
O
O
H O
6
O
e.
17. Treating the reaction product from the prior question with (Ph)2CuLi following by
water yields.
a. O
HO
H
b.
O
O
O
c.
d.
HO
O
Ph
e.
H
Ph
Ph
O
Ph
Ph
18. Starting from cyclohexene, how would one prepare trans-1,2-dimethoxycyclohexane?
a.
b.
c.
d.
e.
OMe
1. MCPBA; 2. 2 equiv. CH3MgBr; 3. H3O+
1. O3; 2. H2O2; 3. CH3OH
1. KMnO4, -OH, H2O, cold; 2. Na; 3. CH3Br
1. MCPBA; 2. NaOMe; 3. CH3Br
none of the above
OMe
19. If ozonolysis of an unknown followed by reductive work-up yielded pentanal and 3heptanone, the unknown would have been:
a.
b.
c.
d.
e.
(E)-4-ethyl-4-nonene only
(Z)-4-ethyl-4-nonene only
either (E)- or (Z)- 4-ethyl-4-nonene
can not be determined from the information given
none of the above
20. Treatment of cyclopentanone with pyrrolidine / cat. H+, followed by benzoyl chloride,
followed by water yields a product that has a pKa that is ____________than/as that
of the starting material:
a.
b.
c.
d.
higher
lower
approximately the same
there is insufficient information given to answer the question
O
Cl
benzoyl chloride
21. Treatment of 1-methyl-1-cyclohexene with cold basic aqueous potassium
permanganate (KmnO4), followed by periodic acid (HIO4) followed by one equivalent
sodium borohydride (NaBH4) in isopropanol yields:
1-methyl-1-cyclohexene
a.
b.
c.
d.
e.
a cyclic compound with a ketone and a secondary alcohol
a cyclic compound with a ketone and a primary alcohol
an acyclic compound with a ketone and a secondary alcohol
an acyclic compound with a ketone and a primary alcohol
none of the above
7
22. Which pair of compounds is best suited to preparing the Robinson annulation
product below?
Ph
NaOH
?

O
a.
b.
O
O
O
O
O
d.
Ph
+
Ph
+
Ph
+
O
c.
e.
+
Ph
+
O
O
O
O
Ph
23. When a solution of (R)-2-methyl-1-phenylbutan-1-one is treated with weak acid it’s
shown to lose its optical activity over time. Which mechanistic step below, best accounts
for this observation:
+
OH
H+
O
OH
b.
a.
c.
Ph
Ph
H
(R)-2-methyl-1-phenylbutan-1-one
H+
O
+ H
O
H2O
+
Ph
H
H
+ H
O
H2O
Ph
Ph
H
H
H
d.
O
O
Ph +
Ph
H
H
24. An acetoacetic ester synthesis employing 1-bromobutane in the second step yields:
a.
b.
c.
d.
e.
5-ethylpentanoic acid
2-heptanone
methyl 3-ethylbutanoate
4-methylacetoacetate
none of the above
"acetoacetic ester"
OEt
O
8
O