Page 1
1.
What type of reaction is the following?
Cl NaOH
A)
elimination
B)
substitution
C)
addition
D)
rearrangement
E)
reduction
2.
What would be the major organic product of the following reaction?
CH3
C
CH3
H3CCCH2
H?
HCl
A)
H3C
C
H3C
H3CCCH2Cl
H
H
B)
C)
D)
E)
Page 2
3.
What would be the major organic product of the following reaction?
H3CCH2CH2CCH2
CH3
H2O, H2SO4?
A)
H3CCH2CH2CCH2
CH3
HOH
B)
H3CCH2CH2CCH3
CH3
OH
C)
H3CCH2CH2CCH2
CH3
OOH
H
D)
H3CCH2CH2CCH3
CH3
OOH
E)
H3CCH2CH2CC
CH3
O
H
H
Page 3
4.
Reaction with ozone, followed by treatment with (CH3)2S, of which of the following
would not yield any CH3CHO?
A)
C C
H
CH3
CH3
H
B)
C C
H
CH3
H
H3C
C)
C C
H3C
CH3
CH3
H
D)
C C
H
H
CH3
H3C
E)
Both B and D
5.
Which of the following sets of reagents would convert 1-methylcyclohexene into
trans-1-methyl-1,2-cyclohexanediol?
CH3
OH
?
CH3OH
A)
1. CH3CO3H
2. CH3ONa, CH3OH
B)
KMnO4, H2O, –OH
C)
1. CH3CO3H
2. H3O+
D)
1. OsO4
2. H2S, H2O
E)
1. O3
2. (CH3)2S
Page 4
6.
What reagent(s) would accomplish the following transformation?
CH2
H3CCH2
CCH2
H3CCH2
H3CCH CH2Br
H3CCH2
?
A)
Br2, h
B)
HBr
C)
PBr3
D)
HBr + peroxides
E)
HgBr2 + NaBH4
7.
Which of the reagents below would best accomplish the following transformation?
OH
OH
?
A)
H2O + cat. H2SO4
B)
CH3CO3H, then NaOH + H2O
C)
Br2 + H2O
D)
O3 then Zn + HCl
E)
KMnO4 + –OH/ H2O
Page 5
8.
What would be the product of the following reaction?
H3C H
CH3
H
Br2?
A)
H3C
Br
CH3
H
B)
H3CCH3
H
H
Br Br
(racemic)
C)
H3C
H
CH3
Br
D)
H3C
H
CH3
H
Br Br
E)
H3C
H
CH2Br
H
9.
Which of the following reagents would best accomplish the following transformation?
CH3CH3
?
A)
NaBH4
B)
LiAlH4
C)
BH3, NaBH4
D)
H2SO4
E)
H2, Pd
10.
Polymerization reactions are thermodynamically favorable (exothermic) because
A)
large molecules are more stable than small ones.
B)
polymers precipitate, which shifts the equilibrium.
C)
a sigma bond is more stable than a bond.
D)
crosslinking stabilizes the product.
E)
alkenes are too unstable to store.
Page 6
11.
Radical polymerization of styrene produces what polymer? (n = large number)
Ph ?
heat
cat.
R-O-O–R
A)
RO
Ph Ph Ph
n
B)
RO Ph Ph Ph
n
C)
RO
Ph Ph Ph
Ph Ph Ph
n
D)
RO
Ph
Phn
E)
None of the above.
Page 7
12.
What would be the expected product of the following reaction?
?
1. ArCO3H
2. H2O, NaOH
A)
OH
HO
B)
OH
HO
C)
H
HO
D)
OH
H
E)
OH
H
13.
Based on your knowledge of the mechanisms involved, which of the reagents below
would you expect to accomplish the following reaction? (Think through the
mechanism!)
OH O
CH2Br
?
A)
HBr
B)
Br2
C)
PBr3
D)
NaBr
E)
HBr + peroxides
Page 8
14.
What type of reaction is the following?
CN
Br NaCN
A)
elimination
B)
addition
C)
substitution
D)
rearrangement
E)
reduction
15.
Which of the following rearrangements would you not expect the cation below to
undergo to any significant extent?
H3CCH CH3
?
+
A)
H3CCCH3
H
+
B)
CH3CH2CH2
+
C)
CH3
CH3
+
D)
None of the above would occur to a significant extent.
E)
All of the above would be significant.
Page 9
16.
What is the major product of the following reaction?
HBr /cat. R2O2
heat ?
A)
B)
Br
C)
Br
D)
Br
Br
E)
CH2Br
Page 10
17.
Predict the major product of the following reaction:
HI / cat. R
2O2?
heat
A)
I
B)
I
C)
I
D)
I
E)
I
I
18.
What reagent(s) might cause the following conversion?
OH
?
A)
1. Br2 2. H2O
B)
NaOH, H2, Pd
C)
H2SO4
D)
1. BH3 2. H2O2, NaOH
E)
Br2, H2O
Page 11
19.
What reagent(s) would accomplish the following reaction?
Br
Br
?
A)
Br2
B)
NBS
C)
Br2 + light
D)
Br2 + FeBr3
E)
HBr
20.
What reagents would be required to accomplish the following transformation?
OH
OH
?
A)
KMnO4, –OH, H2O
B)
BH3 then H2O2
C)
CH3CO3H then H2O, H+
D)
OsO4, tBuOOH, H2O
E)
Br2, H2O
21.
Which reagents would you expect to accomplish the following transformation?
?
OH
A)
BH3 then H2O2, –OH
B)
Hg(O2CCH3)2,
H2O then NaBH4
C)
H2O, H+
D)
KMnO4, H2O, cold
E)
cat. OsO4, H2O2
Page 12
22.
Considering the following reactions, you conclude that the stereochemistry of reactions
#1 and #2 is:
CH3
CC
H3C
Br Br
H
H
Br2
(Rxn #1)
Zn
(Rxn #2)
A)
anti and syn, respectively
B)
syn and anti, respectively
C)
anti and anti, respectively
D)
syn and syn, respectively
E)
None of the above.
23.
Based on your knowledge of the mechanisms involved, which of the reagents below
would you expect to accomplish the following reaction? (Think through the
mechanism!)
OH O
CH3
?
A)
H2/Pd
B)
Br2
C)
PBr3
D)
H2SO4
E)
NaBH4
Page 13
24.
What would be the expected product from the reaction shown?
Br2?
A)
Br
Br
B)
Br
C)
Br Br
D)
Br
Br
E)
Br
Br
25.
What reactant and product types would be most appropriate for the reagents shown?
1. OsO4
2. H2S, H2O
? ?
A)
alkene/alcohol
B)
alkene/anti-1,2-diol
C)
alkene/syn-1,2-diol
D)
alkyne/ketone
E)
alkyne/aldehyde
26.
What reactant and product types would be most appropriate for the reagents shown?
H2O
H2SO4
? ?
A)
alkene/Markovnikov alcohol
B)
alkene/anti-Markovnikov alcohol
C)
alkene/1,2-diol
D)
alkyne/1,2-diol
E)
alcohol/alkene
Page 14
27.
What reactant and product types would be most appropriate for the reagents shown?
? ?
HBr
A)
alkene/Markovnikov alkyl bromide
B)
alkene/anti-Markovnikov alkyl bromide
C)
alkene/syn-1,2-dibromide
D)
alkyne/anti-1,2-dibromide
E)
alcohol/alkene
28.
What reactant and product types would be most appropriate for the reagents shown?
CH3CO3H
? ?
A)
alkene/Markovnikov alcohol
B)
alkene/anti-Markovnikov alcohol
C)
alkene/syn-1,2-diol
D)
alkyne/anti-1,2-diol
E)
alkene/epoxide
29.
What reactant and product types would be most appropriate for the reagents shown?
1. O3
2. Zn, aq HCl
??
A)
alkene/syn-1,2-diol
B)
alkene/anti-1,2-diol
C)
alkene/alcohol
D)
alkene/aldehydes and/or ketones
E)
alkene/epoxide
30.
What reactant and product types would be most appropriate for the reagents shown?
H2O
Br2
? ?
A)
alkene/syn-1,2-dibromide
B)
alkene/anti-1,2-dibromide
C)
alkene/2-bromoalcohol
D)
alkene/1,2-diol
E)
alkene/epoxide
Page 15
31.
Which reagents would be appropriate for the chemical transformation shown below?
H3CC
H3CCH3
CCH2
H
?H3CC
H3CCH3
CH2CH2OH
A)
H2O, H2SO4
B)
BH3, then H2O2, –OH
C)
Hg(OAc)2, H2O, then NaBH4
D)
NaBH4, CH3OH
E)
PCC
32.
Which reagents would be appropriate for the chemical transformation shown below?
H3CC
H3CCH3
CCH2
H
? H3CC
H3CCH3
CCH3
H
HO
A)
H2O, H2SO4
B)
BH3, then H2O2, –OH
C)
Hg(OAc)2, H2O, then NaBH4
D)
NaBH4, CH3OH
E)
PCC
33.
Which reagents would be appropriate for the chemical transformation shown below?
H3CC
H3CCH3
CCH2
H
?C
H3CCH3
CCH2
HCH3
HO
A)
H2O, H2SO4
B)
BH3, then H2O2, –OH
C)
Hg(OAc)2, H2O, then NaBH4
D)
NaBH4, CH3OH
E)
PCC
Page 16
34.
Predict the product of the following reaction:
CH2CH3
CH3
H2, PtO2, CH3CH2OH
A)
CH2CH3
CH3
B)
CH2CH3
CH3
C)
CH2CH3
CH3
D)
CH2CH3
CH3
E)
Equal amounts of A and B.
35.
What is the major product of the following reaction?
HI
A)
I
B)
I
C)
I
I
D)
There is no reaction.
E)
I
Page 17
36.
Predict the major product of the following reaction:
CF
3CO
2H?
A)
F
F
B)
O
C)
O CF3
O
D)
OCF3
O
E)
F
F
37.
How many products are possible in the reaction of trans-2-butene with Br2?
A)
0
B)
1
C)
2
D)
3
E)
4
38.
What is the best method to convert alkenes into alcohols following Markovnikov’s
Rule?
A)
PCC
B)
H2O
C)
hydroboration/oxidation
D)
oxymercuration-demercuration
E)
None of the above.
Page 18
39.
Which of the following reagents will achieve the following reaction:
C C
CH3
HH3C
H
C C
H3C H
HCH3
HO OH
?
A)
1. MCPBA, CH2Cl2
2. H+, H2O
B)
1. OsO4, THF, 25° C
2. H2S
C)
PCC
D)
1. O3/CH2Cl2
2. Zn/CH3CO2H
E)
any of the above
40.
Which of the following products is most likely to form under the reaction conditions?
O
OOH
Cl 1 equivalent
A)
O
O
B)
O
C)
O
D)
OH
E)
OH
Page 19
41.
Which of the following starting materials are most likely to give the product under the
reaction conditions?
1. O3
2. Zn, CH3COOH 10
O
O
?
A)
B)
C)
D)
E)
Page 20
42.
Which of the following products is most likely to form under the reaction conditions?
1. BH3
2. H2O2, NaOH, H2O
D
D
A)
D
D
HO
H
B)
D
OH
C)
H
OH
D
D
D)
H
H
D
D
E)
None of the above.
Page 21
43.
Which of the following products is most likely to form under the reaction conditions?
1) BH3
2) H2O2, NaOH
A)
OH
B)
OH
C)
OH
D)
OH
E)
OH
Page 22
44.
Cholesterol is a major lipid component of atherosclerotic plaques and can be present at
such high concentrations that it forms a crystalline phase within a diseased artery. In
addition to cholesterol, the 5,6-secosterol compound has also been isolated.
5,6-secostereol has been shown to be the product of an unforeseen oxidation reaction in
the body. Which one of these reagents could be used convert cholesterol to the
5,6-secosterol? (Science 2003, 302, 1053)
HO
H H
H
OHO
H H
H
O
H
cholesterol 5,6-secosterol
A)
K2Cr2O7
B)
O3
C)
(CH3)2S
D)
HOOH
E)
LiOH
45.
Select the major product of the olefin metathesis reaction ?
E E
E CO2Me
RRu
Ph
H
Cl
Cl
P(c-hex)3
P(c-hex)3
A)
E
E
R
B)
E
R
E
C)
E
ER
D)
E
E
R
E)
E
E
R
Page 23
46.
What product, if any, would result from the reaction shown below?
CH3
CH3
H2
Pd ?
A)
CH3
CH3
H
H
B)
CH3
CH3
H
H
C)
CH3
CH3
D)
both A and B
E)
no reaction occurs
Page 24
47.
Select the product for the following reaction.
H2/Pt
A)
B)
C)
D)
OO
E)
None of the above.
Page 25
Answer Key
Page 26