Page 1
1.
Which ion would be most stabilized by resonance?
A)
CH2CH2
B)
CHCH3
C)
CH2CH3
D)
CH2CH3
E)
All are equally stabilized.
2.
Which of the following resonance structures of the phenoxide anion would be the major
contributor to the real structure?
A)
B)
O
C)
O
D)
O
E)
All are equally important.
Page 2
3.
What is the main use of azo compounds in general?
N N
R
A)
Antibiotic properties
B)
Fragrances and flavorings
C)
Chemotherapy agents
D)
Herbicides and/or pesticides
E)
Dyes and coloring agents
4.
To which side (if any) would the following equilibrium lie?
C6H5O– + HOH C
6H5OH +
–OH
A)
To the left
B)
To the right
C)
Equally to the left and right
D)
Reaction cannot occur at all
E)
Equilibrium favors a different product
5.
Why does the substitution of ortho or para nitro groups onto chlorobenzene greatly
increase the tendency of the chlorine to be displaced by nucleophiles?
A)
NO2 groups stabilize the SN1 transition state by resonance.
B)
The NO2 groups facilitate removal of a hydrogen to chlorine.
C)
NO2 groups stabilize the SN2 transition state.
D)
NO2 groups stabilize negative charge resulting from addition of a nucleophile.
E)
The NO2 groups exert a general inductive effect which is independent of
substitution position.
Page 3
6.
By which of the following can the N2 group of a benzenediazonium salt not be
substituted?
NN
a benzenediazonium salt
Cl
A)
CN
B)
CH3
C)
H
D)
F
E)
OH
7.
What material is produced easily by means of the Kolbe reaction? (sodium phenoxide +
CO2 + heat/pressure, then H3O+)
A)
Phenol
B)
Benzaldehyde
C)
Succinic acid
D)
Cinnamic acid
E)
Salicylic acid
8.
What product would result from the following reaction?
O?
heat
A)
O
B)
O
C)
O
H
D)
OHC
E)
None of these.
Page 4
9.
What happens when a secondary amine is treated with nitrous acid?
A)
A diazonium salt is formed.
B)
It immediately loses nitrogen to form a carbocation.
C)
A simple acid-base reaction occurs to give an alkyl ammonium nitrite salt.
D)
An N-nitroso amine is formed.
E)
A dealkylation occurs to give a primary amine.
10.
What major product would you expect from the following reaction?
A)
Cl
OCH3
NO2
O2N
B)
CH3O
Cl
NO2
O2N
C)
CH3O
OCH3
NO2
O2N
D)
Cl OCH3
NO2
O2N
E)
both A and D
Page 5
11.
How would you rank the following in decreasing order of reactivity toward nucleophilic
aromatic substitution (most reactive on left)?
ClCl Cl
NO2
O2N
NO2
Cl
NO2
NO2
O2N
1 2 3 4
A)
4 > 1 > 3 > 2
B)
2 > 3 > 1 > 4
C)
3 > 2 > 4 > 1
D)
1 > 3 > 2 > 4
E)
impossible to predict
12.
What would be the result of the following?
O
?
heat
A)
O
B)
O
C)
HO
D)
O
E)
no reaction
Page 6
13.
What would be the expected product of the following reaction?
O
O
?
+
A)
O
O
B)
C)
O
O
D)
O
O
E)
O
Page 7
14.
What product would you expect from the following reaction?
CH2
CH2 KMnO
4
H2O, NaOH
heat
?
A)
O
O
B)
O
O– Na+
2
C)
CH3
2
D)
CH2OH
2
E)
CH3HOCH2
+
Page 8
15.
From what starting materials would the following be made?
NN
NH2
H2N
A)
N2+
NH2
H2N
+
B)
NH2
H2N
N2+
+
C)
Either A or B
D)
Neither A nor B
E)
The compound shown is too unstable to isolate.
16.
What would be the proper ranking of the following in order of decreasing acidity (most
acidic on left)?
OHOH OH
CH3
O2N
NO2
OH
NO2
NO2
O2N
4321
A)
4 > 2 > 1 > 3
B)
3 > 1 > 4 > 2
C)
2 > 4 > 1 > 3
D)
3 > 2 > 4 > 1
E)
2 > 4 > 3 > 1
Page 9
17.
What reagent(s) would be required to accomplish the following reaction?
CH2OCH3HO
+
?
A)
H2SO4/H2O
B)
1. LiAlH4
2. H2O
C)
H2, Pd
D)
HBr, heat
E)
NaBH4, CH3OH
18.
What would be the expected product of the following reaction?
H3CCH3
?
Br2
h
A)
H3CCH3
Br
B)
H3CCH3
Br
C)
H3CCH2Br
D)
H3CCH3
Br
E)
both A and D
Page 10
19.
What would be the expected product(s) from the following reaction?
A)
OH
H3C
B)
OH
H3C
C)
H3C
HO
D)
both A and B
E)
All of the above.
20.
What would be the proper ranking of the following in order of decreasing acidity (most
acidic on left)?
OH OH
OOH
A B C
A)
A > B > C
B)
B > C > A
C)
A > C > B
D)
B > A > C
E)
C > B > A
Page 11
21.
Which of the following is not a valid resonance contributor to the benzyl radical?
A)
CH2
B)
CH2
C)
CH2
D)
CH2
E)
CH2
22.
Predict the major product of the following solvolysis reaction:
H3CO CH2O S
O
O
CH3CH3CH2OH
A)
H3CO CH3
B)
H3COCH3
C)
H3CO CH2OCH2CH3
D)
H3COCH2CH3
E)
None of the above.
Page 12
23.
The following reaction most likely proceeds by what mechanism:
Br + NaN3
A)
SN2
B)
SN1
C)
E2
D)
E1
E)
Free radical halogenation
24.
Which of the following represents a hydrogenolysis reaction?
A)
H2 / Pt
B)
OHO
+
H2 / Pd
C)
OOH
H2 / Pt
D)
OH O
OO
+ CH3OH H
E)
Two or more of these are correct.
Page 13
25.
Considering the mechanism for the following reaction, which of the following is most
likely the rate determining step (RDS)?
Cl
CN
NH2
CN
NH3/heat
A)
Cl
CN
NH3
B)
Cl
CN
Cl
NC NH3
C)
Cl
H
CN
NH3
D)
Cl
CN
NH3
E)
Cl NH3
CN
NH3
CN
Page 14
26.
When considering the mechanism of the reaction shown below, which of the following
is most likely an intermediate along the reaction pathway?
Br OH
1. NaOH / H
2O /340
oC / 150atm
2. H+, H2O
A)
B)
OH
Br
C)
D)
Br
E)
Page 15
27.
Predict the major product of the following reaction:
OH 1) NaOH / H
2O /
2) Heat
Br
A)
O
B)
OH
C)
OH
D)
O
E)
O
Page 16
28.
Which of the following is not a valid resonance contributor in the benzenediazonium
cation?
A)
N
N
B)
N
N
C)
N
N
D)
N
N
E)
All of the above are valid resonance structures.
Page 17
29.
Predict the major product of the following Sandmeyer reaction:
Cl
NH2
1) HBr / NaNO
2
2) CuBr / 100
oC
A)
Br
Br
B)
Cl
Br
C)
Cl
N Br
H
D)
Cl
E)
NH2
NH2
Page 18
30.
Which of the following is not a valid resonance contributor in the benzylic anion?
A)
CH2
B)
C)
D)
CH2
E)
All of these are valid resonance structures.
31.
Arrange the following structures according to decreasing acidity?
A)
1 > 3 > 4 > 2
B)
2 > 4 > 3 > 1
C)
4 > 3 > 1 > 2
D)
3 > 2 > 1 > 4
E)
4 > 1 > 3 > 2
Page 19
32.
Starting with the labeled chlorobenzene (label indicated by *), what is the product of the
following nucleophilic aromatic substitution reaction?
Cl
1) NaOH, H2O
2) H3O+
*
A)
*
B)
OH
*
C)
OH
*
D)
OH
*
E)
structures B and C
Page 20
33.
Which of the reagents given below would accomplish the reaction shown?
CH3
CH3
O2NCO2H
CO2H
O2N
?
A)
H2O2, KOH, heat
B)
Na2Cr2O7, H+, heat
C)
ClCO2H, AlCl3
D)
O3, then H2O
E)
None of these.
Page 21
Answer Key