Page 1
1.
Which nitrogen, if either, is the more basic in nicotine?
N
N
CH3
H
A
B
nicotine
A)
Nitrogen A is more basic.
B)
Nitrogen B is more basic.
C)
The nitrogens are equally basic.
D)
Neither nitrogen is basic.
E)
There is no basis on which to predict this.
2.
How would the heterocyclic amines shown here be ranked in order of decreasing
basicity (more basic > less basic)?
NN
N
HH
III III
A)
III > I > II
B)
I > II > III
C)
II > III > I
D)
I > III > II
E)
II > I > III
Page 2
3.
What product do you expect from the reaction shown below?
A)
B)
NSO3H
C)
D)
N
SO3H
E)
N
NO2
4.
Which atom in the following heterocycle would be the most basic?
N
N
CH3
ON
N
CH3
A
B
C
D
E
A)
A
B)
B
C)
C
D)
D
E)
E
Page 3
5.
The best way to prepare a 2-alkylpyridine from pyridine would be what?
NNR
?
A)
Electrophilic substitution
B)
Free-radical substitution
C)
Nucleophilic substitution
D)
An SN2 reaction
E)
None of the above are correct.
6.
Which of the chloroquinolines shown below would be most reactive toward sodium
methoxide?
A)
N
Cl
B)
N
Cl
C)
N
Cl
D)
N
Cl
E)
These are expected to be equally reactive.
Page 4
7.
Which of the following would be the most reactive diene in a Diels-Alder reaction?
A)
N
H
B)
O
C)
N
D)
These are equally reactive.
E)
None of these undergo Diels-Alder reactions.
8.
What product would be formed in the reaction below?
O
H3CCH3
H2O
H2SO4
?
heat
A)
O
H3CCH3
SO3H
B)
O
H3CCH3
OH
C)
O
H3CCH3
OH
D)
O
H3CCH3
HO OH
E)
O
O
Page 5
9.
What product(s) would you obtain from the reaction below?
S
H3CCH3
Raney Ni
H2
?
A)
S
H3CCH3
H
HH
B)
H3CCH3
C)
S
H3CCH3
HH
HH
H
H
D)
H3CCH3
E)
S
H3CCH3
H
H
10.
What is the name of the following amine?
N
H
A)
Piperidine
B)
Pyrrolidine
C)
Morpholine
D)
Piperazine
E)
Pyridine
Page 6
11.
Which of the following would be the most basic?
A)
B)
NH2
C)
N
CH3
O
H
D)
N
E)
CH3
N
H
Page 7
12.
Which of the following structures represents a quinoline derivative?
A)
N
O
CH3O
CH3O
CH3O
CH3O
B)
N
CH3O
CH3O
C)
N
CH3O
O
D)
S
CH3O
OCH3
OOCH3
OCH3
OCH3
E)
O
OCH3
OH
CH3O
Page 8
13.
Which of the following is not formed as either an intermediate along the reaction
pathway or as a final product for the Chichibabin reaction shown below?
N
1) NaNH2 / NH3 (liq)
2) H3O+?
A)
NNH
B)
N
NH2
H
C)
N
H
NH2
D)
NNH2
E)
N N H
Page 9
14.
Indole is stabilized by several charge-separated resonance contributors. Which of the
following is not a contributing charge-separated resonance structure?
N
Indole H
A)
N
H
B)
N
H
C)
N
H
D)
N
H
E)
N
H
Page 10
15.
Predict the major product of the following reaction.
O
O
O
+Heat ?
A)
O
O
O
B)
O
O
O
C)
O
O
O
D)
O
O
O
E)
O
O
O
O
O
Page 11
16.
Predict the major product of the following reaction.
SCl
O
+SnCl4?
A)
S
O
B)
S
O
C)
S
O
D)
S
O
E)
S
O
17.
Which of the following is one of the oldest known treatment agents for malaria?
A)
Strychnine
B)
Quinine
C)
Taxol
D)
Morphine
E)
Brucine
Page 12
18.
2,5-hexanedione can be dehydrated to give which of the molecules below?
O
O
– H2O?
A)
O CH3
B)
O
C)
O CH3
D)
O
E)
O
19.
Which reagent might convert 2,5-hexanedione to 2,5-dimethylfuran?
O
OO
?
A)
NaBH4, CH3OH
B)
H2, Pt
C)
NaOH, heat
D)
P2O5
E)
Na, EtOH
20.
You would expect a very strong nucleophile (e.g., H2N–) to attack 2-methylpyridine
where?
NH3Ca
b
cde
A)
Position a
B)
Position b
C)
Position c
D)
Position d
E)
Position e
Page 13
21.
You would expect a powerful electrophile (e.g., Br+) to attack 2-methylpyridine mostly
at which carbon?
NH3C
ab
cd
e
A)
Position a
B)
Position b
C)
Position c
D)
Position d
E)
Position e
22.
Which of the following is not aromatic?
A)
N
H
B)
N
C)
N
N
D)
N
N
H
E)
All are aromatic.
Page 14
23.
Which of the following compounds is not a heterocycle?
A)
N
HO
CH3
HO
HO
B)
N
N
Cl
H3CO
C)
N
CH3(CH2)12
H
CO2H
D)
S
F
H
E)
CH3(CH2)12 CH2OH
NH2
OH
Page 15
24.
What is the product of the following reaction?
+ NH3
O
O
CH3
A)
O
O
NHCH3
B)
NH
CH3
C)
N
CH3
D)
NH
CH3
E)
None of the above.
Page 16
25.
Which of the following compounds is not an alkaloid?
A)
B)
C)
D)
E)
All of the above are alkaloids.
Page 17
Answer Key