Page 1
1.
Which of the following would not be aromatic (i.e., which would not be unusually
stable)?
A)
O
B)
H
C)
CH3
H3C
CH3
D)
H
E)
NCH3
2.
How would you name the following?
HO CH3
Cl
A)
3-chloro-5-methylphenol
B)
3-hydroxy-5-chlorotoluene
C)
1-chloro-3-hydroxy-5-methylbenzene
D)
Meta-methy-meta-hydroxytoluene
E)
3-hydroxy-5-methylchlorobenzene
Page 2
3.
Which of the following would you expect to be aromatic?
A)
B)
C)
D)
E)
4.
The best experimental proof of aromaticity is
A)
a pleasant odor.
B)
infrared CH absorption frequency.
C)
NMR chemical shifts.
D)
presence of resonance structures.
E)
presence of conjugation.
5.
Which of the following reactions of aromatics is reversible?
A)
Nitration
B)
Bromination
C)
F-C alkylation
D)
Sulfonation
E)
F-C acylation
6.
What reagents are typically required to accomplish bromination of an aromatic ring?
A)
Br2 + HBr
B)
Br2 + heat
C)
Br2 + light
D)
Br2 + FeBr3
E)
Br2 + H2SO4
Page 3
7.
Which of the following is not a resonance structure involved in electrophilic aromatic
bromination?
A)
Br H
B)
Br
HH
C)
Br H
D)
Br H
E)
All of these are valid resonance structures.
8.
What would be the product of the following reaction?
CH3
H3C
?
1. BH3•T HF
2. H2O2, NaOH
A)
CH3
H3COH
B)
CH3
H3COH
C)
OH
CH3
H3C
D)
CH3
H3C
HO
E)
No reaction occurs.
Page 4
9.
What would be the expected product of the following reactions?
?
3) acetone
4) H3O+
2) Mg / Et
2O
1) Br2 / FeBr3
A)
OH
B)
C)
Br
D)
OH
Ph
H
E)
10.
The reagents listed below all react readily with alkenes. Which one can react (slowly)
irreversibly with an aromatic ring?
A)
HBr + peroxides
B)
CH3CO3H
C)
HBr
D)
H2/catalyst
E)
H2O, H+
Page 5
11.
How many mononitrated (on the aromatic ring) derivatives of meta-xylene (=
1,3-dimethylbenzene) are possible? (Don’t worry about how they might be made or
which would be the major product.)
A)
1
B)
2
C)
3
D)
4
E)
5
12.
Which of the following would you expect to react fastest in an SN1 reaction (consider
the mechanism)?
A)
Br
B)
Br
C)
Br
D)
All would react rapidly.
E)
None would react.
13.
One of the double bonds in phenanthrene, shown below, is much more reactive than the
others. Which one is it?
5
4
3
2
1
A)
1
B)
2
C)
3
D)
4
E)
5
Page 6
14.
Which of the following carbocations would you expect to be most stable?
A)
B)
C)
D)
E)
15.
Which of the following molecules would you predict to be aromatic?
A)
B)
O
C)
D)
E)
H
Page 7
16.
Which would be the best systematic name of vanillan, the primary flavoring ingredient
in vanilla?
OH
CHO
OCH3
vanillin
A)
4-formyl-2-methoxyphenol
B)
3-formyl-6-hydroxyanisole
C)
4-hydroxy-3-methoxybenzaldehyde
D)
5-formyl-2-hydroxyanisole
E)
4-formyl-5-methoxyphenol
17.
Which of the following reactions has an aromatic transition state with (4n + 2) electrons
involved?
A)
C
C
O
Mn
OO
O
+
permanganate
addition:
B)
C
C+
Diels–Alder
reaction:
C)
C
C
O
O
O
+
ozonolysis:
D)
Two of these.
E)
All of these.
18.
Which of the following best describes the electronic nature of cyclooctatetraene?
cyclooctatetraene
A)
This compound is predicted to be aromatic.
B)
This compound is anti-aromatic and very unstable.
C)
This compound is non-planar and non-aromatic.
D)
Not all of the carbon atoms possess the -orbital required for conjugation.
E)
None of these are true.
Page 8
19.
What is the common name for the following compound?
OCH3
A)
Toluene
B)
Anisole
C)
Aniline
D)
Phenol
E)
Cresol
20.
What is/are the major product(s) in the following reaction?
CH3AlCl3
CH2(CH2)2CH2Cl
?
A)
CH3
B)
CH3
C)
CH3
D)
Both A and C
E)
No Reaction
Page 9
21.
What is/are the product(s) from the following reaction?
?
SO3, H2SO4H2O, cat. H2SO4
heat
A)
SO3H
B)
OH
C)
D)
SO3H
SO3H
E)
SO3H
OH
Page 10
22.
What is/are the product(s) in the following Friedel-Crafts Reaction?
H3C
CH3
CH3
Br
+?
FeBr3
A)
B)
C)
CH2
CH(CH3)2CH2
CH(CH3)2
CH2
CH(CH3)2
and
D)
Both A and B.
E)
All of the above.
Page 11
23.
What is the major product of the following reaction?
H2C CH2
+HF ?
0
oC
A)
B)
C)
D)
CH3
E)
no reaction
24.
Which of the following is not an allotrope of carbon?
A)
Graphite
B)
Diamond
C)
Coal
D)
C60
E)
All are allotropes of carbon.
25.
Which of the following statements are not true of benzene?
A)
The carbon-carbon bond lengths alternated between single bonds and double
bonds.
B)
All carbons are sp2 hybridized.
C)
The delocalized electrons form a circular pi-cloud above and below the ring.
D)
It is especially stable according to heats of hydrogenation data.
E)
None of the above. All of these statements are true.
Page 12
26.
If the heat of hydrogenation of the hypothetical 1,3,5-cyclohexatriene is –78.9 kcal/mol,
but the heat of hydrogenation of benzene is –49.3 kcal/mol, what is the stabilization
energy attributed to the resonance in benzene?
A)
–49.3 kcal/mol + (–78.9 kcal/mol) = –128.2 kcal/mol
B)
–49.3 kcal/mol – (–78.9 kcal/mol) = 29.6 kcal/mol
C)
–49.3 kcal/mol
D)
–78.9 kcal/mol
E)
None of the above.
27.
Which of the following molecular orbitals corresponds to the
1 molecular orbital of
benzene?
A)
B)
C)
D)
E)
None of the above.
28.
The infrared spectrum of a dimethylbenzene has a band at 738 cm-1. What is the most
likely structure of the compound?
A)
1,2-dimethylbenzene
B)
1,3-dimethylbenzene
C)
1,4-dimethylbenzene
D)
1,5-dimethylbenzene
E)
Not enough information to determine
Page 13
29.
Which of the following mechanisms best describes electrophilic aromatic substitution of
benzene with bromine?
A)
B)
C)
D)
E)
None of the above.
Page 14
Answer Key