Page 1
1.
What is the molecular formula of limonene, the major volatile compound in orange peel
oil?
limonene
A)
C10H18
B)
C10H20
C)
C10H16
D)
C11H14
E)
C11H18
2.
Of those indicated, which would be the shortest carbon-carbon bond in -selinene?
E
D
C
B
A
A)
A
B)
B
C)
C
D)
D
E)
E
3.
What would be the ideal value for the indicated bond angle?
C
H
Br
A)
120
B)
90
C)
104
D)
180
E)
109
Page 2
4.
Which structure matches the following condensed structure?
CH3CH2CH(CN)CH=CH
2
A)
N
B)
N
C)
N
D)
N
E)
N
Page 3
5.
Which one of the following structures must be incorrect?
A)
OH
B)
O
C)
O
D)
C C
E)
Page 4
6.
Which of the following is not a resonance structure of the others?
A)
OCH3
H
H
+
B)
OCH3
H
H
+
C)
OCH3
H
H
+
D)
OCH3
H
H
+
E)
Page 5
7.
Which one of the resonance structures below would be the most important (i.e., most
stable)?
A)
OCH3
H
H
+
B)
OCH3
H
H
+
C)
OCH3
H
H
+
D)
OCH3
H
H
+
E)
OCH3
H
H
+
8.
How many atoms in ethene are required by sp2 bonding to lie in the same plane?
C C
HH
H
H
ethene
A)
2
B)
3
C)
4
D)
5
E)
6
Page 6
9.
Which one of the following structures is not chemically identical to the others?
A)
H3CCH2
H2CCH
CH2
CH3
CH3
B)
CH3CH 2
H2C
CHCH2CH 3
CH3
C)
H3C
H3CCH2
CCH2
CH2
CH3
H
D)
H3C
H3CCH2
CCH2
CH3
CH3
H
E)
CH3
CH2
HC
CH2
CH2
CH3
CH3
Page 7
10.
Which of the following pairs are not resonance structures of each other?
A)
H2C C C H H2C C CH
and
– –
B)
OO
––
and
C)
CNH2
O
CNH2
O–
+
and
D)
CCH2
O
CCH2
O–
–
and
E)
All are pairs of resonance structures.
11.
How many hydrogen atoms are part of the following steroid?
O
OH
A)
18
B)
20
C)
21
D)
22
E)
24
Page 8
12.
In the following molecule, how many carbon atoms are in the sp3 hybridization state?
OCH3
O
A)
2
B)
4
C)
5
D)
6
E)
11
13.
In the following molecule, how many carbon atoms are in the sp2 hybridization state?
O
O
OH
A)
0
B)
1
C)
2
D)
4
E)
6
14.
In the following molecule, how many carbon atoms are in the sp hybridization state?
A)
2
B)
4
C)
6
D)
12
E)
None of the above.
Page 9
15.
The lone-pair of electrons on nitrogen in the following molecule reside in what type of
orbital?
H
N
A)
sp3
B)
sp2
C)
sp
D)
2p
E)
2s
16.
In the following molecule, how many carbon atoms are in the sp2 hybridization state?
O
A)
1
B)
3
C)
7
D)
8
E)
9
17.
The boxed item most likely represents what?
A)
s orbital
B)
sp3 orbital
C)
p orbital
D)
could be any of A–C
E)
None of the above.
Page 10
18.
The following molecule contains how many carbon atoms in the sp hybridization state?
C O
A)
1
B)
3
C)
8
D)
13
E)
16
19.
The nitrogen of trimethylamine [(CH3)3N] contains how many lone pairs of electrons?
A)
none
B)
one
C)
two
D)
three
E)
there is no nitrogen in this molecule
20.
A positive charge on oxygen generally occurs when:
A)
oxygen has too many electrons.
B)
oxygen has too few electrons.
C)
oxygen is sharing one of its non-bonding electron pairs.
D)
oxygen has too many non-bonding electron pairs.
E)
oxygen is borrowing electrons from another atom.
21.
The carbon atom in CH2Cl2 has what hybridization?
A)
sp
B)
sp2
C)
sp3
D)
sp4
E)
they are not hybridized
Page 11
22.
The molecular formula for piperitone is
O
piperitone
A)
C9H16O
B)
C10H18O
C)
C9H18O
D)
C10H14O
E)
C10H16O
23.
Which structure is different from the others?
A)
Cl
B)
CH3CHClCH(CH3)2
C)
CH3
C
C
Cl
CH3
H3C
H
H
D)
CH3
CH
CH
CH3
CH3
Cl
E)
All are identical.
Page 12
24.
A fairly common algal metabolite is the compound (-)-geosmin, which imparts a musty
odor to water even at concentrations in the ppb range. What is the molecular formula of
geosmin?
(-)-geosmin
CH3
HO CH3
A)
C11H20O
B)
C12H22O
C)
C11H21O
D)
C12H20O
E)
C12H21O
25.
Which of the carbon-carbon bonds indicated would you expect to be the longest in
stilbene?
A
B
C
D
E
A)
A
B)
B
C)
C
D)
D
E)
E
Page 13
26.
Which of the following pairs are not resonance structures of each other?
A)
H2C C C H H2C C CH
and
B)
OO
and
C)
CNH2
O
CNH2
O
and
D)
CCH2
O
CCH2
O
and
E)
All are pairs of resonance structures.
27.
The following molecule has what molecular formula?
O
A)
C39H58O
B)
C40H58O
C)
C39H60O
D)
C44H44O
E)
None of the above.
Page 14
28.
What is the molecular formula of carvone, the major volatile compound in caraway oil?
carvone
O
A)
C10H18O
B)
C10H17O
C)
C10H16O
D)
C10H14O
E)
C10H15O
29.
Of those indicated, which would be the shortest carbon-carbon bond in -cadinene?
E
D
C
B
A
CH3
H3C
A)
A
B)
B
C)
C
D)
D
E)
E
30.
What would be the ideal value for the indicated bond angle?
Br
A)
120
B)
90
C)
104
D)
180
E)
109
Page 15
31.
Which structure matches the following condensed structure?
ClCH2CH(CH3)CH2CH3
A)
Cl
B)
Cl
C)
Cl
D)
Cl
E)
Cl
Page 16
32.
Which one of the following structures must be incorrect?
A)
OH
B)
O
CH3Cl
C)
OH
D)
C C
E)
33.
How many sp2 hybridized carbon atoms are in the potent anticancer compound
hydroxymethylacylfulvene?
O
OH
CH3
CH3
HO
H3C
hydroxymethylacylfulvene
A)
2
B)
4
C)
6
D)
8
E)
None of the above.
Page 17
34.
In the following molecule, how many carbon atoms are in the sp3 hybridization state?
OCH3
O
A)
2
B)
4
C)
5
D)
6
E)
9
35.
Which of the following statements are true of sp orbitals?
A)
Orbitals of the sp type are 50% s and 50% p character.
B)
They are hybrid orbitals.
C)
They are linear.
D)
They result when one s orbital and one p orbital are mixed.
E)
All are correct.
36.
Which of the following molecules are most likely to be held together by a purely
covalent bond?
A)
NaCl
B)
H2
C)
HF
D)
BH3
E)
KI
37.
What is the molecular formula of camphor?
H3CO
camphor
A)
C10H15O
B)
C10H16O
C)
C10H17O
D)
C11H18O
E)
C11H16O
Page 18
38.
Camptothecin is an important anticancer compound; how many carbons are in the sp
hybridization state?
N
N
O
O
O
HO
Camptothecin
A)
0
B)
1
C)
2
D)
3
E)
4
39.
How many sp3 carbons are in the following molecule?
F3C O CF3
O O
A)
0
B)
1
C)
2
D)
3
E)
4
40.
The process of adding electrons one by one to atomic orbitals beginning with the lowest
energy is described by:
A)
the Aufbau Principle.
B)
Hund’s Rule.
C)
the de Broglie Relation.
D)
the Pauli Exclusion Principle.
E)
Coulomb’s Law.
Page 19
41.
Which of the following cannot be a correct Lewis structure?
A)
B)
C)
D)
E)
All are correct.
42.
How many different resonance structures can be drawn for the benzyl cation (shown
below) which place the plus charge on a carbon atom in the ring?
CH2
A)
1
B)
2
C)
3
D)
5
E)
6
Page 20
43.
Which of the following represent resonance contributing Lewis structures for CH2N2?
A)
B)
C)
D)
E)
both A and B are correct
44.
The following molecule belongs to a class of compounds known as allenes. Based on
your knowledge of bonding, predict the hybridization of the carbon atom indicated by
the arrow.
C
C
C
H3CCH3
HH
A)
sp
B)
sp2
C)
sp3
D)
p–p pi
E)
a hypervalent carbon
45.
How many isomers of C4H9Br are possible?
A)
two
B)
three
C)
four
D)
five
E)
six
Page 21
46.
How many isomers of C5H12 are possible?
A)
two
B)
three
C)
four
D)
five
E)
six
47.
Which of the following most correctly defines “structural isomers”?
A)
molecules with different molecular formulas but the same connectivity
B)
compounds that are not constitutional isomers
C)
molecules with the same molecular formula but different connectivity
D)
Anti and gauche conformers
E)
both B and C
48.
How many structural isomers exist for the formula C6H14?
A)
3
B)
4
C)
5
D)
6
E)
7
49.
A hydrocarbon with a double bond and a ring will have the general formula?
A)
CnH2n+2
B)
CnH2n
C)
CnH2n-2
D)
CnH2n-4
E)
C2nH2n
Page 22
50.
What is the hybridization of the each of the labeled atoms for the potent neurotoxin
(-)-gephyrotoxin?
N
H
H
HO
H
H
(-)-gephyrotoxin
source: poison frog
acitivty: neurotoxin
A
BC
D
E
A)
A = sp2, B = sp, C = sp2, D = sp3, E = sp3
B)
A = sp2, B = sp, C = sp3, D = sp3, E = sp2
C)
A = sp2, B = sp, C = sp2, D = sp3, E = sp2
D)
A = sp2, B = sp, C = sp3, D = sp3, E = sp3
E)
A = sp, B = sp, C = sp3, D = sp3, E = sp3
Page 23
Answer Key
Page 24