1.Which of the atoms that are marked with an arrow are sp 2-hybridized?
O
H3C
C
CH3
O
OH
H
C
CH3
I
II
a) I, II, III
b) I, II, IV
H
N
CH3
CH3
III
c) I, III, V
CH3
IV
2. Which statement about contributing structures is false?
a) All contributing structures must have the same number of valence electrons.
b) All contributing structures must obey the rules of covalent bonding.
c) The position of nuclei may change.
d) Third period atoms may have up to 18 electrons around them.
3. Which compounds are classified correctly?
O
C
CH3
CH3
H
OH
H
C
CH3
CH3
N
CH3
alcohol
aldehyde
ketone
amine
I
II
III
IV
a) III, IV, V
b) II, III, IV
c) I, III, V
O
CH3
CH3
C
OH
carboxylic acid
V
d) I, III, IV
4. Which of the three molecules testosterone, methadone and hydrocodone contains an amine?
testosterone
methadone
O
H
H
hydrocodone
N
N
OH
H
O
O
O
I
a) I,II
b) III
II
c) II,III
O
III
d) I, II, III
5. Which ion is the strongest base?
O
CH3CH2O
I
CH3
C
II
O
Cl
CH3CH2
III
IV
a) I
b) II
c) III
C
V
d) III, IV
O
O
CH3
d) IV
6. Which is the order of decreasing acid strength of the following compounds (greatest first)?
OH
O
O
Cl CH2
Br CH2
OH
O
OH
I
CH3
OH
II
b)
O
F CH2
OH
III
III, IV, I, II
c)
IV
a)
II, I, III, IV
III, I, II, IV
d)
IV, II, I, III
7.
Which is the proper reaction mechanism for the reaction of boron trifluoride and diethyl ether?
Assume that the charges are correct and add electron pairs, if needed. Also consider how many
electrons should be in the outer shell of boron trifluoride to make it neutral.
F
BF3
I
CH2CH3
O
F
B
CH2CH3
O
CH2CH3
F
CH2CH3
F
BF3
II
CH2CH3
O
F
B
CH2CH3
CH2CH3
O
F
CH2CH3
F
BF3
III
CH2CH3
O
F
B
CH2CH3
CH2CH3
O
F
CH2CH3
F
BF3
IV
CH2CH3
O
F
B
CH2CH3
CH2CH3
a) I
b) II
c) III
O
F
CH2CH3
d) IV
8. Which of the following molecules are constitutional isomers?
I
II
a)
III
I and IV
b) II and III
c)
I , II, and IV
d)
9.
I, II, and III
How many primary carbons are in cholesterol?
a) 2
b) 3
c) 4
H
H
HO
H
cholesterol
d) 5
IV
10. Which conformation of pentane is most stable?
CH3CH2CH3
H
H
H
H
CH2CH3
H
CH3
H
H
H
a) I
CH3
H
H
c) III
H
H
CH3
II
b) II
CH2CH3
H
H
H
H
I
CH2CH3
III
IV
d) IV
11. In the most stable conformation of cis-1,3-dimethylcyclohexane, what positions do the methyl
groups occupy?
a) axial, axial
b) equatorial, axial
c) equatorial, equatorial
d) axial, equatorial
12. Which compound has the lowest boiling point?
CH3CH2CH2CH2CH3
I
CH3
CHCH2CH3
CH3
I
a)
CH3
CH3
c) III
CH3
CH3
II
b) II
C
III
IV
d) IV
13. Which substances are Lewis bases?
H2O
AlCl3
I
II
.a)
I, II
b)
CH3
CH
F
CH3
IV
III
I, III
c)
III, IV
d)
I, IV
14.Which is the stronger base if the equilibrium lies to the right?
O
CH3
C
I
(Sec. 2.4, HARD)
O
OH
+
CN
CH3
II
C
III
O
+
HCN
IV
a) I
b) II
c) III
d) IV
Difficulty Level: Hard
15. Which is the IUPAC name for the following cycloalkane?
a) 2,4-dimethyl-1-ethylcyclopentane
dimethylcyclopentane
b) 1,3-dimethyl-5-ethylcyclopentane
d) 1-ethyl-3,5-dimethylcyclopentane
c) 1-ethyl-2,4-