Page 1
1.
The correct name of the following molecule would be:
A)
2-ethyl-3,3-dimethylheptane
B)
6-ethyl-5,5-dimethylheptane
C)
3,4,4-trimethyloctane
D)
2-butyl-3-methylpentane
E)
2-sec-butyl-2-methylhexane
2.
What is the name given to the Newman projection of the butane conformation shown
here?
H
CH3
H
CH3
HH
A)
anti
B)
gauche
C)
staggered
D)
eclipsed
E)
skewed
3.
At room temperature, the various conformations of butane
A)
do not interconvert with only the anti form present.
B)
do not interconvert, but all forms are present.
C)
interconvert slowly.
D)
interconvert rapidly.
E)
There is no way to determine if interconversion occurs.
Page 2
4.
What statement is true of the following energy diagram?
prod 1
prod 2
SM
A)
For irreversible reactions, product 1 will dominate.
B)
For reversible reactions, product 2 will dominate at equilibrium.
C)
For reversible reactions, equal amounts of 1 and 2 will be formed.
D)
For irreversible reactions, equal amounts of 1 and 2 will be formed.
E)
None of the above are true.
5.
What would be the correct name of the following?
A)
3-(sec-pentyl)pentane
B)
5-ethyl-4-methylheptane
C)
3-(sec-butyl)hexane
D)
3-ethyl-4-methylheptane
E)
3-ethyl-4-propylpentane
6.
The following Newman projection corresponds to which molecule?
H
CH3CH2H
CH2CH3
H
H
A)
pentane
B)
butane
C)
3-ethylbutane
D)
hexane
E)
3-methylpentane
Page 3
7.
Rotation around the carbon-carbon bond of the molecule depicted by the following
Newman projection requires how much energy?
H
H
H
H
H
H
A)
0 kcal/mol
B)
3 kcal/mol
C)
6 kcal/mol
D)
9 kcal/mol
E)
15 kcal/mol
8.
What is the correct IUPAC name for the following molecule?
A)
1,1,1,4-tetramethylhexane
B)
4-ethyl-1,1,1-trimethylpentane
C)
5-ethyl-2,2-dimethylhexane
D)
3,6,6,6-tetramethylhexane
E)
2,2,5-trimethylheptane
9.
The following represents what functional group?
R R
O
A)
ester
B)
ether
C)
alcohol
D)
thiol
E)
ketone
Page 4
10.
The following represents what functional group?
R H
O
A)
alcohol
B)
aldehyde
C)
carboxylic acid
D)
amide
E)
ketone
11.
The following represents what functional group?
C NR
A)
amide
B)
thiol
C)
ketone
D)
nitrile
E)
amine
12.
What is the correct structure for tert-butyl bromide?
A)
Br
B)
Br
C)
Br
D)
Br
E)
Br
Page 5
13.
The following Newman projection represents which molecule?
H
H3CH2CH2C
CH3
CH2CH3
CH3
CH2CH2CH3
A)
B)
CH3
CH3
C)
D)
E)
Page 6
14.
Name the following functional group:
R O R
O O
A)
ester
B)
ketone
C)
alcohol
D)
carboxylic acid
E)
anhydride
15.
Which isomer of C7H16 shown would have the highest boiling point?
A)
B)
C)
D)
E)
16.
Which of the following contains the isobutyl group?
A)
(CH3)2CHCH2Cl
B)
(CH3)3CCl
C)
CH3CH2CH(CH3)Cl
D)
CH3CH2CH2CH2Cl
E)
None of the above.
Page 7
17.
Which of the following contains the sec-butyl group?
A)
(CH3)2CHCH2Cl
B)
(CH3)3CCl
C)
CH3CH2CH(CH3)Cl
D)
CH3CH2CH2CH2Cl
E)
None of the above.
18.
How would the following molecule be properly named?
CH3
CH
CH
CH3
HC
CH2
CH3
CH3CH2
CH2CH2CH3
A)
3-ethyl-2-methyl-4-propylhexane
B)
3,4-diethyl-2-methylheptane
C)
4-ethyl-3-isopropylheptane
D)
3-isopropyl-4-propylhexane
E)
None of the above.
19.
The IUPAC name for [(CH3)3C]2CHCH3 is:
A)
1,1-di-tert-butylethane
B)
3-tert-butyl-2,2-dimethylbutane
C)
2,2,3,4,4-pentamethylpentane
D)
2,4,4-trimethylheptane
E)
None of the above.
20.
What is the smallest alkane that is liquid at room temperature?
A)
propane
B)
butane
C)
pentane
D)
hexane
E)
All are liquids.
Page 8
21.
All steroids are derivatives of the ring system shown. How many tertiary hydrogens
are in this ring system?
A)
none
B)
2
C)
4
D)
5
E)
6
22.
What is the correct IUPAC name for the following molecule:
A)
2-ethyl-2,6-dimethylheptane
B)
1,1,5,5-tetramethylhexane
C)
1,1,5,5-tetramethylheptane
D)
2,6,6-trimethyloctane
E)
4,4-dimethyl-1-isopropylhexane
23.
What is the name given to the Newman projection of the butane conformation shown
here?
CH3
H
H
CH3
HH
A)
eclipsed
B)
gauche
C)
staggered
D)
anti
E)
skewed
Page 9
24.
Calculate Go for the following reaction at 25 oC and S=0
A)
–10 kcal/mol
B)
10 kcal/mol
C)
34 kcal/mol
D)
–34 kcal/mol
E)
None of the above.
25.
Which of the following has the highest pKa?
A)
HI
B)
NH3
C)
HNO3
D)
CH3COOH
E)
H2SO4
26.
The common name for 1-methylpropyl is:
A)
Isopropyl
B)
Isobutyl
C)
sec-Butyl
D)
tert-Butyl
E)
None of the above.
Page 10
27.
What is the correct Newman projection for the following molecule?
H3C Cl
Br
H3CH2C
A)
CH3
CH3
Cl
(CH2)2CH3
CH2CH3
Br
B)
CH3
CH3
Cl
(CH2)2CH3
BrH3CH2C
C)
CH3
CH3
Cl
CH2CH3
BrH3CH2C
D)
H
CH3
Cl
(CH2)2CH3
CH2CH3
Br
E)
None of the above.
Page 11
28.
Which of the following molecules contain both an alcohol and an aldehyde functional
group?
A)
O
O
B)
H
O
OH
C)
HO NH2
O
D)
O
OH
O
E)
N
CO2H
O
H
Page 12
29.
Consider the potential energy diagram for rotation about the C2–C3 bond in pentane.
The position marked “A” most likely corresponds to which of the following Newman
projections?
A)
CH3
CH2CH2CH3
H
H
H
H
B)
H
CH2CH3
H
H
CH3
H
C)
HH
CH3H
CH2CH3
H
D)
HCH3
HCH2CH3
H
H
E)
Page 13
HH
CH3CH3
H
H
30.
What is the correct IUPAC name for the following molecule?
A)
6-propyl-5,7,8-trimethyldecane
B)
5,7,8-trimethyl-6-propyldecane
C)
3,4,6-trimethyl-5-propyldecane
D)
5-propyl-3,4,6-trimethyldecane
E)
None of the above.
31.
Which of the following is not considered a Lewis acid?
A)
H
B)
CH3OH
C)
AlCl3
D)
C
CH3
CH3
H3C
E)
BF3
Page 14
32.
Which of the following is considered to be a nucleophile?
A)
CH3Cl
B)
CH3CH2I
C)
NH3
D)
E)
C
CH3
H3C
H
33.
Which of the following reactions has a S = 0?
A)
Br2
+Br
Br
B)
CH3CH2Cl + NaOH → CH2=CH2 + H2O + NaCl
C)
Br2
+Br
hv + HBr
D)
•CH3
CH3+ HI CH3
CH3
H3C
I
H
H
E)
None of the above.
34.
How many quaternary carbons are in the following molecule?
A)
0
B)
1
C)
2
D)
3
E)
4
Page 15
35.
How many ester functional groups are in the potent anticancer compound Taxol?
O
OH
O
O
O
O
OCH3
O
O
OH
N
H
O
Taxol
A)
0
B)
1
C)
2
D)
3
E)
4
36.
Arrange these acids in the order of increasing acidity.
HCl HBr HI HF
A)
HBr, HI, HF, HCl
B)
HF, HCl, HBr, HI
C)
HF, HBr, HCl, HI
D)
HI, HCl, HBr, HF
E)
HI, HBr, HCl, HF
37.
Arrange these acids in the order of increasing acidity.
CH4 H2O HF NH3
A)
CH4, H2O, HF, NH3
B)
HF, H2O, CH4, NH3
C)
HF, H2O, NH3, CH4,
D)
CH4, NH3, H2O, HF,
E)
NH3, CH4, H2O, HF,
Page 16
38.
What is the correct IUPAC name for the following molecule?
A)
1-ethyl-2-methylhexane
B)
2-ethyl-1-methylcycloheptane
C)
4-ethyl-5-methylcyclohexane
D)
1-ethyl-2-methylcyclohexane
E)
1-methyloctane
39.
Guanacastepene is a natural product that was recently isolated and shown to be a potent
antibiotic. How many different functional groups does this structure possess?
A)
1
B)
2
C)
3
D)
4
E)
5
Page 17
Answer Key