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Chapter 2
SS2009-08-24
NH2
C)
D)
N
E)
NH2
C) :NF3
D) F
OH
C) CH3OCH2CH3
D) CH3CH2CH2CH2OH
E) CH3CH2OCH2CH3
5.
A)
B)
C)
D)
E)
NH2
H
N
B)
H
E) CH2F2
3.
A)
B)
C)
D)
C)
CH3
E) HOCH2CH2CH2CH2CH2OH
D)
NH2
O
E)
N
H
Chapter 2
Which compound would you expect to have the highest boiling point?
CH3OCH2CH2OCH3
CH3OCH2OCH2CH3
HOCH2CH2CH2CH2OH
CH3OCH2CH2CH2OH
(CH3O)2CHCH3
B)
H
F
H
H
H
H
C) F
H
Of the following compounds, the one with the highest boiling point is:
CH3CH3
CH3CH2Cl
CH3C=O
H
D) CH3CH2OH
E) CH3CH2OCH2CH3
13. This alkane is predicted to have the highest melting point of those shown:
A) CH3CH2CH2CH3
B) CH3CHCH3
CH3
C) CH3CH2CH2CH2CH3
D) CH3CHCH2CH3
CH3
CH3
E)
CH3CCH3
CH3
14. The solid alkane CH3(CH2)18CH3 is expected to exhibit the greatest solubility in which
of the following solvents?
A) CCl4
B) CH3OH
C) H2O
D) CH3NH2
E) HOCH2CH2OH
Chapter 2
A)
B)
C)
D)
E)
OH
OH
OH
OH
II
III
I
II
III
IV
V
IV
Chapter 2
B) Cl
Cl
C)
Cl
20. For a molecule to possess a dipole moment, the following condition is necessary but not
sufficient.
A) Three or more atoms in the molecule
B) Presence of one or more polar bonds
C) A non-linear structure
D) Presence of oxygen or fluorine
E) Absence of a carbon-carbon double or triple bond
21.
A)
B)
C)
D)
E)
Cl
D) Cl
Chapter 2
Cl
Cl
Cl
Cl
Cl
18.
A)
B)
C)
D)
E)
22.
A)
B)
C)
D)
E)
C)
19.
A)
B)
C)
D)
E)
CH3
CH3
CH3COH
CH3
D) CH3CH2CH2CH2OH
E) CH3CH2CH2OCH3
Chapter 2
Chapter 2
NH
O
OH
NH2
C) CH3CH2NH
A)
B)
C)
D)
E)
CH3
D) H3C N CH3
CH3
E) CH3CH2CHNH2
II
III
I
II
III
IV
V
IV
CH3
OH
O
NH
OH
A)
B)
C)
D)
E)
I
II
III
IV
V
II
IV
III
A)
B)
C)
D)
E)
CH3CCH2CH3
O
A)
B)
C)
D)
E)
HCOCH3
D) O
C H
H
E) H3C
CH OH
I
II
III
IV
V
II
III
H3C
Br
Br
IV
Chapter 2
Chapter 2
NH2
H2N
NH
33. The compound shown below is a substance called Capsaicin, found in varying
concentrations in several varieties of hot peppers, and responsible for their respective
degrees of heat. Which functional groups are present in the molecule of capsaicin?
O
A)
B)
C)
D)
E)
I
II
III
IV
V
II
III
IV
HO
A)
B)
C)
D)
E)
A)
B)
C)
D)
E)
OH
Capsaicin
Alkene, ketone, amine, alcohol, ester
Alkene, ketone, alcohol, ether
Alkene, amine, phenol, ether
Ether, phenol, alkene, amide
Ester, phenol, alkene, amide
34. Drawn below is Atropine, found in Atropa belladonna, sometimes used in dilating
pupils during an eye-exam. Which of the following functional groups is NOT in
atropine?
H OH
N
O
O
32. The compound below is an adrenocortical hormone called cortisone. Which functional
group is not present in cortisone?
OH
A)
B)
C)
D)
E)
Atropine
OH
Amine
Ester
Alcohol
Benzene Ring
Ketone
35. The compound shown below is the male sex hormone, testosterone.
OH
OH
A)
B)
C)
D)
E)
OH
Prostaglandin E1
Ketone
2 alcohol
3 alcohol
Carboxylic acid
Alkene
N
H
1 alcohol
2 alcohol
3 alcohol
Ketone
Alkene
A)
B)
C)
D)
E)
10
Chapter 2
Chapter 2
OH
A)
B)
C)
D)
E)
I
II
III
IV
V
II
OH
IV
CH3
OH
HO
OH
CH3
A)
B)
C)
D)
E)
II
O
H3CH2C O
I
II
III
IV
V
II
IV
III
O
OH
III
III
O
OH
OH
IV
A)
B)
C)
D)
E)
I
II
III
IV
V
40.
A)
B)
C)
D)
E)
A)
B)
C)
D)
E)
H 2N
II
III
IV
I
II
III
IV
V
NH2
A)
B)
C)
D)
E)
I
I, II, III
I
II, III
I, IV
V
OH
OH
II
III
IV
42. The number of unique open-chain structures corresponding to the molecular formula
C3H5Cl is:
A) 2
B) 3
C) 4
D) 5
E) 6
Topic: Functional groups
11
12
Chapter 2
Chapter 2
NH2
A)
B)
C)
D)
E)
H 2N
II
III
IV
CH3CCH2CH3
I
II
III
IV
V
Cl
C) CH3CHCH2CH2CH3
Cl
D) CH3CH2CHCl
CH2CH3
E) Two of these
48.
A)
B)
C)
D)
E)
A)
B)
C)
D)
E)
45.
A)
B)
C)
D)
E)
How many constitutional isomers are possible with the formula C4H10O?
3
4
5
6
7
OH
Cl
HO
A)
B)
C)
D)
E)
I
I
II, IV
III, V
IV
All of these
II
III
IV
How many 2 alkyl bromides, neglecting stereoisomers, exist with the formula C6H13Br?
4
5
6
7
8
49. Many organic compounds contain more than one functional group. Which of the
following is both an aldehyde and an ether?
O
O
A)
B)
C)
D)
E)
OCH3
II
III
IV
I,
II, IV
V
I, V
III
50. The following substance is expected to have low solubility in which of the following
solvent(s)?
O Na
O
A)
B)
C)
D)
E)
13
CCl4
C2H5OH
CHCl3
CH2OHCH2CH2CH2CH2CH2OH
The given substance is likely to be quite soluble in all of the solvents described
14
Chapter 2
Chapter 2
53. Draw a structural formula for C8H18 , in which there are two quaternary carbons.
57. Draw all isomers of C6H12O that are aldehydes and contain at least one tertiary carbon
Topic: Molecular Geometry, Dipole Moment
58. Carbon dioxide is non- polar, despite the fact that oxygen is much more electronegative
than carbon. Briefly explain why, using relevant diagrams as appropriate to illustrate
your Ans:wer.
Topic: Intermolecular Forces
59. Ethanol, C2H5OH, and propane, C3H8, have approximately the same molar mass, yet,
ethanol has a much higher boiling point. Briefly explain why.
60. Ethanol, C2H5OH, and dimethyl ether, CH3OCH3, have the same molar mass, yet,
ethanol has a much higher boiling point. Briefly explain why.
15
16
Chapter 2
Chapter 2
Ans:
53
Svar
D
B
E
C
C
D
C
C
E
D
D
D
E
A
A
C
B
D
D
B
A
B
A
C
D
Rtt/Fel
Frga
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
Answers 51-60
Ans:
51
Ans:
52
Svar
B
C
D
B
D
C
B
D
E
C
E
E
C
D
C
D
C
E
B
E
C
E
C
A
A
Rtt/Fel
Ans:
54
OH
Ans:
C3H8O
55
OH
primary alcohol
Ans:
56
ether
Ans:
57
O
secondary alcohol
Ans: The overall dipole moment of a polyatomic molecule depends on two factors: the
58
polarity of various bonds and molecular geometry, since dipole forces have both
magnitude and direction. In some molecules containing bonds of identical
polarity, the molecular geometry may result in a net cancellation of the overall
dipole forces. This is what happens in carbon dioxide: although there are two
polar C-O bonds, because of the linear geometry of the molecule, the net dipole is
zero.
..
..
: O C O:
Ans
59:
17
18