Chapter 2
Chapter 2
SS2009-08-24
MULTIPLE CHOICE QUESTIONS Part 2: Funktionella grp –
intermolekylära krafter
(Answers on pages 17-18)
Topic: Intermolecular forces
1. Which compound would you expect to have the lowest boiling point?
NH2
A)
B)
NH2
C)
H
D)
N
E)
NH2
Topic: Molecular geometry, dipole moment
2. Which molecule would you expect to have no dipole moment (i.e., µ = 0 D)?
A) CHF3
H
B) F
C) :NF3
D) F
OH
C) CH3OCH2CH3
D) CH3CH2CH2CH2OH
E) CH3CH2OCH2CH3
5.
A)
B)
C)
D)
E)
N
H
Topic: Intermolecular forces
4. Which of these would you expect to have the lowest boiling point?
A) CH3CH2CH2OH
B) CH3CHCH3
Which compound would have the highest boiling point?
CH3CH2CH2CH2CH2CH3
CH3CH2OCH2CH2CH3
CH3CH2CH2CH2CH2OH
CH3CH2OCH(CH3)2
CH3OCH2CH2CH2CH3
6. Which of the following is not found in the following substance?
CH3CH2CH2CH2CH2OH
A) Ion-ion
B) van der Waals
C) Dipole-dipole
D) Resonance
E) Hydrogen bonding
7. Which compound would you expect to have the lowest boiling point?
O
A)
F
F
NH2
H
N
B)
H
H
E) CH2F2
O
3.
A)
B)
C)
D)
O
C)
Topic: Intermolecular forces
Which of these compounds would have the highest boiling point?
CH3OCH2CH2CH2OCH3
CH3CH2OCH2CH2OCH3
CH3CH2OCH2OCH2CH3
CH3OCH2CHOCH3
CH3
E) HOCH2CH2CH2CH2CH2OH
N
D)
NH2
O
E)
1
O
N
H
2
Chapter 2
Topic: Intermolecular forces Molecular geometry, dipole moment
8.
A)
B)
C)
D)
E)
Which compound would you expect to have the highest boiling point?
CH3OCH2CH2OCH3
CH3OCH2OCH2CH3
HOCH2CH2CH2CH2OH
CH3OCH2CH2CH2OH
(CH3O)2CHCH3
9. Which of the following would have no net dipole moment
(µ = 0 D)?
A) CBr4
B) cis-1,2-Dibromoethene
C) trans:-1,2-Dibromoethene
D) 1,1-Dibromoethene
E) More than one of these
10. Which molecule has dipole moment greater than zero?
F
A) F
B)
H
F
H
H
F
H
H
C) F
H
Topic: Intermolecular forces
12.
A)
B)
C)
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
F
D) More than one of these
E) None of these
11.
A)
B)
C)
D)
E)
Chapter 2
The strongest of attractive forces is which type?
van der Waals
Ion-dipole
Dipole-dipole
Cation-anion
Hydrogen bonds
15. Which compound would have the lowest boiling point?
O
I
A)
B)
C)
D)
E)
3
OH
OH
OH
OH
II
III
I
II
III
IV
V
4
IV
V
Chapter 2
Topic: Molecular geometry, Polarity
Topic: Molecular geometry, polarity and Intermolecular forces
16. Which molecule(s) has dipole moment equal to zero?
Cl
A)
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
A non-zero dipole moment is exhibited by:
SO2
CO2
CCl4
BF3
Cl
Cl
Cl
Cl
E) None of these have dipole moment equal to zero
17.
A)
B)
C)
D)
E)
Which molecule has a zero dipole moment?
SO2
CO2
CO
CHCl3
None of these
18.
A)
B)
C)
D)
E)
Which molecule has a zero dipole moment?
CH3Cl
CH2Cl2
CHCl3
CCl4
None of these
22.
A)
B)
C)
D)
E)
Topic: Functional groups
23. Which compound listed below is a secondary alcohol?
A) CH3CHCH2CH3
OH
B) CH3CHCH2OH
C)
19.
A)
B)
C)
D)
E)
Which molecule would have a dipole moment greater than zero?
BeCl2
BCl3
CO2
H2O
CCl4
5
Which of these is the weakest of the intermolecular attractive forces?
Ion-ion
van der Waals
Dipole-dipole
Covalent bonding
Hydrogen bonding
CH3
CH3
CH3COH
CH3
D) CH3CH2CH2CH2OH
E) CH3CH2CH2OCH3
6
Chapter 2
Chapter 2
Topic: Functional groups
27. Which compound is an ester?
24. Which compound is a secondary amine?
A) CH3CH2CH2NH2
B) CH3CHCH3
O
O
O
O
NH
O
OH
NH2
C) CH3CH2NH
I
A)
B)
C)
D)
E)
CH3
D) H3C N CH3
CH3
E) CH3CH2CHNH2
II
III
I
II
III
IV
V
IV
V
CH3
28. The compound shown below is a synthetic estrogen. It is marketed as an oral
contraceptive under the name Enovid.
25. Which compound is an aldehyde?
O
O
OH
O
O
NH
O
O
OH
A)
B)
C)
D)
E)
I
II
III
IV
V
I
II
IV
III
26. Which compound is a ketone?
A) O
C OH
H
O
B)
C)
V
A)
B)
C)
D)
E)
In addition to an alkane (actually cycloalkane) skeleton, the Enovid molecule also
contains the following functional groups:
Ether, alcohol, alkyne.
Aldehyde, alkene, alkyne, alcohol.
Alcohol, carboxylic acid, alkene, alkyne.
Ketone, alkene, alcohol, alkyne.
Amine, alkene, ether, alkyne.
29. Which is a 3° alkyl halide?
F
Cl
CH3CCH2CH3
O
A)
B)
C)
D)
E)
HCOCH3
D) O
C H
H
E) H3C
CH OH
I
II
III
IV
V
I
II
III
H3C
7
8
I
Br
Br
IV
V
Chapter 2
Chapter 2
Topic: Functional groups
30. Which is a 3° amine?
Topic: Functional groups
NH2
O
NH2
H2N
N
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
I
II
III
IV
V
II
III
IV
V
31. Which functional group is not contained in prostaglandin E1?
O
O
HO
A)
B)
C)
D)
E)
H
H
H
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.
O
O
OH
OH
O
O
A)
B)
C)
D)
E)
O
OH
Prostaglandin E1
Ketone
2° alcohol
3° alcohol
Carboxylic acid
Alkene
O
N
H
1° alcohol
2° alcohol
3° alcohol
Ketone
Alkene
A)
B)
C)
D)
E)
9
In addition to a cycloalkane skeleton, testosterone also contains the following functional
groups:
Alkene, ester, tertiary alcohol.
Alkene, ether, secondary alcohol.
Alkene, ketone, secondary alcohol.
Alkyne, ketone, secondary alcohol.
Alkene, ketone, tertiary alcohol.
10
Chapter 2
Chapter 2
Topic: Functional groups
Topic: Functional groups
36. Which is a carboxylic acid?
39. Which compound can be classified as an ester as well as a ketone?
O
OH
O
O
A)
B)
C)
D)
E)
I
I
II
III
IV
V
O
O
II
O
O
O
OH
IV
V
37. Which compound is a tertiary alcohol?
CH3
OH
H
O
HO
OH
CH3
A)
B)
C)
D)
E)
O
O
I
II
O
O
H3CH2C O
I
I
II
III
IV
V
II
IV
III
V
O
O
OH
III
O
O
III
O
O
OH
OH
V
IV
A)
B)
C)
D)
E)
I
II
III
IV
V
40.
A)
B)
C)
D)
E)
The C–O–C bond angle in diethyl ether is predicted to be approximately:
90º
105º
110º
120º
180º
41. Which compound(s) contain(s) tertiary carbon atom(s)?
Br
F
38. Which compound is a primary amine with the formula C5H13N?
H 2N
NH
I
A)
B)
C)
D)
E)
N
H 2N
II
III
IV
I
II
III
IV
V
NH2
V
A)
B)
C)
D)
E)
I
I, II, III
I
II, III
I, IV
V
OH
OH
II
III
IV
V
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
43. An example of a tertiary amine is:
H
N
NH2
I
A)
B)
C)
D)
E)
Topic: Functional groups, Isomerism
NH2
H 2N
II
III
IV
N
V
CH3CCH2CH3
I
II
III
IV
V
Cl
C) CH3CHCH2CH2CH3
Cl
D) CH3CH2CHCl
CH2CH3
E) Two of these
44. Which functional groups are present in the following compound?
48.
A)
B)
C)
D)
E)
A)
B)
C)
D)
E)
Alkene, 1º alcohol, ketone
Alkene, 2º alcohol, aldehyde
Alkene, 2º alcohol, ketone
Alkyne, 1º alcohol, aldehyde
Alkyne, 2º alcohol, ketone
45.
A)
B)
C)
D)
E)
How many constitutional isomers are possible with the formula C4H10O?
3
4
5
6
7
46. A tertiary carbon atom is present in which of these compounds?
Cl
OH
Cl
HO
A)
B)
C)
D)
E)
I
I
II, IV
III, V
IV
All of these
47. Which of these compounds is a secondary alkyl chloride?
A) CH3CH2CH2CH2CH2Cl
CH3
B)
II
III
IV
V
How many 2º 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
O
I
A)
B)
C)
D)
E)
O
O
O
OCH3
O
O
II
O
O
III
IV
V
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
SHORT ANSWER QUESTIONS (With answers on page 17-18)
Topic: Isomers, Functional Groups
51. Draw all tertiary amine isomers of C6H15N.
Answers Next Pages (p. 17-18)
52. Draw all isomers of C6H14.
53. Draw a structural formula for C8H18 , in which there are two quaternary carbons.
54. Draw all isomers of C5H10O that are ketones.
55. Draw all isomers of C3H8O and classify each according to functional group
56. Draw all isomers of C6H12O that are aldehydes.
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
ANSWERS MULTIPLE CHOICE QUESTIONS
Part 2: Funktionella grp – intermolekylära krafter
Answers 1-50
Fråga
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
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
Rätt/Fel
Fråga
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
N
N
N
N
N
N
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
Rätt/Fel
O
Ans:
54
O
O
OH
Ans:
C3H8O
55
OH
primary alcohol
Ans:
56
O
O
O
ether
O
O
O
O
Ans:
57
O
O
secondary alcohol
O
O
O
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:
Strong hydrogen bonding between molecules of ethanol leads to elevation in
boiling point. No hydrogen bonding is possible between molecules of propane,
resulting in a lower boiling point compared with ethanol.
Ans: Strong hydrogen bonding between molecules of ethanol leads to elevation in
60
boiling point. No hydrogen bonding is possible between molecules of dimethyl
ether, resulting in a lower boiling point compared with ethanol.
17
18