Chapter 2 Chapter 2

SS2009-08-24
MULTIPLE CHOICE QUESTIONS Part 2: Funktionella grp Topic: Intermolecular forces
4. Which of these would you expect to have the lowest boiling point?
intermolekylra krafter A) CH3CH2CH2OH
(Answers on pages 17-18) B) CH3CHCH3

Topic: Intermolecular forces OH

C) CH3OCH2CH3
1. Which compound would you expect to have the lowest boiling point? D) CH3CH2CH2CH2OH
A) NH2 E) CH3CH2OCH2CH3
B) NH2

5. Which compound would have the highest boiling point?

C) H A) CH3CH2CH2CH2CH2CH3
B) CH3CH2OCH2CH2CH3
N C) CH3CH2CH2CH2CH2OH
D) D) CH3CH2OCH(CH3)2
E) CH3OCH2CH2CH2CH3
N

E)
6. Which of the following is not found in the following substance?
NH2 CH3CH2CH2CH2CH2OH
A) Ion-ion
Topic: Molecular geometry, dipole moment B) van der Waals
C) Dipole-dipole
2. Which molecule would you expect to have no dipole moment (i.e., = 0 D)? D) Resonance
A) CHF3 E) Hydrogen bonding
B) F H

7. Which compound would you expect to have the lowest boiling point?
H F A) O
C) :NF3
D) F F
NH2
B) H
N
H H
E) CH2F2
O
C) O
Topic: Intermolecular forces
N
3. Which of these compounds would have the highest boiling point?
A) CH3OCH2CH2CH2OCH3
B) CH3CH2OCH2CH2OCH3 D)
C) CH3CH2OCH2OCH2CH3 NH2
D) CH3OCH2CHOCH3
O
CH3 E)
O N
E) HOCH2CH2CH2CH2CH2OH H

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Topic: Intermolecular forces Molecular geometry, dipole moment Topic: Intermolecular forces

8. Which compound would you expect to have the highest boiling point? 12. Of the following compounds, the one with the highest boiling point is:
A) CH3OCH2CH2OCH3 A) CH3CH3
B) CH3OCH2OCH2CH3 B) CH3CH2Cl
C) HOCH2CH2CH2CH2OH C) CH3C=O
D) CH3OCH2CH2CH2OH
H
E) (CH3O)2CHCH3
D) CH3CH2OH
E) CH3CH2OCH2CH3
9. Which of the following would have no net dipole moment
( = 0 D)?
13. This alkane is predicted to have the highest melting point of those shown:
A) CBr4 A) CH3CH2CH2CH3
B) cis-1,2-Dibromoethene B) CH3CHCH3
C) trans:-1,2-Dibromoethene
D) 1,1-Dibromoethene CH3
E) More than one of these C) CH3CH2CH2CH2CH3
D) CH3CHCH2CH3

CH3
10. Which molecule has dipole moment greater than zero?
F E) CH3
A) F
CH3CCH3
H H
CH3
B) F H

F H 14. The solid alkane CH3(CH2)18CH3 is expected to exhibit the greatest solubility in which
C) F H of the following solvents?
A) CCl4
B) CH OH
H F
3
D) More than one of these
C) H2O
E) None of these
D) CH3NH2
E) HOCH2CH2OH
11. The strongest of attractive forces is which type?
A) van der Waals
15. Which compound would have the lowest boiling point?
B) Ion-dipole
C) Dipole-dipole OH
OH
D) Cation-anion
E) Hydrogen bonds O OH OH
I II III IV V
A) I
B) II
C) III
D) IV
E) V

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 Chapter 2 Chapter 2

Topic: Molecular geometry, Polarity Topic: Molecular geometry, polarity and Intermolecular forces

16. Which molecule(s) has dipole moment equal to zero? 20. For a molecule to possess a dipole moment, the following condition is necessary but not
A) Cl sufficient.
A) Three or more atoms in the molecule
B) Presence of one or more polar bonds
C) A non-linear structure
B) Cl Cl D) Presence of oxygen or fluorine
E) Absence of a carbon-carbon double or triple bond

C) Cl 21. A non-zero dipole moment is exhibited by:

A) SO2
Cl
B) CO2
C) CCl4
D) Cl Cl D) BF3
E) Cl Cl

Cl
Cl Cl
E) None of these have dipole moment equal to zero

22. Which of these is the weakest of the intermolecular attractive forces?

17. Which molecule has a zero dipole moment? A) Ion-ion
A) SO2 B) van der Waals
B) CO2 C) Dipole-dipole
C) CO D) Covalent bonding
D) CHCl3 E) Hydrogen bonding
E) None of these
Topic: Functional groups

18. Which molecule has a zero dipole moment? 23. Which compound listed below is a secondary alcohol?
A) CH3Cl A) CH3CHCH2CH3
B) CH2Cl2
OH
C) CHCl3
B) CH3CHCH2OH
D) CCl4
E) None of these CH3
C) CH3

19. Which molecule would have a dipole moment greater than zero? CH3COH
A) BeCl2 CH3
B) BCl3
C) CO2 D) CH3CH2CH2CH2OH
D) H2O E) CH3CH2CH2OCH3
E) CCl4

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 Chapter 2 Chapter 2

Topic: Functional groups 27. Which compound is an ester?

24. Which compound is a secondary amine? O O O O

A) CH3CH2CH2NH2
B) CH3CHCH3 NH O
OH
NH2
C) CH3CH2NH I II III IV V
A) I
CH3 B) II
D) H3C N CH3 C) III
CH3 D) IV
E) CH3CH2CHNH2 E) 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? OH

O O O O

NH O
O
OH In addition to an alkane (actually cycloalkane) skeleton, the Enovid molecule also
I II III IV V contains the following functional groups:
A) I A) Ether, alcohol, alkyne.
B) II B) Aldehyde, alkene, alkyne, alcohol.
C) III C) Alcohol, carboxylic acid, alkene, alkyne.
D) IV D) Ketone, alkene, alcohol, alkyne.
E) V E) Amine, alkene, ether, alkyne.

26. Which compound is a ketone?

A) O 29. Which is a 3 alkyl halide?
C OH F Br I
H Br
Cl
B) O
CH3CCH2CH3
C) O I II III IV V
HCOCH3 A) I
D) O B) II
C H C) III
H D) IV
E) H3C E) V
CH OH
H3C

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 Chapter 2 Chapter 2

Topic: Functional groups Topic: Functional groups

30. Which is a 3 amine?
O NH2 33. The compound shown below is a substance called Capsaicin, found in varying
NH2 N concentrations in several varieties of hot peppers, and responsible for their respective
H2N
NH degrees of heat. Which functional groups are present in the molecule of capsaicin?
O
I II III IV V O
N
A) I H
B) II OH
C) III Capsaicin
D) IV A) Alkene, ketone, amine, alcohol, ester
E) V B) Alkene, ketone, alcohol, ether
C) Alkene, amine, phenol, ether
D) Ether, phenol, alkene, amide
31. Which functional group is not contained in prostaglandin E1?
E) Ester, phenol, alkene, amide
O
O H
OH
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
HO atropine?
H
H H OH
N
Prostaglandin E1 O
A) Ketone Atropine
B) 2 alcohol O OH
C) 3 alcohol A) Amine
D) Carboxylic acid B) Ester
E) Alkene C) Alcohol
D) Benzene Ring
E) Ketone
32. The compound below is an adrenocortical hormone called cortisone. Which functional
group is not present in cortisone?
OH
35. The compound shown below is the male sex hormone, testosterone.
O OH
OH O
O

O
O
In addition to a cycloalkane skeleton, testosterone also contains the following functional
A) 1 alcohol
groups:
B) 2 alcohol
A) Alkene, ester, tertiary alcohol.
C) 3 alcohol B) Alkene, ether, secondary alcohol.
D) Ketone C) Alkene, ketone, secondary alcohol.
E) Alkene D) Alkyne, ketone, secondary alcohol.
E) Alkene, ketone, tertiary alcohol.

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 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 O O
O O
OH O
O O O OH
O O O
I II III
I II III IV V
A) I O
O O
B) II O OH
C) III OH
D) IV IV V
E) V A) I
B) II
C) III
37. Which compound is a tertiary alcohol? D) IV
E) V

CH3 OH
HO O OH
H3CH2C O H 40. The COC bond angle in diethyl ether is predicted to be approximately:
CH3 A) 90
B) 105
I II III IV V C) 110
A) I D) 120
B) II E) 180
C) III
D) IV
E) V 41. Which compound(s) contain(s) tertiary carbon atom(s)?
Br
F OH
OH
38. Which compound is a primary amine with the formula C5H13N?
I II III IV V
H2N A) I, II, III
N B) I
NH H2N NH2 C) II, III
D) I, IV
I II III IV V E) V
A) I
B) II 42. The number of unique open-chain structures corresponding to the molecular formula
C) III C3H5Cl is:
D) IV A) 2
E) V B) 3
C) 4
D) 5
E) 6

Topic: Functional groups

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 Chapter 2 Chapter 2

43. An example of a tertiary amine is: Topic: Functional groups, Isomerism

H
N NH2 N 47. Which of these compounds is a secondary alkyl chloride?
NH2 H2N
A) CH3CH2CH2CH2CH2Cl
I II III IV V B) CH3
CH3CCH2CH3
A) I
B) II Cl
C) III C) CH3CHCH2CH2CH3
D) IV Cl
E) V D) CH3CH2CHCl
CH2CH3
E) Two of these
44. Which functional groups are present in the following compound?

48. How many 2 alkyl bromides, neglecting stereoisomers, exist with the formula C6H13Br?
A) 4
A) Alkene, 1 alcohol, ketone B) 5
B) Alkene, 2 alcohol, aldehyde C) 6
C) Alkene, 2 alcohol, ketone D) 7
D) Alkyne, 1 alcohol, aldehyde E) 8
E) Alkyne, 2 alcohol, ketone

45. How many constitutional isomers are possible with the formula C4H10O? 49. Many organic compounds contain more than one functional group. Which of the
A) 3 following is both an aldehyde and an ether?
B) 4
C) 5 O
O O
D) 6 O O OCH3
O O
E) 7 O O O
I II III IV V
A) I,
46. A tertiary carbon atom is present in which of these compounds? B) II, IV
Cl Cl OH C) V
D) I, V
HO E) III
I II III IV V
A) I 50. The following substance is expected to have low solubility in which of the following
B) II, IV solvent(s)?
C) III, V
O Na
D) IV
E) All of these O
A) CCl4
B) C2H5OH
C) CHCl3
D) CH2OHCH2CH2CH2CH2CH2OH
E) The given substance is likely to be quite soluble in all of the solvents described

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 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.

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 Chapter 2 Chapter 2

ANSWERS MULTIPLE CHOICE QUESTIONS Ans:

Part 2: Funktionella grp intermolekylra krafter 53

Answers 1-50 Ans: O O O

54
Frga Svar Rtt/Fel Frga Svar Rtt/Fel
1 D 26 B
2 B 27 C
3 E 28 D
Ans: OH
4 C 29 B
5 C 30 D 55 C3H8O OH
O
6 D 31 C primary alcohol secondary alcohol ether
7 C 32 B
8 C 33 D
9 E 34 E
10 D 35 C Ans:
11 D 36 E 56 O O O O

12 D 37 E
13 E 38 C
14 A 39 D
O O
15 A 40 C O

16 C 41 D
17 B 42 C
18 D 43 E
Ans:
19 D 44 B
57 O O O O
20 B 45 E
21 A 46 C
22 B 47 E
23 A 48 C Ans: The overall dipole moment of a polyatomic molecule depends on two factors: the
24 C 49 A 58 polarity of various bonds and molecular geometry, since dipole forces have both
25 D 50 A magnitude and direction. In some molecules containing bonds of identical
polarity, the molecular geometry may result in a net cancellation of the overall
Answers 51-60 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. ..
Ans:
51 N N N :O C O :

N N N Ans Strong hydrogen bonding between molecules of ethanol leads to elevation in

59: boiling point. No hydrogen bonding is possible between molecules of propane,
resulting in a lower boiling point compared with ethanol.

Ans: Ans: Strong hydrogen bonding between molecules of ethanol leads to elevation in
52 60 boiling point. No hydrogen bonding is possible between molecules of dimethyl
ether, resulting in a lower boiling point compared with ethanol.

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