Organic Chemistry 11th Edition Solomons Test Bank
Organic Chemistry 11th Edition Solomons Test Bank
Organic Chemistry 11th Edition Solomons Test Bank
A) CS2
B) LiF
C) F2
D) CH3F
E) None of these choices.
Answer: D
A) F
F F
B)
F
C)
F
D) F
E) None of these choices.
Answer: D
3) Of the following solvents which one does not have a zero dipole moment?
A) Pentane
B) Cyclohexane
C) Diethyl ether
D) Cyclopentane
E) None of these choices.
Answer: C
A) CH3Cl
B) CH2Cl2
C) CHCl3
D) CCl4
E) None of these choices.
Answer: D
A) CHF3
F H
B) H F
C) :NF3
2
F F
D) H H
E) CH2F2
Answer: B
A) H H
F H
B) F H
F H
C) H F
D) More than one of these choices.
E) None of these choices.
Answer: D
A) CBr4
B) cis-1,2-Dibromoethene
C) trans:-1,2-Dibromoethene
D) 1,1-Dibromoethene
E) More than one of these choices.
Answer: E
3
Section Reference 1: 2.3
Difficulty: Medium
8) For a molecule to possess a dipole moment, which following condition is necessary but not
sufficient?
Answer: B
A) SO2
B) CO2
C) CO
D) CHCl3
E) None of these choices.
Answer: B
A) CO2
B) CH4
C) CH3CH3
D)
4
E) All of these choices.
Answer: E
A) CHCl3
B) CH2Cl2
C) ClHC=CH2
D) trans-ClHC=CHCl
E) None of these choices.
Answer: D
12) Which molecule would have a dipole moment greater than zero?
A) BeCl2
B) BCl3
C) CO2
D) H2O
E) CCl4
Answer: D
A) SO2
B) CO2
5
C) CCl4
D) BF3
Cl Cl
E) Cl Cl
Answer: A
14) Of the following common organic solvents which one is predicted to have the smallest dipole
moment?
A) Chloroform, CHCl3
B) Acetone, (CH3) 2CO
C) Dimethylsulfoxide, (CH3) 2SO
D) Acetonitrile, CH3CN
E) Methanol, CH3OH
Answer: A
A)
Cl Cl
B)
Cl
C) Cl
6
Cl Cl
D) Cl
E) None of these choices have dipole moments equal to zero.
Answer: C
Answer: C
A) Phenyl, pentyl
B) Hexyl, phenyl
C) Benzyl, hexyl
D) Benzyl, heptyl
E) None of these choices.
Answer: C
7
Difficulty: Medium
Answer: D
Answer: A
20) What alkyl group is attached to the oxygen in the following ester?
O
8
A) ethyl
B) propyl
C) sec-propyl
D) isopropyl
E) None of these choices.
Answer: D
Answer: A
22) What alkyl groups are attached to the benzene ring in the following example?
H3CH2CH2C
A) ethyl, butyl
B) ethyl, isobutyl
C) propyl, sec-butyl
D) propyl, butyl
E) None of these choices.
9
Answer: E
23) What common group is attached to both the ether and 3o amine in the following molecule?
OCH2C6H5
NBn
A) benzyl
B) phenyl
C) heptyl
D) ethyl
E) None of these choices.
Answer: A
A) benzyl
B) phenyl
C) heptyl
D) ethyl
E) None of these choices.
Answer: B
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Br
A) 1o alkyl halide
B) 2o alcohol
C) 2o alkyl halide
D) 1o amine
E) 3o alkyl halide
Answer: C
A) I
B) II
C) III
D) IV
E) V
Answer: B
11
27) Which compound(s) contain(s) tertiary carbon atom(s) ?
I II III
Br
OH
OH
IV V
A) I, II, III
B) I
C) II, III
D) I, IV
E) V
Answer: D
A) CH3CH2CH2CH2CH2Cl
CH3
CH3CCH2CH3
B) Cl
CH3CHCH2CH2CH3
C) Cl
D) (CH3) 2CHCHClCH3
E) Two of these choices.
Answer: E
29) How many 2º alkyl bromides, neglecting stereoisomers, exist with the formula C6H13Br?
12
A) 4
B) 5
C) 6
D) 7
E) 8
Answer: C
30) The number of unique open-chain structures corresponding to the molecular formula C3H5Cl
is:
A) 2
B) 3
C) 4
D) 5
E) 6
Answer: C
Topic: Isomers
Section Reference 1: 1.3 and 2.5
Difficulty: Medium
CH3CHCH2CH3
A) OH
CH3CHCH2OH
B) CH3
CH3
CH3COH
C) CH3
D) CH3CH2CH2CH2OH
E) CH3CH2CH2OCH3
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Answer: A
A) 1o alcohol
B) ether
C) 2o alcohol
D) ester
E) 3o alcohol
Answer: E
CH3
OH HO
H3CH2C O
CH3
I II III
O OH
IV V
A) I
B) II
C) III
D) IV
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E) V
Answer: E
Answer: A
I II III
OH
HO
IV V
A) I
B) II, IV
C) III, V
D) IV
E) All of these choices.
Answer: C
15
Topic: Functional groups
Section Reference 1: 2.5 and 2.6
Difficulty: Easy
Answer: D
37) How many constitutional isomers are possible with the formula C4H10O?
A) 3
B) 4
C) 5
D) 6
E) 7
Answer: E
A) CH3CH2CH2NH2
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CH3CHCH3
B) NH2
CH3CH2NH
C) CH3
H3C N CH3
D) CH3
CH3CH2CHNH2
E) CH3
Answer: C
H2N
NH H2N
I II III
N
NH2
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: C
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40) What functional group is present in the following compound?
N
H
A) 1o alkyl bromide
B) 2o amine
C) nitrile
D) 1o amine
E) 3o amine
Answer: B
A) 1o alkyl bromide
B) 2o amine
C) nitrile
D) 1o amine
E) 3o amine
Answer: E
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NH2
H2N
NH
I II III
O NH2
N
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: D
43) What functional groups are present in nicotine, an addictive substance found in tobacco?
Answer: A
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44) An example of a tertiary amine is:
H
N H2N
NH2
I II III
NH2 N
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: E
Answer: D
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O
C OH
A) H
O
B) CH3CCH2CH3
O
C) HCOCH3
O
C H
D) H
H3C
CH OH
E) H3C
Answer: B
O O O
NH O
I II III
OH
IV V
A) I
B) II
C) III
D) IV
E) V
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Answer: D
CHO
A) alcohol
B) ketone
C) aldehyde
D) ester
E) ether
Answer: C
COCH 3
A) alcohol
B) ketone
C) aldehyde
D) ester
E) ether
Answer: B
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50) What functional group(s) is/are present in the following compound?
OHC
Answer: C
51) The compound below is an adrenocortical hormone called cortisone. Which functional group
is not present in cortisone?
OH
O
O OH
A) 1 alcohol
B) Ketone
C) 3 alcohol
D) Carboxylic acid
E) Alkene
Answer: D
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OH O
Answer: B
53) The compound shown below is the male sex hormone, testosterone.
OH
O
O
In addition to a cycloalkane skeleton, testosterone also contains the following functional groups:
Answer: C
54) The compound shown below is a synthetic estrogen. It is marketed as an oral contraceptive
under the name Enovid.
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OH
In addition to an alkane (actually cycloalkanE) skeleton, the Enovid molecule also contains the
following functional groups:
Answer: D
55) Many organic compounds contain more than one functional group. Which of the following
is/are both an aldehyde and an ether?
O O
O
O O O
I II III
O
O O
OCH3
O
IV V
A) I
B) II, IV
C) V
D) I, V
E) III
Answer: A
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56) Which is a carboxylic acid?
OH O
OH
O O O
I II III
O
O O
OH
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: E
CO2H
Answer: B
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58) What functional group(s) is/are present in the following compound?
HO2C
Answer: C
HO H
H H OH
Prostaglandin E1
A) Ketone
B) 2 alcohol
C) 3 alcohol
D) Carboxylic acid
E) Alkene
Answer: C
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O
Answer: D
O O O
NH O
I II III
OH
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: C
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62) What functional group is present in the following compound?
CO2CH3
A) alcohol
B) ketone
C) aldehyde
D) ester
E) ether
Answer: D
OH
Answer: D
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O O O
O
O O O
I II III
O
O O
O OH
OH
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: D
65) 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?
O OH
Atropine
A) Amine
B) Ester
C) Alcohol
D) Benzene Ring
E) Ketone
Answer: E
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66) What functional group(s) is/are present in the following compound?
HO O
NHCH3
Answer: E
67) Many bacterial cells will contain functional groups that are susceptible to antibiotic drugs,
but may, over time, change their functional groups to become resistant to these drugs. What
functional group change is occurring in the transition shown below?
A) Amine to ether
B) Amine to ester
C) Amide to ester
D) Amide to ether
E) None of these choices.
Answer: C
68) The compound shown below is a substance called Capsaicin, found in varying
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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
O
N
H
OH
Capsaicin
Answer: D
69) The compound aspartame is a dipeptide that is often used as a sugar substitute. Which
functional groups are present in aspartame?
Answer: D
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NC NHCH3
Answer: C
A) Dispersion forces
B) Ion-dipole
C) Dipole-dipole
D) Cation-anion
E) Hydrogen bonds
Answer: D
72) Which of these is the weakest of the intermolecular attractive forces taken individually?
A) Ion-ion
B) Dispersion forces
C) Dipole-dipole
D) Covalent bonding
E) Hydrogen bonding
Answer: B
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Difficulty: Easy
73) Which compound would you expect to have the highest melting point?
A) n-Butyl alcohol
B) Isobutyl alcohol
C) sec-Butyl alcohol
D) tert-Butyl alcohol
E) Diethyl ether
Answer: D
A) Ion-ion
B) Dispersion forces
C) Dipole-dipole
D) Covalent bonding
E) Hydrogen bonding
Answer: A
75) Which alkane is predicted to have the highest melting point of those shown?
A) CH3CH2CH2CH3
CH3CHCH3
B) CH3
C) CH3CH2CH2CH2CH3
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CH3CHCH2CH3
D) CH3
CH3
CH3CCH3
E) CH3
Answer: E
A) Ion-ion
B) Dipole-dipole
C) Hydrogen bonds
D) Dispersion forces
E) Covalent bonds
Answer: C
77) Which compound would you expect to have the lowest boiling point?
NH 2
A)
NH2
B)
H
N
C)
N
D)
35
E) NH2
Answer: D
78) Which of these compounds would have the highest boiling point?
A) CH3OCH2CH2CH2OCH3
B) CH3CH2OCH2CH2OCH3
C) CH3CH2OCH2OCH2CH3
CH3OCH 2CHOCH3
D) CH3
E) HOCH2CH2CH2CH2CH2OH
Answer: E
A) CH3CH2CH2CH2CH2CH3
B) CH3CH2OCH2CH2CH3
C) CH3CH2CH2CH2CH2OH
D) CH3CH2OCH(CH3) 2
E) CH3OCH2CH2CH2CH3
Answer: C
36
80) Of the following compounds, the one with the highest boiling point is:
A) CH3CH3
B) CH3CH2Cl
CH3C=O
C) H
D) CH3CH2OH
E) CH3CH2OCH2CH3
Answer: D
81) Which compound would you expect to have the highest boiling point?
A) ethane
B) ethene
C) ethyne
D) bromoethane
E) methane
Answer: D
82) Which compound would you expect to have the highest boiling point?
A) ethyl alcohol
B) ethyl amine
C) chloroethane
D) water
E) ethane
Answer: D
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83) Which of these would you expect to have the lowest boiling point?
A) CH3CH2CH2OH
CH3CHCH3
B) OH
C) CH3OCH2CH3
D) CH3CH2CH2CH2OH
E) CH3CH2OCH2CH3
Answer: C
84) Which compound would you expect to have the lowest boiling point?
A) NH2
H
N
B) O
O
C)
NH2
D) O
O N
E) H
Answer: C
38
Section Reference 1: 2.13
Difficulty: Medium
85) Which compound would you expect to have the highest boiling point?
A) CH3OCH2CH2OCH3
B) CH3OCH2OCH2CH3
C) HOCH2CH2CH2CH2OH
D) CH3OCH2CH2CH2OH
E) (CH3O) 2CHCH3
Answer: C
OH
O OH
I II III
OH
OH
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: A
39
87) 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
Answer: A
88) The following substance is expected to have the lowest solubility in which of the following
solvent(s) ?
O Na
A) CCl4
B) C2H5OH
C) CHCl3
D) CH2OHCH2CH2CH2CH2CH2OH
E) The given substance is likely to be quite soluble in all of the solvents described.
Answer: A
89) The compound NaOH is barely soluble in ethanol. The addition of which of the following
solvents to ethanol would greatly increase its solubility of NaOH?
A) H2O
B) Et2O
C) CH2Cl2
D) Benzene
E) All of these choices.
40
Answer: A
90) For the functional group(s) on the following molecule what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions) ?
CHO
Answer: A
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Easy
91) For the functional group(s) on the following molecule what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions) ?
Answer: C
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Easy
41
92) The IR spectrum of which type of compound will not show evidence of hydrogen bonding?
A) Aldehyde
B) Alcohol
C) Carboxylic acid
D) Phenol
E) Primary amine
Answer: A
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Easy
93) The IR spectrum of which type of compound generally exhibits evidence of hydrogen
bonding?
A) Aldehyde
B) Carboxylic acid
C) Alkene
D) Ester
E) Ketone
Answer: B
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Easy
94) IR evidence for the presence of the C=C would be most difficult to detect in the case of
which of these alkenes?
A)
B)
C)
D)
42
E)
Answer: D
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Easy
95) An oxygen-containing compound shows strong IR absorption at 1630-1780 cm-1 and 3200-
3550 cm-1. What type of compound is it likely to be?
A) an alcohol
B) a carboxylic acid
C) an ether
D) a ketone
E) an aldehyde
Answer: B
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium
96) For the functional group(s) on the following molecule what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions) ?
CN
Answer: D
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium
43
97) For the functional group(s) on the following molecule, what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions) ?
HO
Answer: C
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium
98) For the functional group(s) on the following molecule, what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions) ?
CO2H
Answer: B
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium
99) For the functional group(s) on the following molecule, what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions) ?
44
Br
Answer: E
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium
100) For the functional group(s) on the following molecule, what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions) ?
Answer: A
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium
101) The absorption band for the O-H stretch in the IR spectrum of an alcohol is sharp and
narrow in the case of
45
Answer: C
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium
102) A split peak for the IR absorption due to bond stretching is observed for the carbonyl group
in which of these compounds?
O
A) CH3CH2CH2COH ca
O
B) CH3CH2CCl
C)
O
D) CH3CH2COCH2CH3
O O
E) CH3CH2COCCH2CH3
Answer: E
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium
103) The IR spectrum of which of the following substances is likely to show a small, but sharp
peak at 2200 cm-1?
OH
O
N
H
I II III
IV V
A) I
B) II
46
C) III
D) IV
E) V
Answer: E
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium
Answer: E
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium
105) For the functional group(s) on the following molecule what characteristic IR absorption(s)
would be expected (ignoring C-H absorptions) ?
Answer: D
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
47
106) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions) ?
a. NaNH2
b. CH3CH2I
Answer: C
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
107) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions) ?
O
a. CH3MgBr
OH
b. H3O+
A) A peak around 1710 cm-1 would disappear and a new peak around 3300-3500 cm-1 would
appear.
B) A peak around 1710 cm-1 would appear and a new peak around 1650 cm-1 would disappear.
C) A peak around 2150 cm-1 would disappear and a new peak around 3300-3500 cm-1 would
appear.
D) No change would be observed.
E) None of these choices.
Answer: A
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
108) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions) ?
48
a. NaH
OH OCH3
b. CH3I
Answer: A
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
109) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions) ?
Answer: A
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
110) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions) ?
OH O
PCC
A) A peak around 3300 cm-1 would disappear and nothing new would appear.
B) A new peak around 1710 cm-1 would appear and a peak around 3300 cm-1 would disappear.
49
C) A peak around 2150 cm-1 would disappear and a new peak around 3300 cm-1 would appear.
D) No change would be observed.
E) None of these choices.
Answer: B
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
111) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions) ?
A) A peak around 3300 cm-1 would appear and nothing new would appear.
B) A peak around 1710 cm-1 would disappear and a new peak around 3300 cm-1 would appear.
C) A peak around 2150 cm-1 would disappear and a new peak around 3300 cm-1 would appear.
D) No change would be observed.
E) None of these choices.
Answer: E
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
112) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions) ?
H2, Pd/C
A) A peak around 3300 cm-1 would disappear and nothing new would appear.
B) A peak around 1710 cm-1 would appear and a new peak around 3300 cm-1 would disappear.
C) A peak around 1650 cm-1 would disappear and nothing new would appear.
D) No change would be observed.
E) None of these choices.
50
Answer: C
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
113) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant overall change(s) would be expected by IR (ignoring C-H absorptions) ?
1. Br2, light
2. Zn, HCl
A) A peak around 3300 cm-1 would disappear and nothing new would appear.
B) A peak around 1710 cm-1 would appear and a new peak around 3300 cm-1 would disappear.
C) A peak around 1650 cm-1 would disappear and nothing new would appear.
D) No overall change would be observed.
E) None of these choices.
Answer: D
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
114) For the following reaction sequence (it is not necessary to understand the chemistry) what
significant change(s) would be expected by IR (ignoring C-H absorptions) ?
CN a. DiBAl-H CHO
b. H3O+
A) A peak around 2250 cm-1 would disappear and nothing new would appear.
B) A peak around 1720 cm-1 would appear and a new peak around 3300 cm-1 would disappear.
C) A peak around 2250 cm-1 would disappear and new peak around 1720 cm-1 would appear.
D) A peak around 2250 cm-1 would disappear and new peak around 3300 cm-1 would appear.
E) No change would be observed.
Answer: C
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
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115) The IR stretching frequency occurs at the lowest frequency for which of these bonds?
A) C–H
B) C–O
C) C–Br
D) C–N
E) C–F
Answer: C
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
116) The IR stretching frequency can be predicted to occur at the highest frequency for which of
these bonds?
A) C–H
B) C–F
C) C–Cl
D) C–Br
E) C–I
Answer: A
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
117) The IR absorption due to the stretching of which of these carbon-hydrogen bonds occurs at
the highest frequency?
H
H
H
I II III
H
H
IV V
A) I
B) II
C) III
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D) IV
E) V
Answer: E
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
118) An oxygen-containing compound which shows sharp IR absorption at 2200 cm-1 and 3300
cm-1 is likely to contain which functional group?
A) An ester
B) An alkene
C) An alkyne
D) An ether
E) An aldehyde
Answer: C
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
119) n-Pentane has a higher boiling point than isopentane due to an increased surface to surface
interaction of dispersion forces.
A) True
B) False
Answer: A
120) Carbon dioxide has a higher boiling point than carbon disulfide due to its dipole-dipole
forces.
A) True
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B) False
Answer: B
121) Even though methyl amine (CH3NH2) has a higher molecular weight than water (H2O) , its
boiling point is much lower than water’s boiling point since water has hydrogen bonding
attractive forces.
A) True
B) False
Answer: B
122) Hydrogen bonding will broaden the absorption band in an Infrared spectra.
A) True
B) False
Answer: A
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Easy
123) The higher the wave number in the infrared spectra, the greater the energy that is required
to vibrate the bond.
A) True
B) False
Answer: A
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Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium
124) The molecule N2 does not show up in an IR spectra because the dipole moment of the
molecule does not change with the absorption of IR energy.
A) True
B) False
Answer: A
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
Answer: alkenes
126) All of the carbon-carbon bonds in ___ are equal to one and one-half bonds and have a bond
length in between that of a single bond and a double bond with all of the bond angles at ___.
Answer: Pi bonds
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Topic: Functional Groups
Section Reference 1: 2.1
Difficulty: Easy
128) Draw a structural formula for C8H18, in which there are two quaternary carbons.
Answer:
129) The six p-electrons in benzene are ___ about the ring, which explains why all of the C-C
bonds are the same length.
Answer: delocalized
Topic: General
Section Reference 1: 2.1
Difficulty: Easy
Answer:
Topic: General
Section Reference 1: 2.2
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Difficulty: Easy
132) The ___ is defined as the product of the magnitude of the charge of a particle and the
distance that separates them.
133) 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 Answer.
Answer: The overall dipole moment of a polyatomic molecule depends on two factors: the
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:
134) Nitromethane is a polar molecule but contains 2 equal polar covalent bonds. Briefly explain
why and draw a relevant 3-dimensional structure to show the overall dipole moment of the
molecule.
Answer: The nitro group has 2 polar N-O bonds that are pointing 120o apart which do not
completely cancel out and the C-N bond is polar as well which further add to the net direction of
the dipole.
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Topic: Molecular Geometry, Dipole Moment
Section Reference 1: 2.2 and 2.3
Difficulty: Medium
135) Organic compounds are classified into chemical families on the basis of similarities in
chemical properties; these similarities are primarily due to the presence of characteristic
arrangements of atoms known as ___.
136) Draw all isomers of C3H8O and classify each according to functional group.
OH
C3H8O OH
O
N N N
N N N
Answer:
138) Draw all of the acyclic secondary amines that have the chemical formula C4H9N.
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Answer:
139) A group in which a carbon atom has a double bond to an oxygen atom is called a ___.
Answer: carbonyl
140) Draw all isomers of C6H12O that are aldehydes and contain at least one secondary carbon.
O O O O
Answer:
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O O O O
O O O
Answer:
Answer:
Answer:
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Question type: Essay
144) Ethanol, C2H5OH, and propane, C3H8, have approximately the same molar mass, yet
ethanol has a much higher boiling point. Briefly explain why.
Answer: 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.
145) Even though methanol (CH3OH) and methylamine (CH3NH2) have similar molecular
weights, methanol has a much higher boiling point of 65 oC as opposed to methylamine’s boiling
point of -6 oC. Briefly explain why.
Answer: Both compounds have the same strong intermolecular forces of hydrogen bonding, but
methanol’s O-H bond is much more polarized than methylamine’s N-H as oxygen is more
electronegative than nitrogen. The greater polarization exposes the hydrogen nucleus further and
creates stronger hydrogen bonds.
146) Ethanol, C2H5OH, and dimethyl ether, CH3OCH3, have the same molar mass, yet ethanol
has a much higher boiling point. Briefly explain why.
Answer: Strong hydrogen bonding between molecules of ethanol leads to elevation in boiling
point. No hydrogen bonding is possible between molecules of dimethyl ether, resulting in a
lower boiling point compared with ethanol.
147) Sodium chloride, which is quite soluble in water, is not very soluble in hexane. Why?
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Answer: Sodium chloride, which is an ionic substance, is soluble in a polar solvent such as
water, but not in a non-polar solvent such as hexane.
148) Explain why the compound shown is considered to be capable of being a soap (dissolving
oily substances off of surfaces using water) .
Answer: The compound contains a long hydrophobic “fatty” carbon tail, which attracts grease
particles as they have similar dispersion forces. The polar hydrophilic carboxylate head is forced
to the outside, which the polar water can now dissolve.
149) Examine the following IR spectrum, for substance Q (C7H14O2) . Which oxygen containing
functional group is most likely present in Q?
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Answer: A carboxylic acid
150) Examine the following IR spectrum, for substance P (C3H5NO) . Which oxygen containing
functional group is most likely present in P?
Answer: Alcohol
151) The IR absorption frequencies of the C-H bond in alkanes, alkenes, and alkynes are
measurably different. Briefly explain why.
Answer: IR absorption frequency depends on bond strength; the bond strength of C-H bonds in
alkanes, alkenes and alkynes is different because different atomic orbitals (hybridizeD) of carbon
are involved in the bond: the C-H bond in alkanes is described as (sp3-s) , that in alkenes is (sp2-
s) and in alkynes, it is (sp-s) . The relative % s v. % p character of the hybrid orbitals of carbon
would indicate different bond lengths / bond strengths for alkanes, alkenes and alkynes, with the
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bond length / bond strength being the longest/weakest respectively. This results in different IR
absorption frequencies.
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Hard
152) IR absorption signals of alcohols are typically broad. However, IR spectra of gaseous
samples show sharp peaks. Briefly explain why.
Answer: Broad signals of alcohols are due to hydrogen bonding associated with the O-H group.
In gaseous samples, no hydrogen bonding is possible, and the signal becomes sharp.
Topic: IR Spectroscopy
Section Reference 1: 2.15 and 2.16
Difficulty: Medium
153) An IR spectrum has significant peaks at 3080 and 1650 cm-1. What functional group is
present in the molecule?
Answer: An alkene
154) An IR spectrum has significant peaks at 2200 and 3300 cm-1. What functional group is
present in the molecule?
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