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Organic Chemistry 12th Edition Solomons Test Bank instant download all chapter
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Package Title: Solomons Test Bank
Course Title: Solomons 12e
Chapter Number: 9
1) How many signals would you expect to find in the 1H NMR spectrum of
CH3OCH2CH2OCH3?
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: B
2) Predict the splitting pattern you would observe for the proton at C1 of 2,3-dimethyl-2-
phenylbutane.
A) Doublet
B) Singlet
C) Quartet
D) Septet
E) Octet
Answer: B
1
3) Which one of the following best represents the predicted approximate chemical shift and
coupling for the hydrogen(s) indicated with the arrow?
CH3
O
Answer: C
4) Which one of the following best represents the predicted approximate chemical shift and
coupling for the hydrogen(s) indicated with the arrow?
O
Answer: B
2
5) Which one of the following best represents the predicted approximate chemical shift and
coupling for the hydrogen(s) indicated with the arrow?
Answer: C
6) Which one of the following best represents the predicted approximate chemical shift and
coupling for the hydrogen(s) indicated with the arrow?
O
Answer: E
Answer: C
8) Which one of the following best represents the predicted approximate chemical shift and
coupling for the hydrogen(s) indicated with the arrow in the compound nicotine?
Answer: C
4
9) Which one of the following best represents the predicted approximate chemical shift and
coupling for the hydrogen(s) indicated with the arrow in the compound nicotine?
Answer: E
10) Which one of the following best represents the predicted approximate chemical shift and
coupling for the hydrogen(s) indicated with the arrow?
H
Answer: A
Answer: D
12) Which one of the following best represents the predicted approximate chemical shift and
coupling for the hydrogen(s) indicated with the arrow?
Answer: B
6
13) Which one of the following best represents the predicted approximate chemical shift and
coupling for the hydrogen(s) indicated with the arrow?
Answer: E
14) For the following compound how many different signals would you see in the proton NMR?
(Assume that you can see them all.)
A) 4
B) 5
C) 6
D) 7
E) 8
Answer: A
A) 2
B) 3
C) 4
D) 5
E) None of these choices.
Answer: B
16) For the following compound how many different signals would you see in the proton NMR?
(Assume that you can see them all.)
H3CO
A) 4
B) 5
C) 6
D) 7
E) 8
Answer: C
8
17) For the following compound how many different signals would you see in the proton NMR?
(Assume that you can see them all.)
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: C
18) For the compound adamantine, how many different signals would you see in the proton
NMR? (Assume that you can see them all.)
A) 1
B) 2
C) 3
D) 4
E) None of these choices.
Answer: B
A) CH3CCH2CH3
H
B) C6H5CH2C O
H
C) (CH3)2CHC O
H
D) (CH3)3CC O
O
E) C6H5CH2CCH3
Answer: D
20) For the following compound how many different signals would you see in the proton NMR?
(Assume that you can see them all.)
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: D
10
22) For the following compound how many different signals would you see in the proton NMR?
(Assume that you can see them all.)
A) 4
B) 5
C) 6
D) 7
E) 8
Answer: B
23) Which one of the following best represents the predicted approximate chemical shift and
coupling for the hydrogen(s) indicated with the arrow?
CH3
O
Answer: D
A) Doublet
B) Singlet
C) Quartet
D) Septet
E) Octet
Answer: A
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: C
26) How many chemically distinct 1H NMR signals are there in the following compound?
ClCH2CHCH3
Br
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: D
12
Difficulty Level: Medium
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: C
28) How many 1H NMR signals would you expect from this compound?
OCH3
OCH3
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: B
29) The 1H NMR spectrum of which of these compounds would consist of a triplet, singlet and
quartet only?
A) 2-chloro-4-methylpentane
B) 3-chloro-2-methylpentane
C) 3-chloropentane
D) 1-chloro-2,2-dimethylbutane
E) 3-chloro-3-methylpentane
Answer: E
30) Which one of the following best represents the predicted approximate chemical shift and
coupling for the hydrogen(s) indicated with the arrow?
H
Answer: D
31) Which of the following compounds would not be represented by a lone singlet in the proton
NMR?
A) cyclohexane
B) benzene
C) dimethyl ether (CH3-O-CH3)
D) 1,2-ethanediol
E) none of these choices
Answer: D
32) A compound C5H11Cl which exhibits only two singlets in the 1H NMR spectrum must be:
A) 1-Chloropentane
B) 1-Chloro-2,2-dimethylpropane
C) 1-Chloro-2-methylbutane
D) 3-Chloropentane
E) 1-Chloro-3-methylbutane
Answer: B
14
Difficulty Level: Medium
33) A compound that would show two triplets and a septet in the 1H NMR spectrum could be:
A) 3-ethylpentane
B) 2-bromopropane
C) chlorocyclopropane
D) 1-iodopropane
E) none of these choices
Answer: C
Answer: C
Answer: E
36) The 1H NMR signal for which of the indicated protons will occur at the lowest frequency
(most upfield signal)?
A) I
B) II
C) III
D) IV
E) V
Answer: A
16
37) If all the protons of 1-fluoropentane could be discerned, which would you expect to be at the
lowest field in the 1H NMR spectrum of this compound?
CH3CH2CH2CH2CH2F
V IV III II I
A) Protons on carbon I
B) Protons on carbon II
C) Protons on carbon III
D) Protons on carbon IV
E) Protons on carbon V
Answer: A
38. The 1H NMR signal for which of the indicated protons occurs farthest downfield?
III
Cl H
H C C C C CH3
I H IV
II
V
A) I
B) II
C) III
D) IV
E) V
Answer: E
Answer: B
40) Which proton(s) of the compound below would appear as a doublet in the 1H NMR
spectrum?
I CH3
CH3CH2CH2-O-CH
CH3
V IV III II
I
A) The protons on carbon I.
B) The protons on carbon II.
C) The protons on carbon III.
D) The protons on carbon IV.
E) The protons on carbon V.
Answer: A
18
41) Which proton(s) of the compound below would appear as a triplet in the 1H NMR spectrum?
I CH3
CH3CH2CH2-O-CH
CH3
V IV III II
I
A) The protons on carbon II.
B) The protons on carbon I and V.
C) The protons on carbon III and V.
D) The protons on carbon III and IV.
E) The protons on carbon V.
Answer: C
42) Predict the splitting pattern you would observe for the proton at C3 of 2,3-dimethyl-2-
phenylbutane.
A) Doublet
B) Singlet
C) Quartet
D) Septet
E) Octet
Answer: D
A) Neopentane
B) Hexamethylbenzene
C) Isobutane
D) (Z)-1,2-Dichloroethene
E) (E)-1,2-Dichloroethene
Answer: C
44) Consider the expected splitting of the C2 proton signal in the 1H NMR spectrum of 1,1-
dibromopentane. Presuming that the coupling constants for neighboring protons are sufficiently
different, and that the instrument has sufficient resolving power, what is the theoretical
multiplicity of the C2 proton signal?
A) 3
B) 4
C) 5
D) 6
E) 8
Answer: D
45) Consider the expected splitting of the C2 proton signal in the 1H NMR spectrum of 2-ethyl-
1,3-propanediol. Presuming that the coupling constants for neighboring protons are sufficiently
different, and that the instrument has sufficient resolving power, what is the theoretical
multiplicity of the C2 proton signal?
A) 6
B) 7
C) 8
D) 12
E) 15
Answer: E
20
Difficulty Level: Hard
46) What is the theoretical multiplicity of the C-2 proton signal in the 1H NMR spectrum of 2-
hydroxymethyl-1,3-propanediol, shown below?
OH
HO OH
A) 1
B) 6
C) 7
D) 8
E) 9
Answer: C
47) Consider the 1H NMR spectrum of very pure 1-propanol. Assuming the maximum
multiplicity of signals and non-superposition of peaks, what is the expected signal splitting
pattern for each signal, in the order (a, b, c, d) ?
CH3-CH2-CH2-OH
a b c d
A) 3, 6, 4, 1
B) 3, 6, 4, 3
C) 3, 12, 3, 1
D) 3, 12, 3, 3
E) 3, 12, 6, 3
Answer: E
I II III
O O O
A) I
B) II
C) III
D) IV
E) V
Answer: E
49) The 1H NMR spectrum of which of the compounds below, all of formula C7H12O2, would
consist of three singlets only?
O O
O O
O O
I II III
O O O
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: B
22
50) The 1H NMR spectrum of which of the compounds below, all of formula C7H12O2, would
consist of a singlet, a doublet and a triplet only?
O O
O O
O O
I II III
O O O
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: D
51) A compound with the molecular formula C4H10O gives a 1H NMR spectrum consisting only
of a quartet centered at 3.5 and a triplet at 1.1. The most likely structure for the compound is:
CH3
CH3COH
A) CH3
CH3
B) CH3OCHOH
C) CH3CH2CH2CH2OH
D) CH3CH2OCH2CH3
CH3CHCH2OH
E) CH3
Answer: D
5
2
2
1
12 10 8 6 4 2 0
PPM
CHO
A)
CO2H
B)
CO2H
C)
D) HO2C
CO2H
E)
Answer: C
24
53) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C8H14? Relative integration is shown.
3
2
8 7 6 5 4 3 2 1 0
PPM
A)
B)
C
C)
D)
E)
Answer: D
A) CN
B)
CN
C)
CN
D)
N
E) H
Answer: D
26
55) Determine the most likely structure of a compound, with the molecular formula C9H12, which
gave a 1H NMR spectrum consisting of:
a doublet at 1.25
a septet at 2.90 and
a multiplet at 7.25
I II III IV V ]
A) I
B) II
C) III
D) IV
E) V
Answer: D
56) A compound with the molecular formula C10H13Cl gave the following 1H NMR spectrum:
singlet, 1.6
singlet, 3.1
multiplet, 7.2 (5H)
The most likely structure for the compound is:
Cl Cl
Cl
I II III
Cl
Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: B
57) A compound with the molecular formula C8H9BrO gave the following 1H NMR spectrum:
triplet, 1.4
quartet, 3.9
multiplet, 7.0 (4H)
There was no evidence of an -OH band in the IR spectrum. A possible structure for the
compound is:
O O Br O
Br
Br
I II III
O
Br
Br
O
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: C
28
58) A compound with the molecular formula C6H15N gave the following 1H NMR spectrum:
triplet, 0.90
quartet, 2.4
There were no other signals. The most likely structure for the compound is:
CH3NCH2CH3
A) CH2CH2CH3
CH3NCH2CH2CH2CH3
B) CH3
C) CH3CH2CH2CH2CH2CH2NH2
CH3CH2NCH2CH3
D) CH2CH3
CH3CH2CH2NCH2CH2CH3
E) H
Answer: D
O
Cl
Cl
O
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: A
60) A compound with the molecular formula C3H6Cl2 gave a 1H NMR spectrum consisting only
of a triplet centered at 3.7 and a quintet centered at 2.2. The most likely structure for the
compound is:
A) CH3CH2CHCl2
B) CH3CHClCH2Cl
C) ClCH2CHClCH3
D) ClCH2CH2CH2Cl
E) CH3CCl2CH3
Answer: D
30
61) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C10H20? Relative integration is shown.
3
2
8 7 6 5 4 3 2 1 0
PPM
A)
B)
C)
D)
E)
Answer: C
1 1
8 7 6 5 4 3 2 1 0
PPM
A) O
B) OH
OH
C)
O
D)
O
E)
Answer: D
32
63) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C10H12O2? Relative integration is shown.
3
2 2 2 2
11 10 9 8 7 6 5 4 3 2 1 0
PPM
CHO
A) O
O
O
B)
CO2H
C)
CO2H
D)
CO2H
E)
Answer: C
2 2 2
2 1 0
PPM
A)
O
H
B)
OH
C)
D) O
O
E)
Answer: E
34
65) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C6H10O2? Relative integration is shown.
2 2 2
6 5 4 3 2 1 0
PPM
A) O
O
O
B) H
C) O
O
D) O
O
E) OH
Answer: D
2 2 2 2
1
exchanges with D2O
7 6 5 4 3 2 1 0
PPM
A)
HO
B)
HO
C)
OH
D)
E) HO
Answer: E
36
67) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C5H8O? The IR spectrum does show a characteristic stretch around 1700 cm-
1
. Relative integration is shown.
3 3
1 1
8 7 6 5 4 3 2 1 0
PPM
O
A)
O
B)
O
C)
O
D)
O
E)
Answer: E
I II III
O
O
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: E
A) CH3CH2CHBrCH3
B) CH3CH2CH2CH2Br
C) (CH3)2CHCH2Br
D) (CH3)3CBr
Answer: A
38
70) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C6H12O which shows no characteristic stretches in the IR between 3600-3300
cm-1, but does around 1600 cm-1? Relative integration is shown.
6
1 1 1
6 5 4 3 2 1 0
PPM
A)
O
B)
C) O
O
D)
O
E)
Answer: A
3 3
2 2 2
10 8 6 4 2 0
PPM
A) O
O
B) HO
O
C)
O
D) O
O
E) O
Answer: D
40
72) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C6H12? Relative integration is shown.
3
2
1
8 7 6 5 4 3 2 1 0
PPM
A)
B)
C)
D)
E)
Answer: B
3
2
1 1
6 5 4 3 2 1 0
PPM
A) Br
Br
B)
C) Br
Br
D)
Br
E)
Answer: C
42
74) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C5H10O? The IR spectrum does not show any characteristic stretches around
1700 cm-1. Relative integration is shown.
3 3
2
1 1
7 6 5 4 3 2 1 0
PPM
O
A)
O
B)
O
C)
O
D)
E) O
Answer: A
I II III
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: B
44
76) Determine the likely structure for a compound A (C6H10O), which is found to decolorize
bromine in carbon tetrachloride. Its spectral data is as follows:
1
H NMR IR
triplet, 1.0 singlet, 2.4 2200 cm-1 (sharp)
singlet, 1.4 singlet, 3.4 3300 cm-1 (sharp)
quartet, 1.6 3500 cm-1 (broad)
OH
OH OH
I II III
OH
OH
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: C
Hb Ha
A) Identical
B) Enantiotopic
C) Diastereotopic
D) Homotopic
E) Mesotopic
Answer: C
A) homotopic protons.
B) vicinal protons.
C) enantiotopic protons.
D) diastereotopic protons.
E) isomeric protons.
Answer: C
A) homotopic protons.
B) vicinal protons.
C) enantiotopic protons.
D) diastereotopic protons.
E) isomeric protons.
Answer: D
46
80) In the structure shown, Ha and Hb are classified as:
HO H
Ha H
b
A) homotopic protons.
B) vicinal protons.
C) enantiotopic protons.
D) diastereotopic protons.
E) isomeric protons.
Answer: D
A) homotopic protons.
B) geminal protons.
C) enantiotopic protons.
D) diastereotopic protons.
E) isomeric protons.
Answer: D
O
b
a c d
A) 8
B) 9
C) 12
D) 21
E) 24
Answer: D
83) For the C2 methylene group in 1-bromopropane, the theoretical multiplicity in the 1H NMR
spectrum, presuming that Jab is sufficiently different from Jbc and that the instrument has
sufficient resolving power, is which of these?
CH3 CH2 CH2 Br
c b a
A) 2
B) 5
C) 6
D) 8
E) 12
Answer: E
48
84) Consider the expected splitting of signal “b” in the 1H NMR spectrum of N-methyl-1-
propanamine, shown below. Presuming that Jab is sufficiently different from Jbc and that the
instrument has sufficient resolving power, what is the theoretical multiplicity of signal “b”?
d
b H
N
a c e
A) 2
B) 5
C) 6
D) 8
E) 12
Answer: E
85) Consider the expected splitting of signal “b” in the 1H NMR spectrum of 1,1-dichloro-3-
methylbutane, shown below. Presuming that Jab is sufficiently different from Jbc and that the
instrument has sufficient resolving power, what is the theoretical multiplicity of signal “b”?
a Cl
b d Cl
a c
A) 8
B) 9
C) 12
D) 18
E) 21
Answer: E
A) 2
B) 5
C) 6
D) 8
E) 12
Answer: E
87) Consider the expected splitting of signal “c” in the 1H NMR spectrum of 2-ethyl-1-butanol,
shown below. Presuming that Jbc is sufficiently different from Jcd and that the instrument has
sufficient resolving power, what is the theoretical multiplicity of signal “c”?
b a
OH
a c e
b d
A) 6
B) 7
C) 8
D) 12
E) 15
Answer: E
50
88) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C9H14O? IR data shows no characteristic peak around 1700 cm-1. The 13C-
NMR chemical shifts (ppm): 108.4, 50.9, 31.6, 23.5, 2.0. Relative integration is known.
6
3 3
3 2 1 0
PPM
O
O
A)
O
B) O
O
O
C)
O
D) O
E) O O
Answer: C
2 2
10 9 8 7 6 5 4 3 2 1 0
PPM
CHO
A) H2N
N
B) CHO
C) O
CHO
N
D) H
N CHO
E)
Answer: B
52
90) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C8H15ClO3, which shows a characteristic stretch in the IR around 1750 cm-1
but not around 3500 cm-1, and a characteristic peak at 173 ppm in the 13C-NMR? Relative
integration is shown.
6
2 2
4 3 2 1 0
PPM
O
O
Cl
O
A)
O
O
O
B) Cl
O
O
Cl
O
C)
O
O
Cl
O
D)
O
O
O
E) Cl
Answer: C
91) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C5H11NO? In the 13C-NMR spectrum you notice that the farthest peak
downfield has a chemical shift of 173 ppm. Relative integration is shown.
3 3
2 2
1
exchanges with D2O
9 8 7 6 5 4 3 2 1 0
PPM
N
A) H
O
N
B) H
O
N
C) H
HN
O
D)
O
H N
E)
Answer: A
54
92) The broadband proton-decoupled 13C NMR spectrum of a hexyl chloride exhibits five
signals. Which of these structures could be the correct one for the compound?
CH3
CH3CCH2CH2Cl
A) CH3
Cl
CH3CH2CCH2CH3
B) CH3
CH3 CH3
CH3C CHCH3
C) Cl
CH3
CH3CHCHCH2CH3
D) Cl
CH3
CH3C CHCH3
E) CH3 Cl
Answer: D
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: C
Cl
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: D
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: D
56
96) For the compound dimedone, how many different signals would you see in the 13C NMR?
(Assume that you can see them all.)
A) 3
B) 4
C) 5
D) 6
E) None of these choices.
Answer: C
97) For the compound adamantine, how many different signals would you see in the 13C NMR?
(Assume that you can see them all.)
A) 1
B) 2
C) 3
D) 4
E) None of these choices.
Answer: B
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: E
99) For the following compound how many different signals would you see in the carbon NMR?
(Assume that you can see them all.)
A) 3
B) 4
C) 5
D) 6
E) 7
Answer: C
58
100) In 13C NMR spectroscopy, the signal due to this type of carbon occurs furthest downfield.
A) –CN
C O
B)
C O
C)
C X
D)
E) –CC–
Answer: B
101) The C7 compound which gives 3 signals in the broadband proton-decoupled 13C spectrum
could be:
A) Heptane
B) 2-Methylhexane
C) 3,3-Dimethylpentane
D) 2,4-Dimethylpentane
E) 2,2,3-Trimethylbutane
Answer: D
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: E
103) For the following compound how many different signals would you see in the carbon
NMR? (Assume that you can see them all.)
A) 4
B) 5
C) 6
D) 7
E) 8
Answer: D
60
104) For the following compound how many different signals would you see in the carbon
NMR? (Assume that you can see them all.)
A) 3
B) 4
C) 5
D) 8
E) 9
Answer: A
105) A bromodichlorobenzene which gives four signals in the broadband proton-decoupled 13C
spectrum could be:
Cl Br
Br Cl Br Cl
Cl Cl Cl
I II III
Cl
Br Cl Br
Cl Cl
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: A
S S
A) 4
B) 5
C) 6
D) 7
E) 8
Answer: C
107) Which compound below would give rise to 3 signals in the proton NMR spectrum and 4
signals in the carbon NMR spectrum? (Assume you can separate and see all peaks.)
Br
I II III IV
A) I
B) II
C) III
D) IV
E) None of these choices.
Answer: E
62
108) Which compound below would give rise to 4 signals in the proton NMR spectrum and 4
signals in the carbon NMR spectrum? (Assume you can separate and see all peaks.)
Br
I II III IV
A) I
B) II
C) III
D) IV
E) More than one of the above.
Answer: C
109) Which compound below would give rise to 4 signals in the proton NMR spectrum and 6
signals in the carbon NMR spectrum? (Assume you can separate and see all peaks.)
Br
I II III IV
A) I
B) II
C) III
D) IV
E) More than one of these choices.
Answer: A
OH
I II III IV
A) I
B) II
C) III
D) IV
E) All of these choices fit the criteria.
Answer: C
111) Which compound below would give rise to 5 signals in the proton NMR spectrum and 7
signals in the carbon NMR spectrum? (Assume you can separate and see all peaks.)
Br
I II III IV
A) I
B) II
C) III
D) IV
E) None of these choices.
Answer: D
64
112) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C7H12O4? The 13C-NMR spectrum shows peaks at 14.1, 40.8, 61.0 and 166.8
ppm. Relative integration is shown.
3
2
1
5 4 3 2 1 0
PPM
O O
A) O O
H H
B) O O
O O
C) O O
O
O
D) O
O
O
O
E) O
Answer: A
4
3
2 2
8 7 6 5 4 3 2 1 0
PPM
A)
B) NC
CN
C)
D) CN
H
N
E)
Answer: D
66
114) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C6H10O2? The 13C-NMR shows characteristic chemical shifts at 22.3, 31.1,
117.3, 157.7, and 171.6 ppm. Relative integration is shown.
1
exchanges w/ D2O 1 1 1
13 12 11 10 9 8 7 6 5 4 3 2 1 0
PPM
O
HO
A)
CO2H
B)
O
C) O
CO2H
D)
CO2H
E)
Answer: E
3
2 2 2 2
8 7 6 5 4 3 2 1 0
PPM
A) O
O
O
B)
O
C) O
D) O
E) O
Answer: A
68
116) What is the structure of the compound in the following 1H-NMR spectrum with the
molecular formula C12H17NO and a characteristic IR stretch near 1700 cm-1 and a characteristic
peak in the 13C-NMR at 170 ppm? Relative integration is shown.
3 3 3
22 2 2
8 7 6 5 4 3 2 1 0
PPM
O
A)
B) O
C) HO
O
D)
O
E)
Answer: A
3 3
1 1
6 5 4 3 2 1 0
PPM
O
A)
O
B)
C)
O
O
D)
O
O
E)
Answer: B
70
118) Which is the base peak?
A) 15
B) 29
C) 44
D) 45
E) 100
Answer: B
A) 15
B) 29
C) 44
D) 45
E) 100
Answer: C
A) Alkane
B) Alcohol
C) Ether
D) Ketone
E) Primary amine
Answer: B
A) m/z 15
B) m/z 92
C) m/z 43
D) m/z 57
E) m/z 77
Answer: D
72
122) An organic compound absorbs strongly in the IR at 1687 cm-1. Its 1H NMR spectrum
consists of two signals, a singlet at 2.1 ppm and a multiplet centered at 7.1 ppm. Its mass
spectrum shows significant peaks at m/z 120, m/z 105 and m/z 77. This information is consistent
with which of the following structures?
O
O
O
I II III
IV V
A) I
B) II
C) III
D) IV
E) V
Answer: A
123) Select the structure of a compound C6H14 with a base peak at m/z 43.
A) CH3CH2CH2CH2CH2CH3
B) (CH3CH2)2CHCH3
C) (CH3)3CCH2CH3
D) (CH3)2CHCH(CH3)2
E) None of these choices.
Answer: D
m/z intensity
84 M+• 10.00
85 0.56
86 0.04
A) C5H10O
B) C5H8O
C) C5H24
D) C6H12
E) C4H6O2
Answer: B
m/z intensity
78 M+• 10.00
79 1
80 3.3
81 0.3
A) C6H6
B) C3H5Cl
C) C6H8
D) C6H9
E) C3H7Cl
Answer: E
74
126) The mass spectra of alkyl bromides and chlorides are characterized by an unusually intense
___.
A) base peak
B) parent peak
C) M+• + peak
D) M+• +2 peak
E) None of these choices.
Answer: D
127) The data below from the molecular ion region of the mass spectrum of a halogen-containing
compound are consistent with the presence of what halogen(s) in the original compound?
intensity
M+• 51.0
M+• +2 100.0
M+• +4 49.0
A) One Br
B) One Cl
C) One Br and one Cl
D) Two Br
E) Two Cl
Answer: D
Answer: True
129) Hydrogen that are diastereotopic will show different chemical signals in the proton NMR.
Answer: True
130) The predicted ratio of the relative peak sizes in a quintet signal would be about 1:3:5:3:1.
Answer: False
131) An acceptable solvent to use for a deuterium exchange experiment with an alcohol would
be CDCl3.
Answer: False
132) Compounds that contain a benzylic carbon will often show a peak with a m/z of 91 in a
mass spectrometry experiment.
Answer: True
76
Question type: fill-in-the-blank
Topic: General
Section: 9.1
Difficulty Level: Easy
134) Briefly explain how you might distinguish between 1-butyne and 2-butyne by comparing
their 1H-NMR spectra.
Answer: 1-butyne will show 3 signals whereas 2-butyne will only show one signal
Answer: The main difference would likely be in the chemical shift of the methine proton of the
isopropyl group. The methine proton in I is likely to be more deshielded, and produce a signal
(septet) at about 3.5 ppm, while the analogous proton in II is likely to be found, also as a septet,
at about 2.3 ppm.
O
O
O
O
I ~3.5 ppm II ~2.3 ppm
136) Briefly explain how you might distinguish between the following substances by comparing
their 1H-NMR spectra:
Answer: The key distinguishing will be the carboxylic acid hydrogen which should occur very
far downfield from the other signal and appear as a broad singlet.
78
137) Briefly explain how you might distinguish between the following substances by comparing
their 1H-NMR spectra:
O
O
O
O
I II
Answer: The main difference would likely be in the chemical shifts of the methine proton of the
isopropyl group and the methylene proton closest to the ester function.
The methine proton in I is likely to be more deshielded, and produce a signal (septet) at about 3.5
ppm, while the analogous proton in II is likely to be found, also as a septet, at about 2.3 ppm.
By contrast, the methylene proton in II is likely to be more deshielded, and produce a signal
(triplet) at about 3.4 ppm, while the analogous proton in II is likely to be found, also as a triplet,
at about 2.2 ppm.
I II
O
O
O
O
~3.5 ppm ~2.3 ppm
(septet) (septet)
~2.2 ppm ~3.4 ppm
(triplet) (triplet)
Answer: The main difference would likely be in the chemical shifts of the methine proton of the
isopropyl group and the methylene proton closest to the amide function.
The methine proton in I is likely to be more deshielded, and produce a signal (septet) at about 3.5
ppm, while the analogous proton in II is likely to be found, also as a septet, at about 2.3 ppm.
By contrast, the methylene proton in II is likely to be more deshielded, and produce a signal
(triplet) at about 3.4 ppm, while the analogous proton in II is likely to be found, also as a triplet,
at about 2.2 ppm.
I II
O H
N
N
H O
~3.2 ppm ~2.3 ppm
(septet) (septet)
~2.2 ppm ~3.1 ppm
(triplet) (triplet)
139) Draw the structure for a compound that has the chemical formula C4H8O2 and shows one
singlet, one triplet and one quartet in the proton NMR.
80
140) Predict the 1H NMR spectrum of diethoxymethane, CH3CH2OCH2OCH2CH3.
>
>
O O
>
>
>
~3.4 ppm ~3.4 ppm
quartet ~4.9 ppm quartet
Answer: singlet
Topic: 1H NMR
Section: 9.2
Difficulty Level: Medium
9-10 ppm
triplet
>
Cl
O
>
4-5 ppm
Answer: doublet
Topic: 1H NMR
Section 9.2
Difficulty Level: Medium
Answer: Five
1 2 4
1' 3
OH
5
Topic: 1H NMR
Section: 9.2
Difficulty Level: Easy
143) When measuring the integral for a particular peak in the NMR spectrum, we are not
interested in the peak height as much as in the ___.
144) Examine the 1H NMR spectrum of 1-nitropropane, shown below. Assign the signals to the
respective hydrogen atoms in the molecule.
4.3 ppm
triplet
>
>
triplet
2.0 ppm
Answer: sextet
82
145) An unknown compound, A, has the formula C7H14O. Elucidate the structure of A by
scrutinizing its IR and1H NMR spectra, shown below.
Answer:
4-Heptanone
Topic: General
Section: 9.4
Difficulty Level: Easy
147) What compound is used as the standard “zero” reference in both carbon and proton NMR?
Answer: Rotation about C-C single bonds; chemical exchange of protons attached to
electronegative atoms
Answer:
84
150) Interpret the following 13C/DEPT spectrum of a compound C5H10Br2: elucidate the structure
and assign all the 13C resonances.
32 ppm
>
>
Br Br
>
>
>
33 ppm 33 ppm
Answer: 27 ppm
Answer: Br
4-Bromotoluene
86
152) An unknown compound, F, has the formula C3H6O2. Elucidate the structure of F by
scrutinizing its IR, 1H NMR and 13C NMR spectra, shown below.
Answer: OH
Propanoic acid
153) An unknown compound, L, has the formula C5H10O2. Elucidate the structure of L by
scrutinizing its IR, 1H NMR and 13C NMR spectra, shown below.
Answer: O
Methyl butyrate
88
154) An unknown compound, I, has the formula C3H7NO2. Elucidate the structure of I by
scrutinizing its IR, 1H NMR and 13C NMR spectra, shown below.
Answer: NO2
1-Nitropropane
Answer:
2-Hexanone
90
156) An unknown compound, U, has the formula C6H4Cl2O. Elucidate the structure of U by
scrutinizing its IR, 1H NMR and 13C NMR spectra, shown below.
OH
Cl Cl
Answer:
2,6-dichlorophenol
Topic: Structure Elucidation
Section: 2.16, 9.2, 9.3, 9.8
Difficulty Level: Hard
157) Explain the key differences in the 2-dimensional NMR techniques known as COSY and
heteronuclear correlations.
Answer: A COSY shows correlations between two proton signals, whereas heteronuclear
correlation is designed to show interactions between protons and other non-proton atoms such as
carbon.
92
158) An unknown compound, V, has the formula C8H10O. Elucidate the structure of V by
scrutinizing its IR, 1H NMR and 13C NMR spectra, shown below.
OH
Answer:
2,6-dimethylphenol
159) In mass spectrometry, the most intense peak is assigned an intensity of 100%, and is
referred to as the ___.
161) In electron impact mass spectrometry, a beam of high-energy electrons initially dislodges
one electron from the compound being studied. This produces a positively charged ion called the
___.
162) What can be determined from the relative abundance of the M+• +1 peak?
94
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lasted even through death, and which is still isolated from everything
by the mysterious marble-lace which enfolds them and which floats
above them like a dream.
Very high overhead, as if through a thick vapour, we see the
dome loom through the shadows, although its entire outlines are not
perceptible; its walls seem made of mist, and its marble blocks
appear to have no solidity. Everything is aërial here, nothing is
substantial or real: this is a world of shadowy visions. Even sounds
are unearthly. A note sung under this vault is echoed above our
heads in an invisible region. First, it is as clear as the voice of Ariel,
then it grows fainter and fainter until it dies away and then is re-
echoed very far above, but glorified, spiritualized, and multiplied
indefinitely as if repeated by a distant company, a choir of unseen
angels who soar with it aloft until all is lost save a faint murmur which
never ceases to vibrate over the tomb of the beloved, as if it were
the very soul of a musician.
I have seen the Taj again; this time at noon. Under the vertical
sun the melancholy phantom has vanished, the sweet sadness of
the mausoleum has gone. The great marble table on which it stands
is blinding. The light, reflected back and forth from the immense
surfaces of white marble, is increased a hundred-fold in intensity,
and some of the sides are like burning plaques. The incrustations
seem to be sparks of magic fire; their hundreds of red flowers gleam
like burning coals. The religious texts and the hieroglyphs, inlaid with
black marble, stand out as if traced by the lightning-finger of a
savage god. All the mystical rows of lotus and lilies unfolding in
relief, which just now had the softness of yellowed ivory, spring forth
like flames.—I retrace my steps, passing out of the entrance, and for
an instant I have a dazzling view of the lines and incandescent
surfaces of the building with its unchanging virgin whiteness.—
Indeed, this severe simplicity and intensity of light give it something
of a Semitic character: we think of the flaming and chastening sword
of the Bible. The minarets lift themselves into the blue like pillars of
fire.
I wander outside in the fresh air under the shadows of the leafy
arches until twilight. This garden is the conception of one of the
faithful who wished to glorify Allah. It is the home of religious delight:
—“No one shall enter the garden of God unless he is pure of heart,”
is the Arabian text graven over the entrance-gate. Here are flower-
beds, which are masses of velvet,—unknown blooms resembling
heaps of purple moss. The trunks of the trees are entwined with blue
convolvulus, and flowers like great red stars gleam through the dark
foliage. Over these flowers a hundred thousand delicate butterflies
hover in a perpetual cloud. Many pretty creatures, little striped
squirrels and numerous birds, green parrots and parrots of more
brilliant plumage, disport themselves here, making a little world,
happy and secure, for guards, dressed in white muslin, menace with
long pea-shooters the crows and vultures and protect them from
everything that would bring mischief or cruelty into this peaceful
place.
On the surface of the still waters lilies and lotus are sleeping,
their stiff leaves pinked out and resting heavily upon the dark mirror.
Through the blackness of the boughs English meadows are
revealed, bathed in brilliant sunlight, and spaces of blue sky, across
which a triangle of white storks is sometimes seen flying, and, at
certain moments, the far-away vision of the phantom tomb seems
like the melancholy spectre of a virgin.—How calm, how superb this
solitude, charged with voluptuousness at once solemn and
enervating! Here dwell the beauty, the tenderness, and the light of
Asia, dreamed of by Shelley.
THE Kremlin, always regarded as the Acropolis, the Holy Place, the
Palladium, and the very heart of Russia, was formerly surrounded by
a palisade of strong oaken stakes—similar to the defence which the
Athenian citadel had at the time of the first invasion of the Persians.
Dmitri-Donskoi substituted for this palisade crenellated walls, which,
having become old and dilapidated, were rebuilt by Ivan III. Ivan’s
wall remains to-day, but in many places there are restorations and
repairs. Thick layers of plaster endeavour to hide the scars of time
and the black traces of the great fire of 1812 which was only able to
lick this wall with its tongues of flame. The Kremlin somewhat
resembles the Alhambra. Like the Moorish fortress, it stands on the
top of a hill which it encloses with its wall flanked by towers: it
contains royal dwellings, churches, and squares, and among the
ancient buildings a modern Palace whose intrusion we regret as we
do the Palace of Charles V. amid the delicate Saracenic architecture
which it seems to crush with its weight. The tower of Ivan Veliki is not
without resemblance to the tower of the Vela; and from the Kremlin,
as from the Alhambra, a beautiful view is to be enjoyed, a panorama
of enchantment which the fascinated eye will ever retain.
It is strange that when seen from a distance the Kremlin is
perhaps even more Oriental than the Alhambra itself whose massive
reddish towers give no hint of the splendour within. Above the
sloping and crenellated walls of the Kremlin and among the towers
with their ornamented roofs, myriads of cupolas and globular bell-
towers gleaming with metallic light seem to be rising and falling like
bubbles of glittering gold in the strong blaze of light. The white wall
seems to be a silver basket holding a bouquet of golden flowers, and
we fancy that we are gazing upon one of those magical cities which
the imagination of the Arabian story-tellers alone can build—an
architectural crystallization of the Thousand and One Nights! And
when Winter has sprinkled these strange dream-buildings with its
powdered diamonds, we fancy ourselves transported into another
planet, for nothing like this has ever met our gaze.
We entered the Kremlin by the Spasskoi Gate which opens upon
the Krasnaïa. No entrance could be more romantic. It is cut through
an enormous square tower, placed before a kind of porch. The tower
has three diminishing stories and is crowned with a spire resting
upon open arches. The double-headed eagle, holding the globe in its
claws, stands upon the sharp point of the spire, which, like the story
it surmounts, is octagonal, ribbed, and gilded. Each face of the
second story bears an enormous dial, so that the hour may be seen
from every point of the compass. Add for effect some patches of
snow laid on the jutting masonry like bold dashes of pigment, and
you will have a faint idea of the aspect presented by this queenly
tower, as it springs upward in three jets above the denticulated wall
which it breaks....
Issuing from the gate, we find ourselves in the large court of the
Kremlin, in the midst of the most bewildering conglomeration of
palaces, churches, and monasteries of which the imagination can
dream. It conforms to no known style of architecture. It is not Greek,
it is not Byzantine, it is not Gothic, it is not Saracen, it is not Chinese:
it is Russian; it is Muscovite. Never did architecture more free, more
original, more indifferent to rules, in a word, more romantic,
materialize with such fantastic caprice. Sometimes it seems to
resemble the freaks of frostwork. However, its leading characteristics
are the cupolas and the golden-bulbed bell-towers, which seem to
follow no law and are conspicuous at the first glance.
Below the large square where the principal buildings of the
Kremlin are grouped and which forms the plateau of the hill, a
circular road winds about the irregularities of the ground and is
bordered by ramparts flanked with towers of infinite variety: some
are round, some square, some slender as minarets, some massive
as bastions, and some with machicolated turrets, while others have
retreating stories, vaulted roofs, sharply-cut sides, open-worked
galleries, tiny cupolas, spires, scales, tracery, and all conceivable
endings. The battlements, cut deeply through the wall and notched
at the top like an arrow, are alternately plain and pierced with little
barbicans. We will ignore the strategic value of this defence, but from
a poetic standpoint it satisfies the imagination and gives the idea of a
formidable citadel.