Robert M. Silverstein, Francis X. Webster, David Kiemle-Solutions Manual For Spectrometric Identification of Organic Compounds-Wiley (2005)

Answers for Student Exercises 1.1 to 1.
a
3-ethyloctane
C10H22
CnHmXxNyOz
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD
0
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
# of Atoms
Mass
1.00783
22
10
12.00000
14.0031
0
15.9949
0
31.9721
0
78.9183
0
Exact Mass
Total Mass
22.17226
120.00000
0.00000
0.00000
0.00000
0.00000
142.17226
- (C2H5 )
Rule 3
- (C5H11 )
Rule 3
H
- (CH2=CH2)
Rule 9
3-butylcyclohex-1-ene
C10H18
CnHmXxNyOz
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD
2
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
or
- (C4H9 )
Rule 5 and 6
- (CH2=CH2)
Rule 6
- (C3H7 )
Rule 3
# of Atoms
Mass
1.00783
18
10
12.00000
14.0031
0
15.9949
0
31.9721
0
78.9183
0
Exact Mass
Total Mass
18.14094
120.00000
0.00000
0.00000
0.00000
0.00000
138.14094
Answers for Student Exercises 1.1 to 1.5
2
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
O
c
2-methyl-1-phenylhexan-1-one
C13H18O
CnHmXxNyOz
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD
5
# of Atoms
Mass
1.00783
18
13
12.00000
14.0031
0
15.9949
1
31.9721
0
78.9183
0
Exact Mass
Total Mass
18.14094
156.00000
0.00000
15.99490
0.00000
0.00000
190.13584
- (C6H13 )
Rule 8
O
- (C6H5 )
Rule 8
- (C4H8)
OH
H
Rule 9
O
- (CO)
Rule 8+9
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
d
(E)-undec-3-ene
C11H22
CnHmXxNyOz
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD
1
or
- (CH3)
Rule 5
- (C6H13)
Rule 5
H
- (C7H14)
Rule 9
# of Atoms
Mass
1.00783
22
11
12.00000
14.0031
0
15.9949
0
31.9721
0
78.9183
0
Exact Mass
Total Mass
22.17226
132.00000
0.00000
0.00000
0.00000
0.00000
154.17226

e
1-(hexan-2-yl)benzene
C12H18
CnHmXxNyOz
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD
4
3
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
# of Atoms
Mass
1.00783
18
12
12.00000
14.0031
0
15.9949
0
31.9721
0
78.9183
0
Exact Mass
Total Mass
18.14094
144.00000
0.00000
0.00000
0.00000
0.00000
162.14094
- (CH3 )
Rule 7
- (C4H9 )
Rule 7
- (C4H8 )
Rule 9
H
f
OH
heptan-2-ol
C7H16O
CnHmXxNyOz
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
OH
OH
H
OH
H
OH
IHD
0
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
# of Atoms
Mass
1.00783
16
7
12.00000
14.0031
0
15.9949
1
31.9721
0
78.9183
0
Exact Mass
Total Mass
16.12528
84.00000
0.00000
15.99490
0.00000
0.00000
116.12018
- (C5H11 )
Rule 8
OH
- (CH3 )
Rule 8
OH
- (H )
Rule 8
- (H2O)
Rule 9
OH
COOH
3,5,7-trimethyloctanoic acid
C11H22O2
CnHmXxNyOz
IHD
1
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
4
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
# of Atoms
Mass
1.00783
22
11
12.00000
14.0031
0
15.9949
2
31.9721
0
78.9183
0
Exact Mass
Total Mass
22.17226
132.00000
0.00000
31.98980
0.00000
0.00000
186.16206
O
C
O
- (OH )
OH
Rule 8
O
C
O
OH
- (C10H21 )
Rule 8
- (C9H18)
Rule 9
HO
h
OH
hexan-1-ol
C6H14O
CnHmXxNyOz
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD
0
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
O
C
OH
H
OH
OH
HO
HO
# of Atoms
Mass
1.00783
14
6
12.00000
14.0031
0
15.9949
1
31.9721
0
78.9183
0
Exact Mass
Total Mass
14.10962
72.00000
0.00000
15.99490
0.00000
0.00000
102.10452
H
H
- (CH2=CH2 ) - (H2O)
Rule 9
OH
- (C5H11 )
Rule 8
H 2C
OH
- (H )
OH
Rule 8
OH
OH
2-methylheptan-2-ol
C8H18O
CnHmXxNyOz
IHD
0
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
5
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
# of Atoms
Mass
1.00783
18
8
12.00000
14.0031
0
15.9949
1
31.9721
0
78.9183
0
Exact Mass
Total Mass
18.14094
96.00000
0.00000
15.99490
0.00000
0.00000
130.13584
- (C5H11 )
OH
OH
Rule 8
- (CH3 )
OH
OH
Rule 8
H
H
- (H2O)
- (CH2=C(CH3)2)
Rule 8
Rule 8
S
butyl(propyl)sulfane
C7H16S
CnHmXxNyOz
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD
0
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
# of Atoms
Mass
1.00783
16
7
12.00000
14.0031
0
15.9949
0
31.9721
1
78.9183
0
Exact Mass
- (C3H7 )
Rule 8
- (CH2=CH2)
Rule 9
Total Mass
16.12528
84.00000
0.00000
0.00000
31.97210
0.00000
132.09738
- (C2H5 )
Rule 8
SH

k
OH
(2-hexylphenyl)methanol
C13H20O
CnHmXxNyOz
IHD
4
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
OH
6
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
# of Atoms
Mass
1.00783
20
13
12.00000
14.0031
0
15.9949
1
31.9721
0
78.9183
0
Exact Mass
OH
or
- (C5H11 )
OH
OH
Rule 7
CH2
CH2
- (OH )
OH
Total Mass
20.15660
156.00000
0.00000
15.99490
0.00000
0.00000
192.15150
Rule 7
OH
- (H2O)
Rule 9
O
l
NO2
(4-nitrophenyl)(phenyl)methanone
C13H9NO3
CnHmXxNyOz
IHD
10
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
# of Atoms
Mass
1.00783
9
13
12.00000
14.0031
1
15.9949
3
31.9721
0
78.9183
0
Exact Mass
Total Mass
9.07047
156.00000
14.00310
47.98470
0.00000
0.00000
227.05827
O
- (C6H4NO2 )
NO2
O
Rule 7&8
- (CO)
Rule 8&9
O
O
- (C6H5 )
NO2
Rule 7&8
NO2
3-(ethoxymethyl)heptane
C10H22O
CnHmXxNyOz
IHD
0
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
7
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
# of Atoms
Mass
1.00783
22
10
12.00000
14.0031
0
15.9949
1
31.9721
0
78.9183
0
Exact Mass
- (CH3 )
O
CH2
Rule 8
- (C7H15 )
Total Mass
22.17226
120.00000
0.00000
15.99490
0.00000
0.00000
158.16716
Rule 8
- (C4H9)
Rule 3
O
n
H
Br
2-bromodecanal
C10H19BrO
CnHmXxNyOz
IHD
1
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
# of Atoms
Mass
1.00783
19
10
12.00000
14.0031
0
15.9949
1
31.9721
0
78.9183
1
Exact Mass
Total Mass
19.14877
120.00000
0.00000
15.99490
0.00000
78.91830
234.06197
- (H )
H
Br
Rule 8
Br
O
- (CO )
Rule 9
Br
Br
H
H O
H
Br
- (C8H16)
Rule 9
O
H
H
Br

o
O
O
cyclohexyl acetate
C8H14O2
CnHmXxNyOz
Index = (n) - (m/2) - (x/2) + (y/2) + 1 =
IHD
2
8
Atom Type
Hydrogen
Carbon
Nitrogen
Oxygen
Sulfur
Bromine
- (C6H11O )
# of Atoms
Mass
1.00783
14
8
12.00000
14.0031
0
15.9949
2
31.9721
0
78.9183
0
Exact Mass
Total Mass
14.10962
96.00000
0.00000
31.98980
0.00000
0.00000
142.09942
Rule 8
- (CH3 )
Rule 8
O
H
- (CH2=C=O)
Rule 9

A
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
71
114
99 / C6H11O
15 / CH3
86 / C5H10
28 / C2H4
71 / C4H7O
43 / C3H7
58 / C3H5O
56 / C4H8
43 / C3H7
71 / C4H7O
4-Heptanone
C7H14O
Exact Mass: 114.1045
IHD = 1, match with (k)
OH
4-Bromotoluene
C7H7Br
IHD = 4, match with (v)
Fragement Ion
Fragment Loss
59
116 by CI
115 / C7H15O
1/H
98 / C7H14
18 / H2O
87 / C5H11O
29 / C2H5
69 / C5H9
18 / H2O, 29 / C2H5
59 / C3H7O
57 / C4H9
45 / C2H5O
71 / C5H11
43 / C3H7
73 / C4H9O
41 / C4H5
18 / H2O, 57 / C4H9
Rearrangment
R
R
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
91
170
91 / C7H7
79 / Br
Rearrangment
Tropylium
Ion
75 / C6H3
80 / HBr, 16 / CH4
65 / C5H5
79 / Br, 26 / C2H2
50 / C4H2
120 / C7H5Br
39 / C3H2
131 / C4H5Br
Br
2-Bromopentane
C5H11Br
IHD = 0, match with (r)
Molecular
Ion
C7H16O
IHD = 0, match with (m)
Br
Base Peak
3-Heptanol
Rearrangment
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
71
150
121 / C3H6Br
29 / C2H5
107 / C2H4Br
43 / C3H7
71 / C5H11
79 / Br
55 / C4H7
80 / HBr, 16 / CH4
43 / C3H7
C2H4Br
Rearrangment

O
10
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
43
100
85 / C5H9O
15 / CH3
71 / C4H7O
29 / C2H5
58 / C4H10
42 / C2H2O
57 / C3H5O
43 / C3H7
43 / C3H7
57 / C3H5O
2-Hexanone
C6H12O
IHD = 1, match with (h)
OH
Propionic Acid
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
74
74
73 / C3H5O2
1/H
57 / C3H5O
17 / OH
56 / C3H4O
18 / H2O
45 / CHO2
29 / C2H5
C3H6O2
Exact Mass: 74.0368
IHD = 1, match with(c)
H2N
OH
prop-2-yn-1-ol
C3H4O
Exact Mass: 56.0264
IHD = 2, match with (a)
Rearrangment
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
Rearrangment
73
73
56 / C4H8
17 / NH3
55 / C4H7
18 / NH4
44 / C2H6N
29 / C2H5
43 / C3H7
30 / CH4N
butan-1-amine
C4H11N
Exact Mass: 73.0896
IHD = 0, match with (b)
Rearrangment
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
55
56 by CI
55 / C3H3O
1/H
39 / C3H3
17 / OH
38 / C3H2
18 / H2O
Rearrangment
O
N
O-
11
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
43
89 by CI
90 / C3H8NO2
Addition of H
72 / C3H6NO
17 / OH
43 / C3H7
46 / NO2
42 / C3H6
47 / HNO2
Rearrangment
1-Nitropropane
C3H7NO2
Exact Mass: 89.0477
IHD = 1, match with (d)
OH
O
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
94
138
107 / C7H7O
31 / CH3O
94 / C6H5O
44 / C2H4O
77 / C6H5
61 / C2H5O2
66 / C5H6
72 C3H5O2
51 / C4H3
87 / C4H7O2
39 / C3H2
99 / C5H8O2
2-Phenoxylethanol
C8H10O2
IHD = 4, match with (q)
K
O
Phenetole
O
O
Methyl Butyrate
C5H10O2
IHD = 1, match with (i)
R
R
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
Rearrangment
94
122
94 / C6H5O
28 / C2H4
77 / C6H5
45 / C2H5O
66 / C5H6
56 / C3H4O
51 / C4H3
71 / C4H7O
39 / C3H2
83 / C5H8O
C8H10O
IHD = 4, match with (o)
Rearrangment
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
43
102
87 / C4H7O2
15 / CH3
74 / C3H5O2
28 / C2H4
71 / C4H7O
31 / CH3O
59 / C2H3O2
43 / C3H7
43 / C3H7
59 / C2H3O2
Rearrangment
R

O
M
HN
12
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
Rearrangment
113
113
85 / C5H11N
28 / CO
84 / C5H10N
29 / CHO
56 / C4H8
57 / C2H3NO
55 / C4H7
58 / C2H4NO
42 / C3H6
71 / C3H5NO
Rearrangment
Caprolactam
C6H11NO
IHD = 2, match with (j)
N
N
2-methylpyrazine
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
94
94
67 / C4H5N
27 / CHN
53 / C3H3N
41 / C2H3N
42 / C2H4N
52 / C3H2N
41 / C2H3N
53 / C3H3N
40 / C2H2N
54 / C3H4N
C5H6N2
Exact Mass: 94.0531
IHD =4, match with (e)
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
152
152
135 / C8H7O2
17 / OH
122 / C7H6O2
30 / CH2O
107 / C7H7O
45 / CHO2
Methyl salicylate
105 / C7H5O
17 / OH, 30 / CH2O
C8H8O3
IHD = 5, match with (s)
92 / C6H4O
77 / C6H5
60 / C2H4O2
17 / OH, 58 /
C2H2O2
63 / C5H3
89 / C3H5O3
39 / C3H2
113 / C5H6O3
Fragement Ion
141 /
C6H4ClNO
Fragment Loss
127 / C6H4O
30 / NO
111 / C6H4Cl
46 / NO2
99 / C5H4Cl
58 / CNO2
75 / C6H3
46 / NO2, 36 / HCl
50 / C4H2
107 / C2H2ClNO2
HO
O
O
P
O
N+
-
Cl
1-Chloro-4-Nitrobenzene
C6H4ClNO2
IHD = 5, match with (t)
Base Peak
Molecular
Ion
75 or 157
157
Rearrangment
Rearrangment
16 / O
R

Q
HO
Br
13
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
60
208 by CI
191 / C7H12OBr
17 / OH
149 / C5H10Br
59 / C2H3O2
129 / C7H13O2
79 /Br
111 / C7H11O
79 /Br, 18 / H2O
83 / C6H11
125 / CH2BrO2
60 / C2H4O2
147 / C5H9Br
Rearrangment
7-Bromo Heptanoic Acid

C7H13BrO2
IHD = 1, match with (w)
R
HO
5-Hexyn-1-ol
C6H10O
Exact Mass: 98.0732
IHD = 2, mathc with (g)
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
70
98
97 / C6H9O
1/H
83 / C5H7O
15 / CH3
79 / C6H7
19 / H3O
70 / C4H6O
28 / C2H4
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
43
126
111 / C7H11O
15 / CH3
108 / C8H12
18 / H2O
93 / C7H9
33 / CH5O
83 / C6H11
43 / C2H3O
69 / C5H9
57 / C3H5O
58 / C3H6O
68 / C5H8
55 / C4H7
71 C4H7O
43 / C2H3O
83 / C6H11
6-Methyl-5-hepten-2-one
C8H14O
IHD = 2, match with (p)
T O
HO
Hexanoic acid
C6H12O2
IHD = 1, match with (l)
Rearrangment
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
60
116 by CI
87 / C4H7O2
29 / C2H5
73 / C3H5O2
43 / C3H7
60 / C2H4O2
56 / C4H8
45 / CHO2
71 / C5H11
Rearrangment
Rearrangment

U
HO
Cl
14
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
Rearrangment
162
162
126 / C6H3OCl
36 / HCl
98 / C5H3Cl
64 / CHOCl
63 / C5H3
99 / CHOCl2
Cl
2,6-Dichlorophenol
C6H4Cl2O
IHD = 4, match with (u)
V HO
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
122
122
121/C8H9O
1/H
107/C7H7O
15 / CH3
91 / C7H7
31 / CH3O
77 / C6H5
45 / C2H5O
65 / C5H5
57 / C3H5O
2,6-Dimethylphenol
C8H10O
IHD = 4, match with (n)
2-Cyclohexen-1-one
C6H8O
Exact Mass: 96.0575
IHD = 3, match with (f)
Rearrangment
Base Peak
Molecular
Ion
Fragement Ion
Fragment Loss
Rearrangment
68
96
68 / C4H4O
28 / C2H4
55 / C3H3O
41 / C3H5
53 / C4H5
43 / C2H3O
42 / C2H2O
54 / C4H6
Answers for Student Exercise 2.1 2.9
2.1. Since the indicated carbon of phenylacetonitrile is sp3 hybridized, it is reasonable for this compound to
show CH stretching at less than 3000 cm-1 (2960-2940 cm-1). Where as benzonitrile has only aromatic
CH stretching which is typically between 3100 - 3000 cm-1 (page 87).
CH2
C N
phenylacetonitrile
benzonitrile
2.2.
O
N
H 2N
b. isobutylamine
a. benzonitrile
HO
S
O
c. diphenyl sulfone
d. dioxane
O
g. biphenyl
f. formic acid
N+
O-
e. 1-nitropropane
HO
H 2N
h. benzoic acid
i. benzamide
2.3.
1,3-Cyclohexadiene
Diphenylacetylene
Spectrum B
Spectrum A
1-Octene
Spectrum D
2-Pentene
Spectrum C
2.4.
O
O
NH2
O
H 2N
HO
O
O-
C11H23
Na+
Butyl acetate
Butyramide
Isobutylamine
Lauric acid
Sodium propionate
Spectrum E
Spectrum H
Spectrum I
Spectrum F
Spectrum G
2.5.
HO
O
O
Allyl phenyl ether
Spectrum L
HO
H
Benzaldehyde
Spectrum M
o-Cresol
Spectrum K
m-Toluic acid
Spectrum J
2.6.
HO
N
H 2N
N
H 2N
NH2 Cl
Aniline
Azobenzene
Spectrum Q
Spectrum O
Benzophenone oxime
Spectrum P
2.7.
Methyl isothiocyanate CH3N=C=S
2.8.
This diketone exists primarily (~ 90%) in enol form (in CCl4)

O
Benzylamine
Spectrum N
Dimethylamine
hydrochloride
Spectrum R
enol
Enols such as this display broad, shallow OH stretching bands (here from 3400-2500 cm-1). The
strong band at ~1600 cm-1 is the enolic coupled C=COH band. (See pages 80, 94, and 98)
2.9.
O
OH
4-Heptanone
3-Heptanol
4-Bromotoluene
Br
Br
2-Bromopentane
OH
H 2N
OH
2-Hexanone
Propionic Acid
Butylamine
Propargyl alcohol
OH
O
N+
O-
1-Nitropropane
O
2-Phenoxylethanol
Phenetole
MethylHButyrate
HO
HN
N
O
N+
Cl
Caprolactam
2-methylpyrazine
Methyl salicylate
HO
Br
HO
5-Hexyn-1-ol
HO
Cl
HO
O
Cl
HO
Hexanoic acid
2,6-Dichlorophenol
2,6-Dimethylphenol
2-Cyclohexen-1-one
Answers for Student Exercise 3.1 to 3.3
1
4
Br
(a) 1-bromobutane
3.1(a) 1,2,3,4 are a spin system. Pople notation is A3M2S2X2. 1,2, and 3 are enantiotopic.
3.2 (a)
Spin
1
2
3
4
Appr.
3.40
1.85
1.20
0.85
Table
Appendix A, Chart A.1
Coupled with
2
1,3
3, 4
3
Multiplet (n+1)
Triplet
Quintet
Sextet
Triplet
Integration
2
2
2
3
3.3 (a)
2
5
1
3
O
O 8
(b) (cyclohex-2-enyl)methyl acetate
3.1 (b) 1,2,3,4,5,6,7 are one spin system, and 9 is the second. 4,4 ; 5,5 ; 6,6and 7,7 are
diastereotopic.
3.2 (b)
Spin
Table or Calculation
Coupled with Multiplet (n+1)
Integration
Appr.
1
6,2,7
Sextet*
1
2.80
2
Appendix D, Chart D2
3,1
Triplet*
1
5.59
3
Quartet*
1
5.59
Appendix
D,
Chart
D2
Quartet**
2
1.96
4
4,6
Quartet**
2
1.65
5
1,5
Triplet**
2
1.80
6
1
Doublet**
2
4.05
7
none
Singlet
3
2.10
9
* Coupling constants may not be the same, but make the assumption that they are.
**These are diastereotopic, and are coupled to diastereotopic protons, they would not be first order.
We will assume they are first order for the drawn spectrum.
3.3 (b)
2 and 3
3
2
3
O
1
7
6
4
5
9
8
OH
10
(c) 1-(cyclohexa-1,5-dienyl)-3hydroxy-2-methylpropan-1-one
3.1 (c) 2,3,4,5,6 are a spin system, and 8,9,10 another spin system. 3,3 ; 4,4 ; 9,9 are diastereotopic.
3.2 (c)
Spin
Integration
Appr.
2
Appendix
D,
Chart
D.1
3
Triplet
1
6.68
3
Appendix A, Chart A1
2,4
Quartet***
2
2.05
4
3,5
Quartet***
2
2.05
4,6
Quartet*
1
5
5.68
5
Doublet
1
6.22
6
Appendix
A,
Chart
A.1
9,10
Sextet
1
2.65
8
8
Doublet**
2
3.20
9
8
Doublet
3
1.05
10
1
0.5-4.0 Appendix E
** These are diastereotopic, and are coupled to diastereotopic protons; they would not be first order.
We will assume they are first order for the drawn spectrum.
3.3 (c)
3,4
OH 10
3 2 1
(d) pent-1-yne
3.1 (d) 5,4,3 are a spin system and 1 is second. 5,4,3 is Pople notation is A3M2X2; may have long rang
coupling. 3+4 are enantiotopic.
3.2 (d)
Appr.
0.85
1.50
2.20
1.80
Spin
5
4
3
1

4
Triplet
3,5
Sextet
4
Triplet
none
Singlet
3.3 (d)
Integration
3
2
2
1
5
O
1
5
6
4
(e) hex-3-en-2-one
2
3.1 (e) 3,4,5,6 are a spin system, and 1 is another spin system. Pople notation is A3G2MX. 5 is
enantiotopic.
3.2 (e)
Appr.
1.86
6.09
6.82
2.05
1.00
Spin
1
3
4
5
6
Appendix D, Chart D.2

None
Singlet
4
Doublet
3, 5
Quartet*
4, 6
Quintet*
5
Triplet
Integration
3
1
1
2
3
3.3 (e)
O 2
4
3
(f) 1-methoxybut-1-ene
3.1 (f) 3,4,5,6 are a spin system, and 1 is another spin system. Pople notation is A3G2MX. 4 is
enantiotopic.
3.2 (f)
Appr.
3.20
6.14
4.63
2.05
1.00
Spin
1
2
3
4
5

None
Singlet
3
Doublet
2, 4
Quartet*
3, 5
Quintet*
4
Triplet
Integration
3
1
1
2
3
3.3 (f)
O
N 2 O 3
H
(g) propyl methylcarbamate
3.1 (g) 3,4,5 are a spin system, and 1 is another spin system. Pople notation is A3M2X2. 3 and 4 are
enantiotopic.
3.2 (g)
Spin
Appr.
1
2.95
3
4.10
4
1.60
5
0.85
NH
4.5-7.5 Appendix E
*See Section 3.6.2 for coupling between 1 and N-H.

None
Singlet
3
Triplet
2, 4
Sextet
3, 5
Triplet
*
Singlet
Integration
3
2
2
3
1
3.3 (g)
NH
2 O 3 O
(h) diethoxymethane
3.1 (h) 1 and 2 are a spin system, and 3 is another spin system. Pople notation is A3X2. 2 are
enantiotopic.
3.2 (h)
Spin
1
2
3
Appr.
1.20
3.40
4.95
Appendix B, Table B.1

2
Triplet
1
Quartet
none
Singlet
Integration
3
2
2
3.3 (h)
HO
6
2
(i) 2-methylpentan-2-ol
3.1 (i) 3,4 and 5 is a spin system. 1 and 6 are enantiotopic to each other and 3 and 4 are also
enantiotopic. Pople notation is A3M2X2.
3.2 (i)
Spin
1 and 6
3
4
5
Appr.
1.20
1.50
1.20
0.85
0.5-4.0
Appendix E

none
Singlet
4
Triplet
3,5
Sextet
4
Triplet
none
Singlet
3.3 (i)
1 and 6
Large singlet
of 6 H
OH
1,6,4
Integration
6
2
2
3
1
10
S 2
(j) 1,4-bis(methylthio)butane
3.1 (j) Not First order (no Pople). See Section 3.11.2. Protons 2 and 3 are enantiotopic. Protons on
1,2,3 are Chemical Shift Equivalent.
3.2 (j)
Spin
Appr.
1
Appendix
A,
Chart
A1
none
Singlet
2.10
2
3
Triplet*
2.60
2,3
Quintet*
3
1.60
* Would not be first order. We will assume they are first order for the drawn spectrum.
Integration
6 or 3
4 or 2
4 or 2
3.3 (j)
Actual spectrum would look like this!
PPM
11
3'
4
2'
O
1
7
3
(k) N,N,4-trimethylbenzamide
8
3.1 (k) 2,2; 3,3 are CSE but not ME. 6 and7 are diastereotopic. Pople notation for ring is AA XX
3.2 (k)
Spin
Appr.
2, 2
Appendix
D,
Chart
D1
none
Doublet**
7.80
3, 3
3
Doublet**
7.25
6,7
none
Singlet*
2.95
8
none
Singlet
2.25
* There will be two singlets because of the restricted rotation of the NR2
** These can not be first order. Not magnetically equivalent.
3.3 (k)
2,2
3,3
6,7
Integration
2
2
6*
3
12
6
5
O
1
7
OH
3
(l) 1-(2-hydroxyphenyl)ethanone
3.1 (i) N.A.

3.2 (i)
Spin
Appr.
3
6.85
4
7.05
5
7.25
6
7.70
8
2.40
OH
5.5-12.5 Appendix E
* Will have long range coupling.

4
Doublet*
3,5
Triplet*
4,6
Triplet*
5
Doublet*
none
Singlet
none
Singlet
3.3 (i)
OH
Integration
1
1
1
1
3
1
13
Cl 1
2 H
O
(m) 2-chloroacetaldehyde
3.1(m) 1 and 2 is a spin system. Pople notation is A2X. 2 protons are enantiotopic.
3.2 (m)
Spin
1
Appr.
4.95
Table
2
Triplet
Plus Appendix B, Table B.1*
2
1
Doublet
9.80
extrapolation
Calc is based on Chart A1 3.45 for ClCH2 plus Table B.1 value of 1.50 for HC=O
3.3 (m)
Integration
1
2
14
2H
F
(n) fluoroethene
3.1(n) Charts are not available in text for this problem. Pople notation is AGMX, where X is F.
3.2 (n)
3.3 (n)
4
PPM
Protocol of the H-1 NMR Prediction:

Node
Shift
4.85
6.79
4.23
Base + Inc.
5.25
-0.40
5.25
1.54
5.25
-1.02
Comment (ppm rel. to TMS)

1-ethylene
1 -F cis
1-ethylene
1 -F gem
1-ethylene
1 -F trans
15
3'
4
2'
3
(o) cyclohexyl acetate
3.1 (o) 1,2,2,3,3, and 4 is a spin system, and 6 is another spin system. 2,2,;2,2;3,3;3,3;4,4 protons
are diastereotopic. 2 and 2 are CSE, also 3 and 3 are CSE.
3.2 (o)
Spin
Integration
Appr.
1
Appendix
A,
Chart
A.1
2,2
Quintet
1
4.95
2,2
1,(3or3)
Quartet*
4
1.60
3,3
Appendix C, Table C.1
(2 or 2),4
Quintet*
4
1.44
4
Appendix C, Table C.1
3,3
Quintet*
2
1.44
6
none
Singlet
3
2.00
* These are diastereotopic, and are coupled to diastereotopic protons; they would not be first order. We
will assume they are first order for the drawn spectrum.
3.3 (o)
2,2
3,3, and 4
Answers for Student Exercise 3.4
16
Problem
Problem 3.4
4.3 A
A C7H14O
O
1
4
4-Heptanone
ppm
2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8
Problem 3.4
4.3 B
B C7H16O
Problem
OH
1
OH
3 4 5 6
3-Heptanol
3.5
3.0
Problem 4.3 C C H Br
Problem 3.4 C 7 7 5
2.5
2
1
2.0
1.5
ppm
1.0
3
4
Br
4-Bromotoluene
7.5
7.0
6.5
6.0
Problem 3.4
4.3 D
D C5H11Br
Problem
5.5
5.0
4.5
4.0
3.5
3.0
2.5
Br
ppm
3
5
4
2
2-Bromopentane
2
3
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm

1
Problem
Problem 3.4
4.3 E
E C6H12O
17
O
3
5
2
4
2-Hexanone
2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8
ppm
Problem 3.4
4.3 FF C3H6O2
Problem
x4
HO 1
Propionic Acid
OH
12.0
ppm
11.5
3.5
3.0
2.5
2.0
ppm
1.5
Problem 3.4
4.3 G
G C4H11N
Problem
H2N 1
Butylamine
NH2
2
2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8
Problem 33.4
4.3 HH C3H4O
Problem
1
OH
3
Propargyl alcohol
4.4
OH
4.2
4.0
3.8
3.6
3.4
ppm
3.2
3.0
2.8
2.6
2.4
2.2
2.0
ppm

Problem 3.4 I
Problem 4.3 I C3H7NO2 O
N+ 1
2
O
18
1-Nitropropane
4.5
4.0
3.5
3.0
Problem 3.4 J
Problem 4.3 J C8H10O24
3
2
1
2.5
OH
2.0
1.5
1.0
ppm
O
2-Phenoxylethanol
2200
2150
Hz
2100
1250
1200
1150
Hz
OH
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
ppm
Problem
Problem 3.4
4.3 K
K C8H10O
6
7.5
7.0
2
5
Phenetole
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
1.5 ppm
2.0
Problem
Problem 3.4
4.3 L
L C5H10O2
O
O 1
2 3
5
Methyl Butyrate
3.5
3.0
2.5
2.0
1.5
1.0
ppm
19
Problem
Problem 3.4
4.3 M
M C6H11NO
5
3
O
HN 1 2
NH
5 4
Caprolactam
7.0
6.5
6.0
5.5
5.0
4.5
Problem 3.4
4.3 N
N aCpyrazine
5H6N2 A pyrazine
Problem
3
4.0
3.0
2.5
1.5 ppm
2.0
3.5
4
5
6
1
2-methylpyrazine
5
2520
8.5
8.0
7.5
2510
7.0
6.5
2500
6.0
5.5
HO
Problem
Problem 3.4
4.3 O
O C8H8O3
3
1 proton (x32)
5 O
OH
13
12
7.5
Hz
2490
5.0
1
4.5
3.5
ppm
3.0
4.0
3 4
8
Methyl salicylate
ppm
7.0
6.5
Problem
Problem 3.4
4.3 PP C6H4ClNO2
3
2300
2250
2200
6.0
5.5
5.0
O
-
4.5
Hz
4.0
ppm
7.3
ppm
2
1
N+ 4
2150
Cl
8.2
8.1
8.0
7.9
7.8
7.7
7.6
7.5
7.4

Problem 3.4 Q
Problem 4.3 Q C7H13BrO2 Acid
OH
1 proton (x32)
20
O
2
HO 1
7 Br
2
12
5 4
ppm
11
4.5
4.0
3.5
3.0
2.5
2.0
HO 1
5-Hexyn-1-ol
OH
3.4
3.2
3.0
ppm
1.5
Problem 4.3
3.4 R
R C6H10O Unsaturated alcohol
3.6
2.8
2.6
Problem
ketone ketone
Problem 3.4
4.3 SS Unsaturated
C8H14O Unsaturated
2.4
2 3
2.2
2.0
1.8
ppm
1.6
5
3
2
4
6 7
78
3
1520
5.0
4.5
4.0
Problem
Problem 3.4
4.3 T
T C6H12O2
1510
1500
Hz
3.5
3.0
2.5
1.5 ppm
2.0
HO 1
OH
Hexanoic acid
3
13
12
2.8
ppm
2.6
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
ppm
21
Problem 4.3
3.4 U
U C6H4OCl2
OH
HO
Cl
2
3
Cl
4
2,6-Dichlorophenol
ppm
7.5 7.4 7.3 7.2 7.1 7.0 6.9 6.8 6.7 6.6 6.5 6.4 6.3 6.2 6.1 6.0 5.9 5.8 5.7
HO
Problem 4.3
Problem
3.4 V
V C8H10O
5
1
4
2,6-Dimethylphenol
2120
2100
2080
2060
Hz
4.5
4.0
3.5
OH
7.0
6.5
6.0
5.5
5.0
3.0
ppm
2.5
Problem 4.3
3.4 W
W Unsaturated
ketone ketone
C6H8O Unsaturated
6
O
1
6
2
3
2-Cyclohexen-1-one
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0 ppm
22
3.5A. (1.58(300) 0.90(300))/7 = about 29; (2.36(300) 1.58(300))/7 = about 33

3.5E. (2.38(300) 1.52(300))/7 = about 37; (1.52(300) 1.38(300))/7 = about 6
(1.38(300) 0.87(300))/7 = about 22
3.5F. (2.38(300) 1.13(300))/7 = about 54
3.5G. (2.61(300) 1.35(300))/7 = about 54; (1.35(300) 1.29(300))/7 = about 2 to 3
(1.29(300) 0.84(300))/7 = about 19
3.5H. Long range coupling; cant measure coupling constant
3.5I.
(4.33(300) 2.01(300))/7 = about 99; (2.01(300) 0.99(300))/7 = about 44
3.5K. (4.08(300) 1.44(300))/7 = about 113

3.5L. (2.26(300) 1.62(300))/7 = about 27; (1.62(300) 0.92(300))/7 = about 30
3.5Q. (3.39(300) 1.86(300))/7 = about 66; (2.36(300) 1.65(300))/7 = about 30
(1.86(300) 1.47(300))/7 = about 17; (1.65(300) 1.37(300))/7 = about 12
3.5U. (7.25(300) 6.81(300))/9 = about 15
Answers for Student Exercises 3.6
23
O
1
4
4-Heptanone
A
Pople Notation -- A3M2X2; 2 and 3 (and 5 and 6) are enantiotopic. 3 and 5, 2 and 6 are CSE.
1
OH
3 4 5 6
3-Heptanol
B
One spin system. 2,2; 4,4; 5,5, and 6,6 are diastereotopic.
3
2
5
Br
4-Bromotoluene
C
Two spin systems. Pople Notation -- AAXX. 2 and 2 are CSE but not magnetically equivalent as are
3 and 3.
Br
3
5
4
2
2-Bromopentane
D
One spin system. 3 and 3; 4 and 4 are diastereotopic.
O
1
3
5
2
4
2-Hexanone
Two spin systems. 3, 4, and 5 are enantiotopic.

O
HO 1
Propionic Acid
A3X2. Protons on two are enantiotopic.
24
2
H2N 1
Butylamine
G
Pople Notation A3G2M2X2One spin system. 1, 2, and 3 are enantiotopic.
1
OH
3
Propargyl alcohol
H
One spin system with long range coupling. Protons on 2 enantiotopic.
O
-
N+ 1
1-Nitropropane
Pople Notation -- A3M2X2. 1 and 2 are enantiotopic.

3
4
3'
2
1
OH
2'
2-Phenoxylethanol
J
Two spins systems; Pople Notation -- AAMMX and A2X2. 2 and 2are CSE but not magnetically
equivalent as are 3 and 3. 5 and 6 are enantiotopic.
6
2
5
2'
3'
Phenetole
K
Two spins systems; Pople Notation -- AAMMX and A3X2. 2 and 2are CSE but not magnetically
equivalent as are 3 and 3. 5 and 6 are enantiotopic.
O
O 1
2 3
5
Methyl Butyrate
L
Two spin systems; Pople Notation --A3M2X2. 2 and 3 are enantiotopic.
25
O
HN 1 2
6
5 4
Caprolactam
M
One spin system. 2,2; 3,3; 4,4; 5,5 and 6,6 are diastereotopic.
4
6
1
2-methylpyrazine
N
Pople Notation AB for 5 and 6. Three spins systems.
HO
O
O
3 4
8
Methyl salicylate
Two spin systems. Pople Notation AGMX.

3
O
-
2
1
N+ 4
Cl
O
3'
2'
P
One spin system. 2 and 2 are CSE but not magnetically equivalent as are 3 and 3.
O
HO 1
Q
One spin system. 2, 3, 4, 5, 6, and 7 are enantiotopic.
7 Br
26
6
2
HO 1
5-Hexyn-1-ol
R
One spin system with long range coupling. 1, 2, 3, and 4 are enantiotopic.
8
5
3
2
4
6 7
S
At 2 spins systems (7 and 8 probably have long range coupling). 3 and 4 are enantiotopic.
O
2
HO 1
Hexanoic acid
One spin system. 2, 3, 4, and 5 are enantiotopic.

HO
Cl
2
3
Cl
3'
4
2,6-Dichlorophenol
U
One spin system. 3 and 3 are CSE but not magnetically equivalent.
HO
5
1
3'
4
2,6-Dimethylphenol
V
One spin system. 3 and 3 are CSE but not magnetically equivalent. 5 and 6 are CSE.
O
1
6
5
2
3
2-Cyclohexen-1-one
One spin system. 4, 5, and 6 are enantiotopic.
JAX
JXA
AX
27
1
JXA
JAX
1
A2X
1
1
A2
1
2
1
X
JXA
1
JAX
1
A3X
A2X2
1
2
1
1
JXA
JAX
1
1
2
1
1
A3
JXA
JAX
1
A3X2
A3
1
2
X2
1
2
A2
1
3
X2
28
With the AMX systems A and X do not change; they are

represented as follows: JAM
JMX
1
JAM
AMX
1
1
A
JMX
JAM
1
2
1
1
A2MX
A2
JAM
A3MX
3
4
JMX
A3
1
3
1
3
1
4
1 JMX
29
Answers for Student Exercise 3.8 Continued

JAM
A2MX2
1
X2
1
2
1
1
A2
1
3
JMX
1
4
JAM
M
A2MX3
1
A2
1
1
1
1
3
4
1 JMX
3
6
10
4
10
1
5
JAM
A3MX3
1
1
1
1
3
4
15
1
3
6
10
A3
1
4
10
20
X3
1
5
15
JMX
1
X3
30

With the AMX systems A and X do not change; they are
represented as follows: JAM
JMX
1
The following are for M:

JAM
AMX
1
1
1
1
JMX
A2MX
JAM
1
1
2
1
1
A3MX
1
2
1 JMX
JAM
1
1
2
1
1
1
3
1
3
3
JMX
31
Answers for Student Exercise 3.9 Continued
JAM
A2MX2
1
1
1
1
2
1
2
2
4
A2MX3
JMX
1 1
3
JAM
1
1
2
1
1
1
1
1
2
3
4
7
1
1
3
2
5
JMX
JAM
A3MX3
1
2
1
1
1
1
1
3
1
2
3
3
4
3
3
6
10
3
6
12
3
6
12
4
10
1
2
6
JMX
1
32
Answers for Student Exercise 3.10A
Spin System ab2c3

Coupling
a-b 6 Hz
b-c 12Hz
a-c 3 Hz
(c)
1 Jcb
1
1
1
2
1
1
(b)
3
1
1 Jca
1
1
1
2
2
3
2
4
Jab
1
(a)
1
3
1
2
1
3
Jac
1
Jbc
1
Jba
33
Answers for Student Exercise 3.10B
Spin System ab2c3

Coupling
a-b 6 Hz
b-c 4Hz
a-c 9 Hz
1
(c)
1 Jca
1 1
1
1
(b)
1 Jcb
2
1
Jba
1
2 1 1 2
Jbc
1
3 1 3 3 1 3
(a)
1
1
1
3
1
3
3
1
3
Jac
1 Jab
34
Answers for Student Exercise 3.10C
Spin System a2b2c2

Coupling
a-b 6 Hz
b-c 4Hz
a-c 9 Hz
1 Jca
(c)
1
1
1 2
1
1
1
1 2
2 1
1 Jbc
2 2 1 4 1 2 2
1
2
1 Jba
(a)
1 Jcb
(b)
1 Jac
2
1
1
2
Jab
1
2
1
OH
2 O
O 2
S 2
1
2 S
2'
1'
N
1'
2'
OAc
2
1
o
Answers for Student Exercise 4.2 - 3 (a)
a
3
1 Br
1-bromobutane
Atom
C1
Base
Other
-Br
Methane
-2.5
9.1
9.4
-2.5
C2
Methane
1,3
-2.5
18.2
9.4
11
C3
Methane
4,2
-Br
-2.5
18.2
9.4
C4
Methane
-2.5
9.1
9.4
-2.5
45
40
35
Calc Shift
20
are from Table 4.4
33.5
Other is from table 4.6
-Br
36.1
30
Comments
The base and shifts
22.1
13.5
25
20
15
10
ppm
Answers for Student Exercise 4.2 - 3 (b)
6
1
7
3
O
O
CH3
Methane
2,6,7
OCOR,3,5
3(3(2))
-2.5
3*9.1
6+9.4+9.4
-2.5
3*(-3.7)
value
-2.5
27.3
24.8
-2.5
-11.1
C2
ethylene
1,4'
6,7,5'
5,6'
-OCOR, Zcis
(-3)+(-1.1)
Atom
Base
C1
C3
C4
C5
Other
10.6+-7.9
7.2+7.2+-1.8
(-1.5)+(-1.5)
123.3
2.7
12.6
-3
-4.1
ethylene
4,1'
5,6',7'
6,5'
Zcis
-1.1
10.6+-7.9
7.2+2(-1.8)
(-1.5)+(-1.5)
123.3
2.7
3.6
-3
Methane
3,5
6,2
1,1
2(9.1)
2(9.4)
2(-2.5)
0.3
-2.5
18.2
18.8
-5
0.3
Methane
4,6
1,3
7,2,2
2(9.1)
2(9.4)
3(-2.5)
18.2
18.8
-7.5
-2.5
C6
Methane
-2.5
2,4,7
2(3),OCOCH3
3(9.4)
2(-2.5)+(-3)
-2.5
18.2
28.2
-8
-2.5
6,2
3,5
2(3)
15.2
-4
0.3
-2.5
C8
Table 4.12
C9
Table 4.12
61
20.7
140
120
Other is from table 4.6
are from Table 4.4
131.5
125.5
2(3)
170.5
160
36
27
1,5
Table 4.12 1,OCOCH3
Comments
The base and shifts
29.8
2(9.1)
C7
-2.5
-1.1
Calc Shift
100
80
60
33.4
67.5
170.5
Table 4.12
20.7
Table 4.12
40
20
ppm
Answers for Student Exercise 4.2 - 3 (c)
O
1
4
7 OH
8
(c) 3-hydroxy-2-methyl1-phenylpropan-1-one
Atom
from table 4.12
Base
Other
Calc Shift
Table 4.12
C1
128.5
7.8
136.3
C2
128.5
-0.4
128.1
C3
128.5
-0.4
128.1
C4
128.5
2.8
131.3
From Table 4.19 the C=O is approximately 197.6 ppm,
C5
C6
C7
C8
methane
7,8,5
OH,Ph
3(2,3)
-2.5
2(9.1)+24
10+9
(-3.7)+(-9.5)
-2.5
42.2
19
-13.2
methane
OH, 6
8, 5
2(3)
-2.5
48+9.1
9.4+1
-2
-2.5
-2.5
57.1
10.4
-2
-2.5
methane
7,5
OH,Ph
1(3)
-2.5
9.1
9.4+1
(-5)+(-2)
-1.1
-2.5
9.1
10.4
-7
-1.1
180
160
140
120
198
Base
200
100
Comments
These compare nicely
Other
80
Calc Shift
Table 4.4 +
Table 4.6
45.5
60.5
8.9
60
40
20
ppm
Answers for Student Exercise 4.2-3 (d)
3 2
(d) pent-1-yne
Atom
Base
Other
C1
Table 4.11
Comments
The base and shifts
67.0-68.1
are from Table 4.11
67.6
C2
Calc Shift
Increments from table 4.6
67.6
Table 4.11
84.7-84.5
84.6
C3
C4
C5
84.6
4,c
5,c
9.1+4.5
9.4+5.5
-2.5
13.6
13.9
Methane
5,3
2(9.1)
5.5
-2.5
18.2
5.5
Methane
-c
-2.5
9.1
9.4
-3.5
-2.5
9.1
9.4
-3.5
Methane
85
80
75
70
65
Base shifts Table 4.4

25
21.2
60
55
50
45
40
35
12.5
30
25
20
15
10
ppm
Answers for Student Exercise 4.2-3 (e)
O
1
5
6
4
(e) hex-3-en-2-one
2
Atom
Base
C1
methane
Comments
The base and shifts
-2.5
24
9.4
-2.5
0.3
0.1
are from Table 4.4
-2.5
24
9.4
-2.5
0.3
0.1
Table 4.10
1,3
C2
Other
Calc Shift
28.8
Table 4.10
196.9
C3
C4
C5
C6
approximate
196.9
ethylene
2,5'
6'
123.3
24+(-7.9)
-1.8
123.3
16.1
-1.8
ethylene
5,2'
123.3
10.6+1
7.2
137.6
123.3
11.6
7.2
methane
6,4
-2.5
2(9.1)
9.4
-2
0.3
-2.5
18.2
9.4
-2
0.3
142.1
0.3
0.1
methane
-2.5
9.1
9.4
-2.5
-2.5
9.1
9.4
-2.5
140
120
180
Increments from Table 4.6
160
100
23.4
13.9
80
60
40
20
ppm
Answers for Student Exercise 4.2-3 (f)
O 2
4
3
(f) (1-methoxybut-1-ene
Atom
C1
C2
C3
C4
C5
Base
Other
Comments
Calc Shift
methane
O-R
The base and shifts
-2.5
51
9.4
-2.5
0.3
0.1
are from Table 4.4
-2.5
51
9.4
-2.5
0.3
0.1
55.8
Table 4.10
153.2
4'
5'
153.2
-7.9
-1.8
Table 4.10
84.2
10.6
7.2
Table 4.10
143.5
84.2
10.6
7.2
methane
5,3
-OR
102
-2.5
9.1+9.1
9.4
-2
-2.5
18.2
9.4
-2
23.1
methane
-2.5
9.1
9.4
-2.5
0.1
-2.5
9.1
9.4
-2.5
0.1
140
130
120
110
100
90
80
70
13.6
60
50
40
30
20
ppm
Answers for Student Exercise 4.2-3 (g)
N 2 O 3
H
(g) propyl methylcarbamate

Comments
Atom
Base
C1
methane
NH
COO
The base and shifts
-2.5
31
-2.5
0.3
0.1
are from Table 4.4
-2.5
31
-2.5
0.3
0.1
Other
Calc Shift
28.4
C2 Table 4.20
Table 4.20
157.8
C3
C4
C5
157.8
methane
3,OCOR
NHR
-2.5
9.1+51
9.4
-4
-2.5
60.1
9.4
-4
methane
5,3
OCOR
-2.5
9.1+9.1
-2.5
18.2
methane
OCOR
-2.5
9.1
9.4
-3
-2.5
9.1
9.4
-3
150
140
130
120
63
20.7
110
100
13
90
80
70
60
50
40
30
20
ppm
Answers for Student Exercise 4.2-3 (h)
2 O 3 O
(h) diethoxymethane
Atom
Base
C1
methane
OCOR
Comments
The base and shifts
-2.5
9.1
are from Table 4.4
-2.5
9.1
methane
1,OCOR
-2.5
9.1+45
9.4
-2.5
54.1
9.4
methane
2(OR)
2(2)
2(1)
-2.5
51(2)
9.4(2)
2(-2.5)
-2.5
102
18.8
-5
110
100
C2
C3
90
Other
Calc Shift
11.6

See Table 4.15 for
comparison
61
80
113.3
70
60
50
40
30
20
10
ppm
Answers for Student Exercise 4.2-3 (i)
HO
(i) 2-methylpentan-2-ol
Atom
Base
C1
methane
6,3,OH
1(4)
-2.5
9.1
2(9.4)+10
-2.5
0.3
C2
C3
C4
C5
C6
0.3
Other
Calc Shift
Comments
The base and shifts
-3.4
are from Table 4.4

29.8
-2.5
9.1
28.8
-2.5
methane
1,6,3,OH
-3.4
4(2(1)+2)
-2.5
3(9.1)+48
9.4
-2.5
(2)(-1.5)+-8.4
-2.5
75.3
9.4
-2.5
-11.4
methane
2,4
1,6,OH,5
2(4)
-2.5
9.1(2)
3(9.4)+10
-7.2
-2.5
18.2
38.2
-7.2
methane
3,5
1,6,OH
-2.5
2(9.1)
9.4
2(-2.5)+(-5)
-2.5
18.2
9.4
-10
methane
1,6
-2.5
9.1
9.4
-2.5
(2).3
-2.5
9.1
9.4
-2.5
0.6
6,3,OH
1(4)
-2.5
9.1
2(9.4)+10
-2.5
0.3
-3.4
-2.5
9.1
28.8
-2.5
0.3
-3.4
100
90
80
70
comparison
68.3
46.7
15.1
methane
110
See Table 4.14 for
60
14.1
50
29.8
40
30
20
10
ppm
10
Answers for Student Exercise 4.2-3 (j)
S 2
(j) 1,4-bis(methylthio)butane
Atom
Base
C1
methane
SR
Comments
The base and shifts
-2.5
20
are from Table 4.4
-2.5
20
methane
SR,3
SR
See Table 4.18 for
-2.5
20+9.1
9.4
-2.5
Comparison
-2.5
29.1
9.4
-2.5
methane
2,2
3,SR
SR
-2.5
2(9.1)
9.4+7
-2.5
-2.5
18.2
16.4
-2.5
35
30
C2
C3
45
40
Other
Calc Shift
17.5
33.5
29.6
25
20
15
10
ppm
11
Answers for Student Exercise 4.2-3 (k)
O
1
4
3
(k) N,N,4-trimethylbenzamide
Atom
Base
from table 4.12
Table 4.12 C=ONH2
Other
Calc Shift
CH3
C1
128.5
-2.9
130.6
C2
128.5
-1.2
-0.1
127.2
C3
128.5
0.7
129.2
C4
128.5
3.4
9.3
141.2
From Table 4.20 the C=O is approximately 171 ppm,
C5
C6
C7
Base
methane
NR2
C=O
Ph
-2.5
42
-2
-2.5
42
-2
methane
NR2
C=O
Ph
-2.5
42
-2
-2.5
42
-2
171
Other
Calc Shift
Table 4.4 +
Table 4.6
38.5
38.5
C8 Table 4.12
160
Comments
Table 4.12
Table 4.12
21.3
140
120
100
80
60
40
20
ppm
12
Answers for Student Exercise 4.2-3 (l)
6
5
O
1
7
2
OH
3
(l) 1-(2-hydroxyphenyl)ethanone
Atom
Base
from table 4.12
Table 4.12 C=OCH3
Other
Calc Shift
OH
C1
128.5
7.8
-12.7
123.6
C2
128.5
-0.4
26.6
154.7
C3
128.5
-0.4
-12.7
115.4
C4
128.5
2.8
1.6
132.9
C5
128.5
-0.4
-7.3
120.8
C6
128.5
-0.4
1.6
129.7
C7
From Table 4.19 the C=O is approximately 197.6 ppm,
197.6
C8
From Table 4.19 the CH3 is approximately 26.3 ppm,
26.3
180
160
140
120
100
80
60
Comments
Table 4.12
Table 4.19
40
20
ppm
13
Answers for Student Exercise 4.2-3 (l)
Cl
2 H
O
(m) 2-chloroacetaldehyde
Atom
Base
C1
methane
Cl, CHO
Comments
The base and shifts
-2.5
31+31
are from Table 4.4
-2.5
62
Other
Calc Shift
59.5
C2 Table 4.19

See Table 4.18 for
Cl
Comparison
199.7
199.7
200
199.7
180
160
140
120
100
80
60
40
20
ppm
14
Answers for Student Exercise 4.2-3 (n)
F
(n) fluoroethene
Atom
Base
C1
Ethylene
Comments
The base
123.2
68
are from Table 4.9
123.2
68
C2
Other
Calc Shift
191.2
Ethylene
See Table 4.9 for
123.2
Comparison
123.2
132.2
Note -- These are not close to observed values, but are the only answer from given tables.
19F couplings not shown
200
180
160
140
120
100
80
60
40
20
ppm
15
Answers for Student Exercise 4.2-3 (n)
1
2
5
6
3
(o) cyclohexyl acetate
Atom
Base
C1
Table 4.7
OCOR
Comments
The base and shifts
26.9
51
are from Table 4.7
26.9
51
C2
C3
C4
C5
Other
Calc Shift
77.9
Table 4.7
OCOR
26.9
26.9
32.9
Table 4.7
OCOR
26.9
-3
26.9
-3
23.9
Table 4.7
OCOR
26.9
26.9
26.9
Table 4.20
Approx
168
C6
methane
COO
2,2
3,3
Table 4.20
The base and shifts
-2.5
25
-2.5
2(.3)
2(.1)
are from Table 4.4
-2.5
25
-2.5
0.6
0.2
160
168
140
120
100
80
20.8
60
40
20
ppm
Answers for Student Exercise 4.4 A-C
16
Problem
Problem 5.7A
4.4 A
4
4-Heptanone
4
200
180
160
1
Problem 5.7B
4.4 B
Problem
140
OH
120
100
80
60
40
20
ppm
3 4 5 6
3-Heptanol
85
80
75
70
65
5
Problem
Problem 5.7C
4.4 C
60
55
50
45
40
35
30
25
20
15
10
ppm
Br
4-Bromotoluene
3
5
1
140
131 ppm
4
130
120
110
100
90
80
70
60
50
40
30
20
10 ppm
Answers for Student Exercise 4.4 D-F
17
Br
Problem
Problem 5.7D
4.4 D
3
5
4
2
2-Bromopentane
95
90
85
80
75
70
Problem 5.7E
4.4 E
Problem
65 60
O
1
55
50
3
5
2
4
2-Hexanone
45
40
35
30
25
20
15
ppm
10
4 5
200
180
160
Problem
Problem 5.7F
4.4 F
140
O
HO 1
120
2
100
80
60
40
ppm
20
Propionic Acid
2
1
180
160
140
120
100
80
60
40
20
ppm
Answers for Student Exercise 4.4 G-I

Problem
Problem 5.7G
4.4 G
H2N 1
18
Butylamine
95
90
85
80
75
70
65
1
Problem 5.7H
4.4 H
Problem
60
55
OH
50
85
35
30
25
20
15
10
ppm
Note that it is often the case that the DEPT

spectra are incorrect for alkynes. Intensities
of the CH are quite different than the C,
which is apparent here.
90
40
3
Propargyl alcohol
95
45
80
75
70
Problem
Problem 5.7I
4.4 I
65
-
60
O
55
N+ 1
50
45
40
35
30
25
20
15
10
ppm
10
ppm
1-Nitropropane
77.5
95
90
85
80
75
70
65
ppm
77.0
60
55
50
45
40
35
30
25
20
15
Answers for Student Exercise 4.4 J-L

Problem
Problem 5.7J
4.4 J
2
1
OH
19
O
2-Phenoxylethanol
2
4
1
170
160
150
140
130
120
110
100
90
Problem 5.7K
4.4 K
Problem
60 ppm
70
2
5
80
4
Phenetole
2
4
1
160 150 140 130 120 110 100
90
80
70
60
O
O 1
2 3
5
Problem
Problem 5.7L
4.4 L
50
40
30
20
ppm
Methyl Butyrate
3 4
5
1
170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
20
ppm
Answers for Student Exercise 4.4 M-O

Problem
Problem 5.7M
4.4 M
20
HN 1 2
6
5 4
Caprolactam
2 53
1
180
160
140
120
100
80
60
ppm
20
Problem 5.7N
4.4 N
Problem
40
5
6
1
2-methylpyrazine
365
7
2
150
140
130
120
110
100
90
80
70
60
HO
Problem
Problem 5.7O
4.4 O
O
O
50
1
40
30
20
ppm
3 4
8
Methyl salicylate
170
160
34
130
120
150
140
110
100
90
80
70
60 ppm
21
Answers for Student Exercise 4.4 P-R

Problem 5.7P
4.4 P
Problem
3
O
-
2
1
N+ 4
Cl
ppm
148 146 144
155 150 145 140 135 130 125 120 115 110 105 100
95
90
85
80
ppm
20
ppm
Problem
Problem 5.7Q
4.4 Q
HO 1
7 Br
276453
1
180
160
140
120
Problem 5.7R
4.4 R
Problem
100
HO 1
80
3
5-Hexyn-1-ol
40
Note that it is often the case that the DEPT

spectra are incorrect for alkynes. Intensities
of the CH are quite different than the C,
which is apparent here.
60
25
20
85
80
75
70
65
60
55
50
45
40
35
30
15
10
ppm
Answers for Student Exercise 4.4 S-U

Problem
Problem 5.7S
4.4 S
22
5
3
2
4
6 7
7 4
5
6
2
200
180
160
140
120
100
80
60
40
20
ppm
Problem 5.7T
4.4 T
Problem
HO 1
Hexanoic acid
2 4 35
1
180
160
140
120
100
HO
Problem
Problem 5.7U
4.4 U
80
1
Cl
60
40
20
ppm
80
ppm
2
3
Cl
4
2,6-Dichlorophenol
4
2
121.2
155 150 145 140 135 130 125 120 115 110 105 100
ppm
95
90
85
Answers for Student Exercise 4.4 V-W
23
Problem
Problem 5.7V
4.4 V
HO
5
1
2
3
4
2,6-Dimethylphenol
3
5
1
150
2
140
130
120
110
100
90
80
70
60
50
40
ppm
30
20
45
Problem
Problem 5.7W
4.4 W
1
6
5
2
3
2-Cyclohexen-1-one
1
200
180
160
140
120
100
80
60
40
20
ppm

4.5
2nI +1 rule
ID =1
24
Example
CDCl3
CD2Cl2
1
CD3Cl
Answers for Student Exercise 4.6 A-C
25
Problem 5.6A
4.6A
Problem
C5H10Br2
Br
2
Br
1
3
1,5-dibromopentane
1 2
3
75
70
65
60
55
50
45
40
35
30
Problem 5.6B
4.6B
Problem
C8H8O2
25
20
HO
15
10
5 ppm
O
7
1
4
2-methylbenzoic acid
5
8
132
170 160 150 140 130 120 110 100
Problem 5.6C
4.6C
Problem
C12H27N
130
90
128
80
70
60
50
40
30
20
ppm
6 N
dihexylamine
75
70
ppm
65
60
55
50
5 3
45
40
35
30
25
20
15
10
5 ppm
Answers for Student Exercise 4.6 D-F

Problem 5.6D
4.6D
Problem
C16H22O4
26
O
4 O 5
O
O
dibutyl phthalate
3 2
170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
20
ppm
Problem 5.6E
4.6E
Problem
C7H12O
O
5-methylhex-5-en-2-one
3 41 7
2
200
180
160
140
Problem 5.6F
4.6F
Problem
C8H14O
120
100
80
4
6
5
3
oct-3-yn-1-ol
80
20
ppm
85
40
OH
1
60
75
27
82
70
65
60
55
80
50
78
45
40
ppm
35
30
25
20
15
10
ppm
27
2
3
3
O
1
4 O 5
4 O 5
6
6
O
ortho-diethyl phthalate
There is one mirror image. There are 6 nonequivalent carbons, and there are 4 distinct proton
signals, 2,3,5,6 with a integration ratio of 2:2:4:6, or 1:1:2:3.
DEPT 90
DEPT 135
Carbon - 13
4
180
160
1,3,2
140
120
100
PPM
80
60
40
20
28
O
7
6 O 51
2
1 5 O 6
2
3
meta-diethyl phthalate
There is one mirror image. There are 7 nonequivalent carbons, and there are 5 distinct proton
signals, 2,3,4,5,6 with a integration ratio of 2:1:1:4:6..
DEPT 90
DEPT 135
Carbon - 13
21
4
3
180
160
140
120
100
PPM
80
60
40
20
29
O
O
2
3
3
1
1
2
para-diethyl phthalate
There are two mirror images. There are 5 nonequivalent carbons, and there are 3 distinct proton
signals, 2,4,5 with a integration ratio of 4:4:6, or 1:1:3.
DEPT 90
DEPT 135
Carbon - 13
180
160
140
120
100
PPM
80
60
40
20

3.5
ppm
3.0
2.5
1
2.0
1.5
1.0
0.5
0.5
1.0
COSY
ppm
(a)
0.5
1.0
1.5
1.5
2
F1 2.0
2.0
2.5
2.5
3.0
3.0
Group #
1
2
3
4
H
3.40
1.85
1.20
0.85
3.5
F2
HMQC
ppm
5
10
10
15
15
20
20
F1 25
25
30
30
35
35
40
40
45
45
3.0
2.8
2.6
2.4
2.2
2.0
F2
1.8
1.6
1.4
1.2
1.0
ppm
Br
(a) 1-bromobutane
1
3.5
C
33.5
36.1
22.1
13.5
ppm
HMBC
(a)
5
10
15
1 Br
(a) 1-bromobutane
20
F1 25
30
1
2
35
Group #
1
2
3
4
H
3.40
1.85
1.20
0.85
C
33.5
36.1
22.1
13.5
40
45
50
3.0
2.8
2.6
2.4
2.2
2
Hz
2.0
1.8
1.6
F2
1.4
1.2
ppm
1.0
INADEQUATE
4
Center
Frequency
-3000
-3000
-2000
-2000
-1000
-1000
F1 0
1000
1000
2000
2000
3000
3000
45
40
35
30
F2
25
20
15
10
ppm

ppm 6.0
5.5
5.0
4.5
4.0
3
3.5
3.0
2.5
2.0
1.5
5
1.5
9
2.0
COSY
ppm
5
1.5
2.0
1
3
(b)
7
O
O 8
2.5
2.5
3.0
3.0
F1 3.5
3.5
7
4.0
4.0
4.5
4.5
5.0
5.0
2
5.5
Group #
1
2
3
4
5
6
7
8
9
H
2.80
5.59
5.59
1.96
1.65
1.80
4.05
NA
2.10
5.5
F2
HMQC
ppm
20
20
5
6
40
40
60
60
7
7
F1
80
80
100
100
120
120
2
3
6.0
5.5
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
ppm
C
36.0
131.5
125.5
29.8
27.0
33.4
67.5
170.5
20.7

3
2
4
7
ppm
HMBC
9 46 5
56
9 41
40
1
3
(b)
7
O
O 8
60
Group #
1
2
3
4
5
6
7
8
9
80
F1
100
32
120
140
H
2.80
5.59
5.59
1.96
1.65
1.80
4.05
NA
2.10
C
36.0
131.5
125.5
29.8
27.0
33.4
67.5
170.5
20.7
160
8
180
6.0
Hz
5.5
5.0
4.5
4.0
3.0
2.5
2.0
1.5 ppm
F2 Center
Frequency
2 3
3.5
INADEQUATE
16 4 5 9
-10000
-10000
-5000
-5000
F1 0
5000
5000
10000
10000
180
160
140
120
100
F2
80
60
40
20
ppm

ppm 7
7
6
5
3
9
8
ppm
COSY
(c)
10
1
OH
10
34
OH
Group #
1
2
3
4
5
6
7
8
9
10
OH
8
9
F1
4
H
NA
6.68
2.05
2.05
5.68
6.22
NA
2.65
3.20
1.05
0.5-4
5
6
F2
HMQC
ppm
10
20
20
4
40
3
40
8
9
60
60
F1 80
80
100
100
120
140
120
140
F2
ppm
C
143.2
150.0
28.3
30.7
122.1
131.1
206.7
45.5
60.5
8.9
NA

2 6
4
3
HMBC
10
(c)
10
ppm
20
34 8
40
F1
Group #
10
3
4
8
9
5
6
1
2
7
OH
100
56 1 2
140
160
180
200
9
8
OH
10
80
120
1
6
60
H
1.05
2.05
2.05
2.65
3.20
5.68
6.22
NA
6.68
NA
0.5-4
C
8.9
28.3
30.7
45.5
60.5
122.1
131.1
143.2
150.0
206.7
NA
7
7
4
2 1
Hz
F2 Center
6
5 Frequency
ppm
INADEQUATE
9
43
10
-10000
-10000
-5000
-5000
F1 0
5000
5000
10000
10000
15000
15000
200
180
160
140
120
F2
100
80
60
40
20
Hz

ppm
2.5
2.0
7
1.5
1.0
0.5
COSY
ppm
(d)
0.5
0.5
3 2
5
1.0
1.0
4
1.5
F1
1.5
Group #
1
2
3
4
5
H
1.80
NA
2.20
1.50
0.85
1
2.0
2.0
2.5
2.5
F2
HMQC
ppm
5
10
20
F1
10
20
30
30
40
40
50
50
60
60
70
70
80
80
2.5
2.0
1.5
F2
1.0
0.5
ppm
C
67.6
84.6
25.0
21.2
12.5

1
ppm
8
4
HMBC
(d)
10
20
3 2
H
1.80
NA
2.20
1.50
0.85
C
67.6
84.6
25.0
21.2
12.5
4
3
30
Group #
1
2
3
4
5
F1 40
50
60
1
70
80
2
90
2.5
1
2.0
2
1.5
1.0
F2 Center
Frequency
0.5
ppm
INADEQUATE
3 4
Hz
-4000
-4000
-2000
-2000
F1 0
2000
2000
4000
4000
6000
6000
90 85 80 75 70 65 60 55 50 45 40 35 30 25 20 15 10
F2
Hz
ppm 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
6
1
5
(e)
F1 4
5
3
COSY
ppm
Group #
1
2
3
4
5
6
H
1.86
NA
6.09
6.82
2.05
1.00
F2
HMQC
ppm
6
5
20
F1
20
40
40
60
60
80
80
100
100
120
120
140
3
140
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
F2
ppm
C
28.8
196.9
137.6
142.1
23.4
13.9

ppm
10
5 1
HMBC
6
6
5
1
20
40
60
(e)
O
1
Group #
1
2
3
4
5
6
F1 80
100
120
4
H
1.86
NA
6.09
6.82
2.05
1.00
C
28.8
196.9
137.6
142.1
23.4
13.9
3
4
140
160
180
200
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5
4 3
ppm
INADEQUATE
F2 Center
Frequency
15
Hz
-10000
-10000
-5000
-5000
F1 0
5000
5000
10000
10000
15000
200
180
160
140
120
F2
100
80
60
40
20
15000
Hz
11
ppm 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
5
1
4
1 1
ppm
O 2
Group #
1
2
3
4
5
F1
4
COSY
(f)
4
3
H
3.20
6.14
4.63
2.05
1.00
4
3
5
2
F2
HMQC
ppm
5
4
20
40
20
40
F1
60
60
80
80
3
100
100
120
140
120
2
140
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
F2
ppm
C
55.8
143.5
102.0
23.1
13.6

2
12
3
ppm
HMBC
(f)
5
20
O 2
40
Group #
1
2
3
4
5
F1 60
80
100
H
3.20
6.14
4.63
2.05
1.00
C
55.8
143.5
102.0
23.1
13.6
120
140
2
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5
ppm
INADEQUATE
F2 Center
2
Hz
Frequency
-5000
-5000
F1 0
5000
5000
10000
10000
150 140 130 120 110 100
90
80
F2
70
60
50
40
30
20
10
Hz
13
ppm 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
5
ppm
1 1
F1
3
5
NH
F2
HMQC
ppm
20
40
60
F1
20
40
60
80
80
100
100
120
120
140
140
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
F2
(g)
4
H
C
Group #
1
2.95
28.4
2
NA 157.8
3
4.10
63.0
4
1.60
20.7
5
0.85
13.0
NH
4.5-7.5 NA
1
3
O
N 2 O 3
H
4
2
COSY
ppm
14
3
ppm
HMBC
5
5
20
F1
H
C
Group #
1
2.95
28.4
2
NA 157.8
3
4.10
63.0
4
1.60
20.7
5
0.85
13.0
NH
4.5-7.5 NA
80
100
(g)
N 2 O 3
H
40
60
120
140
2
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5
ppm
F2 Center
Frequency 3
INADEQUATE
1
4 5
Hz
-10000
-10000
-5000
-5000
F1 0
5000
5000
10000
10000
140
120
100
F2
80
60
40
20
Hz

ppm 6.0
5.5
5.0
4.5
4.0
15
3.5
3.0
2.5
2.0
1.5
1.0
ppm
1.0
1.0
1.5
1.5
2.0
2.0
2.5
2.5
F1 3.0
3.0
3.5
COSY
2 O 3 O
(h)
Group #
1
2
3
H
1.20
3.40
4.95
3.5
4.0
4.0
4.5
4.5
5.0
5.0
5.5
5.5
F2
HMQC
ppm
F1
20
20
40
40
2
60
60
80
80
100
100
3
120
120
6.0
5.5
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
1.0
ppm
C
11.6
61.0
113.3

3
16
2
HMBC
ppm
1
20
(h)
40
F1
2 O 3 O
60
Group #
1
2
3
H
1.20
3.40
4.95
C
11.6
61.0
113.3
80
100
3
120
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
ppm
1.5
INADEQUATE
F2 Center
Frequency
2
3
Hz
-8000
-8000
-6000
-6000
-4000
-4000
-2000
-2000
F1 0
2000
2000
4000
4000
6000
6000
8000
8000
120
110
100
90
80
70
F2
60
50
40
30
20
10
Hz

ppm 2.0
1.8
1.6
17
1.4
1.2
1.0
0.8
0.6
0.6
0.6
5
0.8
0.8
1.0
1.0
F1 1.2
1.4
1.2
1.4
1.6
COSY
ppm
(i)
HO
H
Group #
1
1.20
2
NA
3
1.50
4
1.20
5
0.85
6
1.20
OH
0.5-4.0
1.6
OH
1.8
1.8
F2
HMQC
ppm
10
10
20
20
6 1
30
F1 40
30
40
50
50
60
60
70
70
80
80
ppm
2.0
1.8
1.6
1.4
1.2
F2
1.0
0.8
0.6
4
C
29.8
68.3
46.7
15.1
14.1
29.8
NA
18
6
4
1
HMBC
ppm
10
20
F1
HO
16
30
40
3
50
(i)
H
Group #
1
1.20
2
NA
3
1.50
4
1.20
5
0.85
6
1.20
OH
0.5-4.0
C
29.8
68.3
46.7
15.1
14.1
29.8
NA
60
2
70
2.0
1.8
1.6
1.4
1.2
1.0
ppm
0.8
F2 Center
3 Frequency
2
Hz
INADEQUATE
45
1,6
-4000
-4000
-2000
-2000
F1 0
2000
2000
4000
4000
6000
75
70
65
60
55
50
45
F2
40
35
30
25
20
15
10
6000
Hz

ppm 3.0
2.8
2.6
2.4
19
2.2
2.0
1.8
1.6
1.4
1.2
ppm
COSY
(j)
1.2
1.2 1
1.4
1.4
3
1.6
F1
1.6
1.8
1.8
2.0
Group #
1
2
3
3
H
2.10
2.60
1.60
2.0
2.2
2.2
2.4
2.4
2
2.6
S 2
2.6
2.8
2.8
F2
HMQC
ppm
15
15
1
20
20
F1 25
25
3
30
30
2
35
35
40
40
ppm
3.0
2.8
2.6
2.4
2.2
2.0
F2
1.8
1.6
1.4
1.2
C
17.5
33.5
29.6
20
1
HMBC
ppm
(j)
1
S 2
15
1
20
F1
Group #
1
2
3
3
H
2.10
2.60
1.60
C
17.5
33.5
29.6
25
3
30
2
35
40
3.0
2.8
2.6
2.4
2.2
2.0
1.8
1.6
ppm
1.4
F2 Center
Frequency
INADEQUATE
Hz
-1500
-1500
-1000
-1000
-500
-500
F1 0
500
500
3 to 3'
1000
1000
1500
1500
2000
2000
40
38
36
34
32
30
28
26
F2
24
22
20
18
16
14
12
Hz
21
ppm 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
COSY
ppm
(k)
6,7
3
4
8
5
2
H
NA
7.80
7.25
NA
NA
2.95
2.95
2.25
3
2
F2
HMQC
ppm
40
40
6,7
60
60
80
80
100
100
120
120
F1
2
3.0
3
2.8
2.6
2.4
2.2
2.0
F2
1.8
1.6
1.4
1.2
ppm
N
7
3
Group #
1
2
3
4
5
6
7
8
F1
C
130.6
127.2
129.2
141.2
171.0
38.5
38.5
21.3

2
22
7
6
HMBC
ppm
(k)
67
40
4
8
60
F1 80
23
1
4
140
3
Group #
1
2
3
4
5
6
7
8
100
120
H
NA
7.80
7.25
NA
NA
2.95
2.95
2.25
C
130.6
127.2
129.2
141.2
171.0
38.5
38.5
21.3
160
5
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0
5
Hz
ppm
F2 Center
Frequency
13 2
INADEQUATE
7
6
-10000
-10000
-5000
-5000
F1 0
5000
5000
10000
10000
160
140
120
100
F2
80
60
40
20
Hz
23
ppm 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
COSY
ppm
(l)
2
3
3
7
F2
HMQC
ppm
8
40
40
60
60
80
80
100
100
F1
120
3.0
120
4
2.8
2.6
2.4
2.2
2.0
F2
1.8
1.6
1.4
1.2
OH
H
Group #
1
NA
2
NA
3
6.85
4
7.05
5
7.25
6
7.70
7
NA
8
2.40
OH 5.5-12.5
F1
ppm
4
4
C
123.6
154.7
115.4
132.9
120.8
129.7
197.6
26.3
NA

6
24
54 3
HMBC
ppm
40
(l)
6
5
60
3
51
64
140
160
80
120
1
7
F1 100
OH
H
Group #
1
NA
2
NA
3
6.85
4
7.05
5
7.25
6
7.70
7
NA
8
2.40
OH 5.5-12.5
C
123.6
154.7
115.4
132.9
120.8
129.7
197.6
26.3
NA
180
7
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0
ppm
INADEQUATE
F2
Center
4 6 1 5 3 Frequency
Hz
-10000
-10000
-5000
-5000
F1 0
5000
5000
10000
10000
180
160
140
120
F2
100
80
60
40
Hz

ppm 11
10
25
8
ppm
COSY
(m)
1
Cl
2 H
O
6
F1 7
Group #
1
2
H
4.95
9.80
9
2
10
10
F2
HMQC
ppm
1
60
60
80
80
100
100
F1 120
120
140
140
160
160
180
180
2
200
11
200
10
F2
ppm
C
59.5
199.7
26
HMBC
2
ppm
60
(m)
Cl
80
2 H
100
Group #
1
2
F1
120
H
4.95
9.80
C
59.5
199.7
140
160
180
2
200
11
10
F2 Center
Frequency
ppm
INADEQUATE
Hz
-10000
-10000
-5000
-5000
F1 0
5000
5000
10000
10000
200
180
160
140
F2
120
100
80
60
Hz

ppm 8.0
7.5
7.0
6.5
27
6.0
5.5
5.0
4.5
ppm
(n)
1trans
4.5
COSY
1cis
4.5
1cis
5.0
5.0
5.5
5.5
6.0
6.0
6.5
6.5
F1
H
1trans
Group #
1cis
1trans
2
F
H
4.85
4.23
6.79
7.0
7.0
7.5
7.5
F2
HMQC
ppm
1
130
130
140
140
150
150
F1 160
160
170
170
180
180
2
190
190
200
8.0
7.5
7.0
6.5
6.0
F2
5.5
5.0
4.5
200
ppm
C
132.2
132.2
191.2
28
1cis
HMBC
1trans
ppm
(n)
130
140
H
1trans
150
F1
Group #
1cis
1trans
2
160
170
1cis
F
H
4.85
4.23
6.79
C
132.2
132.2
191.2
180
190
2
7.0
6.5
6.0
2
5.5
5.0
4.5
F2 Center
Frequency
ppm
INADEQUATE
Hz
-4000
-4000
-2000
-2000
F1 0
2000
2000
4000
4000
6000
6000
Hz
190
180
170
F2
160
150
140
130

ppm 6.0
5.5
5.0
4.5
4.0
29
3.5
3.0
2.5
2.0
1.5
33' 4
1.5
F1
1.5
22'
6
2.0
3'
2'
2.5
3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5
1
Group #
1
2,2'
3,3'
4
5
6
H
4.95
1.60
1.44
1.44
NA
2.00
5.5
F2
HMQC
ppm
33'
4
6
22'
40
60
40
60
F1
80
80
100
100
120
120
140
140
160
160
6.0
5.5
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
ppm
5
6
5.0
5.5
(o)
2.0 4
2.5
5.0
COSY
ppm
C
77.9
32.9
23.9
26.9
168.0
20.8
30
6
ppm
33'
22' 4
HMBC
6
3 3'
4
2
40
2'
(o)
4
60
3
1
F1 80
Group #
1
2,2'
3,3'
4
5
6
100
120
H
4.95
1.60
1.44
1.44
NA
2.00
C
77.9
32.9
23.9
26.9
168.0
20.8
140
160
5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
F2
Center
Frequency 1
2.5
2.0
ppm
INADEQUATE
2 43 6
Hz
-10000
-10000
-5000
-5000
F1 0
5000
5000
10000
10000
160
140
120
100
F2
80
60
40
20
Hz
31
CH2
H
g= geminal
v= vicinal
lr= long range
5
4
HO
7
8 CH2
H3C
1
CH3
CH3
1
CH2=
5 5'
OH
2
3 3'
ppm
0.5
v
1.0
1.5
g
v
2.0
lr
2.5
3.0
F1
3.5
4.0
4.5
5.0
lr
5.5
6.0
6.5
7.0
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
1.0
0.5
ppm
32
CH2
H
HO
8 CH2
H3C
CH3
1
Carbon 13 Signals
1
Bonded
Bonded
Bonded
Bonded
Bonded
Bonded
Bonded
CH3
CH2=
CH3
CH2=
Bonded
Bonded

1
33
H NMR 600 MHz
5
3
1300
Hz 1250
Hz
Hz
1150
3
6
1000 Hz
1050
2.3
13
2.2
2.1
860 840 820 Hz
2.0
1.9
1.8
1.7
620 600 580 Hz
1.6
1.5
1.4
1.3
1.2
ppm
1.1
1.0
3 4
C/DEPT 600 MHz
O
6
1
2
5
3 4
2-methylcyclopentanone
220
200
180
160
140
120
100
80
60
40
20
ppm

ppm
COSY 600 MHz
1.0
1.0
1.2
1.2
1.4
1.4
ppm 2.4
F1
34
2.2
2.0
1.8
1.6
1.4
1.2
1.0
1.6
1
2
5
3 4
1.6
4
1.8
1.8
2.0
2.0
2.2
2.2
5 3 2 5
ppm
F2
5
2
3
5
HMQC 600 MHz
2-methylcyclopentanone
6
15
15
20
20
25
25
F1 30
30
35
35
40
40
45
45
2.4
2.2
2.0
1.8
1.6
F2
1.4
1.2
1.0
ppm

1
35
H NMR 600 MHz

7
4750 Hz
4800
4400 Hz
4450
1700 Hz 1550
4300 Hz
4350
1750
1500 Hz
1200 Hz
1250
4
3
7 8 6
O
9
10
8
7
8.0
13
7.5
7.0
6.5
6.0
5.5
2
3
5.0
4.5
4.0
3.5
3.0
2.0 ppm
2.5
C/DEPT 600 MHz
8 6 97
200
180
160
140
10
120
100
80
60
40
ppm

ppm
36
5
COSY 600 MHz
8.0
7.5
7.0 ppm
7.0
10
7
6
3
4
8.0
9
8
7.5
3
ppm
F1
ppm
F2
HMQC 600 MHz
ppm
40
60
40
ppm
125
7
9
6
130
F1
80
60
80
135
8.2 8.0 7.8 7.6 7.4 7.2
ppm
100
100
120
120
140
140
9
F2
ppm

1
H NMR 600 MHz
Hz
5470
4
5200
Hz
5190
2590
Hz
2580
790
Hz
780
4900 Hz
4910
4360 Hz
4370
5480
37
CH2
8
CH3
ethyl nicotinate
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
ppm
13
13C/DEPT
MHz
C/DEPT600
NMR
150.9 MHz
8
2
160
150
140
130
120
110
100
90
80
70
60
50
40
30
ppm
ppm
ppm
3
4
CH2
8
CH3
ethyl nicotinate
F1 5
ppm
F1
COSY 600 MHz

8
2
3
38
5 3
F2
4
3
5
1
HMQC 600 MHz
20
20
40
40
60
60
80
80
100
100
120
120
140
140
4
3
1
160
160
9
F2
ppm
39
INADEQUATE
600
MHz
INADEQUATE
150.9
MHz
Hz
-25000
-20000
-15000
-10000
-25000
-20000
CH2
CH3
-15000
-10000
ethyl nicotinate
-5000
F1
-5000
5000
5000
10000
10000
15000
15000
20000
20000
25000
25000
160
140
120
5
Hz
100
80
60
F2
40
ppm
20
12000
12000
13000
13000
F1
14000
14000
15000
15000
16000
16000
17000
17000
165
160
155
150
145
F2
140
135
130
125
ppm

8
INADEQUATE 150.9 MHz
13
40
Hz
-10000
-10000
15
H3C
-5000
H3C
14
CH3
12
11
5
9
10
-5000
O
6
F1
CH2
13
8-7
8-9
5000
5000
8-13
10000
10000
160 150 140 130 120 110 100
5
90
1 9
80
70
60 50
14
11
67 2
10 3
40
30
15
ppm
20
12
Hz
-9000
-9000
11-15
11-14
3-2
-8000
C6-C7
-8000
10-11
4-12
F1-7000
-7000
1-2
1-11
5-6
-6000
9-10
-6000
4-3
-5000
-5000
1-9
-4000
-4000
5-4
65
60
55
50
45
F2
40
35
30
25
20
15
ppm
41
The following correlations can be found in the INADEQUATE spectrum of caryophyllene oxide
Carbon 1 correlates with carbons 2, 9, and 11
Carbon 2 correlates with carbons 1 and 3
Carbon 5 correlates with carbons 4, and 6
Carbon 11 correlates with carbons 1, 10, 14, and 15
Carbon 12 correlates with carbons 4
15
H3C
H3C
14
CH3
12
11
5
9
10
6
8
H
CH2
13

1
42
H NMR 600 MHz

2
1
6
3500
Hz
3450
3050
OH
3000
Hz
1400
Hz
1350
10
10
1200
Hz
1150
950
Hz 9 750
900
Hz
700
OH
4
5
OH
7
8
10
3,7-dimethylocta-1,6-dien-3-ol
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
ppm
1.5
13
13 C/DEPT
NMR
150.9 MHz
C/DEPT 600
MHz
1
6
140
130
150
120
110
100
90
80
10
70
60
50
40
30
20 ppm

ppm 6.0 5.5 5.0 4.5 4.0 3.5
43
3.0
2.5
2.0
1.5
ppm
COSY 600 MHz

9
1.5
1.5
2.0
2.0
9
2.5
3.0
F1
4
5
3.5
4.0
2.5
OH
10
5
OH
3.0
3.5
4.0
7
8
10
4.5
4.5
5.0
5.0
5.5
5.5
1
6
1
2
ppm
F2
1,6,1
8 10
4
5
HMQC 600 MHz
20
20
40
40
60
60
10
F1
80
80
100
100
1
120
120
6
7
140
140
6.0
5.5
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
ppm
8
9
HMBC 600 MHz
161
OH
ppm
20
4
5
44
4
10
40
10
5
8
9
OH
60
F1
7
8
10
80
100
1
120
6
7
140
160
6.0
5.5
5.0
4.5
4.0 F2 3.5
3.0
2.5
2.0
ppm
1.5
ppm
20
20
40
40
60
60
F1
ppm
ppm
120
120
140
140
6.0
5.9
5.8
ppm
5.2
5.0
F2
ppm
2.0
1.5
ppm
ppm

2
45
1
INADEQUATE
150.9
INADEQUATE
600MHz
MHz
9 85
10
Hz
9
4
-15000
-10000
OH
3
6
-15000
7
8
10
-10000
-5000
-5000
F1
0
5000
5000
10000
10000
15000
15000
140
120
100
80
F2
60
40
20
ppm
ppm
5.2 5.0 4.8 4.6 4.4 4.2 4.0
F1
3.6
2
4
5
3
4
3.8
3
6
5
TOCSY 600 MHz
3.8 3.6 3.4
3.4
4.0
46
3.4
G2
3.6
G3
G5
G6
3.8
G4
4.0
4.2
4.2
4.4
4.4
4.6
4.6
4.8
4.8
5.0
5.0
5.2
5.2
5.2 5.0 4.8 4.6 4.4 4.2 4.0
3.8 3.6 3.4
G1
1
HDO
1
ppm
F1
Correlations from the three anomeric protons are drawn. These correlations show the ring protons
for the three monosaccharide residues of lactose. Correlations among the ring protons are difficult
to decipher due to overlap. Results from the 1D HOHAHA in Figure 5.26 agree with these
findings.

1
47
H NMR 600 6MHz

CH2OH
O
H
HO CH2OH
5
H
4
O
H H 1
HO
HO
H
HHO
3 H 2
H
HO
H
HO
6
CH52
H
HO
4 H
HO HO
3
H
HO
-Galactose
Ring A
C3
CH2
O
H
O
H
O
H
H1
3.9
HO
3.7
CH2OH
-Fructose
Ring C
C1
B2 B4
3.6
ppm
3.5
C3
A1
A6
C1
A2 B3
C6 C6
B6
3.8
CH2OH
HO
HO
5H
HO
HO
HDO
B1
-Glucose
Ring B
4.0
CH2OH
2 CH2HOH
H2
HO
C4 B5
B6 A4 A5 C5
A3
4.1
C4
5.4 5.3 5.2 5.1 5.0 4.9 4.8 4.7 4.6 4.5 4.4 4.3 4.2 4.1 4.0 3.9 3.8 3.7 3.6
ppm
13
13C/DEPT
150.9 MHz
C/DEPT NMR
600 MHz
74.0
B5
B3
C3
73.5
73.0
100
72.0
71.5
95
71.0
C5
B1
A1
C2
72.5
A5
B2
90
85
A3 B4 A4
70.5
70.0
69.5
C3 C4
80
75
A2
69.0
C6 C1A6
B6
70
ppm
65
ppm
48
Mixing time 300 ms 5.40 ppm irradiated
1-d TOCSY 600 MHz
B6
B6
Mixing time 80 ms
B5
B4
Mixing time 40 ms
B3
B2
Mixing time 20 ms
4.05
4.00
3.95
3.90
3.85
3.80
3.75
3.70
3.65
3.60
Mixing time 300 ms 4.97 ppm irradiated
A5
3.55
3.50
ppm
1-d TOCSY 600 MHz
A6
Mixing time 80 ms
A4
A3
Mixing time 40 ms
Mixing time 20 ms
A2
4.05
4.00
3.95
3.90
3.85
3.80
3.75
3.70
3.65
3.60
H NMR 600 MHz
3.55
3.50
ppm
49
Mixing time 80 ms
1-d TOCSY 600 MHz

C6 C6
Mixing time 40 ms
C5
Mixing time 20 ms
C4
4.05
4.00
3.95
3.90
3.85
6 CH2OH
HO
H
HO
H
H
HO
O
H
3.70
CH2
H
HO
HO
-Galactose
Ring A
3.75
3.65
3.60
3.55
3.50
3.80
H NMR 600 MHz
2
HO
-Glucose
Ring B
CH2OH
H
HO
3
HO
4
H
-Fructose
Ring C
5
CH2OH
ppm

ppm
F1
5.4 5.2 5.0 4.8 4.6
50
4.4 4.2 4.0 3.8 3.6
COSY 600 MHz
ppm
3.6
3.6
3.8
3.8
4.0
4.0
4.2
4.2
4.4
4.4
4.6
4.6
4.8
4.8
5.0
5.0
5.2
5.2
5.4
5.4
C3
HDO
A1
B1
COSY 600 MHz
ppm
B4
B2
3.5
3.6
C1
B6
3.7
F1
C6B3
C6 A2
C5
A3
A5
A4
B6 B5
C4
3.8
3.9
4.0
4.1
C3
4.2
4.2
4.1
4.0
3.9
3.8
F2
3.7
3.6
3.5
ppm
A6

ppm 5.4 5.2 5.0 4.8 4.6 4.4 4.2 4.0 3.8 3.6
F1
ppm
3.6
3.6
3.8
3.8
4.0
4.0
4.2
4.2
4.4
4.4
4.6
4.6
4.8
4.8
5.0
5.0
5.2
5.2
5.4
5.4
51
TOCSY 600 MHz
C3
HDO
A1
B1
TOCSY 600 MHz
ppm
B4
B2
3.5
3.6
C1
B6
3.7
F1
C6B3
C6 A2
C5
A3
A5
A4
B6 B5
C4
3.8
3.9
4.0
4.1
C3
4.2
4.2
4.1
4.0
3.9
3.8
F2
3.7
3.6
3.5
ppm
A6

B1
A1
C1
B5A4
A6
C3
C4 B6
C6 C6
A5 A3C5 A2 B3 B6
ppm 5.5
ppm
4.1
4.0
3.9
3.8
3.7
3.6
52
HMQC 600 MHz

B2 B4
3.5
ppm
60
A6
C1
C6
F1
65
B6
ppm
A2
A4
B4
A3
69
70
B2
A5
B5
71
72
B3
73
C4
74
F1
75
76
C3
77
78
79
80
81
C5
ppm
B1
95
F1
A1
100
C2
105
5.5
ppm
4.1
4.0
F2
3.9
3.8
3.7
3.6
3.5
ppm

B1
HMQC-TOCSY
600 MHz
C1
B5A4
A6
C4 B6
C6 C6
A5 A3C5 A2 B3 B6
B2 B4
A1
C3
ppm 5.5
ppm
53
4.1
4.0
3.9
3.8
3.7
3.6
3.5
ppm
60
A6
C1
C6
F1
65
B6
ppm
A2
A4
B4
A3
69
70
B2A5
B5
71
72
B3
73
C4
74
F1
75
76
C3
77
78
79
80
81
C5
ppm
B1
95
F1
A1
100
C2
105
5.5
ppm
4.1
4.0
F2
3.9
3.8
3.7
3.6
3.5
ppm

B1
A1
C1
B5A4
A6
C3
C4 B6
C6 C6
A5 A3C5 A2 B3 B6
ppm 5.5
ppm
4.1
4.0
3.9
3.8
3.7
3.6
54
HMBC 600 MHz

B2 B4
3.5
ppm
60
A6
C1
C6
F1
65
B6
ppm
A2
A4
B4
A3
69
70
B2A5
B5
71
72
B3
73
C4
74
F1
75
76
C3
77
78
79
80
81
C5
ppm
B1
95
F1
A1
100
C2
105
5.5
ppm
4.1
4.0
F2
3.9
3.8
3.7
3.6
3.5
ppm

1
55
H NMR 600 MHz

22
23
Hz
3200 7,8,24,25
3100
2
11
15
1000
2200
Hz
14
HO
HO
10
600 Hz
CH3
CH3
18
20
CHCH
3 3
13
15
Hz
1100
29
27 26
18
500
Hz
29
16
1000 Hz
28
23
24
27
25
26
16
HH
4.5
600
22
17
14
5.0
12
21
9
700
19
11
CH
33 H
1 CH
1300
19
21
20
Hz
2100
17 15
28
16 12
28
900
12
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
13
13
C/DEPT600
NMR
150.9 MHz
C/DEPT
MHz
21
8 25
22
23
130
120
7
32.0
27
29
11
2
ppm
ppm
21.5
140
110
100
90
80
70
18
13 20
12
1417 9 24 4
15
1 16 28
10
19
26
60
50
40
30
20 ppm
56
ppm 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
COSY 600 MHz
ppm
18
19
4
29
21
311
19
HO
1 CH3
10
CH3 20
13
9
8
CH3
28
22
12 18
17
14
15
23
27
24
25
26
16
20
24
4 7
23
22
6
COSY 600 MHz
ppm
0.6
0.8
9 14
1.0
29 to 28
1.2
29 to 28
1.4
F1
1.6
27 26 to 25
15
7
1.8
16
17
15
15 to 14
1
8
2.0
7,11
2.2
7 2lr
17
1 15
28 17
12
16
2.2
2.0
1.8
1.6
1.4
21
7
12
20
21
F2
1.27 1.0
0.8 7 0.6
21
28
2 11
7 8 24 25
15
16
2.4
2.4
18
26
27
ppm
17
29
19

6
22
23
4
ppm 5.5
ppm
3.6
ppm
57
8
29
25
21
HMQC
600 MHz
711
1927 26
242 12 2815 14
2
18
12 1 16 15 28 16 17 1 9
20 7
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
ppm
18
29
15
26
19
27
2111
15
28
20
25
16
2
30
35
725
8
10
F1
1
12
20
13
4
40
45
50
9
24
55
17
14
60
65
29
21
19
70
3
HO
11
1 CH3
10
CH3 20
23
17
14
ppm
12 18
13
28
22
CH3
15
24
27
25
26
16
23
130
22
140
5
5.5
ppm
3.6
ppm
2.2
2.0
F2
1.8
1.6
1.4
1.2
1.0
0.8
0.6
ppm

22
23
4
ppm 5.5
ppm
3.6
ppm
2.2
2.0
1.8
1.6
1.4
1.2
12-18
15
23-26
6-19
22,23-21
0.8
0.6
ppm
18
14-18
29
28-29
13C Satellite peaks
24 25-26
26
19
27-26
19
2711
21
15
28
28
12-11
22,23-28
25
1.0
17-18
24-29 28-29
20
24+25-27
9-11
14-15
16-15
24 25-28
26-27
29-28
17 15 14-16
30
6-7 22,23-25
3-2
4-2
7-8
1-2
15-8
12-8
6-10
3-1
F1
4-10
1,2-10
8,7,-10
2-1
22,23-20
40
2-1
11-12
3-4
12-13
6-4
45
50
22,23-24
55
22,23-17
2-4
7-14
1 CH3
HO
10
5
6
6-3
4-3
CH3
CH3 20
27,29,26-24
15
17
14
18-17
18-14
29
28
22
23
27
24
17
14
9
24
21
16 12 15-14
12 18
13
28-24
16 12
21
11
18-13
12 1-9 19-9
15 8-14
19
1
12
20
13
4
9-1
21-20 18-12
17-12
16-20
17-20
25-24 28-24
10
9-10
19
16-17
60
70
119
7,8,11
25
26
16
1,2 -3
725
8
27 26-25
16-13 15,11-13 12,15,17-13 14-13
12-9, and 7-9
65
16
2
24,28-25 28-25 15-8 14,9-(7,8)
35
58
8
25
21
HMBC 600 MHz
711
19272926
242 12 2815 14
2
18
12 1 16 15 28 16 17 1 9
20 7
3
2-3
1-3
ppm
6
4-6
22-23
130
7-6 1-6(4b)
20-23
20-22
140
6-5
24,25 28-23
24-22
23
28-23
27 26-23(4b)
17-22 21-22
22
3-5
4-5
5.5
7-6
ppm
3.6
ppm
2.2
7-5
2.0
F2
1-5
1.8
7-5
1.6
19-5
1.4
1.2
1.0
0.8
0.6
ppm
59
H NMR 600 MHz

0o C in 5%/95% D2O/H2O
KNH
T2
SNH
S3
T3 K2
S2
5400
5300
5200
Hz
5100
2700
2600
T4
K6
K3 K3
2500
Hz
2400
T4
Impurity
K4
K5
K6
1800 Hz
1100
800 Hz
900
KNH
SNH
9.0
1000
8.5
8.0
# of protons
7.5
7.0
6.5
6.0
5.5
5.0
2 3
4.5
4.0
11 2 2 3
2
3.5
3.0
2.5
2.0
TNH
SNH
Threonine (Thr) (T) Serine (Ser) (S)

Lysine (Lys) (K)
13
O
O
O
2
H 2
H 2
C/DEPT 600 MHz
H2N
CH C
HO CH
CH C
3 CH2
OH
4 CH3
CH C
3 CH2
ppm
OH
KNH
4 CH2
5
CH2
6 CH
2
K1
S1 NH2
T1
T3
T2 K2
S3
175
170
ppm
S2
K6
K3 K5
70 65 60 55 50 45 40 35 30 25
K4 T4
ppm

ppm 9
F1
60
5
ppm
COSY 600 MHz

K5 K4
T4
K3K3
K6
S3
K2 T3T2
S2
TNH
KNH
SNH
COSY 600 MHz
ppm
F1
1.0
1.0
1.5
1.5
2.0
2.0
2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5
ppm
4.5
4.0
3.5
3.0
2.5
F2
2.0
1.5
1.0
T4
K4
K5
K3K3
K6
S3
T2
T3K2
S2

ppm 9
F1
61
5
ppm
TNH
TOCSY 600 MHz

K5 K4
T4
K3K3
K6
S3
K2 T3T2
S2
KNH2
KNH
SNH
TOCSY 600 MHz
ppm
F1
1.0
1.0
1.5
1.5
2.0
2.0
2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
K4
K5
K3K3
K6
S3
T2
T3K2
S2
4.5
4.5
4.0
3.5
3.0
2.5
F2
2.0
1.5
1.0
4.5
ppm
T4
62
COSY 600 MHz

SNH
KNH
1.5
H2N
CH C
3 CH2
KNH
ROESY 600 MHz

SNH
KNH2
KNH
KNH2
T4
K4
K5
K3
Lysine (Lys) (K)
H
N
CH C
3 CH2
OH
4 CH3
2.0
H
N
CH C
HO CH
F1
SNH
KNH2
ppm
1.0
TOCSY 600 MHz
OH
4 CH2
5
CH2
6 CH
2
2.5
K6
NH2
3.0
S3
T2
K2
T3
3.5
4.0
S2
4.5
9.0
8.5
8.0
ppm
7.5
8.5
F2
8.0
7.5
ppm
F2
8.5
8.0
7.5
7.0 ppm
F2
HMQC 600 MHz
T3 T2S3
K2
S2
ppm
20
H2N
30
CH C
3
HO CH
4 CH3
F1
K6
H
N
CH C
3 CH2
OH
K5 K4
K3
T4
T4
Lysine (Lys) (K)
H
N
CH C
3 CH2
K4
K5
OH
K3
4 CH2
5
K6
CH2
40
6 CH
2
NH2
50
K2
S2T2
S3
60
T3
4.5
4.0
3.5
3.0
F2
2.5
2.0
1.5
1.0
ppm

ppm 9.0 8.5 8.0
ppm
63
4.0
3.5
3.0
2.5
2.0
1.5
1.0
HMBC 600 MHz

ppm
T3 T2
20
K2
F1
K3 K5
K6
K3
T4
K4
K5
K4
K2
KNH-K3
30
K6
K5
K4
K3
K5
K4
K6
40
50
KNH-K2
K2
S2
T2
S3
K3 K3 K4
S3
T3
60
T4
S2
T2
T4
T3
F2
SNH
KNH
KNH2
S2
ppm
168
170
S2-T1
SNH-T1
T2
K2 S3
T3
T3-T1
T4
K5
K4
K3
K6
T2-T1
T1
KNH-S1
S2-S1 K2-S1
T2,S3-S1
F1 172
H2N
CH C
3
HO CH
174
4 CH3
H
N
CH C
3 CH2
OH
S1
Lysine (Lys) (K)
H
N
CH C
3 CH2
OH
4 CH2
5
CH2
6 CH
2
176
NH2
178
KNH-K1
K2-K1
K3-K1
K1
180
9.0 8.5 8.0
ppm
4.0
3.5
F2
3.0
2.5
2.0
1.5
1.0
ppm
Answers for Student Exercise6.1

1
1
NOTE: The formula should be C5H10N2
H NMR 300 MHz
ppm
2.75 2.70 2.65 2.60 2.55 2.50 2.45 2.40 2.35 2.30 2.25 2.20 2.15 2.10
13
C/DEPT NMR 75.5 MHz
4
1
C5H10N2
Mol. Wt.: 98
3-(dimethylamino)propanenitrile
130
15
120
110
100
90
80
70
60
50
40
30
20
ppm
20
ppm
N NMR 30.4 MHz

N
240
220
200
180
160
140
120
100
80
60
40

1
H NMR 300 MHz

1
1
2 Si Cl
1 3
C6H15ClSi
Mol. Wt.: 151
tert-butylchlorodimethylsilane
1.3
13
1.2
1.1
1.0
0.9
0.8
0.7
0.6
0.5
0.4
0.3
0.1 ppm
0.2
C/DEPT NMR 75.5 MHz
1
3
35
29
30
25
20
15
10
ppm
-5
Si NMR 59.6 MHz
55
50
45
40
35
30
25
20
15
10
ppm

1
3
2
H NMR 300 MHz
3
4
H3C 1
P
2
34
Br
C19H18BrP
Mol. Wt.: 357
2340
8.5
13
8.0
7.5
7.0
6.5
2320
Hz
2300
6.0
5.5
5.0
4.5
4.0
3.0 ppm
3.5
C/DEPT NMR 75.5 MHz

4
10200
Hz
10000 Hz
2
3
2
c
9800
Hz 9000
8900 Hz
800
Hz
750
1
ab c
130
31
d
120
e
110
100
90
80
70
60
50
40
30
20
10 ppm
2 ppm
P NMR 121.5 MHz, 1H Decoupled
28
26
24
22
20
18
16
14
12
10

% of Base Peak
MASS
105
175
100
244
77
50
127
50
205
100
m/z
IR
F3C
50
OH
CF3
5'
2 3
4
5
6'
6
7
717
F NMR 282.4 MHz

See Table 6.2
5,5
972
1000
19
6,6
1165
1219
1273
H NMR
1504
3070
4000
1
200
C9H6F6O
Mol. Wt.: 244
1,1,1,3,3,3-hexafluoro2-phenylpropan-2-ol
3000
2000
Wavenumber (cm-1)
3548
3602
%Transmittance
100
150
OH
7.8
7.5
13
7.0
6.5
7.7
6.0
7.6
5.5
7.5 ppm
5.0
4.5
4.0
ppm
6,6
5,5
128
126
130
ppm
-74.7
Septet caused by 6 F two

bond coupling (JCCF) to
carbon 2
C/DEPT
-74.6
C1 and C3, with coupling to

3F, J value of 288 Hz
124
122
120
118 ppm
78
77
76
ppm
% of Base Peak
MASS
100
103
100
72
43
50
CI Reagent gas methane
x 30
57
50
85
40
50
60
70
m/z
IR
85
80
90
143
131
100
100
m/z
833
3000
H NMR 600 MHz
972
1049
2870
2954
4000
1
1149
1388
1458
50
3417
%Transmittance
100
2000
Wavenumber (cm-1)
1000
6
OH
2680 2660 2640 2620 2600 2580
4.5
4.0
2140 2120 2100 2080 2060 2040 Hz
Hz
2 is closer to CH2OH in space, therefore is

more deshielded than 4. NOE experiments
would confirm this.
OH
3.5
3.0
2.5
2.0
ppm
1.5
13
13
C/DEPT
MHz
C/DEPT NMR
NMR 150.9
600 MHz
3-methyl-3-oxetanemethanol
5 CH2OH
2
1O
24
CH3
3
4
C5H10O2
Mol. Wt.: 102
6
3
80
75
70
65
60
55
50
45
40
35
30
25
20 ppm

ppm
1.5
4.5
4.0
3.5
3.0
2
2.5
2.0
1.5
ppm
3-methyl-3-oxetanemethanol
5 CH2OH
2
2.0
1O
1.5
CH3
3
4
2.0
C5H10O2
Mol. Wt.: 102
2.5
COSY 600 MHz
2.5
F1
3.0
3.0
3.5
3.5
4.0
4.0
4.5
OH
5
2
4
4.5
ppm
OH
F2
HMQC 600 MHz
20
20
30
30
40
40
F1 50
50
60
60
70
70
80
80
4.5
4.0
3.5
3.0
F2
2.5
2.0
1.5
ppm
2 4
MASS
% of Base Peak
221
100
50
97
55
203
177
50
IR
137
81
100
150
m/z
236
200
100
%Transmittance
1003
910
1381
1458
2924
4000
3000
H NMR 600 MHz
11
11
2000
Wavenumber (cm-1)
12
2300
Hz
1200
800
Hz
1150
750
1000
16
Hz
1050
Hz
700
Hz
900
600
850
15
31
5
9 4
8
2350
1000
Hz
550
Hz
13 14
Hz
500
16
(-)-ambroxide 11
13
CH3 12
4
5
3
6
1 10
9
14
H3C 15CH3
O
CH3
16
C16H28O
Mol. Wt.: 236
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
13
13
C/DEPT
NMR 600
150.9
MHz
C/DEPT NMR
MHz
3
11
7
1
15
13
10
80
75
70
65
60
11
11
55
50
45
40
35
30
25
51
43
ppm
20
15 ppm
HMQC 600 MHz
16
12
9
14,16
12 8 4
1513 14
13
4
8 16
14
12
20
30
6
15
2
F1 40
39
5
(-)-ambroxide 11
13
CH3 12
50
4
5
60
3
6
14
ppm
1.9
1.8
O
CH3
16
1.7
1.6
H3C 15CH3
4.0
1 10
7
1
11
F2
1.5
1.4
1.3
1.2
1.1
1.0
0.9
0.8
ppm
Answers for Student Exercise 7.8C

11
11
12
9
ppm
4.0
3.9
ppm
2.0
8
1.8
51
4 3 8
9
4
1.6
1.4
HMBC 600 MHZ

HMQC 600 MHz
16
1513 14
5 3 7
1.2
1.0
0.8
ppm
13
15
4
20
8
14,16
12
ppm
34
15
(-)-ambroxide 11
F1
13
CH3 12
36
4
5
38
3
6
14
40
1 10
H3C 15CH3
O
CH3
16
9
3
42
5
ppm
58
60
62
64
11
ppm
10
80
82
4.0
3.9
ppm
2.0
1.8
F2
1.6
1.4
1.2
1.0
0.8
ppm
Answers for Student Exercise 7.8D
INADEQUATE
MHz
INADEQUATE150.9
600 MHz
11
1
10
539
1416
12 8 4
15
13
Hz
(-)-ambroxide 11
13
-7000
CH3 12
4
5
-6000
-5000
2-13
6-14 or 15
3
7
O
1 10
2
CH3
9
3-4
9-8
16
14
H3C 15CH3
-7000
-6000
5-4
-5000
6-15 or 14
-4000
-4000
5-6
7-8
-3000
3-2
-3000
1-12
-2000
-2000
11-12
7-6
7-2
-1000
-1000
1-2
F1
10-8
1000
1000
2000
2000
10-9
3000
3000
4000
4000
5000
5000
10-1
6000
6000
7000
7000
80
75
70
65
60
55
50
F2
45
40
35
30
25
20
15
ppm
CHAPTER 8 ASSIGNED PROBLEMS

Problem 8.1
% of Base Peak
MASS
68
55
100
41
112
84
50
97
40
50
60
70
IR
m/z
O
90
100
110
1 2
3
4
50
Cycloheptanone
C7H12O
Mol. Wt.: 112
11
856
941
2000
Wavenumber (cm-1)
1161
3000
1342
1454
4000
1701
2858
2927
%Transmittance
100
80
1000
NMR 300 MHz

HHNMR
2
3
2.7
2.6
2.5
2.4
2.3
2.2
2.1
2.0
1.9
1.8
1.7
1.5 ppm
1.6
1313
C/DEPT NMR 75.5 MHz

C/DEPT
200
180
160
140
120
100
80
60
40
ppm

Problem 8.2
MASS
% of Base Peak
124
100
94
50
53
50
60
95
81
66
70
80
m/z
IR
100
110
120
OH
100
50
687
768
837
945
1041
1149
11
1284
3000
m-Methoxyphenol
C 7H 8 O 2
Mol. Wt.: 124
1493
1601
2839
2947
3005
4000
OCH3
3398
%Transmittance
90
2000
Wavenumber (cm-1)
1000
H NMR
NMR 300 MHz
H
6
2
4
2150
2140
Hz
1960
1950
Hz
1920 Hz
1930
OH
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
ppm
13
13
C/DEPT NMR 75.5 MHz

C/DEPT
4
1
3 2
3
1
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm

Problem 8.3
MASS
% of Base Peak
55
M-1
83
100
39 41
50
53
40
45
65
50
55
IR
m/z
60
84
66
65
70
75
80
85
50
741
2000
Wavenumber (cm-1)
1014
11
1138
1227
1319
3000
1454
4000
2229
2291
2877
2939
2978
3332
%Transmittance
100
1000
H
H NMR
NMR 300 MHz
5
1
4
1280
4.0
1260 Hz
3.5
OH
660 Hz
680
3.0
2.5
2.0
ppm
1.5
13
13C/DEPT
C/DEPT NMR 75.5 MHz
HO
H 2C
CH2
5 CH3
2-Pentyn-ol
C5 H 8 O
Mol. Wt.: 84
CDCl3
5
4
1
78.0 77.5 77.0 76.5
95
90
85
80
75
70
65
ppm
60
55
50
45
40
35
30
25
20
ppm

Problem 8.4
MASS
% of Base Peak
75
100
49
61
50
77 99
97
m/z
IR
146
148
146
100
113
100
112 M
114
50
x 30
111
110
75
77
50
150
148
150
152
115
100
150
m/z
Cl
Cl 1 CH 3 Cl
CH2 2 CH2
90
80
1,2,3-Trichloropropane
C3H5Cl3
Mol. Wt.: 146
70
H NMR
NMR 300 MHz
663
717
1
1H
2000
Wavenumber (cm-1)
910
3000
1219
1288
4000
1435
2962
3016
%Transmittance
100
1000
1+3
4.35
4.30
4.25
4.20
4.15
4.10
4.05
4.00
3.95
3.90
3.85
ppm
3.80
13
13C/DEPT
C/DEPT NMR 75.5 MHz
1+3
2
75
70
65
60
55
50
45
ppm

Problem 8.5
% of Base Peak
MASS
m/z
126 (M)
127 (M+1)
128 (M+2)
100
50
%M
100.0
8.2
4.9
111
126
39
43
40
83
57
49
50
60
70
80
m/z
IR
90
100
110
120
130
50
11
590
2000
Wavenumber (cm-1)
725
856
933
1061
1273
3000
1415
4000
1662
3089
%Transmittance
100
1000
H
H NMR
NMR 300 MHz
3
2300
2280 Hz
7.5
7.0
6.5
6.0
5.5
5.0
2120 Hz
2140
4.5
13
13 C/DEPT
C/DEPT NMR 75.5 MHz
4.0
2
3.5
3.0
2.5
ppm
O
5
6 CH3
Ethanone, 1-(2-thienyl)2-Acetylthiophene
C6H6OS
Mol. Wt.: 126
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm

Problem 8.6
% of Base Peak
MASS
x 10
105
100
186
184
50
77
51
50
IR
100
150
m/z
100
80
70
2260
2250
2240
2230
2220
13
7.0
6.5
6.0
1000
2210
5.5
5.0
C/DEPT NMR 75.5 MHz
1590
1580
1570
Hz
640
630
620
Hz
Hz
2200
7.5
594
694
764
H NMR 300 MHz
2000
Wavenumber (cm-1)
964
3000
1211
4000
1450
1496
2985
3032
%Transmittance
90
4.5
H3C
6
4.0
3.5
3.0
2.5
ppm
Br
1
2
3
4
(1-Bromoethyl)benzene
C8H9Br
Mol. Wt.: 184
4
3
1
140
130
120
110
100
90
80
70
60
50
40
30 ppm

Problem 8.7
MASS
% of Base Peak
109
124
100
81
53
50
63
50
75
60
70
80
IR
90
m/z
100
110
120
50
513
733
825
2000
Wavenumber (cm-1)
1034
11
1234
3000
1512
1612
1701
4000
1859
2835
2951
3348
%Transmittance
100
1000
H
H NMR
NMR 300 MHz
2
OH
7.0
6.5
6.0
5.5
5.0
4.5
4.0
ppm
3.5
OH
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
4
3
2
1
OCH3
5
3
1
p-Methoxyphenol
C 7H 8 O 2
Mol. Wt.: 124
150
140
130
120
110
100
90
80
70
60
50
ppm

Problem 8.8
MASS
% of Base Peak
128
100
64
130
50
92
73
50
60
70
80
IR
90
m/z
100
110
120
130
50
2000
Wavenumber (cm-1)
OH
1
1H
H NMR
NMR 300 MHz
6
4
6
1000
Cl
2
3
679
748
3000
1030
4000
1200
1338
1454
1481
1585
3039
3074
3464
3521
%Transmittance
100
OH
o-Chlorophenol
C6H5ClO
Mol. Wt.: 128
7.4
7.2
7.0
6.8
6.6
6.4
6.2
6.0
5.8
5.6
5.4
ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
155
150
145
140
135
130
125
120
115
ppm

Problem 8.9
x 20
55
87
100
115
196
194
73
135
50
100
137
165
150
m/z
IR
163
1203
50
1365
1435
% of Base Peak
MASS
50
3000
2000
Wavenumber (cm-1)
1
1H
H NMR
NMR 300 MHz
748
4000
1736
2954
%Transmittance
100
1000
O
6
6
Br
Methyl 5-bromo valerate

C6H11BrO2
Mol. Wt.: 194
2
4
3.6
3.4
3.2
3.0
2.8
2.6
2.4
2.2
2.0
1.8
1.6
ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
5 2
6
1
33.0
32.5
170 160 150 140 130 120 110 100
32.0
90
ppm
80
70
60
50
40
30
ppm

Problem 8.10
MASS
% of Base Peak
54
100
67
84
93
50
111
50
60
70
80
IR
m/z
90
100
126
110
120
1
1H
H NMR
NMR 300 MHz
2000
4
OH
5
1
Wavenumber
(cm-1)
2
849
3000
1045
1331
4000
1466
2873
2931
2958
3344
%Transmittance
100
1000
3-Octyn-1-ol
C8H14O
Mol. Wt.: 126
6
7
OH
3.5
3.0
2.5
2.0
1.5
ppm
1.0
13
13C/DEPT
C/DEPT NMR 75.5 MHz
2
84
82
80
85
ppm
78
3
80
75
70
65
60
55
50
45
40
35
30
25
20
ppm
% of Base Peak
MASS
Problem 8.11
162
100
164
63
98
50
126
73
50
60
70
80
90
100 110
m/z
IR
120
128
130
140
150
160
50
1
1H
H NMR
NMR 300 MHz
2000
Wavenumber (cm-1)
1000
OH
Cl
OH
7.4
7.2
7.0
555
3000
725
814
4000
1188
1277
1404
1477
1585
3097
3521
%Transmittance
100
6.8
6.6
Cl
2,4-Dichlorophenol
C6H4Cl2O
Mol. Wt.: 162
6.4
6.2
6.0
5.8
5.6
5.2 ppm
5.4
13
13C/DEPT
C/DEPT NMR 75.5 MHz
155
150
145
140
135
130
125
120
115
ppm

Problem 8.12
% of Base Peak
MASS
123
100
95
75
50
50
63
70
80
90
m/z
100
110
120
1157
1265
1358
60
1597
1685
50
IR
138
130
140
50
3000
2000
Wavenumber (cm-1)
H NMR 300 MHz

2
567
4000
841
960
3005
3074
3356
%Transmittance
100
1000
19
F NMR 282.4 MHz
H Coupled
H Decoupled
6
2400
2390
2380
Hz
2140
Hz
2130
ppm
8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0
13
-104.5 ppm
-104.4
5
C/DEPT NMR 75.5 MHz
COCH3
1
2
3
4
F
4-Fluoroacetophenone
C8H7FO
Mol. Wt.: 138
130 128 126 124 122 120 118
6
ppm
1
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm

Problem 8.13
MASS
% of Base Peak
96
100
50
70
50
50
55
60
65
75 77
70
m/z
IR
75
80
85
90
95
100
2
3
4
95
2000
Wavenumber (cm-1)
756
3000
1234
4000
1504
1604
1697
Fluorobenzene
C 6H 5 F
Mol. Wt.: 96
3062
3749
%Transmittance
1000
11H
19
NMR 300 MHz

H NMR
F NMR 282.4 MHz

1
H Coupled
7.4
7.3
7.2
7.1
ppm
-80.1
-80.3 ppm
-80.2
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
2
4
130
128
126
124
122
120
118
116 ppm
1
165
160
155
150
145
140
135
130
125
120
115 ppm

Problem 8.14
MASS
% of Base Peak
82
100
50
138
54
95
67
50
60
70
80
90
m/z
IR
123
100
110
120
130
140
50
1750
1740 Hz
Hz
640
570
1000
89
525
H NMR
NMR 300 MHz
2000
Wavenumber (cm-1)
903
1
1H
1246
3000
1381
4000
1670
2870
2958
%Transmittance
100
560 Hz
300
3.5
3.0
Hz
290
6.0
5.5
5.0
4.5
4.0
2.5
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
2.0
ppm
1.5
CH3
3
4
9
2
5
H 3C
H3 C
1
6
89
Isophorone
C9H14O
Mol. Wt.: 138
2
1
200
6 4
3
180
160
5
140
120
100
80
60
40
ppm

Problem 8.15
MASS
% of Base Peak
54
68
50
81
79
50
60
70
93
80
90
IR
95
m/z
107
100
109
149
147
119
110
121
120
130
140
150
100
%Transmittance
90
80
H
H NMR
NMR 300 MHz
Br
756
2000
Wavenumber (cm-1)
2
11
1250
3000
1435
4000
2245
2970
70
1000
N
4-Bromobutanoyl nitrile
C4H6BrN
Mol. Wt.: 147
3.6
3.5
3.4
3.3
3.2
3.1
3.0
2.9
2.8
2.7
2.6
2.5
2.4
2.3
ppm
2.2
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
4
1
120
110
100
90
80
70
60
50
40
30
20
ppm

Problem 8.16
MASS
% of Base Peak
106
100
137
50
77
50
60
70
80
IR
m/z
90
100
110
120
130
140
90
80
1
1H
H NMR
NMR 300 MHz
2000
Wavenumber (cm-1)
1000
3
2
OH
5
7.5
825
3000
1049
1442
1512
1620
4000
2931
3194
3348
%Transmittance
100
7.0
6.5
6.0
5.5
5.0
ppm
4.5
4.0
3.5
3.0
2.5
2.0
1.5 ppm
OH
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
5
1
OH
2
3
NH2
1
140
130
p-Aminophenylethanol
C8H11NO
Mol. Wt.: 137
120
110
100
90
80
70
60
50
40
ppm

Problem 8.17
MASS
% of Base Peak
119
100
50
91
64
76
50
60
70
80
m/z
IR
90
100
110
120
90
80
70
H NMR
NMR 300 MHz
2
671
787
1
1H
1342
3000
1481
1589
4000
2245
3309
%Transmittance
100
2000
Wavenumber (cm-1)
1000
OH
7.6
7.5
7.4
7.3
7.2
7.1
7.0
6.9
6.8
6.7
6.6
6.5
6.4
6.3
ppm
6.2
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
2
5
3
4
OH
p-Cyanophenol
C7H5NO
Mol. Wt.: 119
165
160
155
150
145
140
135
130
125
120
1
115
110
ppm

Problem 8.18
MASS
% of Base Peak
163
100
178
50
91
77
50
135
100
IR
150
m/z
%Transmittance
100
50
2000
Wavenumber (cm-1)
748
11
1149
1203
3000
1458
2870
2962
3572
4000
1000
H
H NMR
NMR 300 MHz
2100 Hz
2150
950 Hz
1000
450
OH
7.0
6.5
6.0
5.5
5.0
Hz
400
4.5
4.0
3.5
13
13C/DEPT
C/DEPT NMR 75.5 MHz
2.5
1.5 ppm
2.0
OH
1
3.0
5
6
3
4
2,6-Diisopropyl phenol
C12H18O
Mol. Wt.: 178
6
5
4
1
150
2
140
130
120
110
100
90
80
70
60
50
40
30
20 ppm

Problem 8.19
MASS
% of Base Peak
106
78
100
121
51
50
50
60
70
80
m/z
IR
90
100
110
120
50
1000
4
7
2720
9.0
702
H NMR
NMR 300 MHz
957
1
1H
2000
Wavenumber (cm-1)
3
1273
3000
1419
1689
4000
3047
3363
%Transmittance
100
2700 Hz
8.5
2580 Hz
2600
8.0
7.5
7.0
2440
6.5
6.0
2420 Hz
5.5
13
13C/DEPT
2180 Hz
2200
5.0
4.5
4.0
3.5
ppm
3.0
C/DEPT NMR 75.5 MHz
7
6
CH3
5
6
2-Acetylpyridine
C7H7NO
Mol. Wt.: 121
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm

Problem 8.20
MASS
% of Base Peak
108
123
100
53
50
40
80
50
60
70
80
IR
90
m/z
100
110
120
50
2000
Wavenumber (cm-1)
1000
7.0
2060
3
6.5
Hz
Hz 1820
2020
633
741
H NMR
NMR 300 MHz
1095
1
1H
1404
3000
1651
4000
2947
3109
%Transmittance
100
Hz
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
ppm
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
3
4
H3C5
2
7
6
CH3
1-Methyl-2-acetylpyrrole
C7H9NO
Mol. Wt.: 123
6
180
160
140
120
100
80
60
40
ppm

Problem 8.21
% of Base Peak
MASS
100
159
100
85
57
50
x 20
43
103
158
50
50
100
m/z
IR
187
150
150
m/z
50
2000
Wavenumber (cm-1)
11
1034
1149
3000
1319
4000
1651
1720
2962
%Transmittance
100
1000
H
H NMR
NMR 300 MHz
7
1
3
5
6
3.5
3.0
2.5
2.0
1.5
ppm
1.0
13
13C/DEPT
C/DEPT NMR 75.5 MHz

7
1
2
O
O
Isobutylacetoacetate
C8H14O3
Mol. Wt.: 158
200
180
160
140
120
100
80
60
40
ppm

Problem 8.22
MASS
% of Base Peak
119
100
50
91
64
76
50
60
70
80
IR
90
m/z
100
110
120
100
80
70
11
H NMR 600
300 MHz
42
5
671
787
3000
1342
4000
1481
1589
2245
3309
%Transmittance
90
2000
Wavenumber (cm-1)
OH
1000
3
4
2
1
OH
m-Cyanophenol
C7H5NO
Mol. Wt.: 119
7.4
7.3
7.2
7.1
7.0
6.9
6.8
6.7
6.6
6.5
6.4
6.3
ppm
6.2
13
13 C/DEPT
NMR 600
75.5MHz
MHz
C/DEPT NMR
7
155
150
145
140
135
130
125
120
115
ppm

Problem 8.23
MASS
% of Base Peak
x 20
183
185
100
155
75
50
100
157
150
m/z
IR
224
200
198
264
262
260
226
200
250
50
H NMR
NMR 300 MHz
617
1
1H
810
2000
Wavenumber (cm-1)
995
1068
3000
1223
1396
1485
1585
1685
4000
2962
3059
3089
3356
%Transmittance
100
1000
7.9
7.8
7.7
7.6
ppm
3.6
3.4
13
13C/DEPT
C/DEPT NMR 75.5 MHz
3.2
3.0
6
2.8
2.6
ppm
2.4
COCH2CH2CH2Cl
1
2
3
4
5
1
Br
4Bromo-4-chlorobutyrophenone
C10H10BrClO
Mol. Wt.: 260
190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
ppm

Problem 8.24
% of Base Peak
MASS
100
100
55
50
147
69
74
83
50
128
175
50
100
150
150
m/z
187
200
m/z
IR
50
H NMR
NMR 300 MHz
930
1
1H
1238
1277
1419
1466
3000
1709
4000
2669
2978
3039
%Transmittance
100
2000
Wavenumber (cm-1)
1000
2x OH
x64
3
2
12
11
ppm
2.6
2.4
2.2
2.0
1.8
1.6
1.2 ppm
1.4
13
13C/DEPT
C/DEPT NMR 75.5 MHz

O
HO 1
CH2 C 5
CH
CH2 OH
2
CH3
15
2-Methyl glutaric Acid

C6H10O4
Mol. Wt.: 146
180 170 160 150 140 130 120 110 100
90
80
70
60
50
4 3
40
30
ppm

Problem 8.25
91
66
100
93
92
50
100
51
% of Base Peak
MASS
50
50
60
m/z
IR
70
80
80
90
90
m/z
90
80
2000
Wavenumber (cm-1)
H NMR 300 MHz
725
802
1065
3000
1342
4000
1720
2962
3055
%Transmittance
100
1000
2
1
2050
7.0
13
6.5
Hz
2040
6.0
5.5
1080 Hz
1090
5.0
4.5
Hz
615 610 605
4.0
3.5
3.0
2.5
2.0
ppm
C/DEPT NMR 75.5 MHz
Bicyclo[2,2,1] hepta-2-5-diene
C7 H 8
Mol. Wt.: 92
140
130
120
110
100
90
80
70
60
50
ppm

Problem 8.26
% of Base Peak
MASS
M
156
100
M+2
63
158
50
98
50
60
70
80
121
90
100
110
m/z
IR
120
130
140
150
160
1041
H NMR 600 MHz
1234
1473
3000
802
933
50
4000
1
586
2900
%Transmittance
100
2000
Wavenumber (cm-1)
1000
6.85
6.80
6.75
6.70
6.65
ppm
6.00 5.95
ppm
1313
C/DEPT
MHz
C/DEPTNMR
NMR600
150.9
MHz
3
4
O
7
5
1
Cl
5-chloro-1,3-benzodioxole
C7H5ClO2
Mol. Wt.: 156
1
155
150
2
145
36
140
135
130
125
120
115
110
105 ppm

Problem 8.27A
% of Base Peak
MASS
55
42
100
84
50
114
70
40
50
60
70
IR
m/z
80
90
100
110
50
O
2
1000
1
O
2
6
3
4
571
H
H NMR
NMR 300 MHz
2000
Wavenumber (cm-1)
856
11
1057
1165
3000
1442
4000
1728
2931
%Transmittance
100
3 5
-Caprolactone
C6H10O2
Mol. Wt.: 114
4.0
3.5
3.0
2.5
2.0
ppm
1.5
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
43
170
160
150
140
130
120
110
100
90
80
70
60
50
40
ppm

Problem 8.27B
ppm 4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.5
ppm
1.5
COSY 300 MHz
4
1
2.0
2
2.5
2.0
O
F1
2.5
3
4
-Caprolactone
C6H10O2
Mol. Wt.: 114
3.0
5
3
3.0
3.5
3.5
4.0
4.0
6
F2
ppm
HETCOR
75.5MHz
MHz
HETCO 300
4 3
1.5
1.5
2.0
2.0
2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5
ppm
F1
65
60
55
50
45
F2
40
35
30
25

Problem 8.28A
MASS
% of Base Peak

55
x 10
69
100
82
137
120
118
90
50
139
92
50
100
m/z
IR
130
140
m/z
150
50
H NMR 600 MHz

1
2000
Wavenumber (cm-1)
648
725
3000
1057
4000
1458
2862
2939
3332
%Transmittance
100
1000
6
HO 1
5
6
Cl
1-Hexanol-6-chloro
C6H13ClO
Mol. Wt.: 136
4 3
OH
3.6
3.4
3.2
3.0
2.8
2.6
2.4
2.2
2.0
1.8
1.4 ppm
1.6
1313
C/DEPT
MHz
C/DEPTNMR
NMR600
150.9
MHz
60
55
50
45
40
35
30
25
ppm

Problem 8.28B
3.5
ppm
3.0
2.5
1.5
ppm
1.5
1.5
2.0
2.0
HO 1
F1
2.0
5
6
Cl
1-Hexanol-6-chloro
C6H13ClO
Mol. Wt.: 136
2.5
2.5
3.0
3.0
3.5
3.5
OH
ppm
F2
HMQC 600 MHz
2 4 3
25
30
COSY 600 MHz
25
4
OH
30
35
35
40
F1
40
45
ppm
45
50
32
50
55
55
33
60
2.0
3.5
3.0
1.8
2.5
F2
1.6
1.4
2.0
ppm
1.5
60
1
ppm

Problem 8.29A
MASS
% of Base Peak
95
100
67
45
50
69
55
110
81
50
60
70
80
IR
128
113
90
m/z
100
110
120
130
%Transmittance
100
50
2000
Wavenumber (cm-1)
11
825
1041
1126
3000
1377
1450
2924
2966
3344
4000
1000
HNMR
NMR 300 MHz
H
1
7
Hz
1540
Hz
1140
480 Hz
500
4.5
Hz
440
5.0
4.0
3.5
3.0
2.5
OH
2.0
ppm
1.5
13
13
C/DEPT
C/DEPT NMR 75.5 MHz
OH
5
120
110
100
90
80
6-Methyl-5-hepten-2-ol
C8H16O
Mol. Wt.: 128
130
8
7
70
60
50
40
30
20 ppm

Problem 8.29B
ppm 5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0 ppm
1.0
COSY 300 MHz
1.0
1
1.5
2.0
2.0
OH
4
2.5
2.5
F1 3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5
5.0
5.0
1.5
7
8
F2 2
ppm
84 1
HETCOR300
75.5
MHz
HETCO
MHz
1.0
7
OH
1.5
5
F1
2.0
2.5
6-Methyl-5-hepten-2-ol
C8H16O
Mol. Wt.: 128
3.0
3.5
OH
4.0
4.5
5.0
5.5
120
100
80
60
F2
40
20
ppm

Problem 8.30A
MASS

223
225
100
69
100
143
50
100
177
159
179
50
194
150
m/z
230
240 250
m/z
IR
263
265
50
251
253
% of Base Peak
88
260
%Transmittance
100
50
1000
3.5
1034
H NMR
NMR 300
600 MHz
MHz
4.0
1188
2000
Wavenumber (cm-1)
11
H
1458
3000
1736
2870
2939
4000
3.0
2.5
2.0
ppm
1.5
13
13
C/DEPT
NMR 75.5
600 MHz
C/DEPT NMR
MHz
Br
2,6,5
7
4 3
8
Ethyl 6-Bromohexanoate
C8H15BrO2
Mol. Wt.: 222
170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
ppm

Problem 8.30B
ppm
4.0
3.5
3.0
2.5
2.0
1.5
1.0
1.0
F1
ppm
COSY 300 MHz
1.0
1.5
1.5
2.0
2.0
2.5
8
4
3
5
2
2.5
1
1
3.0
3.0
6
3.5
3.5
4.0
4.0
F2 2 6 5 4 3
HETCOR
HETCO75.5
300MHz
MHz
ppm
1.0
Br
1.0
O
1.5
Ethyl 6-Bromohexanoate
C8H15BrO2
Mol.
Wt.: 222
2.0
1.5
2.0
F1 2.5
2.5
3.0
3.0
4
3
5
2
3.5
3.5
4.0
4.0
60
55
50
45
40
35
F2
30
25
20
15
ppm

Problem 8.31A
MASS
% of Base Peak
134
100
41
94
50
65
40
50
77
60
119
91
105
70
80
IR
m/z
90
100
110
120
130
50
2000
Wavenumber (cm-1)
690
752
3000
1242
4000
1496
1601
2866
2916
3032
3066
%Transmittance
100
1000
H NMR 600 MHz

5
3
4
3680
Hz 3300
3660
Hz 3220
3280
Hz
3200
7.4
7.2
7.0
6.8
6.6
6.4
6.2
2760
2740
Hz
6.0
5.8
5.6
5.4
5.2
5.0
ppm
4.8
13
13
C/DEPT NMR
NMR 150.9
600 MHz
C/DEPT
MHz
5
OCH2CH=CH2
1
2
3
4
6
160
150
140
130
2
4
120
Allylphenyl ether
C9H10O
Mol. Wt.: 134
110
100
90
80
70
ppm

Problem 8.31B
ppm 7.5
7.0
6.5
6.0
5.5
5.0
4.5
ppm
4.5
4.5
5.0
5.0
5.5
5.5
6.0
6.0
6.5
6.5
7.0
7.0
COSY 600 MHz
F1
F2
ppm
5
OCH2CH=CH2
70
HMQC 600 MHz
70
1
2
80
80
90
90
Allylphenyl ether
C9H10O
Mol. Wt.: 134
100
100
F1 110
110
diastereotopic
120
120
130
130
3
6
140
140
150
150
1
7.5
7.0
6.5
6.0
F2
5.5
5.0
4.5
ppm

Problem 8.32A
% of Base Peak
MASS
x 20
95
100
50
110
109
67
55
70
80
90
IR
100
m/z
110
120
130
1365
60
1712
50
139
136
121
154
140
150
50
H NMR 600 MHz
2000
Wavenumber
(cm-1)
3
829
3000
1057
4000
1227
2877
2951
3317
%Transmittance
100
1000
8
9 10
OH
2400
Hz
1350 Hz 1150
Hz 1050
Hz
950 Hz
4.0
3.5
3.0
Hz
750
In the above insets each tick mark is 10 Hz 3
2.5
550 Hz
5 4
2.0
500 Hz
5 6
ppm
1.5
13
13
C/DEPT NMR
NMR 150.9
600 MHz
C/DEPT
MHz
10
H 3C
CH3
7
1
4
CH3
3 OH
Borneol
C10H18O
Mol. Wt.: 154
9 10
25
20
1 7
75
70
65
60
55
50
45
40
35
30
15 ppm

Problem 8.32B
ppm
4.0
3.5
3.0
2.5
7
2.0
1.5
1.0
ppm
COSY 600 MHz

9.10,8
1.0
1.0
1.5
1.5
2.0
2.0
F1
10
2.5
3.0
5
3.5
CH3
3.0
1
4
2.5
CH3
7
5
6
3
H 3C
OH
3 OH
3.5
Borneol
C10H18O
Mol. Wt.: 154
4.0
4.0
F2
HMQC 600 MHz
ppm
8
ppm
20
10
9
20
6
5
15
30
30
20
40
F1
diastereotopic
25
0.90
0.85
40
ppm
50
50
60
60
70
70
7
1
4.0
3.5
3.0
2.5
F2
2.0
1.5
1.0
ppm

Problem 8.33A
MASS
% of Base Peak
85
100
50
57
70
50
60
70
IR
114
m/z
80
90
100
110
656
1180
1774
4000
1
972
50
1358
1466
2885
2970
%Transmittance
100
3000
H NMR 600 MHz
1000
6
2
2000
Wavenumber (cm-1)
3 5
-Caprolactone
C6H10O2
Mol. Wt.: 114
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
13
13
C/DEPT NMR
NMR 150.9
600 MHz
C/DEPT
MHz
180
29
160
140
120
100
80
28
60
ppm
40
20
ppm

Problem 8.33B
ppm 4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
COSY 600 MHz
ppm
1.0
1.0
1.5
1.5
5
3
2.0
2.0
3
F1 2.5
2.5
2
3.0
3.0
-Caprolactone
C6H10O2
Mol. Wt.: 114
3.5
3.5
4.0
4.0
4
F2
HMQC 600 MHz
ppm
10
10
20
20
30
30
diastereotopic
40
40
ppm
F1 50
3
5
2
28
60
50
60
30
2.5
2.0
1.5 ppm
70
70
80
80
4.5
4.0
3.5
3.0
2.5
F2
2.0
1.5
1.0
ppm

Problem 8.34A
MASS
% of Base Peak
41
69
100
81
55
95
50
123
109
60
70
80
90
IR
m/z
100
110
120
130
140
1057
50
156
1381
1450
40
138
150
160
50
4000
1
3000
HO
H NMR 600 MHz
2000
9
10
Wavenumber
(cm-1)
CH3
CH3
3
4
833
2924
3332
%Transmittance
100
1000
8
10
CH3
8
Citronellol
C10H20O
Mol. Wt.: 156
5.0
4.5
5
OH
4.0
3.5
3.0
2.5
2.0
1.5
ppm
1.0
13
13
C/DEPT NMR
NMR 150.9
600 MHz
C/DEPT
MHz
24
10
130
26
120
110
25
100
ppm
90
80
70
60
50
40
30
20 ppm

Problem 8.34B
ppm 5.5
F1
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
1.0
1.0
1.5
1.5
2.0
2.0
2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5
5.0
5.0
F2
COSY 600 MHz

10
4
2
3
8
9
OH
5
HMQC 600 MHz
ppm
HO
20 CH3
2
10
10
20
CH3
40
95
3
4
2
60
CH3
40 4 5
Citronellol
C10H20O
Mol.
60 Wt.: 156
ppm
F1 80
80
20
100
100
30
40
120
120
5.5
5.0
4.5
4.0
3.5
3.0
F2
2.5
2.0
ppm
2.0 1.5 1.0

1.5
1.0
ppm

Problem 8.35A
MASS
% of Base Peak
95
81
100
41
108
69
55
50
152
137
50
60
70
80
90
100
m/z
IR
130
140
10CH3
2954
Camphor
C10H16O
Mol. Wt.: 152
1743
3000
1041
748
1450
50
1273
4
2
4000
2000
Wavenumber (cm-1)
1000
H NMR 600 MHz
2.3
8 9
2.4
150
%Transmittance
120
H3C 7 CH3
100
110
3
5
2.2
2.1
2.0
1.9
6
1.8
1.7
6
1.6
1.5
1.4
10
1.3
1.2
1.1
30
25
1.0
ppm
0.9
13
13
C/DEPT NMR
NMR 150.9
600 MHz
C/DEPT
MHz
4 3
2
220
ppm
10
55
50
45
40
35
20
15
ppm

Problem 8.35B
ppm
F1
2.4
2.2
2.0
1.8
1.6
1.4
1.2
1.0
0.8
0.6
ppm
0.6
0.6
0.8
0.8
1.0
1.0
1.2
1.2
1.4
1.4
1.6
1.6
COSY 600 MHz
10
9
8
5
6
6
1.8
1.8
2.0
2.0
2.2
2.2
2.4
2.4
F2
HMQC 600 MHz
ppm
10
10
10
20
20
8
9
30
30
H3C 7 CH3
F1
3
2
40
40
1
10CH3
Camphor
C10H16O
Mol. Wt.: 152
50
5
6
3
7
50
1
2.4
2.2
2.0
1.8
1.6
F2
1.4
1.2
1.0
0.8
0.6
ppm

Problem 8.35C
INADEQUATE
INADAQUATE150.9
150.9MHz
MHz
2
Hz
9
-20000
-20000
H3C 7 CH3
-15000
-15000
3
2
-10000
-10000
10CH3
-5000
-5000
Camphor
C10H16O
Mol. Wt.: 152
F1 0
5000
5000
10000
220
200
180
160
140
120
100
F2
80
60
9 8
40
10000
ppm
20
Hz
7 43
10
-25000
-25000
-24000
-24000
-23000
-23000
-22000
-22000
F1
-21000
-21000
-20000
-20000
-19000
-19000
-18000
-18000
-17000
-17000
ppm
65
60
55
50
45
40
35
F2
30
25
20
15
10

Problem 8.36A
% of Base Peak
MASS
x 30
43
70
100
55
50
40
50
130
115
60
70
80
IR
m/z
90
100
110
120
130
1041
2962
1242
1743
50
4000
1373
1466
2877
%Transmittance
100
3000
2000
Wavenumber (cm-1)
1
H NMR 600 MHz
2350 Hz
2300 Hz
1000 Hz
850
Hz
1000
7 is doublet
6 is triplet
Hz
700
Hz
550
In the above insets each tick mark is 10 Hz
3.5
3.0
2.5
2.0
5
ppm
1.5
13
13
C/DEPT NMR
NMR 150.9
600 MHz
C/DEPT
MHz
O
3
H3C 2 O
CH3
7 CH3
5
4
2-Methylbuty acetate
C7H14O2
Mol. Wt.: 130
170 160 150 140 130 120 110 100
90
80
70
60
50
40
7 6
1
30
20
ppm

Problem 8.36B
ppm 4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
COSY 600 MHz

6
1.0
1.0
1.5
1.5
5
5
2.0
2.0
2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
F1
F2
HMQC 600 MHz
ppm
10
10
ppm
10
20
20
6
7
1
5
15
30
30
7
0.95
40
0.90
ppm
0.85
40
F1
O
50
50
3
4
H3C 2 O
60
CH3
60
7 CH3
2-Methylbuty acetate
C7H14O2
Mol. Wt.: 130
70
4.5
4.0
3.5
3.0
2.5
F2
2.0
1.5
70
1.0
ppm

Problem 8.37A
MASS
m/z
151 (M-1)
152 (M)
153 (M+1)
154 (M+2)
% of Base Peak
111
100
%M
37.5
100.0
12.7
5.2
152
50
83
69
50
60
70
80
90
IR
m/z
100
110
120
130
140
150
1234
1419
1651
3000
2000
Wavenumber (cm-1)
H NMR 600 MHz
725
957
50
4000
1
1057
3008
3093
%Transmittance
100
1000
7 and 8 are diastereotopic

78
Hz
4680
7.5
7.0
4260 Hz 1520
Hz
4560
Hz 740
720 Hz
Hz
600
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
ppm
1.5
13
13
C/DEPT NMR
NMR 150.9
600 MHz
C/DEPT
MHz
O
S
1
2
1
5
C
5
7
8
cyclopropyl(thiophen-2-yl)methanone
C8H8OS
Mol. Wt.: 152
7 8
6
4
180
160
140
120
100
80
60
40
20
ppm

Problem 8.37B
ppm
ppm
COSY 600 MHz

87
F1
F2
2
1
3
HMQC 600 MHz
ppm
20
20
O
S
40
1
2
60
40
60
cyclopropyl(thiophen-2-yl)methanone
C8H8OS
Mol. Wt.: 152
F1
78
80
80
100
100
120
120
2
3
1
F2
ppm
IR
164
121
70
80
90
100
m/z
110
120
130
149
136
103
91
77
50
60
140
150
160
3940
3920
2000
Wavenumber (cm-1)
Hz
3880
663
764
3000
1265
1412
1473
1550
1612
2962
50
H NMR 600 MHz
949
2870
3201
%Transmittance
100
4000
1
Problem 8.38A
100
65
% of Base Peak
MASS
1000
3860 Hz
9 10
Hz
3720
Hz
1280
320
Hz
300
OH
9
13
C/DEPT NMR 150.9 MHz
171.5
10
150
140
130
120
CH3
-Thujaplicin
C10H12O2
Mol. Wt.: 164
537
171.0 ppm
160
OH
H 3C 8
170
ppm
O
7
110
100
90
80
70
10
60
50
40
30
ppm

Problem 8.38B
ppm
1
2
ppm 6.8
6.6
6.4
6.2
ppm
ppm
9 10
6.2
6.4
1
2
36
6.6
F1
COSY 600 MHz
H 3C 8
10
CH3
9
-Thujaplicin
C10H12O2
Mol. Wt.: 164
F2
HMQC 600 MHz
ppm
20
20
9 10
ppm
40
40
7
3
5
125
60
60
130
F1 80
80
135
6
140
100
6.8
6.6
6.4
100
ppm
6.2
120
120
140
140
7
F2
OH
ppm
7
3
5
6

Problem 8.38C
INADEQUATE
600 MHz
INADEQUATE
150.9 MHz
4
9
10
Hz
-20000
-20000
-15000
-15000
-10000
-10000
-5000
-5000
F1
5000
5000
10000
10000
15000
15000
20000
20000
160
2 1
140
120
4
100
80
F2
60
40
3 7
20
ppm
Hz
0
5000
5000
F1
10000
10000
15000
15000
O
7
1
2
OH
20000
20000
5
175
170
165
160
155
3
4
H C 8 CH3
150 3 10
145 140
135
9
F2
-Thujaplicin
C10H12O2
Mol. Wt.: 164
130
125
120
115
ppm

Problem 8.39A
% of Base Peak
MASS
123
100
83
55
41
50
151
69
95
232
230
110
50
100
4000
3000
150
m/z
200
IR
1034
1219
1365
1442
1473
80
70
1751
90
2954
%Transmittance
100
2000
Wavenumber (cm-1)
1000
10
H NMR 600 MHz

8
2800
Hz
1350
1300
1250
1200
1150
1100
1050
4.5
4.0
3.5
3.0
H3 C
900
2.0
Hz
850
ppm
1.5
CH3
4
5
6
950
9
13
2.5
1000
Br
CH3 O
3-Bromocamphor
C10H15BrO
Mol. Wt.: 230
10
20.0
200
180
19.9
160
19.8
140
ppm
120
100
80
60
10
40
20
ppm

Problem 8.39B
ppm 5.0
F1
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
ppm
1.0
1.0
1.5
1.5
2.0
2.0
2.5
2.5
3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5
F2
COSY 600 MHz
10
8
6
6
5
5
4
HMQC 600 MHz
ppm
8
10
H3 C
20
6
CH3 O
3-Bromocamphor
C10H15BrO
Mol. Wt.: 230
F1
20
89
5
30
Br
10
30
10
10
CH3
40
40
7
50
50
3
1
60
60
5.0
4.5
4.0
3.5
3.0
F2
2.5
2.0
1.5
1.0
ppm

Problem 8.39C
INADEQUATE
150.9
INADEQUATE
600MHz
MHz
13
2
Hz
-20000
-20000
-15000
-15000
-10000
-10000
F1
-5000
-5000
5000
5000
200
180
3
160
4
140
120
100
6
F2
80
60
40
ppm
20
10
Hz
-25000
-25000
-24000
-24000
-23000
-23000
-22000
-22000
8
F1
H3 C
-21000
-20000
1
CH3
-21000
3
Br
CH3 O
3-Bromocamphor
C10H15BrO
Mol. Wt.: 230
-19000
10
-18000
-17000
60
55
50
45
40
35
F2
30
25
20
15
10
-20000
-19000
-18000
-17000
ppm

Problem 8.40A
% of Base Peak
MASS
FM (found) = 154.1351 154
108
100
81
71
139
111
93
55
50
136
50
60
70
80
90
m/z
IR
100
110
120
130
140
150
841
1080
987
4000
1
1219
1373
1466
50
2970
%Transmittance
100
3000
2000
Wavenumber (cm-1)
H NMR 600 MHz
1000
8,9
10
4,6
3,7
3,7
4,6
2
2.1
2.0
1.9
1.8
1.7
1.6
1.5
1.4
1.3
1.2
1.0 ppm
1.1
13
13
C/DEPT
MHz
C/DEPT NMR
NMR 150.9
600 MHz
6
10
CH3
7
4
3
5
2
O
CH3
8
9 CH3
75
Cineole
C10H18O
Mol. Wt.: 154
70
4,6
65
60
55
50
8,9
10
45
40
35
3,77
30
25
ppm

Problem 8.40B
ppm 2.2
2.0
1.8
1.6
1.4
1.2
1.0
ppm
1.0
1.0
1.2
1.2
1.4
1.4
1.6
1.6
1.8
1.8
2.0
2.0
COSY 600 MHz

10
8,9
2
3,7
4,6
F1
4,6
3,7
F2
HMQC 600 MHz
ppm
22
22
3,7
7 10
24
6
5
26
4
24
CH3
1
O
2
26
CH3
10
F1 28
9 CH3
28
Cineole
C10H18O
Mol. Wt.: 154
30
8,9
30
4,6
32
32
2
34
34
2.2
2.0
1.8
1.6
F2
1.4
1.2
1.0
ppm

Problem 8.41A
MASS
% of Base Peak
82
67
100
155
54
FM (found) = 155.0711 by CI
100
50
110
50
183
100
m/z
IR
50
160
195
170 180
m/z
190
903
1219
1790
4000
1
1450
50
1859
2862
2947
%Transmittance
100
3000
H NMR 600 MHz
2000
Wavenumber (cm-1)
O
1000
2
1
O
1,2-cyclohexanedicarb
oxylic acid anhydride
C8H10O3
Mol. Wt.: 154
3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4
ppm
13
13
C/DEPT NMR
NMR 150.9
600 MHz
C/DEPT
MHz
2
3
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
ppm

Problem 8.41B
ppm
3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2
1.5
ppm
COSY 600 MHz
1.5
2.0
2.0
2.5
2.5
3.0
3.0
F1
F2
HMQC 600 MHz
ppm
4
3
25
25
30
O
2
30
F1
35
O
1,2-cyclohexanedicarb
oxylic acid anhydride
C8H10O3
Mol. Wt.: 154
35
40
40
45
45
ppm
3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2
F2

Problem 8.42A
MASS
% of Base Peak
104
100
121
50
131
91
77
164
65
50
146
60
70
80
90
100 110
m/z
IR
130
140
150
160
5
6
100
OH
10
1720
50
OCH3
6 7
4400
4350
1000
10
Hz
2750
2700
Hz 2000
1950
Hz
1650
7.0
6.5
748
2000
Wavenumber (cm-1)
H NMR 600 MHz

8
972
3000
1-methoxy-2-indanol
C10H12O2
Mol. Wt.: 164
1088
4000
1350
1466
2831
2939
3402
%Transmittance
3
2
4
7
120
6.0
5.5
5.0
1600 Hz
4.5
4.0
3.5
OH
3.0
ppm
13
13
C/DEPT NMR
NMR 150.9
600 MHz
C/DEPT
MHz
3
10
140
130
120
110
100
90
80
70
60
50
40
ppm

Problem 8.42B
ppm 7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
ppm
COSY 600 MHz

3
3.0
3.0
6
4
3.5
4.0
3
2
3.5
OH
F1
4.5
1-methoxy-2-indanol
C10H12O2
Mol. Wt.: 164
5.0
10
4.0
10
OCH3
4.5
OH
2
1
5.0
5.5
5.5
6.0
6.0
6.5
6.5
7.0
7.0
F2
5 7
6
8
HMQC 600 MHz
ppm
3
40 ppm
40
58
126
60
10
60
128
130
7.4
80
7.3
7.2
ppm
80
1
F1
100
100
120
120
7.5
7.0
6.5
6.0
5.5
5.0
F2
4.5
4.0
3.5
3.0
ppm

Problem 8.42C
8
10
1
2
ppm
7.5
7.4
HMBC 600 MHz
7.3
7.2
7.1 ppm
4.5
4.0
3.5
OH
3.0
40
ppm
ppm
3
40
5
50
50
6
4
7
F160
9
8
3
2
10
OH
60
10
OCH3
1-methoxy-2-indanol
C10H12O2
Mol. Wt.: 164
70
70
80
80
90
90
F1
ppm
ppm
125
125
130
130
135
135
140
140
145
145
ppm
7.5
7.4
7.3
7.2
7.1 ppm
F2
4.5
4.0
3.5
3.0
94
8
7

Problem 8.43A
% of Base Peak
MASS
x 30
43
100
131
85
109
95
182
185
200
50
50
100
IR
150
m/z
200
100
HO
3000
H NMR
600 MHz
6
2000
Wavenumber (cm-1)
10
1000
11
Ethyl 3-hydroxy-3,6dimethylhept-6-enoate
C11H20O3
Mol. Wt.: 200
1260
1240
Hz
780
740 Hz
760
OH
4.5
887
O4000
1034
10
1188
1373
1458
1
C
1728
70
2978
H3C
3
11 4
80
3518
%Transmittance
90
4.0
3.5
3.0
2.5
2.0
ppm
1.5
13
13
C/DEPT
MHz
C/DEPT NMR
NMR 150.9
600 MHz
3
1
170
160
150
11
140
130
120
110
100
90
80
70
60
50
40
30
10
ppm

Problem 8.40A
ppm 5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.5
F1
ppm
1.5
2.0
2.0
2.5
2.5
3.0
3.0
6
3.5
3.5
4.0
COSY 600 MHz

11
10
4
5
2
OH
4.0
9
4.5
4.5
7
F2
HMQC 600 MHz
ppm
10
20
20
11
40
40
60
60
H3C
3
11 4
F1 100
1
C
2
5
10
80
120
C11H20O3
Mol. Wt.: 200
140
100
120
160
140
160
1
5.0
4.5
4.0
3.5
3.0
F2
HO
80
5
4
2.5
2.0
1.5
ppm

Problem 8.43C
HMBC 600 MHz

8
OH
10
11
ppm
10
20
8
11
30
5
4
40
50
9
60
70
F180
F1
HO
90
H3C
3
11 4
100
1
C
2
5
10
110
C11H20O3
Mol. Wt.: 200
120
130
140
150
160
170
5.0
4.5
4.0
3.5
F2
3.0
2.5
2.0
1.5
ppm

Problem 8.44A
MASS
% of Base Peak
121
100
136
50
93
65
178
149
50
100
IR
150
m/z
50
H NMR 600 MHz
2000
Wavenumber (cm-1)
841
3000
1173
1211
1281
4000
1597
1658
2962
3325
%Transmittance
100
1000
3
7
6
OH
8.0 7.8 7.6 7.4 7.2 7.0 6.8 ppm
3.0
2.5
2.0
ppm
1.5
13
13
C/DEPT
MHz
C/DEPT NMR
NMR 150.9
600 MHz
O
5
8
7
1
2
3
4
2
5
200
180
160
3
1
140
120
OH
4'-Hydroxy valerphenone
C11H14O2
Mol. Wt.: 178
100
80
60
40
8
7
ppm

Problem 8.44B
ppm
ppm
COSY 600 MHz

9
1
6
8
7
1
2
F1
OH
C11H14O2
Mol. Wt.: 178
6
OH
F2
3
2
HMQC 600 MHz
ppm
9
20
20
8
7
40
40
60
60
F1 80
80
100
100
120
120
2
F2
ppm

Problem 8.44C
HMBC 600 MHz
OH
ppm
8.0
7.5
7.0
ppm
3.0
2.5
2.0
1.5
1.0
15
ppm
ppm
15
6
O
5
20
8
7
20
F1
8
3
25
25
30
OH
C11H14O2
Mol. Wt.: 178
30
35
35
6
ppm
ppm
120
120
130
130
1
2
140
140
150
150
160
160
170
170
180
180
190
190
200
200
210
210
ppm
8.0
7.5
7.0
ppm
F2
3.0
2.5
2.0
1.5
1.0

Problem 8.45A
MASS
% of Base Peak
68
100
108
53
50
79
50
153
151
125
93
100
m/z
IR
168
150
50
7
3
887
933
H NMR 600 MHz
1242
2000
Wavenumber (cm-1)
5,4
7
4
1412
1442
1705
3000
2669
2893
2962
3078
%Transmittance
100
1000
5
10
1
2900
Hz
2850
1600
1550
x64
Hz
1200
1150
1100
Hz
1050
OH
ppm
12
4.5
4.0
3.5
3.0
2.5
2.0
1.5
5 10 4
1
ppm
9
C/DEPT
MHz
C/DEPT
NMR 150.9
600 MHz
H2CNMR
13
13
3
1
7
8
HO
2
6
CH3
10
O
2-((1R,2S)-1-methyl-2-(prop-1-en-2yl)cyclobutyl)acetic acid
C10H16O2
Mol. Wt.: 168
8
180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
ppm

Problem 8.45B
5.0
ppm
4.5
4.0
3.5
3.0
2.5
2.0
1.5
COSY 600 MHz
ppm
10
1.5
1.5
2.0
2.0
2.5
2.5
54
5,4
7
7
3
F1 3.0
3.0
3.5
3.5
4.0
4.0
4.5
4.5
9
5.0
5.0
F2
HMQC 600 MHz
ppm
20
H2C
40
20
H
4
1
7
8
HO
60
40
CH3
60
10
O
2-((1R,2S)-1-methyl-2-(prop-1-en-2yl)cyclobutyl)acetic acid
ppm
80 C10H16O2
Mol. Wt.: 168
F1
100
20
120
30
140
80
1
10
100
120
140
40
160
160
50
180
180
3.0
5.0
4.5
4
1 10
5
7
4.0
3.5
2.5
3.0
F2
2.0
2.5
1.5
2.0
ppm
1.5
ppm

Problem 8.45C
HMBC 600 MHz

9
1
3
5.0
ppm
4.8
ppm
2.6
7
2.4
2.2
5,4
2.0
4
1.8
10
5
1.6
1.4
1.2
ppm
4
20
1
25
9
H2C
30
10
H
3
1
7
8
HO 35
CH3
10
O
F1
2-((1R,2
S)-1-methyl-2-(prop-1-en-2yl)cyclobutyl)acetic acid
C10H16O2
40
Mol. Wt.: 168
7
6
45
50
ppm
150
8
5.0
4.8
ppm
2.6
2.4
F2
2.2
2.0
1.8
1.6
1.4
1.2
ppm

% of Base Peak
100
50
53
IR
91
77
122
65
50
60
70
80
90
100
110
m/z
120
151
148
133
130
140
166
150
160
787
1365
1466
%Transmittance
100
50
2916
1049
3332
4000
1
Problem 8.46A
105
MASS
3000
H NMR 600 MHz
2000
Wavenumber (cm-1)
1000
10
4
2180
2160 Hz
1440
1420
1400
1380
1360
1340
1320
1300
1280
1260
1240
1220 Hz
7
3
11
5.0
13
4.5
4.0
OH
3.5
3.0
2.5
2.0
1.5
ppm
1.0

10 11
CH2CH2OH
2
1
3
8
7
4
130
120
Nopol
C11H18O
Mol. Wt.: 166
140
11
110
100
90
80
5 10
4
7
70
60
50
40
30
ppm

Problem 8.46B
ppm 5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
COSY 600 MHz
ppm
1.0
1.0
1.5
1.5
2.0
2.0
4
7
5
10
2.5
2.5
4
9
F1 3.0
3.0
3.5
3.5
4.0
2
4.5
4.0
5.0
5.0
5.5
5.5
1
OH
11
4.5
F2
HMQC 600 MHz
ppm
10 11
20
8
7
20
CH2CH2OH
2
1
40
3
8
40
Nopol
C11H18O
Mol. Wt.: 166
60
F1
ppm
30
80
11
60
4
9
80
6
10
5
100
35
100
40
120
2.5
5.5
2
OH
5.0
4.5
4.0
3.5
2.4
3.0
F2
2.3
2.2
2.5
2.0
2.1
1.5
ppm
1.0
120
ppm

Problem 8.46C
INADEQUATE
MHz
INADEQUATE
150.9600
MHz
11
Hz
-15000
-15000
-10000
-10000
10 11
-5000
-5000
CH2CH2OH
2
F1
5000
3
8
7
4
5000
Nopol
C11H18O
Mol. Wt.: 166
10000
10000
15000
15000
140
130
120
110
10
100
90
F2
80
70
9 4
60
7
50
40
30
20
ppm
Hz
-16000
-16000
-14000
-14000
-12000
-12000
-10000
-10000
-8000
-8000
-6000
-6000
F1
-4000
-4000
-2000
-2000
2000
2000
4000
4000
45
40
35
F2
30
25
20
ppm

Problem 8.47A
% of Base Peak
MASS
105
100
277
100
77
50
136
154
50
FM (found) = 277.1083 by CI
100
150
IR
50
200
m/z
305
250
m/z
317
300
2877
2939
3000
H NMR 600 MHz

3
1281
1712
1751
4000
2000
Wavenumber (cm-1)
1000
12
10
4800
4700
4600
717
50
1072
3456
%Transmittance
100
10
OH
4500 Hz 3300
3200
O
3100
3000 Hz
1500
11
1400
Hz
1300
8 12
O 13
9
O
10
CO
12
8
O
C O
5
1
O
O
CH2OH
11
2200 Hz
2250
1750
1700 Hz
3.0
2.5
2
HOH
2C
4
5-(Benzoyloxy)hexahydro-4(hydroxymethyl)
C15H16O5
Mol. Wt.: 276
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
ppm

Problem 8.47B
ppm 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
ppm
COSY 600 MHZ

7
O
O 13
9
10
6
O
C O
5
41
12
8
7
11
CH2OH
11
2
4
F1 5-(Benzoyloxy)hexahydro-4(hydroxymethyl)
C15H16O5
Mol. Wt.: 276
9
6
6
O
C
O
O
7
3
HOH2C
COSY 600 MHZ
ppm
2.5
2.5
3.0
3.0
3.5
3.5
10
12
10
12
8
11
F1
4.0
4.0
4.5
4.5
5.0
5.0
5.5
5.5
5.5
5.0
4.5
4.0
3.5
F2
3.0
2.5
ppm
9
6

Problem 8.47C
13
2 3
13
180
170
160
3
129 ppm
130
150
140
77.5
130
11
8 1012
ppm
77.0
120
110
100
90
80
70
40 ppm
50
HMQC 600 MHz
11
60
ppm
O
40
O 13
9
10
50
C O
5
60
12
O
7
13
OH
HOH2C
CH2OH
11
11
13
70
4
8
6
12
8 10
F1805-(Benzoyloxy)hexahydro-4(hydroxymethyl)
C15H16O5
Mol. Wt.: 276
12 8
90
ppm
100
35
12
10
10
12
10
8
110
40
120
3.0
2.9
2.8
2.7
2.6
2.5
2.4
ppm
130
2
4
8.0
7.5
7.0
6.5
6.0
5.5
5.0
F2
4.5
4.0
3.5
3.0
2.5
ppm

Problem 8.47D
HMBC 600 MHz
2
4
ppm
8.2
8.0
7.8
7.6
40
7.4 ppm
11
5.0
4.5
4.0
12 8
3.5
3.0
10
7 OH
2.5
ppm
12
10
8
O
O 13
9
10
50
O
C
5 O
60
12
8
7
CH2OH
11
11
2
4
70
5-(Benzoyloxy)hexahydro-4(hydroxymethyl)
C15H16O5
Mol. Wt.: 276
80
F1
ppm
3
2
130
4
140
150
160
5
170
13
180
8.2
8.0
7.8
7.6
7.4 ppm
5.0
F2
4.5
4.0
3.5
3.0
2.5
ppm

Robert M. Silverstein, Francis X. Webster, David Kiemle-Solutions Manual For Spectrometric Identification of Organic Compounds-Wiley (2005)

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Robert M. Silverstein, Francis X. Webster, David Kiemle-Solutions Manual For Spectrometric Identification of Organic Compounds-Wiley (2005)

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Answers for Student Exercises 1.1 to 1.

Answers for Student Exercises 1.1 to 1.5

Answers for Student Exercises 1.1 to 1.5

Answers for Student Exercises 1.1 to 1.5

Index = (n) - (m/2) - (x/2) + (y/2) + 1 =

Answers for Student Exercises 1.1 to 1.5

Index = (n) - (m/2) - (x/2) + (y/2) + 1 =

Answers for Student Exercises 1.1 to 1.5

Index = (n) - (m/2) - (x/2) + (y/2) + 1 =

Index = (n) - (m/2) - (x/2) + (y/2) + 1 =

Answers for Student Exercises 1.1 to 1.5

Index = (n) - (m/2) - (x/2) + (y/2) + 1 =

Index = (n) - (m/2) - (x/2) + (y/2) + 1 =

Answers for Student Exercises 1.1 to 1.5

Index = (n) - (m/2) - (x/2) + (y/2) + 1 =

Answers for Student Exercises 1.6 to 1.11

Answers for Student Exercises 1.6 to 1.11

Answers for Student Exercises 1.6 to 1.11

Answers for Student Exercises 1.6 to 1.11

Answers for Student Exercises 1.6 to 1.11

7-Bromo Heptanoic Acid

Answers for Student Exercises 1.6 to 1.11

Answers for Student Exercise 2.1 2.9

Answers for Student Exercise 2.1 2.9

Methyl isothiocyanate CH3N=C=S

This diketone exists primarily (~ 90%) in enol form (in CCl4)

Answers for Student Exercise 2.1 2.9

7-Bromo Heptanoic Acid

Answers for Student Exercise 3.1 to 3.3

Answers for Student Exercise 3.1 to 3.3

(b) (cyclohex-2-enyl)methyl acetate

Answers for Student Exercise 3.1 to 3.3

Answers for Student Exercise 3.1 to 3.3

Coupled with Multiplet (n+1)

Answers for Student Exercise 3.1 to 3.3

Coupled with Multiplet (n+1)

Answers for Student Exercise 3.1 to 3.3

Coupled with Multiplet (n+1)

Answers for Student Exercise 3.1 to 3.3

(g) propyl methylcarbamate

Coupled with Multiplet (n+1)

Answers for Student Exercise 3.1 to 3.3

Coupled with Multiplet (n+1)

Answers for Student Exercise 3.1 to 3.3

Coupled with Multiplet (n+1)

Answers for Student Exercise 3.1 to 3.3

Actual spectrum would look like this!

Answers for Student Exercise 3.1 to 3.3

Answers for Student Exercise 3.1 to 3.3

3.1 (i) N.A.

Coupled with Multiplet (n+1)

Answers for Student Exercise 3.1 to 3.3

Answers for Student Exercise 3.1 to 3.3

Protocol of the H-1 NMR Prediction:

Comment (ppm rel. to TMS)

Answers for Student Exercise 3.1 to 3.3

Answers for Student Exercise 3.4

Answers for Student Exercise 3.4

Answers for Student Exercise 3.4

Answers for Student Exercise 3.4

Answers for Student Exercise 3.4

7-Bromo Heptanoic Acid

Answers for Student Exercise 3.4