ch08 solutions

CHAPTER 8 ASSIGNED PROBLEMS

MASS% of Base Peak 55 68

Problem 8.1

10041 112 84 97

50

40

50

60

70

IR100 %Transmittance

m/z O

80

90

100

110

1 2 3 4

502858 2927

Cycloheptanone C7H12O Mol. Wt.: 1121701 1342 1454 1161 856 941

400011

3000

2000 Wavenumber (cm-1)

1000

H NMR H NMR 300 MHz2 3

4

2.71313

2.6

2.5

2.4

2.3

2.2

2.1

2.0

1.9

1.8

1.7

1.6

1.5 ppm

C/DEPT C/DEPT NMR 75.5 MHz

2

4

3

1

200

180

160

140

120

100

80

60

40

ppm


MASS% of Base Peak

Problem 8.2124

10094

50

53

66

81

95

50

60

70

80

IR1004

m/zOH3

90

100

110

120

2 1 6 7

%Transmittance

50

5

OCH31493 1601 1284 687 768 837 945 1041 1149

m-Methoxyphenol C 7H 8 O 2 Mol. Wt.: 124

3398

2839 2947 3005

40001 1

3000


1000

H NMR H NMR 300 MHz5 6 4

2

7

2150

2140

Hz

1960

1950

Hz

1930

1920 Hz

OH

7.513 13

7.0

6.5

6.0

5.5

5.0

4.5

4.0

3.5

ppm

C/DEPT C/DEPT NMR 75.5 MHz

4 1 3 5

3 2

7

1 190 180 170 160 150 140 130 120 110 100

90

80

70

60

50

40

ppm


MASS55 % of Base Peak

Problem 8.3M-1 83 39 41 M 53 65 66 84

100 50

40

45

50

55


m/z

60

65

70

75

80

85

503332 2877 2939 2978 2229 2291 1454 1138 1227 1319 1014 741

40001 1

3000


1000

H NMR 300 MHz H NMR

5 11280 1260 Hz 680 660 Hz

4 OH

4.013 13C/DEPT

3.5

3.0

2.5

2.0

1.5

ppm

C/DEPT NMR 75.5 MHz

HO H 2C1

4

C2

C3

CH25 CH3

3

CDCl3

2-Pentyn-ol C5 H 8 O Mol. Wt.: 84

5 4

1 278.0 77.5 77.0 76.5 ppm

95

90

85

80

75

70

65

60

55

50

45

40

35

30

25

20

ppm



Problem 8.4CI Reagent gas methane110 49 61 77 99 97 112 M 114 148 146 111 x 30 113 146 75 77 115 148 150 152

100 50

100 50

50

IR100 %Transmittance 90 80 70

m/z

100

150Cl Cl 1 CH 3 Cl CH2 2 CH2 1,2,3-Trichloropropane C3H5Cl3 Mol. Wt.: 1462962 3016

100

m/z

150

1435

1219 1288

910

663 717

40001 1H

3000

H NMR 300 MHz NMR


1000

1+3

2

4.3513 13C/DEPT

4.30

4.25

4.20

4.15

4.10

4.05

4.00

3.95

3.90

3.85

3.80

ppm

C/DEPT NMR 75.5 MHz

1+3 2

75

70

65

60

55

50

45

ppm


MASS% of Base Peak

Problem 8.5m/z 126 (M) 127 (M+1) 128 (M+2) %M 100.0 8.2 4.9

111

100 5039 43 49 57 83

126

40

50

60

70


80 m/z

90

100

110

120

130

50

3089

1662

1415

1273

856 933 1061

725

590

40001 1

3000


1000

H NMR 300 MHz H NMR3 1 2 6

2300

2280 Hz

2140

2120 Hz

4

5ppm

7.513 13 C/DEPT

7.0

6.5

6.0

5.5

5.0

4.52 1

4.0

3.5

3.0

2.5

C/DEPT NMR 75.5 MHz

3

S

4

O5 6 CH3

1

3

2

Ethanone, 1-(2-thienyl)2-Acetylthiophene C6H6OS Mol. Wt.: 126

6

5

4

190 180 170 160 150 140 130 120 110 100

90

80

70

60

50

40

ppm


MASS% of Base Peak 105

Problem 8.6x 10 186 184 51 77

100 50

IR100 90 %Transmittance 80 70

50

100

m/z

150

2985 3032

1450 1496

1211

964

594 694 764

40001

3000

H NMR 300 MHz3


1000

2

41590 Hz 640 630 620 Hz 1580 1570 Hz

6

2260

2250

2240

2230

2220

2210

2200

5

7.513

7.0

6.5

6.0

5.5

5.0H3C6

4.5Br

4.0

3.5

3.0

2.5

ppm

C/DEPT NMR 75.5 MHz

5 1

2 3 4

4 3 1140 130 120 110 100

2

(1-Bromoethyl)benzene C8H9Br Mol. Wt.: 184

5

6

90

80

70

60

50

40

30 ppm


MASS% of Base Peak

Problem 8.7109 124 81 53 63 75

100 50

50

60

70

80


m/z

90

100

110

120

50

3348

2835 2951

1859

1512 1612 1701

1234

1034

733 825

513

40001 1

3000


1000

H NMR 300 MHz H NMR2 3 5

OH

7.013 13

6.5

6.0

5.5

5.0OH4 3 2 1

4.5

4.0

3.5

ppm

C/DEPT NMR 75.5 MHz C/DEPT

OCH35

3 1 4

2

p-Methoxyphenol C 7H 8 O 2 Mol. Wt.: 124

5

150

140

130

120

110

100

90

80

70

60

50

ppm


MASS% of Base Peak

Problem 8.8128

10064 130 92 73

50

50

60

70

80


m/z

90

100

110

120

130

50

3464 3521

3039 3074

1200 1338 1454 1481 1585

1030

679 748

40001 1 H

3000

H NMR 300 MHz NMR3 6 5 4

2000 Wavenumber (cm-1) OH1 6 5 4 2 3

1000

Cl

OH

o-Chlorophenol C6H5ClO Mol. Wt.: 128

7.413 13

7.2

7.0

6.8

6.6

6.4

6.2

6.0

5.8

5.6

5.4

ppm


5 3

4

6

1

2

155

150

145

140

135

130

125

120

115

ppm


MASS% of Base Peak 55 87 73

Problem 8.9x 20 115 196 194 135 137 163 165

100 50 0 50 100 %Transmittance

100

IR

m/z

150

50

2954

1736

1365 1435

1203

748

40001 1 H

3000

H NMR 300 MHz NMR6Br5 4

2000 Wavenumber (cm-1)O6 3 2 1

1000

O

5

Methyl 5-bromo valerate C6H11BrO2 Mol. Wt.: 194

2 4 3

3.613 13

3.4

3.2

3.0

2.8

2.6

2.4

2.2

2.0

1.8

1.6

ppm


5 2

4 6

3

1

33.0

32.5

32.0

ppm

170 160 150 140 130 120 110 100

90

80

70

60

50

40

30

ppm



Problem 8.1067 84 93 111 126

100 50

50

60

70

80


m/z

90

100

110

120

3344

2873 2931 2958

1466

1331

1045

849

40001 1 H

8

30007 6

H NMR 300 MHz NMR

2000 4 5 1 OH Wavenumber (cm-1) 23

1000

3-Octyn-1-ol C8H14O Mol. Wt.: 126

8 6 7

1

2

5

OH

3.513 13 C/DEPT

3.0

2.5

2.0

1.5

1.0

ppm

C/DEPT NMR 75.5 MHz

1

6 2 7

5

8

84

82

80

78

ppm

485 80 75

370 65 60 55 50 45 40 35 30 25 20 ppm


MASS% of Base Peak

Problem 8.11162 164 98 73 126 128

10063

50

50

60

70

80

90


100 110 m/z

120

130

140

150

160

503521 3097 1188 1277 1404 1477 1585 725 814 555

40001 1 H

3000

H NMR 300 MHz NMR3 6 5

2000 Wavenumber (cm-1)OH1 6 5 4 2 3

1000

Cl

OH

7.413 13 C/DEPT

7.2

7.0

6.8

6.6

Cl 2,4-Dichlorophenol C6H4Cl2O Mol. Wt.: 162 6.4 6.2 6.0

5.8

5.6

5.4

5.2 ppm

C/DEPT NMR 75.5 MHz

3 1

5

6

4

2

155

150

145

140

135

130

125

120

115

ppm

CHAPTER 8 ASSIGNED PROBLEMS Problem 8.12

MASS% of Base Peak

123 95 75 50 63 138

100 50


50

60

70

80

90 m/z

100

110

120

130

140

50

3356

3005 3074

1597 1685

1157 1265 1358

841 960

567

40001

3000

2000 Wavenumber (cm-1)1

100019

H NMR 300 MHz2 3 6

F NMR 282.4 MHz

H Coupled

1

H Decoupled

2400

2390

2380

Hz

2140

2130

Hz

8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.013

ppm5 1

-104.4COCH32 3 4 6

-104.5 ppm

C/DEPT NMR 75.5 MHz

2

3

F 4-Fluoroacetophenone C8H7FO Mol. Wt.: 138130 128 126 124 122 120 118 ppm

6

5

4 1

190 180 170 160 150 140 130 120 110 100

90

80

70

60

50

40

ppm


MASS% of Base Peak

Problem 8.1396

100 5050

70

75 77

50

55

60

65


70 m/zF1 2 3

75

80

85

90

95

953749 3062

4

Fluorobenzene C 6H 5 F Mol. Wt.: 96

1504 1604 1697

1234

756

40001 1H

3000

2000 Wavenumber (cm-1)19

1000

NMR H NMR 300 MHz

F NMR 282.4 MHz1

H Coupled

3

2 4

7.413 13

7.3

7.2

7.1

ppm

-80.1

-80.2

-80.3 ppm


3 4130 128 126 124 122 120 118 116 ppm

2

1165 160 155 150 145 140 135 130 125 120 115 ppm



Problem 8.14

100 50138 67 95 123

54

50

60

70

80


90 m/z

100

110

120

130

140

502870 2958 1670 1381 1246 903 525

40001 1 H

3000

H NMR 300 MHz NMR


1000

6 4

7

89

1750

1740 Hz

640

Hz

570

560 Hz

300

290

Hz

2ppm

6.013 13

5.5

5.0

4.5

4.0

3.5

3.0

2.57

2.0

1.5

C/DEPT NMR 75.5 MHz C/DEPT4 9

CH33 2 5 6 1

H 3C H3 C8

O

89 6 4 5

2 1200 180

Isophorone C9H14O Mol. Wt.: 138

7

3160 140 120 100 80 60 40

ppm



Problem 8.15

50

68 81 79 93 95 107 109 119 121

149 147

50

60

70

80

90


m/z

100

110

120

130

140

150

2245

1435

1250

756

40001 1

3000

H NMR 300 MHz H NMR4Br4 3

2000 Wavenumber (cm-1) 22 1

1000

N 4-Bromobutanoyl nitrile C4H6BrN Mol. Wt.: 147

3

3.613 13

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

2.2

ppm


3 4 1120 110 100 90 80 70 60 50 40 30 20

2

ppm



Problem 8.16

100 5077 137

50

60

70

80

IR100 %Transmittance 90 803348 3194 2931

m/z

90

100

110

120

130

140

1442 1512 1620

1049

825

40001 1H

3000

H NMR 300 MHz NMR3 25 4


1000

6 OH3 2 ppm

5

7.513 13

7.0

6.5

6.0

5.5

5.0

4.5OH

4.0

3.5

3.0

2.5

2.0

1.5 ppm


6

5 1 2 3

OH

2

3

4

NH2 p-Aminophenylethanol C8H11NO Mol. Wt.: 137

6

5

4140

1130 120 110

100

90

80

70

60

50

40

ppm


MASS% of Base Peak

Problem 8.17119

100 50

64 76

91

50

60

70


80 m/z

90

100

110

120

2245

1481 1589

1342

671 787

40001 1H

3000

H NMR 300 MHz NMR2


1000

3

OH

7.613 13

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

ppm

C/DEPT NMR 75.5 MHz C/DEPT2 5 3 4 1

N

C

OH

p-Cyanophenol C7H5NO Mol. Wt.: 119

2

3

4

5

1115 110 ppm

165

160

155

150

145

140

135

130

125

120


MASS% of Base Peak

Problem 8.18163

100 5077 91 135 178

50

100


m/z

150

50

3572

2870 2962

1458

1149 1203

748

40001 1

3000


10006

H NMR 300 MHz H NMR

3

2150

2100 Hz

1000

950 Hz

450

400

Hz

4

OH

51.5 ppm

7.013 13C/DEPT

6.5

6.0

5.5

5.0

4.5

4.0

3.56 2 3 4 5

3.0

2.5

2.0

C/DEPT NMR 75.5 MHz

OH1

6

3 4 1150 140

2,6-Diisopropyl phenol C12H18O Mol. Wt.: 178

6 5

2130 120 110 100 90 80 70 60 50 40 30 20 ppm


MASS% of Base Peak

Problem 8.19106 78 121

100 5051

50

60

70


80 m/z

90

100

110

120

50

3363

3047

1689

1419

1273

957

702

40001 1H

3000

H NMR 300 MHz NMR5

2

2000 Wavenumber (cm-1) 3

1000

4 7

2720

2700 Hz

2600

2580 Hz

2440

2420 Hz

2200

2180 Hz

9.013 13C/DEPT

8.5

8.0

7.5

7.0

6.5

6.0

5.5

5.03 4 5

4.5

4.0

3.5

3.0

ppm

C/DEPT NMR 75.5 MHz

2 1 7 6

N

C O

CH3

5 6

4

3 1

2

2-Acetylpyridine C7H7NO Mol. Wt.: 121

7

190 180 170 160 150 140 130 120 110 100

90

80

70

60

50

40

ppm


MASS% of Base Peak

Problem 8.20108 123

100 5053 80

40

50

60

70

80


m/z

90

100

110

120

50

3109

2947

1651

1404

1095

633 741

40001 1H

3000

H NMR 300 MHz NMR


1000

5

7

4

2060 3

Hz

2020

Hz 1820

Hz

2

7.013 13

6.5

6.0

5.5

5.0

4.5

4.0

3.5

3.0

2.5

ppm

C/DEPT NMR 75.5 MHz C/DEPT3 4 2 1 7 6

N

CH3

4 1 6180 160 140

2

3

H3C5

O

1-Methyl-2-acetylpyrrole C7H9NO Mol. Wt.: 123

5

7

120

100

80

60

40

ppm


MASS% of Base Peak 43 x 20 85 159

Problem 8.21CI Reagent gas methane 100103 158

100 5057

50 50 100 150 150 m/z

187


m/z

502962 1651 1720 1319 1034 1149

40001 1

3000


1000

H NMR 300 MHz H NMR7 1 3 5 6

3.513 13C/DEPT

3.0

2.5

2.0

1.5

1.0

ppm

C/DEPT NMR 75.5 MHz7 1 2 3 4

O

5

6 7

O O Isobutylacetoacetate C8H14O3 Mol. Wt.: 158

5

3 1

6

7

2

4

200

180

160

140

120

100

80

60

40

ppm


MASS% of Base Peak

Problem 8.22119

100 50

64 76

91

50

60

70

80

IR100 90 %Transmittance 80 703309

m/z

90

100

110

120

2245

1481 1589

1342

671 787

40001 1

3000

H NMR 600 MHz 30042 5 64 5

2000 Wavenumber (cm-1) OH3 2 1 6 7

1000

C

N

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

6.2

ppm

13 13 C/DEPT

NMR 75.5 MHz C/DEPT NMR 600 MHz

5 3

6

4

2

7155 150 145 140 135 130 125 120 115

1

ppm


MASS% of Base Peak 183 185 200 198

Problem 8.23x 20

100 5075 155 157

224

226

264 262 260

100


150 m/z

200

250

50

3356

2962 3059 3089

1396 1485 1585 1685

1223

995 1068

810

617

40001 1H

3000

H NMR 300 MHz NMR2 3

2000 Wavenumber (cm-1)6 8 5

1000

7

7.9

7.8

7.7

7.6

ppm

3.6

3.4

3.25 1 2 3 4 6

3.07 8

2.8

2.6

2.4

ppm

13 13C/DEPT

C/DEPT NMR 75.5 MHz

COCH2CH2CH2Cl

3 5 1

2

Br 4Bromo-4-chlorobutyrophenone C10H10BrClO Mol. Wt.: 260

6

7

8

4

190 180 170 160 150 140 130 120 110 100

90

80

70

60

50

40

ppm


MASS% of Base Peak

100 55 69 74 83 147

100 50

CI Reagent gas methane

128

50175 187

50 m/z

100

150

150

m/z

200


50

2978 3039

2669

1709

1238 1277 1419 1466

930

40001 1H

3000

H NMR 300 MHz NMR2x OHx64


1000

4 3 2

6

1213 13C/DEPT

11

ppm

2.6

2.4

2.2

2.0

1.8

1.6

1.4

1.2 ppm

C/DEPT NMR 75.5 MHzO HO 12

CH2 C 5 CH CH2 OH CH36 4

3

O

15

2-Methyl glutaric Acid C6H10O4 Mol. Wt.: 146

2

4 3

6

180 170 160 150 140 130 120 110 100

90

80

70

60

50

40

30

ppm


MASS% of Base Peak

91

92

CI Reagent gas methane 100 5093

100 5066 51

50

60

IR100 %Transmittance 90 80

m/z

70

80

90

80

m/z

90

2962 3055

1720

1342

1065

725 802

40001

3000


1000

H NMR 300 MHz1

2

3

2050

2040

Hz

1090

1080 Hz

615 610 605

Hz

7.013

6.5

6.0

5.5

5.0

4.5

4.0

3.5

3.0

2.5

2.0

ppm

C/DEPT NMR 75.5 MHz

3

2

1

1

Bicyclo[2,2,1] hepta-2-5-diene C7 H 8 Mol. Wt.: 92

2

3

140

130

120

110

100

90

80

70

60

50

ppm


MASS% of Base Peak

Problem 8.26

M 156 M+2

10063

5098 121

158

50

60

70

80

90

IR100

100 110 m/z

120

130

140

150

160

586

%Transmittance

2900

50

933 1041

802

1234

1473

40001

3000

H NMR 600 MHz6 4


1000

3

7

6.8513 13

6.803 4 5

6.75

6.70

6.65

ppm

6.00 5.95

ppm

C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz2

O7

Cl

1 6

O

5-chloro-1,3-benzodioxole C7H5ClO2 Mol. Wt.: 156

4

36

7

1155 150

2145 140 135 130

5

125

120

115

110

105 ppm


MASS% of Base Peak 42 55

Problem 8.27A

100 5084 70 114

40

50

60

70


m/z

80

90

100

110

50

2931

1728

1442

1057 1165

856

571

400011

3000O2 1


1000

H NMR 300 MHz H NMR63 4

1O6 5

2 3 5

4

-Caprolactone C6H10O2 Mol. Wt.: 114

4.013 13 C/DEPT

3.5

3.0

2.5

2.0

1.5

ppm

C/DEPT NMR 75.5 MHz

6 1

43 2 5

170

160

150

140

130

120

110

100

90

80

70

60

50

40

ppm

CHAPTER 8 ASSIGNED PROBLEMS Problem 8.27B

ppm 4.5

4.0

3.5

3.0

2.5

2.0

1.5

ppm

COSY 300 MHz

1.5 2.02

1.5O1

41 2 3 4 5 6

2.0O6

5 3

2.5

3 4 5

2.5 3.0 3.5 4.0

2

F13.0 3.5 4.0


6

F2ppm6 2 5 4 3

HETCOR 75.5 MHz HETCO 300 MHz

1.5 2.0 2.5

1.5 2.0 2.5 3.0 3.5 4.0 4.5 ppm

F13.0 3.5 4.0 4.5 65 60 55 50 45 40 35 30 25

F2


MASS% of Base Peak 55 x 10 82 90 92 120 118

Problem 8.28ACI Reagent gas methane

100 50 50

69

137

5

139


m/z

100

130

m/z

140

150

50

3332

2862 2939

1458

1057

648 725

40001

3000

H NMR 600 MHz1 6


1000

HO 1

2

3

4

5 6

Cl

1-Hexanol-6-chloro C6H13ClO Mol. Wt.: 136

5

2

4 3

OH

3.613 13 C/DEPT

3.4

3.2

3.0

2.8

2.6

2.4

2.2

2.0

1.8

1.6

1.4 ppm

C/DEPTNMR 600 MHz NMR 150.9 MHz

1

6

5

2

4

3

60

55

50

45

40

35

30

25

ppm


ppm

3.5

3.0

2.5

2.0

1.5

ppm

COSY 600 MHz

1.5

1.5

2.0HO 12 3 4 5 6

2.0Cl

F1

2.5

1-Hexanol-6-chloro C6H13ClO Mol. Wt.: 136

2.5

3.0

3.0

3.5

3.5

1

6

ppm

OH

F2

5

2 4 3

HMQC 600 MHz

25 30 35 405 2 OH

254

3

30 35 40 45 50 55 33 2.0 1.8 2.5 1.6 1.4 2.0 ppm 1.5 601 6

F145 50 55 60

ppm 32

3.5

3.0

ppm

F2



Problem 8.29A

100 5045 67 55 69 81 110 113 128

50

60

70

80


m/z

90

100

110

120

130

503344 2924 2966 1377 1450 1041 1126 825

400011

3000


1000

H NMR H NMR 300 MHz7 8

1

1540

Hz

1140

Hz

500

480 Hz

440

Hz

3 4 OH

5

2

5.013 13 C/DEPT

4.5

4.0

3.5

3.0

2.5

2.0

1.5

ppm

C/DEPT NMR 75.5 MHz

7 5 8 6 4 3

OH2 1

5 6

6-Methyl-5-hepten-2-ol C8H16O Mol. Wt.: 128

2

3 8

4

1 7

130

120

110

100

90

80

70

60

50

40

30

20 ppm


ppm 5.5 1.0 1.5 2.0 2.5

5.0

4.5

4.0

3.5

3.0

2.5

2.0

1.5

1.0 ppm 1.0

COSY 300 MHz1

1.5 2.0 2.5 3.0 3.5

3 OH 4

7 8

F1 3.03.5 4.0 4.5 5.084 1 7

2

4.0 4.5 5.05

5

F2 2

3

HETCOR 75.5 MHz HETCO 300 MHz

ppm 1.07

1.55

OH4 3 2 1

2.0 2.5

8

6

6-Methyl-5-hepten-2-ol C8H16O Mol. Wt.: 128

F1

3.0 3.5 4.0 4.5 5.0 5.5 120 100 80 60 40 20 ppmOH

F2


MASS88 % of Base Peak 223 225

Problem 8.30ACI Reagent gas methane 100251 253 143 159 177 179 50 194 263 265

10069

50 0

50 100

100

m/z

150

230

IR

240 250 m/z

260

%Transmittance

502870 2939 1736 1458 1188 1034

400011 H

3000

H NMR 300 MHz NMR 600 MHz


1000

8

7

6

2

5

3

4

4.013 13 C/DEPT

3.5

3.0

2.5

2.0

1.5

ppm

NMR 600 MHz C/DEPT NMR 75.5 MHz

Br

6

5

4

3

2

1

O

7

8

2,6,5 7

4 3 8

O

1

Ethyl 6-Bromohexanoate C8H15BrO2 Mol. Wt.: 222

170 160 150 140 130 120 110 100

90

80

70

60

50

40

30

ppm


ppm 1.0

4.0

3.5

3.0

2.5

2.0

1.5

1.0

ppm 1.0

COSY 300 MHz8 4 3 5 2

1.5

1.5

2.0

2.0

F1

2.51 1

2.5

3.0

3.06

3.5

3.57

4.07

4.0

F2 2 6 5 4 3

8

HETCOR 75.5 MHz HETCO 300 MHz1.0

ppm 1.0Br6 5 3 1

4

2

O

7

8

8 4 3 5 2

O 1.5 Ethyl 6-Bromohexanoate C8H15BrO2 Mol. Wt.: 222 2.0

1.5

2.0

F1 2.53.0

2.5

3.06

3.5

3.57

4.0 60 55 50 45 40 35 30 25 20 15

4.0 ppm

F2


MASS% of Base Peak

Problem 8.31A134

10041 94

50

65

77

91 105

119

40

50

60

70

80


m/z

90

100

110

120

130

502866 2916 3032 3066 1496 1601 1242 690 752

40001

3000


1000

H NMR 600 MHz3 4 2 5

3680

3660

Hz 3300

3280

Hz 3220

3200

Hz

2760

2740

Hz

6

7

7.413 13

7.2

7.0

6.8

6.6

6.4

6.2

6.0

5.8

5.6

5.4

5.2

5.0

4.8

ppm

C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz5 1 2 6 7

OCH2CH=CH2

3 4 1 6 7

24

3

Allylphenyl ether C9H10O Mol. Wt.: 134

5

160

150

140

130

120

110

100

90

80

70

ppm


ppm 7.5 4.5

7.0

6.5

6.0

5.5

5.0

4.5

ppm 4.5

COSY 600 MHz

5.0

5.0

5.5

5.5

F16.0 6.0

6.5

6.5

7.0

7.0

3

4

2 65 6 7

F2

ppm 70 80 90 1004

7

5

HMQC 600 MHz

OCH2CH=CH21 2 3

70 80 90 100diastereotopic

5

Allylphenyl ether C9H10O Mol. Wt.: 134

F1 110120 130 140 150

1102

120 1306

7

4 3

140 1501

7.5

7.0

6.5

6.0

5.5

5.0

4.5

ppm

F2

CHAPTER 8 ASSIGNED PROBLEMS Problem 8.32A

MASS% of Base Peak 95 x 20

100 5055 67 110 109 121 139 136 154

50

60

70

80

90


100 m/z

110

120

130

140

150

50

3317

2877 2951

1712

1365

1227

1057

829

40001

3000

H NMR 600 MHz

2000 Wavenumber (cm-1) 3

1000

8 9 10

OH

2400

Hz

1350 Hz 1150

Hz 1050

Hz

950 Hz

750

Hz

550 Hz

500 Hz

2

In the above insets each tick mark is 10 Hz 3

6

5 4

5 6

3

4.013 13

3.5

3.0

2.5

2.0

1.5

ppm

C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz10 9

H 3C6 5 4

CH37 1

8 2

CH3

3 OH

2

Borneol C10H18O Mol. Wt.: 154

4

3

5

6

9 10

8

1 7

75

70

65

60

55

50

45

40

35

30

25

20

15 ppm


ppm

4.0

3.5

3.0

2.5

7 2.0

1.5

1.0

ppm

COSY 600 MHz9.10,8 3 5 6

1.0 1.5 2.0

1.0 1.5 2.010 9

OH 5 6 3

4

F12.5 3.05

H 3C6 4

CH37 1

2.5 3.0 3.5 4.02

8 2

CH3

3 OH

3.5 4.0

Borneol C10H18O Mol. Wt.: 154

F2ppm ppm 20 15 30 20 40 25 0.90diastereotopic

HMQC 600 MHz8

20 30 40 50 60 702 7 1

10 9 6 5

3 4

F150 60 70

0.85

ppm

4.0

3.5

3.0

2.5

2.0

1.5

1.0

ppm

F2



Problem 8.33A

100 50

57

70

114

50

60

70

IR100

m/z

80

90

100

110

656

2885 2970

1358 1466

%Transmittance

972

50

1180

1774

40001

3000

H NMR 600 MHz6 5 3 4 2 1


1000

6

4

O

O

2 3 3 5 5


4.013 13

3.5

3.0

2.5

2.0

1.5

1.0

ppm

C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHz

2 4

5

3 6

1

29

28

ppm

180

160

140

120

100

80

60

40

20

ppm


ppm 4.5 1.0 1.5 2.0

4.0

3.5

3.0

2.5

2.0

1.5

1.0

ppm 1.0 1.53

COSY 600 MHz6

5

2.03

F1 2.56

2.53 4 5 2 1

2

3.0 3.5 4.0

O

O

3.0 3.5 4.04


F2ppm 10 20 30diastereotopic

HMQC 600 MHz6

10 20 30ppm

40

403 5 22.5 2.0 1.5 ppm

F1 5060 70 80

28

50 60 70 804

30

4.5

4.0

3.5

3.0

2.5

2.0

1.5

1.0

ppm

F2



Problem 8.34A69 55 81 95 109 123 138 156

100 50

40

50

60

70

80

90


m/z

100

110

120

130

140

150

160

503332 2924 1381 1450 1057 833

40001

3000HO1

H NMR 600 MHz

2000 9 10 Wavenumber (cm-1) CH3 CH36 2 3 4 5 7

1000

9

8 10

CH38

Citronellol C10H20O Mol. Wt.: 156

6

1

5 OH3.5 3.0 2.5 2.0

3

2

4

5.013 13

4.5

4.0

1.5

1.0

ppm


6 7

9

5 1 24 3

8

1026 25 ppm

130

120

110

100

90

80

70

60

50

40

30

20 ppm


ppm 5.5 1.0 1.5 2.0 2.5

5.0

4.5

4.0

3.5

3.0

2.5

2.0

1.5

1.0

ppm

COSY 600 MHz10 4 2 OH 5 3 8 9

1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0

F1

3.0 3.5 4.0 4.5 5.0

1

6

F2ppmHO1 2 10 9 6

HMQC 600 MHz10

20 CH33

CH37

20

8 95 3 4 2

40 4 5 Citronellol C10H20O Mol. Wt.: 156 60

CH38

40

60 ppm

1

F1 8020 100 30 40 2.0 1.5 1.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 ppm 1.0

80

100

120

1207

6

ppm

F2



Problem 8.35A81 41 55 69 108 152 137

100 50

50

60

70

80


90 100 m/z9

110

120

130

140

150

H3C 7 CH35 6 1 10CH3 4 3

8

1273

748

1450

2

1041

502954

O1743

Camphor C10H16O Mol. W 152 t.:

40001

3000


1000

H NMR 600 MHz

8 9

10

3

4 52.2 2.1 2.0 1.9

3 61.8 1.7 1.6 1.5

61.4

5

2.413 13

2.3

1.3

1.2

1.1

1.0

0.9

ppm


4 3 2 1 7

6

5

9

8

10

220

ppm

55

50

45

40

35

30

25

20

15

ppm


ppm 0.6 0.8 1.0 1.2

2.4

2.2

2.0

1.8

1.6

1.4

1.2

1.0

0.8

0.6

ppm 0.6 0.8 1.0 1.2 1.4 1.6

COSY 600 MHz

10 9 8 5 6 6

F1

1.4 1.6 1.8 2.0 2.2 2.4

1.8 2.0 2.2 2.43 5 4

3

F2ppm 10 10

HMQC 600 MHz

10

20

20

8 9 5 6

30

9

F140

H3C 7 CH35 6 1 10CH3 4 3 2

8

30

40O

4 3 7

50


501

2.4

2.2

2.0

1.8

1.6

1.4

1.2

1.0

0.8

0.6

ppm

F2

CHAPTER 8 ASSIGNED PROBLEMS Problem 8.35C

INADEQUATE 150.9 MHz INADAQUATE 150.9 MHz2Hz9 8

1

3

-20000 -15000 -10000 -5000

H3C 7 CH35 6 1 10CH3 4 3 2

-20000 -15000 -10000

O

F1 05000 10000 220 Hz


-5000 0 5000 10000 ppm

200

180

160

140

120

F2

100

80

60

40

20

1-25000 -24000 -23000 -22000

7 43

6

5

9 8

10-25000 -24000 -23000 -22000 -21000 -20000 -19000 -18000 -17000 ppm

F1-21000 -20000 -19000 -18000 -17000 65 60 55 50 45 40 35

F2

30

25

20

15

10

5



Problem 8.36Ax 30 70 55 115 130

100 50 40 50

60

70

80

IR100

m/z

90

100

110

120

130

1373 1466

%Transmittance

2877 2962

1041

50 4000 3000 2000 Wavenumber (cm-1) 1

1242

1743

1

1000 7 is doublet

H NMR 600 MHz

6 is triplet

2350 Hz

2300 Hz

1000 Hz

850

Hz

700

Hz

550

Hz

3

In the above insets each tick mark is 10 Hz 4 51.5

5ppm

3.513 13

3.0

2.5

2.0


O3

H3C 2 O1

4

5

6

CH3

7 CH3

3 5 4 1 7 6

2

2-Methylbuty acetate C7H14O2 Mol. Wt.: 13090 80 70 60 50 40

170 160 150 140 130 120 110 100

30

20

ppm


ppm 4.5

4.0

3.5

3.0

2.5

2.0

1.5

1.0

ppm

COSY 600 MHz6

1.0 1.5 2.0

1.0 1.5 2.0 2.5 3.0 3.53 5 5 4 1 7

F12.5 3.0 3.5 4.0

4.0

F2ppm 10ppm 10

HMQC 600 MHz

106

6 7 1 5

20 30 4015

20 30

70.95 0.90 0.85 ppm

4

40 504 5 6

F150 60 701

O3

H3C 2 O

CH3

7 CH3

60 703

2-Methylbuty acetate C7H14O2 Mol. Wt.: 130

4.5

4.0

3.5

3.0

2.5

2.0

1.5

1.0

ppm

F2



Problem 8.37Am/z 151 (M-1) 152 (M) 153 (M+1) 154 (M+2) %M 37.5 100.0 12.7 5.2

100 5069 83

152

50

60

70

80

90

IR1003008 3093

m/z

100

110

120

130

140

150

%Transmittance

1057

501419 1234 1651

957

725

40001

3000


1000

H NMR 600 MHz

7 and 8 are diastereotopic 78

4680

Hz

4560

Hz

4260 Hz 1520

Hz 740

720 Hz

600

Hz

3

1

2

6

7.513 13

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

C/DEPT NMR 600 MHz C/DEPT NMR 150.9 MHzO S1 2 3 4

C5

6 8

7

1 5180 160

3

2

cyclopropyl(thiophen-2-yl)methanone C8H8OS Mol. Wt.: 152

7 8 6

4140 120 100 80 60 40 20 ppm


ppm 1 2 3 4 5 6 7 8

8

7

6

5

4

3

2

1

ppm 1 2

COSY 600 MHz87

6

3 4 5 6 7 82 1 3

F1

F2ppm

HMQC 600 MHz

20S4 3

O C5 6 8 1 2 7

20

6

78

40

40

60

F180

cyclopropyl(thiophen-2-yl)methanone C8H8OS Mol. Wt.: 152

60

80

100

100

120

1202 3 1

8

7

6

5

4

3

2

1

ppm

F2

CHAPTER 8 ASSIGNED PROBLEMS% of Base Peak 121

MASS100103 77 91

Problem 8.38A164 136

60

70

80

90

100

m/z

110

120

130

140

150

149

65

50

160

IR%Transmittance

1002870 663 764

949

3201

2962

1265 1412 1473 1550 1612

50

40001

3000


1000

H NMR 600 MHz3 6

7

5

8

9 10

3940

3920

Hz

3880

3860 Hz

3720

Hz

1280

Hz

320

300

Hz

OH

913

8

7

6

5

4

3

2

1

ppm

C/DEPT NMR 150.9 MHz7 6 5 1

O2 3 4

OH

2

1 6 537

H 3C 810

CH39

9 8

10

171.5

171.0 ppm

4

-Thujaplicin C10H12O2 Mol. Wt.: 164

170

160

150

140

130

120

110

100

90

80

70

60

50

40

30

ppm


ppm

7

6

5

4

3

2

1

ppm

COSY 600 MHz9 10O

1 2 3

ppm 6.8

6.6

6.4

6.2

ppm

15 7

6.2 6.4 6.6

2 3

86

7

1 2 3 4

OH

F14 5 6 7

36

5

4 5 6 7

H 3C 810

CH39

-Thujaplicin C10H12O2 Mol. Wt.: 164

F2ppm 20 40 60ppm

HMQC 600 MHz

209 10

407 3 5

8

125 130

60 80

F1 80100 120 140 7

135

6140 6.8 6.6 6.4 6.2 ppm

100 120 140

7 3 5 6

6

5

4

3

2

1

ppm

F2


INADEQUATE 600 MHz INADEQUATE 150.9 MHz4Hz -20000 -15000 -10000 -5000 -20000 -15000 -10000 -5000 0 5000 10000 15000 20000 160 2 1 Hz 0 0 140 120 4 100 80 60 40 3 7 20 ppm

8

9 10

F1

0

5000 10000 15000 20000

F2

6

5

5000

5000

F110000 10000

150007 6 1

O2 3 4

15000

OH20000

200005

175

170

165

160

155

H C 8 CH3 150 3 10 145 140 135 9

F2 -Thujaplicin

130

125

120

115

ppm

C10H12O2 Mol. Wt.: 164


MASS% of Base Peak

Problem 8.39A123 83 55 151 69 95 110 232 230

100 5041

50

100

m/z

150

200

IR100 %Transmittance 90 802954 1219 1365 1442 1473 1034

70

1751

40001

3000


1000

H NMR 600 MHz8

10 9

2800

Hz

1350

1300

1250

1200

1150

1100

1050

1000

950

900

850

Hz

3

4

5

5

6

6

4.513

4.0

3.5

3.09 8 7

2.5

2.0

1.5

ppm

C/DEPT NMR 150.9 MHz

H3 C5 6

CH34 3

1 10

2

Br

8

9

CH3 O 3-Bromocamphor C10H15BrO Mol. Wt.: 230

3

4

6

5

10

2

20.0

19.9

19.8

ppm

1

7ppm

200

180

160

140

120

100

80

60

40

20

CHAPTER 8 ASSIGNED PROBLEMS Problem 8.39Bppm 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

COSY 600 MHz

1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5

1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5

9 8 6 6 5 5 4

10

F1

3

F2ppm 109 8 7

HMQC 600 MHz

H3 C5 6

CH34 3

10

10

20

1 10

2

20Br

89 5 6

30

F140


30

40

750 50

4 3 1

60 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0

60 ppm

F2


INADEQUATE 150.9 MHz INADEQUATE 600 MHz2Hz

13

-20000 -15000 -10000

-20000 -15000 -10000 -5000 0 5000

F1-5000 0 5000

200

1Hz

180 3

160 4

140

120

7

F2

100 6

80

60

40

5

20 10

ppm

-25000 -24000 -23000 -22000

-25000 -24000 -23000 -220009 8 7

F1-21000 -20000

H3 C5 6

CH34 3

-21000 -20000 -19000 -18000 -17000 ppm

1 10

2

Br

-19000 -18000 -17000 60 55 50 45 40 35


F2

30

25

20

15

10

5


MASS% of Base Peak

Problem 8.40A108 81 71 93 111 139 55 136FM (found) = 154.1351 154

100

50

50

60

70

80

90

IR100

m/z

100

110

120

130

140

150

841

%Transmittance

1373 1466

1080

1219

502970

987

40001

3000

H NMR 600 MHz


1000

8,9 4,6 3,7

10

3,7

4,6 2

2.113 13

2.0

1.9

1.8

1.7

1.6

1.5

1.4

1.3

1.2

1.1

1.0 ppm

C/DEPT NMR 150.9 MHz C/DEPT NMR 600 MHz6 7 4 3 2 5 1 10

CH3 O CH38

9 CH3

4,6 2

8,9 10

3,7 7

1

5

Cineole C10H18O M Wt.: 154 ol.

75

70

65

60

55

50

45

40

35

30

25

ppm


ppm 2.2 1.0

2.0

1.8

1.6

1.4

1.2

1.0

ppm 1.0

COSY 600 MHz10

1.2

1.22

8,9

1.4

1.4

3,7 4,6

4,6

F11.6 1.6

1.8

1.83,7

2.01 4 5 6

2.0

F2ppm

HMQC 600 MHz

22 246 7 10

223,7

24 26

CH31 O 2

264

5 3

CH38

F1 2830 32 34 2.2 2.0

10

9 CH3

28 30

Cineole C10H18O M Wt.: 154 ol.

8,9

4,6

322

34 1.8 1.6 1.4 1.2 1.0 ppm

F2



10054

67

CI Reagent gas methane155

100110

FM (found) = 155.0711 by CI

50 50 160183 195

50

IR100

m/z

100

170 180 m/z

190

1450

%Transmittance

2862 2947

50

1859 1790

1219

903

40001

30003 4

H NMR 600 MHz2

2000 Wavenumber (cm-1) O2 1

1000

4

O O 1,2-cyclohexanedicarb oxylic acid anhydride C8H10O3 Mol. W 154 t.:

3

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 1.413 13

ppm


2 3 1 4

170

160

150

140

130

120

110

100

90

80

70

60

50

40

30

ppm


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

ppm

COSY 600 MHz

1.5

1.5

4

3

2.0

2.0

F12.5 2.5

3.0

3.0

2

F2ppm

HMQC 600 MHz

4 3

25O2 1

25

3

30

4

30O

F135O 1,2-cyclohexanedicarb oxylic acid anhydride C8H10O3 Mol. W 154 t.:

35

40

40

2

45 3.4 3.2 3.0 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2

45 ppm

F2



100121

5065

77

91

131 164 146

50

60

70

80

906

IR100 %Transmittance7

100 110 m/z5 4 9 8 1 3 2

120

130

140

150

160

1720

OH

502831 2939 3402

OCH31350 1466 972

10

1-methoxy-2-indanol C10H12O2 Mol. Wt.: 164

748

1088

40001

3000


1000

H NMR 600 MHz8 6 7 5

10

4400

4350

Hz

2750

2700

Hz 2000

1950

Hz

1650

1600 Hz

1

2

3

OH

3

7.013 13

6.5

6.0

5.5

5.0

4.5

4.0

3.5

3.0

ppm


9

4

6

7

8

5 1

2 10

3

140

130

120

110

100

90

80

70

60

50

40

ppm


ppm 7.5 3.0

7.0

6.5

6.0

5.5

5.0

4.5

4.0

3.5

3.0

ppm

COSY 600 MHz3 OH 3 10

5 6 4 7 8 9 1 3 2

3.0 3.5OH

3.5 4.0 4.5

OCH3

10

4.0 4.5 5.0 5.5 6.0 6.5 7.05 7 6 8 2 1

F1

5.0 5.5 6.0 6.5 7.0

1-methoxy-2-indanol C10H12O2 Mol. Wt.: 164

F2ppm 40 ppm58126

HMQC 600 MHz3

407 10

60

128 130

6067.4 7.3 7.2 ppm

80

801

2

F1100 100

120

120

7.5

7.0

6.5

6.0

5.5

5.0

4.5

4.0

3.5

3.0

ppm

F2

CHAPTER 8 ASSIGNED PROBLEMS Problem 8.42C 8 6 7 5 1 2 3 OH 3 10

HMBC 600 MHz

ppm 40

7.5

7.4

7.3

7.2

7.1 ppm

4.5

4.0

3.5

3.0

ppm ppm 403

50

5 6 4 7 9 8 1 3 2

5010OH

F16070

OCH3 1-methoxy-2-indanol C10H12O2 Mol. Wt.: 164

10

60

702

80

801

90

90 ppm

F1ppm

125

125

5

8 7

130

130

6

135

135

140

140

94

145 7.5 7.4 7.3 7.2 7.1 ppm 4.5 4.0 3.5 3.0

145 ppm

F2



Problem 8.43Ax 30 85 95 131 109 182 185 200

100 50 50

100

IR100 90 %Transmittance 80 701 C O 9 10

m/z

150

200

HO

3518

2978

1728

1373 1458

1188

1034

887

H3C 3 11 41

2 5

O 4000

3000

H NMR 600 MHz 68


1000

7

10

11 8

Ethyl 3-hydroxy-3,6dimethylhept-6-enoate C11H20O3 Mol. Wt.: 200

9 7

1260

1240

Hz

780

760

740 Hz

2 OH 5

4

4.513 13

4.0

3.5

3.0

2.5

2.0

1.5

ppm

C/DEPT NMR 150.9 MHz C/DEPT NMR 600 MHz

7 3 1 6

9

2

4

5 11

8

10

170

160

150

140

130

120

110

100

90

80

70

60

50

40

30

ppm


ppm 5.0

4.5

4.0

3.5

3.0

2.5

2.0

1.5

ppm

COSY 600 MHz11 10 4 5 2 8

1.5 2.0 2.5

1.5 2.0 2.5 3.06

F1

3.0 3.5 4.0 4.5

3.5 4.0

OH

9

4.57

F2ppm

HMQC 600 MHz10

20 40 60 80HO H3C 3 11 4 2 5 6 7 8 1 C O O 9 10

2011

8 5 4 2 9 3

40 60 80 100 120 140 1601 6

F1 100120 140 160

7


5.0

4.5

4.0

3.5

3.0

2.5

2.0

1.5

ppm

F2


HMBC 600 MHz7 9 8 OH 2 5 4 10 11

ppm10

20 30 40 50 60 709 11

8 5 4 2

3

F180F1

90 100 110 120 130 140

HO H3C 3 11 4 2 5 6 7 8 1 C O O 9

10

7


6

150 160 1701

5.0

4.5

4.0

3.5

F2

3.0

2.5

2.0

1.5

ppm



Problem 8.44A

100136

50

65

93

149

178

50

100


m/z

150

50

3325

2962

1597 1658

1173 1211 1281

841

40001

3000

H NMR 600 MHz3 2


1000

9 7 6 OH

8

8.0 7.8 7.6 7.4 7.2 7.0 6.8 ppm13 13

3.0

2.5O5 1 2 3 4 6 7

2.08 9

1.5

ppm

C/DEPT NMR 150.9 MHz C/DEPT NMR 600 MHz

2 5 4

3 1

OH 4'-Hydroxy valerphenone C11H14O2 Mol. Wt.: 178

6

8 7

9

200

180

160

140

120

100

80

60

40

ppm


ppm 1 2 3 4 5 6 7 8

8

7

6

5

4

3

2

1

ppm 1

COSY 600 MHz9 8 7 6

O5 1

6 7 2 3 4

8 9

2 3 4 5 6OH

F1


7 8

3 2

F2ppm

HMQC 600 MHz9

20

207 6

8

40

40

60

60

F1 80100

80

1003

120

1202

8

7

6

5

4

3

2

1

ppm

F2

CHAPTER 8 ASSIGNED PROBLEMS Problem 8.44C 2 3 6 OH 7 8

HMBC 600 MHz9

ppm

8.0

7.5

7.0

ppm

3.0

2.5

2.0

1.5

1.0

ppm ppm

15O6 5 1 2 7 8 9

15

9

20

208

F1254

3

257

30


30

35

356

ppm 120 130 140 150 160 170 180 190 200 210 8.0 7.5 7.0 ppm 3.0 2.5 2.0 1.5 1.0

ppm 120 130 140 150 160 170 180 190 200 210 ppm5 4 1

3

2

F2



Problem 8.45A

100108

50 0

53 79 93 125 153 151 168

50 100

IR

100 m/z

150

%Transmittance

50

2893 2962 3078

2669

1705

1412 1442

1242

887 933

30001

H NMR 600 MHz7 3

2000 Wavenumber (cm-1) 5,4 7 4

1000

5 1 10

2900

2850

Hz

1600

1550

Hz

1200

1150

1100

1050

Hz

x64

9

OH

1213 13

ppmH

4.5

4.0

3.5

3.0

2.5

2.0

1.5

ppm

9 C/DEPTC C/DEPT NMR 150.9 MHz H2 NMR 600 MHz 3 1 7 8 2 6 10 5 4

HO

CH3

O 2-((1R,2S)-1-methyl-2-(prop-1-en-2yl)cyclobutyl)acetic acid C10H16O2 Mol. Wt.: 168 8

9

3

7 6

5 10 4 1

2

180 170 160 150 140 130 120 110 100

90

80

70

60

50

40

30

ppm


ppm

5.0

4.5

4.0

3.5

3.0

2.5

2.0

1.5

ppm

COSY 600 MHz10

1.5 2.0 2.5

1.5 2.0 2.53 54 5,4 7 7

1

F1 3.03.5 4.0 4.5 5.0

3.0 3.5 4.0 4.59

5.0

F2ppm 20 409

HMQC 600 MHz204 1 10 5 7 3

H2C1 7 8 2

H3 6 10 4 5

40 60 801 10

O 2-((1R,2S)-1-methyl-2-(prop-1-en-2yl)cyclobutyl)acetic acid ppm 80 C10H16O2 M Wt.: 168 ol.

HO 60

CH3

F1

100 120 140 160

20

100 120 140 160

9

30

40

50

1803.0 2.5 2.0 1.5 ppm

180

5.0

4.5

4.0

3.5

3.0

2.5

2.0

1.5

ppm

F2


HMBC 600 MHz9 3ppm 5.0 4.8 ppm

1 72.4 2.2

10

7

5,4

41.8

51.6 1.4 1.2 ppm

2.6

2.0

420

1259

H2C 301 7 8 2

10H3 6 10 4 5

5

HO 35

CH3

F1 O 2-((1R,2S)-1-methyl-2-(prop-1-en-2yl)cyclobutyl)acetic acid C10H16O2 40 Wt.: 168 Mol.6

7

45

50

3

ppm

9 2 85.0 4.8 ppm 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2 ppm

150

F2


MASS% of Base Peak

105

Problem 8.46A

100 5053 65 91 122 133 151 148 166

77

50

60

70

80

90

100

110 m/z

120

130

140

150

160

IR%Transmittance

100787

1365 1466

503332 2916

1049

40001

3000

H NMR 600 MHz4


1000

10 9 9 5 1

2180

2160 Hz

1440

1420

1400

1380

1360

1340

1320

1300

1280

1260

1240

1220 Hz

7 3 11 OH 4

8

5.013

4.5

4.0

3.5

3.0

2.5

2.0

1.5

1.0

ppm

C/DEPT NMR 150.9 MHz10 11

CH2CH2OH2 1 8 9 5 6 7 4 3

3 2

11

Nopol C11H18O M Wt.: 166 ol.

1

5 10

9

4 7 8

6

140

130

120

110

100

90

80

70

60

50

40

30

ppm


ppm 5.5 1.0 1.5 2.0 2.5

5.0

4.5

4.0

3.5

3.0

2.5

2.0

1.5

1.0

ppm

COSY 600 MHz8

1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.54

4 7 5 10 9

F1 3.03.51 OH

11

4.0 2 4.5 5.0 5.5

3

F2ppm 201 10 11

HMQC 600 MHz

CH2CH2OH2 3 8 9 5 6 7 4

206

8 7

40

40

1

60

F180

Nopol C11H18O M Wt.: 166 ol.

60ppm 30

11

4 9 6 10 52.5 2.4 2.3 2.2 2.1 ppm

80

35

10040

100

120 5.5 2OH

120 ppm

3

5.0

4.5

4.0

3.5

3.0

2.5

2.0

1.5

1.0

F2

CHAPTER 8 ASSIGNED PROBLEMS Problem 8.46CINADEQUATE 600 MHz INADEQUATE 150.9 MHz

2Hz -15000 -10000 -5000

3

11

1

-15000 -1000010 11

CH2CH2OH2 1 8 6 5 7 4 9 3

-5000 0 5000 10000 15000

F1

0

5000 10000 15000 140 130 120 110 10

Nopol C11H18O M Wt.: 166 ol.100 90 80 70 60 7 50 40 30 20

1Hz -16000 -14000 -12000 -10000 -8000 -6000

5

6

F2

ppm

9 4

8

-16000 -14000 -12000 -10000 -8000 -6000 -4000 -2000 0 2000 4000 45 40 35 30 25 20 ppm

F1-4000 -2000 0 2000 4000

F2


MASS% of Base Peak

105

CI Reagent gas methane277

100 100 5077 136 154

FM (found) = 277.1083 by CI305 317

50 200 250

50

100

150

IR100

m/z

m/z

300

2877 2939

%Transmittance

3456

50

717

1072

1712 1751

1281

40001

3000

H NMR 600 MHz3 4


1000

2

6

9

12

10 10OH

7

4800

4700

4600

4500 Hz 3300

3200 OO 13

3100

3000 Hz

1500

1400

1300

Hz

11

8 12

O10

9 8 6 7 11

12

C O O O C 51

O O2250 2200 Hz 1750 1700 Hz

CH2OH

2 HOH2C 4 3

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

3.0

2.5

ppm


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 2.5O O 13

ppm

COSY 600 MHZ7

3O

9 10 6 8 7 11

12

311

4 14 3

C O 52

CH2OH

4

F1 5-(Benzoyloxy)hexahydro-4(hydroxymethyl)C15H16O5 Mol. Wt.: 276

5

5

9 6

6O C O O HOH2C O

6

7

74 3 2

8

8

ppm 2.5 2.5

COSY 600 MHZ7 10 12 10 12 8

3.0

3.0

3.5

3.511

F14.0 4.0

4.5

4.5

5.0

5.0

9 6

5.5 5.5 5.0 4.5 4.0 3.5 3.0 2.5

5.5 ppm

F2

CHAPTER 8 ASSIGNED PROBLEMS Problem 8.47C13

C/DEPT NMR 150.9 MHz

1130 129 ppm

2 3 477.5 77.0 ppm

9

6

11

7

8 1012

13180

5170

2

160 3

150

140

130

120

110

100

90

80

70

60

50

40 ppm

4

6

9

11

HMQC 600 MHz7

ppmO

409

O 1310 8 6 7

O O O O

C

12 8 10 13 7 11 13 6 12 8 12 10 10 9

12

50O

60 704 3

C O 51 2

11

CH2OH

OH HOH2C

F1 5-(Benzoyloxy)hexahydro-480 (hydroxymethyl)C15H16O5 Mol. Wt.: 276

90 100 110

ppm 35

12 10 83.0 2.9 2.8 2.7 2.6 2.5 2.4 ppm

40

120

3 2 4

130

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

F2

CHAPTER 8 ASSIGNED PROBLEMS Problem 8.47D 2 4

HMBC 600 MHz3 6 9 11 12 8 10 7 OH

ppm

8.2

8.0

7.8

7.6

7.4 ppm

5.0

4.5

4.0

3.5

3.0

2.5

ppm

40O 139

O

12 10 8

50O C

10 6 5 O

12 8 7 11

7 11

CH2OH

604

1 2 3

70

5-(Benzoyloxy)hexahydro-4(hydroxymethyl) C15H16O5 Mol. Wt.: 276

6 9

80

F1ppm 130

1 4

3 2

140

150

160

5170

13180 8.2 8.0 7.8 7.6 7.4 ppm 5.0 4.5 4.0 3.5 3.0 2.5 ppm

F2

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