Midterm 1 MPS

Question 1

CH. 12 Recommended Probs

65a

Answer 1

See CH.12 Rec. Problem Solutions

Question 2

CH. 12 Recommended Probs

45o

Answer 2

See CH.12 Rec. Problem Solutions

Question 3

Give the HNMR chemical shift range typical of this FG

Iodoalkane

Answer 3

3.1-3.3 ppm

Question 4

There is a “gap” at around 5.2 ppm in HNMR of alkenes where there is little to no activity. What is important about this “gap”?

Answer 4

This “gap” can be used to determine if an alkene is internal or terminal.

Since H’s attached to the terminal end of alkenes have a ppm shift of 4.6-5.2 ppm, you can assume that any signals to the left of this gap are H’s attached to the terminal end of an alkene (and thus, that the alkene is terminal).

Since H’s attached to the internal end of of alkenes have a ppm shift of 5.2-6.0 ppm, you can assume that any signals to the right of this gap are H’s attached to the internal end of an alkene.

Question 4

CH. 11 Recommended Problems

30c

Answer 4

See CH. 11 Recommended Probs Key

Question 5

SP2010 MT1

2i

Answer 5

See key

Question 6

See Properties of Alkenes & pi-bonds

2

Answer 6

See key

Question 7

SP2010 MT1

3g

Answer 7

See key

Question 8

See NMR Practice Problems

15

Answer 8

See key

Question 8

See NMR Practice Problems

23

Answer 8

See key

Question 8

CH. 12 Recommended Probs

45e

Answer 8

See CH.12 Rec. Problem Solutions

Question 8

CH. 12 Recommended Probs

64b

Answer 8

See CH.12 Rec. Problem Solutions

Question 8

SP2013 MT1

7d

Answer 8

See solutions

Question 9

Give the HNMR chemical shift range typical of this FG

Bromoalkane

Answer 9

3.4-3.6 ppm

Question 10

CH. 11 Recommended Problems

30d

Answer 10

See CH. 11 Recommended Probs Key

Question 11

Give the HNMR chemical shift range typical of this FG

Chloroalkane

Answer 11

3.6-3.8 ppm

Question 11

CH. 12 Recommended Probs

49m

Answer 11

See CH.12 Rec. Problem Solutions

Question 11

CH. 12 Recommended Probs

49o

Answer 11

See CH.12 Rec. Problem Solutions

Question 11

CH. 12 Recommended Probs

60b

Answer 11

See CH.12 Rec. Problem Solutions

Question 11

CH. 11 Recommended Problems

29d

Answer 11

See CH. 11 Recommended Probs Key

Question 11

CH. 11 Recommended Problems

37c

Answer 11

See CH. 11 Recommended Probs Key

Question 11

Workshop Spectroscopy Practice #1-26

26

Answer 11

See key

Question 11

Alicia PS #1

2c

Answer 11

See key

Question 13

CH. 12 Recommended Probs

44b

Answer 13

See CH.12 Rec. Problem Solutions

Question 14

# Workshop Spectroscopy Practice #1-26 11

Answer 14

See key

Question 15

# CH. 12 Recommended Probs 57a

Answer 15

See CH.12 Rec. Problem Solutions

Question 15

# CH. 12 Recommended Probs 57b

Answer 15

See CH.12 Rec. Problem Solutions

Question 15

# CH. 11 Recommended Problems 37e

Answer 15

See CH. 11 Recommended Probs Key

Question 16

# See Properties of Alkenes & pi-bonds 1

Answer 16

See key

Question 17

# SP2013 MT1 2b

Answer 17

See solutions

Question 18

What is the IR wavenumber range for **Aromatics**?

Answer 18

~3030 cm^-1

Question 18

What is the IR wavenumber range for **-CC- Alkynes**?

Answer 18

2100-2260 cm^-1

Question 18

# Give the HNMR chemical shift range typical of this FG Aromatic (Benzene-H)

Answer 18

6.5-9.5 ppm, usually 7-8 ppm

Question 18

# CH. 12 Recommended Probs 42a

Answer 18

See CH.12 Rec. Problem Solutions

Question 19

# CH. 12 Recommended Probs 46j

Answer 19

See CH.12 Rec. Problem Solutions

Question 20

# CH. 12 Recommended Probs 49c

Answer 20

See CH.12 Rec. Problem Solutions

Question 21

# See NMR Practice Problems 19

Answer 21

See key

Question 21

# CH. 12 Recommended Probs 64a

Answer 21

See CH.12 Rec. Problem Solutions

Question 21

# SP2010 MT1 1a

Answer 21

See key

Question 21

# SP2010 MT1 2h

Answer 21

See key

Question 22

# CH. 12 Recommended Probs 59b

Answer 22

See CH.12 Rec. Problem Solutions

Question 23

**Alcohol (-OH)** For the above FG, give the following: 1. Wavenumber range 2. Signal characteristics (strong, broad, sharp, etc)

Answer 23

1. 3400-3650 cm^-1 2. Broad, strong

Question 23

# CH. 11 Recommended Problems 30i

Answer 23

See CH. 11 Recommended Probs Key

Question 24

# CH. 11 Recommended Problems 55a

Answer 24

See CH. 11 Recommended Probs Key

Question 25

# CH. 12 Recommended Probs 41a

Answer 25

See CH.12 Rec. Problem Solutions

Question 25

# CH. 12 Recommended Probs 49f

Answer 25

See CH.12 Rec. Problem Solutions

Question 25

# CH. 12 Recommended Probs 53e

Answer 25

See CH.12 Rec. Problem Solutions

Question 25

# CH. 12 Recommended Probs 57c

Answer 25

See CH.12 Rec. Problem Solutions

Question 25

# CH. 11 Recommended Problems 66b

Answer 25

See CH. 11 Recommended Probs Key

Question 26

# CH. 11 Recommended Problems 31b

Answer 26

See CH. 11 Recommended Probs Key

Question 27

# Alicia PS #1 4

Answer 27

See key

Question 28

# Give the HNMR chemical shift range typical of this FG Next to aromatic (Benzene-CH)

Answer 28

2.2-2.5 ppm

Question 28

# Workshop Spectroscopy Practice #1-26 19

Answer 28

See key

Question 29

# CH. 12 Recommended Probs 45p

Answer 29

See CH.12 Rec. Problem Solutions

Question 30

# CH. 12 Recommended Probs 34

Answer 30

See CH.12 Rec. Problem Solutions

Question 30

# CH. 11 Recommended Problems 33

Answer 30

See CH. 11 Recommended Probs Key

Question 30

# Alicia PS #1 1b

Answer 30

See key

Question 30

# Alicia PS #1 2e

Answer 30

See key

Question 30

# SP2013 MT1 3b

Answer 30

See solutions

Question 30

# SP2013 MT1 3h

Answer 30

See solutions

Question 30

# SP2010 MT1 3e

Answer 30

See key

Question 31

# See Alkene Nomenclature PS 16

Answer 31

See key

Question 32

# CH. 11 Recommended Problems 41g

Answer 32

See CH. 11 Recommended Probs Key

Question 33

# CH. 11 Recommended Problems 51a

Answer 33

See CH. 11 Recommended Probs Key

Question 34

# CH. 11 Recommended Problems 29b

Answer 34

See CH. 11 Recommended Probs Key

Question 35

# CH. 11 Recommended Problems 43

Answer 35

See CH. 11 Recommended Probs Key

Question 36

# Give the HNMR chemical shift range typical of this FG Ester

Answer 36

3.5-4.5 ppm

Question 36

# SP2010 MT1 1f

Answer 36

See key

Question 36

# SP2010 MT1 9

Answer 36

See key

Question 37

# CH. 11 Recommended Problems 34c

Answer 37

See CH. 11 Recommended Probs Key

Question 38

# SP2010 MT1 7c

Answer 38

See key

Question 39

# Workshop Spectroscopy Practice #1-26 2

Answer 39

See key

Question 40

# CH. 11 Recommended Problems 51e

Answer 40

See CH. 11 Recommended Probs Key

Question 41

# See NMR Practice Problems 3

Answer 41

See key

Question 41

# CH. 12 Recommended Probs 66b

Answer 41

See CH.12 Rec. Problem Solutions

Question 41

# CH. 11 Recommended Problems 55c

Answer 41

See CH. 11 Recommended Probs Key

Question 42

# CH. 12 Recommended Probs 39

Answer 42

See CH.12 Rec. Problem Solutions

Question 44

# CH. 11 Recommended Problems 55b

Answer 44

See CH. 11 Recommended Probs Key

Question 45

# CH. 11 Recommended Problems 51f

Answer 45

See CH. 11 Recommended Probs Key

Question 46

# Workshop Spectroscopy Practice #1-26 23

Answer 46

See key

Question 47

# CH. 12 Recommended Probs 40c

Answer 47

See CH.12 Rec. Problem Solutions

Question 47

# CH. 12 Recommended Probs 46d

Answer 47

See CH.12 Rec. Problem Solutions

Question 47

# CH. 11 Recommended Problems 34d

Answer 47

See CH. 11 Recommended Probs Key

Question 47

# Alicia PS #1 5

Answer 47

See key

Question 48

# See NMR Practice Problems 13

Answer 48

See key

Question 49

# CH. 12 Recommended Probs 58b

Answer 49

See CH.12 Rec. Problem Solutions

Question 50

# CH. 11 Recommended Problems 32a

Answer 50

See CH. 11 Recommended Probs Key

Question 51

# SP2013 MT1 3a

Answer 51

See solutions

Question 53

# SP2013 MT1 1f

Answer 53

See solutions

Question 54

# Give the HNMR chemical shift range typical of this FG Ether/Alcohol

Answer 54

3.3-4.0 ppm

Question 54

# CH. 12 Recommended Probs 62

Answer 54

See CH.12 Rec. Problem Solutions

Question 56

# See NMR Practice Problems 22

Answer 56

See key

Question 57

What is the IR wavenumber range for **C=C benzene double bonds**?

Answer 57

1660-2000 cm^-1 and 1450-1600 cm^-1

Question 58

# CH. 11 Recommended Problems 37d

Answer 58

See CH. 11 Recommended Probs Key

Question 59

# See Alkene Nomenclature PS 6

Answer 59

See key

Question 60

# See Alkene Nomenclature PS 12

Answer 60

See key

Question 61

Give the coupling constant (J) and coupling pattern for geminal, *trans*-vicinal, *cis*-vicinal, allylic and alkane H-coupling.

Answer 61

* _Geminal:_ 0-3 Hz; doublet (d) * _*trans-*vicinal:_ 10-18 Hz, usually ~16 Hz; doublet (d) * *_cis-_*_vicinal:_ 6-14 Hz, usually ~10 Hz; doublet (d) * _Allylic:_ 0-3 Hz; doublet (d), triplet (t) or quartet (q) * _Alkane:_ 4-10 Hz, usually ~7 Hz; doublet (d), triplet (t), or quartet (q)

Question 63

# CH. 12 Recommended Probs 50

Answer 63

See CH.12 Rec. Problem Solutions

Question 64

# SP2013 MT1 4

Answer 64

See solutions

Question 65

# Alicia PS #1 2b

Answer 65

See key

Question 66

# CH. 12 Recommended Probs 42c

Answer 66

See CH.12 Rec. Problem Solutions

Question 68

# See NMR Practice Problems 11

Answer 68

See key

Question 69

Explain what the **fragmentation** obtained from mass spectrometry is, and why it is important?

Answer 69

* When atoms are deflected, they can create fragments of the compound. * Some fragments are harder to make than others; but are usually made in specific ratios. * These ratios of framentation can be used as a "fingerprint" for the compound, and are important in identifying unknown compounds.

Question 70

# CH. 12 Recommended Probs 59a

Answer 70

See CH.12 Rec. Problem Solutions

Question 71

# CH. 11 Recommended Problems 61a

Answer 71

See CH. 11 Recommended Probs Key

Question 72

# CH. 12 Recommended Probs 45a

Answer 72

See CH.12 Rec. Problem Solutions

Question 72

# CH. 11 Recommended Problems 27

Answer 72

See CH. 11 Recommended Probs Key

Question 72

# SP2010 MT1 3d

Answer 72

See key

Question 73

# CH. 12 Recommended Probs 42f

Answer 73

See CH.12 Rec. Problem Solutions

Question 74

# CH. 12 Recommended Probs 63c

Answer 74

See CH.12 Rec. Problem Solutions

Question 75

# CH. 11 Recommended Problems 63f

Answer 75

See CH. 11 Recommended Probs Key

Question 76

# SP2010 MT1 3c

Answer 76

See key

Question 77

# Workshop Spectroscopy Practice #1-26 8

Answer 77

See key

Question 77

# Alicia PS #1 3

Answer 77

See key

Question 77

# SP2013 MT1 1a

Answer 77

See solutions

Question 78

# CH. 11 Recommended Problems 30b

Answer 78

See CH. 11 Recommended Probs Key

Question 80

# CH. 11 Recommended Problems 30e

Answer 80

See CH. 11 Recommended Probs Key

Question 81

# CH. 12 Recommended Probs 66f

Answer 81

See CH.12 Rec. Problem Solutions

Question 82

# See Alkene Nomenclature PS 18

Answer 82

See key

Question 83

# CH. 11 Recommended Problems 29c

Answer 83

See CH. 11 Recommended Probs Key

Question 84

# CH. 11 Recommended Problems 41c

Answer 84

See CH. 11 Recommended Probs Key

Question 84

# CH. 11 Recommended Problems 41f

Answer 84

See CH. 11 Recommended Probs Key

Question 85

**Amines** For the above FG, give the following: 1. Wavenumber range 2. Signal chracteristics

Answer 85

1. 3250-3500 cm^-1 2. Broad, strong

Question 86

# CH. 12 Recommended Probs 35b

Answer 86

See CH.12 Rec. Problem Solutions

Question 87

# CH. 12 Recommended Probs 63a

Answer 87

See CH.12 Rec. Problem Solutions

Question 88

# See NMR Practice Problems 6

Answer 88

See key

Question 88

# CH. 11 Recommended Problems 29a

Answer 88

See CH. 11 Recommended Probs Key

Question 88

# CH. 11 Recommended Problems 34b

Answer 88

See CH. 11 Recommended Probs Key

Question 88

# SP2010 MT1 1b

Answer 88

See key

Question 89

# CH. 12 Recommended Probs 31

Answer 89

See CH.12 Rec. Problem Solutions

Question 90

# CH. 12 Recommended Probs 43c

Answer 90

See CH.12 Rec. Problem Solutions

Question 91

# CH. 12 Recommended Probs 42e

Answer 91

See CH.12 Rec. Problem Solutions

Question 91

# CH. 12 Recommended Probs 65e

Answer 91

See CH.12 Rec. Problem Solutions

Question 91

# SP2010 MT1 3b

Answer 91

See key

Question 92

# Alicia PS #1 1a

Answer 92

See key

Question 93

# CH. 12 Recommended Probs 40a

Answer 93

See CH.12 Rec. Problem Solutions

Question 95

# CH. 11 Recommended Problems 49a

Answer 95

See CH. 11 Recommended Probs Key

Question 96

# CH. 12 Recommended Probs 45m

Answer 96

See CH.12 Rec. Problem Solutions

Question 97

# See Alkene Nomenclature PS 7

Answer 97

See key

Question 98

# See Alkene Nomenclature PS 8

Answer 98

See key

Question 99

# CH. 12 Recommended Probs 57e

Answer 99

See CH.12 Rec. Problem Solutions

Question 99

# CH. 11 Recommended Problems 63b

Answer 99

See CH. 11 Recommended Probs Key

Question 99

# Alicia PS #1 2d

Answer 99

See key

Question 100

What is the IR wavenumber range for **Esters**?

Answer 100

1735-1750 cm^-1

Question 101

# CH. 12 Recommended Probs 46g

Answer 101

See CH.12 Rec. Problem Solutions

Question 102

# CH. 12 Recommended Probs 69

Answer 102

See CH.12 Rec. Problem Solutions

Question 103

# CH. 11 Recommended Problems 30f

Answer 103

See CH. 11 Recommended Probs Key

Question 105

Explain how mass spectrometry can be used to detect the presence of isotopes.

Answer 105

* Since mass spec can determine the mass of compounds (and individual molecules) it can also determine the ratio of masses. * By knowing the isotopic ratio of a compound in nature, you can compare to the relative ratios and masses of isotopes in compound to "match" the isotopes in the compound to the isotopes found in nature.

Question 107

# CH. 12 Recommended Probs 46b

Answer 107

See CH.12 Rec. Problem Solutions

Question 108

# CH. 12 Recommended Probs 37e

Answer 108

See CH.12 Rec. Problem Solutions

Question 109

# See NMR Practice Problems 5

Answer 109

See key

Question 110

What is the IR wavenumber range for **Nitriles**?

Answer 110

2220-2260 cm^-1

Question 112

# Workshop Spectroscopy Practice #1-26 7

Answer 112

See key

Question 113

# CH. 12 Recommended Probs 46l

Answer 113

See CH.12 Rec. Problem Solutions

Question 114

What is the IR wavenumber range for the **C=C bond of a****lkenes**?

Answer 114

1620-1680 cm^-1

Question 115

# SP2013 MT1 2a

Answer 115

See solutions

Question 116

# CH. 11 Recommended Problems 63

Answer 116

See CH. 11 Recommended Probs Key

Question 116

# Workshop Spectroscopy Practice #1-26 9

Answer 116

See key

Question 117

What is the wavenumber range for **Alkenes**?

Answer 117

3050-3150 cm^-1

Question 119

# See NMR Practice Problems 21

Answer 119

See key

Question 120

# SP2010 MT1 5

Answer 120

See key

Question 121

Explain the difference in orientation between geminal, trans-vicinal, cis-vicinal, allylic, and alkane coupling in HNMR.

Answer 121

* _Geminal:_ two H's attached to the same C in a C=C bond. * _*trans*-vicinal:_ two H's that are *trans* to each other across a C=C bond. * _*cis-*vicinal:_ two H's that are *cis* to each other across a C=C bond. * _Allylic:_ one H attached to a C in a C=C bond, and one H attached to a C which is bonded to one side of the C=C bond (so a H attached to this --\>C-C=C)\ * _Alkane:_ two H's on either side of a C-C bond.

Question 121

# CH. 12 Recommended Probs 57f

Answer 121

See CH.12 Rec. Problem Solutions

Question 121

# CH. 11 Recommended Problems 34a

Answer 121

See CH. 11 Recommended Probs Key

Question 122

# See Alkene Nomenclature PS 11

Answer 122

See key

Question 124

# SP2010 MT1 7b

Answer 124

See key

Question 125

# CH. 11 Recommended Problems 41h

Answer 125

See CH. 11 Recommended Probs Key

Question 127

# CH. 12 Recommended Probs 35c

Answer 127

See CH.12 Rec. Problem Solutions

Question 128

# CH. 11 Recommended Problems 38a

Answer 128

See CH. 11 Recommended Probs Key

Question 130

# CH. 12 Recommended Probs 45g

Answer 130

See CH.12 Rec. Problem Solutions

Question 131

# CH. 12 Recommended Probs 70b

Answer 131

See CH.12 Rec. Problem Solutions

Question 132

# CH. 12 Recommended Probs 46k

Answer 132

See CH.12 Rec. Problem Solutions

Question 133

# CH. 12 Recommended Probs 67b

Answer 133

See CH.12 Rec. Problem Solutions

Question 134

# CH. 11 Recommended Problems 61d

Answer 134

See CH. 11 Recommended Probs Key

Question 135

# CH. 11 Recommended Problems 61b

Answer 135

See CH. 11 Recommended Probs Key

Question 135

# Workshop Spectroscopy Practice #1-26 22

Answer 135

See key

Question 137

# See NMR Practice Problems 16

Answer 137

See key

Question 138

# CH. 12 Recommended Probs 64c

Answer 138

See CH.12 Rec. Problem Solutions

Question 139

# See NMR Practice Problems 10

Answer 139

See key

Question 140

# CH. 12 Recommended Probs 70a

Answer 140

See CH.12 Rec. Problem Solutions

Question 140

# SP2013 MT1 8

Answer 140

See solutions

Question 141

# SP2013 MT1 6a

Answer 141

See solutions

Question 142

# Workshop Spectroscopy Practice #1-26 12

Answer 142

See key

Question 143

# See NMR Practice Problems 20

Answer 143

See key

Question 143

# CH. 11 Recommended Problems 50

Answer 143

See CH. 11 Recommended Probs Key

Question 144

# Give the HNMR chemical shift range typical of this FG Alkyl (primary)

Answer 144

0.7-1.3 ppm

Question 145

# CH. 12 Recommended Probs 43a

Answer 145

See CH.12 Rec. Problem Solutions

Question 146

# CH. 12 Recommended Probs 65g

Answer 146

See CH.12 Rec. Problem Solutions

Question 147

# CH. 12 Recommended Probs 60a

Answer 147

See CH.12 Rec. Problem Solutions

Question 149

# CH. 12 Recommended Probs 66c

Answer 149

See CH.12 Rec. Problem Solutions

Question 150

# CH. 11 Recommended Problems 55d

Answer 150

See CH. 11 Recommended Probs Key

Question 151

# Workshop Spectroscopy Practice #1-26 21

Answer 151

See key

Question 156

# See Alkene Nomenclature PS 14

Answer 156

See key

Question 157

# CH. 12 Recommended Probs 53a

Answer 157

See CH.12 Rec. Problem Solutions

Question 158

# SP2013 MT1 3d

Answer 158

See solutions

Question 159

# CH. 11 Recommended Problems 32c

Answer 159

See CH. 11 Recommended Probs Key

Question 160

# CH. 12 Recommended Probs 37b

Answer 160

See CH.12 Rec. Problem Solutions

Question 160

# Workshop Spectroscopy Practice #1-26 3

Answer 160

See key

Question 161

# CH. 12 Recommended Probs 38

Answer 161

See CH.12 Rec. Problem Solutions

Question 162

# CH. 12 Recommended Probs 66d

Answer 162

See CH.12 Rec. Problem Solutions

Question 163

# CH. 11 Recommended Problems 30a

Answer 163

See CH. 11 Recommended Probs Key

Question 164

# CH. 12 Recommended Probs 58d

Answer 164

See CH.12 Rec. Problem Solutions

Question 165

# CH. 11 Recommended Problems 61g

Answer 165

See CH. 11 Recommended Probs Key

Question 166

# CH. 12 Recommended Probs 68

Answer 166

See CH.12 Rec. Problem Solutions

Question 169

# SP2010 MT1 4

Answer 169

See key

Question 170

What is the IR wavenumber range for **Alkanes**?

Answer 170

2850-3000 cm^-1

Question 171

# CH. 12 Recommended Probs 44c

Answer 171

See CH.12 Rec. Problem Solutions

Question 172

# CH. 12 Recommended Probs 45c

Answer 172

See CH.12 Rec. Problem Solutions

Question 173

# CH. 12 Recommended Probs 43d

Answer 173

See CH.12 Rec. Problem Solutions

Question 174

# CH. 11 Recommended Problems 39

Answer 174

See CH. 11 Recommended Probs Key

Question 175

# CH. 11 Recommended Problems 49c

Answer 175

See CH. 11 Recommended Probs Key

Question 176

# CH. 12 Recommended Probs 45d

Answer 176

See CH.12 Rec. Problem Solutions

Question 177

# CH. 11 Recommended Problems 34e

Answer 177

See CH. 11 Recommended Probs Key

Question 178

# CH. 11 Recommended Problems 38c

Answer 178

See CH. 11 Recommended Probs Key

Question 181

# CH. 12 Recommended Probs 43b

Answer 181

See CH.12 Rec. Problem Solutions

Question 182

# CH. 12 Recommended Probs 45b

Answer 182

See CH.12 Rec. Problem Solutions

Question 183

# CH. 12 Recommended Probs 46f

Answer 183

See CH.12 Rec. Problem Solutions

Question 184

# CH. 12 Recommended Probs 51

Answer 184

See CH.12 Rec. Problem Solutions

Question 185

# CH. 12 Recommended Probs 65f

Answer 185

See CH.12 Rec. Problem Solutions

Question 186

# CH. 11 Recommended Problems 41e

Answer 186

See CH. 11 Recommended Probs Key

Question 187

# CH. 12 Recommended Probs 59c

Answer 187

See CH.12 Rec. Problem Solutions

Question 188

# CH. 11 Recommended Problems 46a

Answer 188

See CH. 11 Recommended Probs Key

Question 191

**-CCH Alkynes** For the above FG, give the following 1. Wavenumber length 2. Signal characteristics

Answer 191

1. 3260-3330 cm-1 2. Sharp

Question 192

# CH. 12 Recommended Probs 49h

Answer 192

See CH.12 Rec. Problem Solutions

Question 193

# Workshop Spectroscopy Practice #1-26 25

Answer 193

See key

Question 196

# CH. 12 Recommended Probs 49j

Answer 196

See CH.12 Rec. Problem Solutions

Question 197

# SP2013 MT1 7c

Answer 197

See solutions

Question 198

# CH. 12 Recommended Probs 49k

Answer 198

See CH.12 Rec. Problem Solutions

Question 199

# CH. 12 Recommended Probs 66g

Answer 199

See CH.12 Rec. Problem Solutions

Question 200

# Workshop Spectroscopy Practice #1-26 20

Answer 200

See key

Question 201

# CH. 12 Recommended Probs 63d

Answer 201

See CH.12 Rec. Problem Solutions

Question 202

# SP2010 MT1 1e

Answer 202

See key

Question 204

# CH. 12 Recommended Probs 45l

Answer 204

See CH.12 Rec. Problem Solutions

Question 205

# CH. 12 Recommended Probs 46m

Answer 205

See CH.12 Rec. Problem Solutions

Question 206

# CH. 11 Recommended Problems 51c

Answer 206

See CH. 11 Recommended Probs Key

Question 207

# CH. 11 Recommended Problems 61e

Answer 207

See CH. 11 Recommended Probs Key

Question 208

# CH. 11 Recommended Problems 49b

Answer 208

See CH. 11 Recommended Probs Key

Question 210

What is the IR wavenumber range for **Acyl halides**?

Answer 210

1790-1815 cm^-1

Question 211

What is the IR wavenumber range for **Amides**?

Answer 211

1650-1690 cm^-1

Question 212

# CH. 12 Recommended Probs 71

Answer 212

See CH.12 Rec. Problem Solutions

Question 213

# SP2010 MT1 3f

Answer 213

See key

Question 214

# CH. 12 Recommended Probs 63b

Answer 214

See CH.12 Rec. Problem Solutions

Question 215

# CH. 12 Recommended Probs 67a

Answer 215

See CH.12 Rec. Problem Solutions

Question 215

# Workshop Spectroscopy Practice #1-26 10

Answer 215

See key

Question 215

# Workshop Spectroscopy Practice #1-26 15

Answer 215

See key

Question 216

# SP2010 MT1 1c

Answer 216

See key

Question 217

# CH. 11 Recommended Problems 31c

Answer 217

See CH. 11 Recommended Probs Key

Question 218

# CH. 12 Recommended Probs 63e

Answer 218

See CH.12 Rec. Problem Solutions

Question 219

# See Properties of Alkenes & pi-bonds 5

Answer 219

See key

Question 219

# CH. 11 Recommended Problems 35

Answer 219

See CH. 11 Recommended Probs Key

Question 220

# CH. 12 Recommended Probs 46e

Answer 220

See CH.12 Rec. Problem Solutions

Question 222

# CH. 12 Recommended Probs 49p

Answer 222

See CH.12 Rec. Problem Solutions

Question 223

# CH. 12 Recommended Probs 53d

Answer 223

See CH.12 Rec. Problem Solutions

Question 224

# CH. 12 Recommended Probs 66h

Answer 224

See CH.12 Rec. Problem Solutions

Question 225

# SP2013 MT1 3c

Answer 225

See solutions

Question 226

# CH. 11 Recommended Problems 28

Answer 226

See CH. 11 Recommended Probs Key

Question 228

# See Alkene Nomenclature PS 9

Answer 228

See key

Question 229

# Workshop Spectroscopy Practice #1-26 4

Answer 229

See key

Question 230

# Workshop Spectroscopy Practice #1-26 5

Answer 230

See key

Question 231

# See NMR Practice Problems 18

Answer 231

See key

Question 233

# See NMR Practice Problems 12

Answer 233

See key

Question 236

# Give the HNMR chemical shift range typical of this FG Alkyl (secondary)

Answer 236

1.2-1.6 ppm

Question 237

# CH. 11 Recommended Problems 61c

Answer 237

See CH. 11 Recommended Probs Key

Question 238

# CH. 12 Recommended Probs 53b

Answer 238

See CH.12 Rec. Problem Solutions

Question 239

# CH. 11 Recommended Problems 66a

Answer 239

See CH. 11 Recommended Probs Key

Question 240

# CH. 11 Recommended Problems 66d

Answer 240

See CH. 11 Recommended Probs Key

Question 242

# CH. 12 Recommended Probs 45j

Answer 242

See CH.12 Rec. Problem Solutions

Question 243

# Workshop Spectroscopy Practice #1-26 14

Answer 243

See key

Question 244

# CH. 12 Recommended Probs 61

Answer 244

See CH.12 Rec. Problem Solutions

Question 247

What three things does mass spectrometry determine?

Answer 247

1. Mass 2. Fragmentation 3. Presence of isotopes

Question 248

# CH. 11 Recommended Problems 31a

Answer 248

See CH. 11 Recommended Probs Key

Question 251

# CH. 12 Recommended Probs 35a

Answer 251

See CH.12 Rec. Problem Solutions

Question 252

How do the polarities of -cis and -trans alkenes compare?

Answer 252

* cis* alkenes are mor polar than *trans* alkenes because the dipole moments of *trans* alkenes cancel each other out due to them being in opposite directions. * cis* alkenes by contrast have both their dipole moments going away the C=C bond, creating a net dipole moment.

Question 253

# Workshop Spectroscopy Practice #1-26 24

Answer 253

See key

Question 254

What causes alkenes to be so downshifted (i.e. deshielded)?

Answer 254

* Applying a magnetic field to an alkene causes electrons to circle the magnetic field lines in one direction. * The pi-bond of an alkene creates an addt'l local magnetic field reinforcing the external field created by the applied magnetic field. * This causes the extra shift & deshielding on the alkene protons.

Question 256

Ex. 118B (Workshop Spectroscopy Problem)

Answer 256

See key

Question 257

# SP2010 MT1 1d

Answer 257

See key

Question 258

# SP2013 MT1 2c

Answer 258

See solutions

Question 261

# See Alkene Nomenclature PS 5

Answer 261

See key

Question 262

# See NMR Practice Problems 4

Answer 262

See key

Question 263

# CH. 11 Recommended Problems 29e

Answer 263

See CH. 11 Recommended Probs Key

Question 264

**Allylic** and **geminal** coupling in alkenes have the same Hz range. How can you tell them apart?

Answer 264

Geminal coupling only occurs in doublets (d); allylic can occur in doublet (d), triplet (t) or quartet (q) patterns. So if you see a coupling pattern of 0-3 Hz with a triplet or quartet, you would know it was a geminal coupling.

Question 267

# CH. 12 Recommended Probs 42d

Answer 267

See CH.12 Rec. Problem Solutions

Question 268

# CH. 12 Recommended Probs 45n

Answer 268

See CH.12 Rec. Problem Solutions

Question 269

# CH. 11 Recommended Problems 38b

Answer 269

See CH. 11 Recommended Probs Key

Question 270

# CH. 12 Recommended Probs 49e

Answer 270

See CH.12 Rec. Problem Solutions

Question 273

# See Alkene Nomenclature PS 17

Answer 273

See key

Question 274

# CH. 12 Recommended Probs 49n

Answer 274

See CH.12 Rec. Problem Solutions

Question 275

# CH. 12 Recommended Probs 66e

Answer 275

See CH.12 Rec. Problem Solutions

Question 276

# CH. 11 Recommended Problems 63c

Answer 276

See CH. 11 Recommended Probs Key

Question 277

# CH. 11 Recommended Problems 37b

Answer 277

See CH. 11 Recommended Probs Key

Question 279

# Give the HNMR chemical shift range typical of this FG Formyl (XCHO)

Answer 279

8-8.5 ppm

Question 280

# CH. 11 Recommended Problems 41a

Answer 280

See CH. 11 Recommended Probs Key

Question 283

# See NMR Practice Problems 1

Answer 283

See key

Question 284

# CH. 12 Recommended Probs 43f

Answer 284

See CH.12 Rec. Problem Solutions

Question 285

# SP2010 MT1 3a

Answer 285

See key

Question 286

# SP2013 MT1 1b

Answer 286

See solutions

Question 287

# Alicia PS #1 2a

Answer 287

See key

Question 288

# See NMR Practice Problems 2

Answer 288

See key

Question 289

**Carboxylic acids** For the above FG, give the following: 1. Wavenumber range 2. Signal characteristics

Answer 289

1. 2500-3100 cm^-1 2. Broad, strong

Question 290

# CH. 12 Recommended Probs 40d

Answer 290

See CH.12 Rec. Problem Solutions

Question 291

# See Alkene Nomenclature PS 15

Answer 291

See key

Question 292

# SP2013 MT1 1d

Answer 292

See solutions

Question 293

# SP2010 MT1 3h

Answer 293

See key

Question 294

# CH. 12 Recommended Probs 45k

Answer 294

See CH.12 Rec. Problem Solutions

Question 296

# See Alkene Nomenclature PS 10

Answer 296

See key

Question 297

What is the IR wavenumber range for **Aldehydes**?

Answer 297

2850 & 2750 cm^-1

Question 299

# See Properties of Alkenes & pi-bonds 4

Answer 299

See key

Question 300

# See NMR Practice Problems 17

Answer 300

See key

Question 301

# CH. 12 Recommended Probs 37c

Answer 301

See CH.12 Rec. Problem Solutions

Question 302

# CH. 12 Recommended Probs 65d

Answer 302

See CH.12 Rec. Problem Solutions

Question 303

# Workshop Spectroscopy Practice #1-26 6

Answer 303

See key

Question 305

# CH. 12 Recommended Probs 65c

Answer 305

See CH.12 Rec. Problem Solutions

Question 306

# See NMR Practice Problems 9

Answer 306

See key

Question 307

# SP2013 MT1 7a

Answer 307

See solutions

Question 309

# See NMR Practice Problems 24

Answer 309

See key

Question 310

# CH. 12 Recommended Probs 58a

Answer 310

See CH.12 Rec. Problem Solutions

Question 311

Explain how mass spectrometry works, and how it differs from spectroscopy.

Answer 311

* Compound is exposed to ionizing radiation (e.g. X-Rays) that removes electrons, creating ions of the compound. * Ionized molecules are accelerated through a tube, where they are exposed to a magnetic field. * Like charges repel, so the charged ions are deflected by the charge. * Since heavier compounds are not as easily moved, the amount of deflection can be used to determine the mass of the compound.

Question 312

# CH. 12 Recommended Probs 45i

Answer 312

See CH.12 Rec. Problem Solutions

Question 313

# CH. 12 Recommended Probs 45f

Answer 313

See CH.12 Rec. Problem Solutions

Question 314

# CH. 12 Recommended Probs 65b

Answer 314

See CH.12 Rec. Problem Solutions

Question 315

# CH. 11 Recommended Problems 42

Answer 315

See CH. 11 Recommended Probs Key

Question 316

# CH. 11 Recommended Problems 48

Answer 316

See CH. 11 Recommended Probs Key

Question 317

# SP2013 MT1 3e

Answer 317

See solutions

Question 318

# CH. 12 Recommended Probs 46c

Answer 318

See CH.12 Rec. Problem Solutions

Question 319

# SP2010 MT1 6

Answer 319

See key

Question 320

What is the IR wavenumber range for **Anhydrides**?

Answer 320

1740-1790 cm^-1 and 1800-1850 cm^-1

Question 323

# Give the HNMR chemical shift range typical of this FG Internal alkene

Answer 323

5.2-6.0 ppm

Question 324

# Workshop Spectroscopy Practice #1-26 18

Answer 324

See key

Question 325

# SP2013 MT1 1e

Answer 325

See solutions

Question 326

# See Alkene Nomenclature PS 13

Answer 326

See key

Question 327

# See NMR Practice Problems 25

Answer 327

See key

Question 328

# CH. 11 Recommended Problems 65

Answer 328

See CH. 11 Recommended Probs Key

Question 329

# Give the HNMR chemical shift range typical of this FG Allylic

Answer 329

1.6-2.2 ppm

Question 329

# CH. 12 Recommended Probs 58c

Answer 329

See CH.12 Rec. Problem Solutions

Question 331

# Give the HNMR chemical shift range typical of this FG Next to C=O

Answer 331

2-2.5 ppm

Question 332

# CH. 12 Recommended Probs 53c

Answer 332

See CH.12 Rec. Problem Solutions

Question 333

# CH. 12 Recommended Probs 40b

Answer 333

See CH.12 Rec. Problem Solutions

Question 334

# SP2013 MT1 3g

Answer 334

See solutions

Question 335

# CH. 12 Recommended Probs 44d

Answer 335

See CH.12 Rec. Problem Solutions

Question 336

# Workshop Spectroscopy Practice #1-26 13

Answer 336

See key

Question 337

1. Which bond is stronger, sigma bonds or pi bonds? 2. Why?

Answer 337

1. Sigma bonds 2. Sigma bonds have better overlap (end-to-end), while pi bonds have side-side overlap and have less contact overall.

Question 340

# CH. 12 Recommended Probs 41b

Answer 340

See CH.12 Rec. Problem Solutions

Question 341

# See NMR Practice Problems 8

Answer 341

See key

Question 342

What is the IR wavenumber range and typical value for **Aldehydes**?

Answer 342

1690-1750 cm^-1, usually 1735 cm^-1

Question 343

# Workshop Spectroscopy Practice #1-26 16

Answer 343

See key

Question 344

# Give the HNMR chemical shift range typical of this FG Fluoroalkane

Answer 344

4.3-5.0 ppm

Question 345

What is the IR wavenumber range for a **H attached to a C=C bond (alkene)**?

Answer 345

~3050-3150 cm^-1

Question 346

# CH. 12 Recommended Probs 37a

Answer 346

See CH.12 Rec. Problem Solutions

Question 347

# CH. 12 Recommended Probs 66a

Answer 347

See CH.12 Rec. Problem Solutions

Question 348

# CH. 11 Recommended Problems 61h

Answer 348

See CH. 11 Recommended Probs Key

Question 349

# CH. 11 Recommended Problems 57

Answer 349

See CH. 11 Recommended Probs Key

Question 350

# CH. 12 Recommended Probs 46a

Answer 350

See CH.12 Rec. Problem Solutions

Question 351

# See NMR Practice Problems 7

Answer 351

See key

Question 352

# Give the HNMR chemical shift range typical of this FG Alkyl (tertiary)

Answer 352

1.4-1.8 ppm

Question 353

# Give the HNMR chemical shift range typical of this FG Terminal alkene

Answer 353

4.6-5.2 ppm

Question 354

# CH. 11 Recommended Problems 61f

Answer 354

See CH. 11 Recommended Probs Key

Question 355

If alkenes have shorter and stronger C-H bonds than alkanes, then why are they more acidic?

Answer 355

Due to the hybridization. Alkenes are sp² hybridized, meaning that the orbitals have more *s* character (1/3) compared to alkanes (1/4). Remember, *s* orbitals are spherical and hang out near the C in the C-H bond. If the hybridized orbital has more *s* character, than the electrons will remain closer to the C atom, making it easier for the H⁺ proton to leave.

Question 356

# SP2010 MT1 8

Answer 356

See key

Question 357

# CH. 12 Recommended Probs 32

Answer 357

See CH.12 Rec. Problem Solutions

Question 358

# CH. 12 Recommended Probs 42b

Answer 358

See CH.12 Rec. Problem Solutions

Question 360

What is the IR wavenumber range for **Carboxylic acid carbonyl groups**?

Answer 360

1710-1760 cm^-1

Question 361

# CH. 11 Recommended Problems 30h

Answer 361

See CH. 11 Recommended Probs Key

Question 363

# CH. 12 Recommended Probs 37d

Answer 363

See CH.12 Rec. Problem Solutions

Question 364

# CH. 12 Recommended Probs 36

Answer 364

See CH.12 Rec. Problem Solutions

Question 365

# CH. 12 Recommended Probs 46h

Answer 365

See CH.12 Rec. Problem Solutions

Question 366

# CH. 11 Recommended Problems 41d

Answer 366

See CH. 11 Recommended Probs Key

Question 367

# CH. 12 Recommended Probs 57d

Answer 367

See CH.12 Rec. Problem Solutions

Question 368

# Alicia PS #1 2f

Answer 368

See key

Question 369

# SP2013 MT1 7b

Answer 369

See solutions

Question 370

# SP2013 MT1 5

Answer 370

See solutions

Question 371

# CH. 11 Recommended Problems 63d

Answer 371

See CH. 11 Recommended Probs Key

Question 372

# CH. 12 Recommended Probs 46n

Answer 372

See CH.12 Rec. Problem Solutions

Question 373

# SP2013 MT1 6b

Answer 373

See solutions

Question 374

# CH. 12 Recommended Probs 46i

Answer 374

See CH.12 Rec. Problem Solutions

Question 376

What is the IR wavenumber range and typical value for **Ketones**?

Answer 376

1690-1750 cm^-1, usually 1715 cm^-1

Question 377

# SP2013 MT1 1c

Answer 377

See solutions

Question 378

# SP2013 MT1 3f

Answer 378

See solutions

Question 379

# SP2010 MT1 7a

Answer 379

See key

Question 380

# See NMR Practice Problems 14

Answer 380

See key

Question 381

# Give the HNMR chemical shift range typical of this FG Alkyne

Answer 381

1.7-3.1 ppm

Question 382

# Give the HNMR chemical shift range typical of this FG Aldehyde (R-CHO)

Answer 382

9.5-10.0 ppm

Question 383

# CH. 12 Recommended Probs 44a

Answer 383

See CH.12 Rec. Problem Solutions

Question 384

# CH. 12 Recommended Probs 45h

Answer 384

See CH.12 Rec. Problem Solutions

Question 385

# CH. 11 Recommended Problems 63e

Answer 385

See CH. 11 Recommended Probs Key

Question 386

# See Properties of Alkenes & pi-bonds 3

Answer 386

See key

Question 387

# CH. 11 Recommended Problems 51b

Answer 387

See CH. 11 Recommended Probs Key

Question 388

# SP2010 MT1 2g

Answer 388

See key

Question 389

# CH. 11 Recommended Problems 67

Answer 389

See CH. 11 Recommended Probs Key

Question 390

# CH. 12 Recommended Probs 46o

Answer 390

See CH.12 Rec. Problem Solutions

Question 391

# CH. 11 Recommended Problems 66c

Answer 391

See CH. 11 Recommended Probs Key

Question 392

# CH. 11 Recommended Problems 37a

Answer 392

See CH. 11 Recommended Probs Key

Question 393

# CH. 11 Recommended Problems 41b

Answer 393

See CH. 11 Recommended Probs Key

Question 394

# See NMR Practice Problems 26

Answer 394

See key

Question 395

# CH. 11 Recommended Problems 51d

Answer 395

See CH. 11 Recommended Probs Key

Question 396

# CH. 11 Recommended Problems 62a

Answer 396

See CH. 11 Recommended Probs Key

Question 397

# CH. 11 Recommended Problems 38d

Answer 397

See CH. 11 Recommended Probs Key

Question 398

# CH. 12 Recommended Probs 43e

Answer 398

See CH.12 Rec. Problem Solutions

Question 399

# CH. 11 Recommended Problems 64

Answer 399

See CH. 11 Recommended Probs Key

Question 400

# Workshop Spectroscopy Practice #1-26 17

Answer 400

See key

Question 401

# See Alkene Nomenclature PS 4

Answer 401

See key

Question 402

# Give the HNMR chemical shift range typical of this FG Amines

Answer 402

2.4-3.5 ppm

Question 403

# CH. 12 Recommended Probs 45q

Answer 403

See CH.12 Rec. Problem Solutions

Question 404

# CH. 12 Recommended Probs 60c

Answer 404

See CH.12 Rec. Problem Solutions

Question 405

# CH. 11 Recommended Problems 46b

Answer 405

See CH. 11 Recommended Probs Key

Question 406

# Ch. 12 Recommended Probs 54a

Answer 406

See key

Question 407

# Ch. 12 Recommended Probs 54b

Answer 407

See key

Question 408

# Ch. 12 Recommended Probs 54c

Answer 408

See key

Question 409

# Ch. 12 Recommended Probs 54d

Answer 409

See key

Question 410

# Ch. 12 Recommended Probs 54e

Answer 410

See key

Question 411

# Ch. 12 Recommended Probs 55a

Answer 411

See key

Question 412

# Ch. 12 Recommended Probs 55b

Answer 412

See key

Question 413

# Ch. 12 Recommended Probs 55c

Answer 413

See key

Question 414

# Ch. 12 Recommended Probs 55d

Answer 414

See key

Question 415

# Ch. 12 Recommended Probs 55e

Answer 415

See key

Question 416

# CH. 11 Recommended Problems 30g

Answer 416

See CH. 11 Recommended Probs Key

Question 417

# CH. 11 Recommended Problems 32b

Answer 417

See CH. 11 Recommended Probs Key

Question 418

# Workshop Spectroscopy Practice #1-26 1

Answer 418

See key