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Answers for Student Exercises 1.1 to 1.5

1

Atom Type

# of Atoms

Mass

Total Mass

Hydrogen

22

1.00783

22.17226

a

Carbon

10

12.00000

120.00000

Nitrogen

0

14.0031

0.00000

Oxygen

0

15.9949

0.00000

Sulfur

0

31.9721

0.00000

Bromine

0

3-ethyloctane C

10

H

22

Cn HmX xNy Oz

IHD

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

0

78.9183 Exact Mass

0.00000 142.17226

- (C 2H 5 )

Rule 3

- (C5H 11 ) Rule 3

H

- (CH 2=CH 2) Rule 9

b

Atom Type

# of Atoms

Mass

Total Mass

Hydrogen

18

1.00783

18.14094

Carbon

10

12.00000

120.00000

Nitrogen

0

14.0031

0.00000

Oxygen

0

15.9949

0.00000

Sulfur

0

31.9721

0.00000

Bromine

0

3-butylcyclohex-1-ene C

10

H

18

Cn HmX xNy Oz

IHD

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

2

78.9183 Exact Mass

or

- (C4H 9 )

Rule 5 and 6

- (CH2 =CH2) Rule 6

- (C3H 7 )

Rule 3

0.00000 138.14094

Answers for Student Exercises 1.1 to 1.5

2

O

Atom Type

# of Atoms

Mass

Hydrogen

18

1.00783

18.14094

Carbon

13

12.00000

156.00000

Nitrogen

0

14.0031

0.00000

Oxygen

1

15.9949

15.99490

Sulfur

0

31.9721

0.00000

78.9183

0.00000

c

2-methyl-1-phenylhexan-1-one C13 H18O

Cn Hm Xx Ny O z

IHD

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

5

Bromine

0

Exact Mass

O

O

Total Mass

190.13584

O

- (C6 H13 )

Rule 8 O

O

- (C6 H5 ) Rule 8

H O

O

- (C4H8 )

OH

H

Rule 9

O - (CO)

Rule 8+9

d

E)-undec-3-ene

Atom Type

# of Atoms

Mass

Hydrogen

22

1.00783

Total Mass 22.17226

Carbon

11

12.00000

132.00000

Nitrogen

0

14.0031

0.00000

Oxygen

0

15.9949

0.00000

Sulfur

0

31.9721

0.00000

(

C 11 H 22

Cn Hm Xx Ny O z

IHD

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

1

Bromine

0

78.9183 Exact Mass

or

- (CH3) Rule 5

- (C6 H13 ) Rule 5

H - (C7 H14 ) Rule 9

0.00000 154.17226

Answers for Student Exercises 1.1 to 1.5

e

1-(hexan-2-yl)benzene C

12

3

Atom Type

# of Atoms

Mass

Hydrogen

18

1.00783

Total Mass 18.14094

Carbon

12

12.00000

144.00000

Nitrogen

0

14.0031

0.00000

Oxygen

0

15.9949

0.00000

Sulfur

0

31.9721

0.00000

Bromine

0

78.9183

0.00000

H

18

Cn Hm X xNy Oz

IHD

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

4

Exact Mass

162.14094

- (CH3 ) Rule 7

- (C4 H9 ) Rule 7

H

H

- (C4 H8 ) Rule 9

H Atom Type f

OH heptan-2-ol C H 7

16

O

Cn Hm Xx Ny Oz

IHD

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

0

# of Atoms

Mass

Total Mass

Hydrogen

16

1.00783

16.12528

Carbon

7

12.00000

84.00000

Nitrogen

0

14.0031

0.00000

Oxygen

1

15.9949

15.99490

Sulfur

0

31.9721

0.00000

Bromine

0

78.9183 Exact Mass

0.00000 116.12018

- (C5 H11 ) OH Rule 8

OH

- (CH3 ) OH Rule 8

H

- (H ) OH

OH Rule 8

H

OH

- (H2 O)

OH Rule 9

Answers for Student Exercises 1.1 to 1.5

g

COOH 3,5,7-trimethyloctanoic acid C

11

H

O

22

4

Atom Type

# of Atoms

Mass

Hydrogen

22

1.00783

22.17226

Carbon

11

12.00000

132.00000

Nitrogen

0

14.0031

0.00000

Oxygen

2

15.9949

31.98980

Sulfur

0

31.9721

0.00000

2

Cn Hm Xx Ny O z

IHD

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

1

Total Mass

Bromine

78.9183

0

0.00000

Exact Mass

186.16206

O C O

- (OH ) OH

Rule 8 O C

O O

- (C10 H 21 )

O

C

OH

C

OH

Rule 8

OH

H

H

O

- (C9 H18)

O

OH

HO

Rule 9

HO

HO

h

OH hexan-1-ol C H 6

14

O

Cn Hm Xx Ny Oz

IHD

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

0

Atom Type

# of Atoms

Mass

Total Mass

Hydrogen

14

1.00783

14.10962

Carbon

6

12.00000

72.00000

Nitrogen

0

14.0031

0.00000

Oxygen

1

15.9949

15.99490

Sulfur

0

31.9721

0.00000

Bromine

0

78.9183

0.00000

Exact Mass

102.10452

H O

- (CH2 =CH 2 ) - (H2O)

H

Rule 9

- (C5H11 ) OH Rule 8

H 2C

OH

- (H ) OH

OH Rule 8

Answers for Student Exercises 1.1 to 1.5

i

OH 2-methylheptan-2-ol C H 8

18

O

Cn Hm Xx Ny Oz

IHD

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

0

5

Atom Type

# of Atoms

Mass

Total Mass

Hydrogen

18

1.00783

18.14094

Carbon

8

12.00000

96.00000

Nitrogen

0

14.0031

0.00000

Oxygen

1

15.9949

15.99490

Sulfur

0

31.9721

0.00000

Bromine

0

78.9183

0.00000

Exact Mass

130.13584

- (C5H11 ) OH

OH

Rule 8

- (CH 3 ) OH

OH Rule 8

H O H

- (H2O)

- (CH 2 =C(CH 3) 2) Rule 8

Rule 8

j

S butyl(propyl)sulfane C H 7

16

S

Cn Hm Xx Ny Oz

IHD

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

0

Atom Type

# of Atoms

Mass

Total Mass

Hydrogen

16

1.00783

16.12528

Carbon

7

12.00000

84.00000

Nitrogen

0

14.0031

0.00000

Oxygen

0

15.9949

0.00000

Sulfur

1

31.9721

31.97210

Bromine

0

78.9183

0.00000

Exact Mass

- (C

132.09738

H7 )

3

S Rule 8

S

- (CH2 =CH2 )

S

SH Rule 9

H

- (C2H 5 ) S

S Rule 8

Answers for Student Exercises 1.1 to 1.5

k

6

Atom Type

# of Atoms

Mass

Hydrogen

20

1.00783

20.15660

Carbon

13

12.00000

156.00000

Nitrogen

0

14.0031

0.00000

Oxygen

1

15.9949

15.99490

OH

(2-hexylphenyl)methanol C

H

13

20

O

Cn Hm Xx Ny Oz

IHD

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

4

OH

Sulfur

0

31.9721

0.00000

Bromine

0

78.9183

0.00000

Exact Mass

192.15150

OH

or

- (C 5H11 )

OH

Total Mass

OH

Rule 7 CH 2 CH 2

- (OH )

OH

Rule 7

- (H 2O)

OH H

Rule 9

O l

NO 2 (4-nitrophenyl)(phenyl)methanone C

H NO

13

9

3

Cn Hm Xx Ny Oz

IHD

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

10

Atom Type

# of Atoms

Mass

Hydrogen

9

1.00783

9.07047

Carbon

13

12.00000

156.00000

Nitrogen

1

14.0031

14.00310

Oxygen

3

15.9949

47.98470

Sulfur

0

31.9721

0.00000

Bromine

0

78.9183

0.00000

Exact Mass

Total Mass

227.05827

O

O - (C6 H4NO 2 ) Rule 7&8 NO 2 O - (CO)

Rule 8&9 O

O

- (C6H5 ) Rule 7&8 NO 2

NO2

Answers for Student Exercises 1.1 to 1.5

m

O

7

Atom Type

# of Atoms

Mass

Hydrogen

22

1.00783

Total Mass 22.17226

Carbon

10

12.00000

120.00000

Nitrogen

0

14.0031

0.00000

Oxygen

1

15.9949

15.99490

3-(ethoxymethyl)heptane C

H

10

O

22

Cn Hm Xx Ny Oz

IHD

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

0

Sulfur

0

31.9721

0.00000

Bromine

0

78.9183

0.00000

Exact Mass

- (CH

3

158.16716

) O

O Rule 8

CH2

- (C7H 15 )

O

O

Rule 8

- (C4 H 9)

O

O

Rule 3

O n

H Br 2-bromodecanal C

10

H

19

Atom Type

# of Atoms

Mass

Hydrogen

19

1.00783

Total Mass 19.14877

Carbon

10

12.00000

120.00000

Nitrogen

0

14.0031

0.00000

Oxygen

1

15.9949

15.99490

BrO

Cn Hm Xx Ny Oz

IHD

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

1

Sulfur

0

31.9721

0.00000

Bromine

1

78.9183

78.91830

Exact Mass

234.06197

O

O - (H ) H Rule 8

Br

Br

O - (CO ) Rule 9

Br

H

Br

H

O H

O - (C8H16 ) H

Br

H

Rule 9 Br

Answers for Student Exercises 1.1 to 1.5

o

O

O cyclohexyl acetate C H 8

14

O

2

Cn Hm Xx Ny Oz

IHD

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

2

O

O

8

Atom Type

# of Atoms

Mass

Total Mass

Hydrogen

14

1.00783

14.10962

Carbon

8

12.00000

96.00000

Nitrogen

0

14.0031

0.00000

Oxygen

2

15.9949

31.98980

Sulfur

0

31.9721

0.00000

Bromine

0

78.9183

0.00000

Exact Mass

- (C6 H 11O )

142.09942

O

Rule 8

O

O

- (CH3 )

O

O

Rule 8

O

H

O

O - (CH2=C=O) Rule 9

H

Answers for Student Exercises 1.6 to 1.11

9

Molecular

O

A

Base Peak

Ion

Fragement Ion

Fragment Loss

71

114

99 / C6H11O

15 / CH3

86 / C5H10

28 / C2H4

Rearrangment

R

4-Heptanone C H 7

O

14

Exact Mass: 114.1045 IHD = 1, match with (k)

71 / C4H7O

43 / C3H7

58 / C3H5O

56 / C4H8

43 / C3H7

71 / C4H7O

R

Molecular

B

OH

Base Peak

Ion

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

R

Rearrangment

3-Heptanol C7H16O

Rearrangment

R

R

Exact Mass: 116.1201 IHD = 0, match with (m)

C

Molecular

Br

Base Peak

Ion

Fragement Ion

Fragment Loss

91

170

91 / C7H7

79 / Br

Ion

75 / C6H3

80 / HBr, 16 / CH4

R

65 / C5H5

79 / Br, 26 / C2H2

R

50 / C4H2

120 / C7H5Br

39 / C3H2

131 / C4H5Br

Tropylium 4-Bromotoluene C7H7Br Exact Mass: 169.9731 IHD = 4, match with (v)

D

Br

2-Bromopentane C 5H11Br

Molecular Base Peak

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

Exact Mass: 150.0044 IHD = 0, match with (r)

R

Answers for Student Exercises 1.6 to 1.11

10

Molecular E

O

Base Peak

Ion

Fragement Ion

Fragment Loss

43

100

85 / C5H9O

15 / CH3

71 / C4H7O

29 / C2H5

2-Hexanone C6H12O

58 / C4H10

42 / C2H2O

57 / C3H5O

43 / C3H7

43 / C3H7

57 / C3H5O

Rearrangment

R

Exact Mass: 100.0888 IHD = 1, match with (h)

O

F

Molecular

OH

Base Peak

Ion

Fragement Ion

Fragment Loss

74

74

73 / C3H5O2

1 / H

57 / C3H5O

17 / OH

56 / C3H4O

18 / H2O

45 / CHO2

29 / C2H5

Rearrangment

Propionic Acid C 3H6 O2 Exact Mass: 74.0368 IHD = 1, match with(c)

R

Molecular G

H 2N

Base Peak

Ion

Fragement Ion

Fragment Loss

Rearrangment

73

73

56 / C4H8

17 / NH3

R

55 / C4H7

18 / NH4

R

44 / C2H6N

29 / C2H5

43 / C3H7

30 / CH4N

butan-1-amine C4 H 11N Exact Mass: 73.0896 IHD = 0, match with (b)

H

Molecular

OH

prop-2-yn-1-ol

Base Peak

Ion

Fragement Ion

Fragment Loss

55

56 by CI

55 / C3H3O

1 / H

39 / C3H3

17 / OH