Solution Manual for Spectrometric Identification of Organic Compounds 8th by Silverstein

Solution Manual for Spectrometric Identification of

Organic Compounds 8th by Silverstein

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 CHAPTER 6
Answers for Student Exercise 6.1
1 NOTE: The formula should be C5H10N2
H NMR 300 MHz
4

3 2

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 ppm

13
C/DEPT NMR 75.5 MHz

4 4
1 3
N
2 4 3 2
N
C5H10N2
Mol. Wt.: 98
3-(dimethylamino)propanenitrile

130 120 110 100 90 80 70 60 50 40 30 20 ppm

15
N NMR 30.4 MHz

N
N

240 220 200 180 160 140 120 100 80 60 40 20 ppm

145
Answers for Student Exercise 6.2 2
1
H NMR 300 MHz
1 3
1
1 2 Si Cl 3
1 3
C6H15ClSi
Mol. Wt.: 151
tert-butylchlorodimethylsilane

1.3 1.2 1.1 1.0 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 ppm

13
C/DEPT NMR 75.5 MHz

35 30 25 20 15 10 5 0 -5 ppm

29
Si NMR 59.6 MHz

55 50 45 40 35 30 25 20 15 10 5 ppm
Answers for Student Exercise 6.3 3 3
2 4
1 5
H NMR 300 MHz H3C 1
2 P
34 Br 5

C19H18BrP
Mol. Wt.: 357

2340 2320 2300 Hz

8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 ppm

13
C/DEPT NMR 75.5 MHz
4 3

a b

10200 Hz 10000 Hz
2
3 1 5
2
c d e

4
9800 Hz 9000 8900 Hz 800 750 Hz 5

ab c d e

130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

31
P NMR 121.5 MHz, 1H Decoupled

28 26 24 22 20 18 16 14 12 10 8 6 4 2 ppm
Answers for Student Exercise 6.4 4
MASS
105
175
% of Base Peak
100
244
77
50 127
205

50 100 150 200

m/z
IR
OH
100 F3C CF3
1 2 3
4
5' 5
%Transmittance

50 6' 6
7
C9H6F6O
Mol. Wt.: 244
3602
3548

3070

1504

1273
1219
1165
972

717
1,1,1,3,3,3-hexafluoro-
2-phenylpropan-2-ol
4000 3000 2000 1000
Wavenumber (cm-1)
1
H NMR 19
F NMR 282.4 MHz
6,6’

See Table 6.2

7
5,5’

OH
7.8 7.7 7.6 7.5 ppm

7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 ppm -74.6 -74.7 ppm
Septet caused by 6 F two
13
C/DEPT bond coupling (JCCF) to
carbon 2

7 6,6’ 5,5’ C1 and C3, with coupling to

3F, J value of 288 Hz
4

130 128 126 124 122 120 118 ppm 78 77 76 ppm

Solution Manual for Spectrometric Identification of Organic Compounds 8th by Silverstein

6.5 Using the information in the appendix, calculate the Larmor frequencies of 7Li, 23Na, and 207Pb in a
magnetic field of 21.1 T.

𝛾𝐵0
𝜈=
2𝜋

B0 = 21.1 T; π = 3.14159265

For 7Li, γ = 10.3977013 x 107 rad T-1 s-1 and so the Larmor frequency, ν, is 349.17 MHz.

For 23Na, γ = 7.0808493 x 107 rad T-1 s-1 and so the Larmor frequency, ν, is 237.87 MHz.

For 207Pb, γ = 5.58046 x 107 rad T-1 s-1 and so the Larmor frequency, ν, is 187.40 MHz.

6.6 When the NMR spectra of heteronuclei show J couplings to protons, why are these couplings
essentially never ‘strong’ in the sense of Pople (AB)?

Consider the case of a 13C-1H spin pair, for example. In a typical magnetic field of 9.4 T, the proton
Larmor frequency is about 400 MHz and that of 13C is about 100 MHz. To demonstrate whether a spin
pair comprises an AX or AB spin system, one must consider the ratio ∆ν/J. If this ratio is greater than
about 8, we say the spin system is weakly coupled and is represented by the letters AX. If the ratio is
smaller than about 8, we say the spin system is strongly coupled and is represented by the letters AB. In
the case of the 13C-1H spin pair, J is about 125 Hz and ∆ν is about 300 MHz in this example. This gives a
ratio of 3.75 x 107, which is much larger than 8. This will always be the case for heteronuclear coupling
to protons because the value of ∆ν will always be on the order of several MHz, resulting in a very large
∆ν/J ratio.

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