Spectroscopy Problem Set - CHEM 3720 – Summer 2001 – Answer Key

1
1. For the following compounds, draw the structure and predict the H NMR. (Number of peaks, position of
peaks, intensity of peaks, and splitting of peaks).

a) 1,2-dimethoxyethane
O
3.50
3.36 δ 3.50 (s, 4H), 3.36 (s, 6H).
3.36 O
3.50

b) p-bromotoluene δ 7.33 (d, J = 8 Hz, 2H), 6.94 (d, J = 8 Hz, 2H),

Br 2.28 (s, 3H).
7.33 7.33

6.94 6.94

CH3
2.28

c) ethyl propanoate
O δ 4.15 (q, J = 7.1 Hz, 2H), 2.13 (q, J = 7.4 Hz, 2H),
1.14 4.15 1.27 (t, J = 7.1 Hz, 3H), 1.14 (t, J = 7.4 Hz, 3H).
O 1.27
2.13

d) 3-buten-2-one 6.32 δ 6.32 (dd, J = 18.7, 6.5 Hz, 1H), 6.25 (dd, J =
H 18.7, 1.1 Hz, 1H), 5.62 (dd, J = 6.5, 1.1 Hz), 2.25
5.62 H 2.25 (s, 3H)

H O
6.25

2. Propose a structure for each of the following compounds, based on the spectroscopic data provided.

a) C3H6Br2: H NMR δ 3.52 (t, 4H), 2.34 (quintet, 2H); C NMR δ 34.9
1 13 31.1
2.34
(t), 31.1 (t).
Br Br
3.52 3.52
34.9 34.9

b) C5H12O: H NMR δ 3.21 (s, 3H), 1.19 (s, 9H); C NMR δ 74.3 (s),
1 13 1.19
27.0
49.4 (q), 27.0 (q).
CH3
1.19 74.3
27.0 CH3 C O CH3 3.21
49.4

CH3
1.19
27.0

c) C5H10O: H NMR δ 2.42 (q, 4H), 1.07 (t, 6H); C NMR δ 212.0 (s),
1 13

35.5 (t), 7.92 (q). 1.07

O
1.07
7.92 7.92
212.0
2.42 2.42
35.5 35.5
 Spectroscopy Problem Set - CHEM 3720 – Summer 2001 – Answer Key

d) C5H10O2: H NMR δ 3.68 (s, 3H), 2.55 (septet, 1H), 1.16 (d, 6H);
1
O
C NMR δ 177.5 (s), 51.5 (q), 33.9 (d), 19.0 (q).
13
1.16 3.68
19.0 177.5
2.55 51.5
33.9 O
1.16
19.0

e) C4H6O2: C NMR δ 178.2 (s), 68.9 (t), 22.7 (t), 22.3 (t).
13
O
178.2
22.7 O
22.3 68.9

f) C8H10O2: H NMR δ 6.85 (s, 4H), 3.75 (s, 6H); C NMR δ 153.8 (s),
1 13 6.85 6.85
114.6 114.6
114.6 (d), 55.7 (t).
3.75 3.75
153.8
55.7 CH3O 153.8 OCH3 55.7

6.85 6.85
114.6 114.6

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g) C4H11N: H NMR δ 2.68 (1H, septet), 2.40 (3H, s), 1.50 (1H, broad 1.05
singlet), 1.05, (6H, d). IR (selected peaks): 3450 - 3300 cm-1 (strong, CH3
broad) 1.05 2.40
CH3 CH CH3
2.68 N
H
1.50
3450-3300

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h) C6H1013O3: H NMR δ 3.73 (3H, s), 3.48 (2H, s), 2.57 (2H, q), 1.08 203.2 167.7
(3H, t); C NMR δ 203.2 (s), 167.7 (s), 52.3 (q), 48.7 (t), 36.3 (t), 7.54 O O
(q). 1.08 3.73
7.54 52.3
2.57 3.48
O
36.3 48.7

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i) C8H8O: C1NMR δ 197.2 (s), 137.1 (s), 133.0 (d), 128.5 (d), 128.2
O
(d), 26.5 (q). H NMR δ 7.94 - 7.28 (5H, multiplet), 2.50 (3H, s) 128.5 197.2
128.2 137.1 2.50
26.5
133.0 128.5
128.2
7.94 - 7.28

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j) C7H14O2: H NMR δ 1.16 (9H, s), 1.21 (3H, t), 4.05 (2H, q). IR 1735
(selected peaks) 1735 cm-1 (strong), 1300 - 1050 cm-1 (two bands, O
1.16 4.05
strong).
1.16 O 1.21
1300 - 1050
1.16
 Spectroscopy Problem Set - CHEM 3720 – Summer 2001 – Answer Key

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k) C10H10O2: H NMR δ 8.01 (4H, s), 2.65 (6H, s). C NMR δ 197.4 128.4 128.4
2.65
8.01 8.01
(s), 140.1 (s), 128.4 (d), 26.9 (q). O
197.4 140.1 140.1 197.4

2.65 8.01 8.01 O

128.4 128.4

l) C5H8O: C NMR δ 213.9 (s), 37.0 (t), 22.3 (t). IR (selected peaks)
13 1740
-1
1740 cm O
213.9
37.0 37.0

22.3 22.3

m) C5H10O2: H NMR δ 4.15 (2H, q), 2.31 (2H, q), 1.27 (3H, t), 1.14
1
9.15 O 60.2
(3H, t), C NMR δ 174.4 (s), 60.2 (t), 27.2 (t), 14.2 (q), 9.15 (q).
13
1.14 174.4 4.15

O 1.27
2.13 14.2
27.2

n) C4H7NO: C NMR δ 173.0 (s), 42.4 (t), 30.3 (t), 20.8 (t). IR
13 1690
(selected peaks, cm-1) 1690, 3550 - 3050 one band, strong, broad. O
173.0
3550 - 3050
30.3 N H
20.8 42.4