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(30 Points) : 1. Match The Following To Their IR Spectra

1. The document contains 4 chemistry problems involving matching IR spectra, calculating UV maxima, explaining mass spectrometry fragmentation patterns, and comparing mass spectra of two compounds. 2. The problems cover topics like interpreting spectroscopic data from IR, UV-Vis, and mass spectrometry to determine structural information about unknown organic compounds. 3. Solving the problems requires understanding principles of vibrational spectroscopy, electronic transitions, and mass spectrometry fragmentation to deduce structural information from experimental data.

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Ika Sanjiwani
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119 views12 pages

(30 Points) : 1. Match The Following To Their IR Spectra

1. The document contains 4 chemistry problems involving matching IR spectra, calculating UV maxima, explaining mass spectrometry fragmentation patterns, and comparing mass spectra of two compounds. 2. The problems cover topics like interpreting spectroscopic data from IR, UV-Vis, and mass spectrometry to determine structural information about unknown organic compounds. 3. Solving the problems requires understanding principles of vibrational spectroscopy, electronic transitions, and mass spectrometry fragmentation to deduce structural information from experimental data.

Uploaded by

Ika Sanjiwani
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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1.

Match the following to their IR spectra (30 points)

H O O OH

O
O OH

b
a
1466

3333
2941 1716

c 3026
1650
d
1450 3034 1685 1617
3341

3086

e f 2817
2716

2820 2766 1703 2966


1731
1. Circle the structure of the product that corresponds to the 1H NMR and IR data below. Circle
only one structure
N N
C C

N
NO2 NO2 Br Br Br
C NO2

Br
Br O Br Br
Br O Br

O OMe
O
O
OMe MeO O

1H NMR 8.07 ppm (d, J=7.9 Hz, 2H)


7.32 ppm (d, J=7.9 Hz, 2H)
2.35 ppm (s, 3H)

IR
3109

1596

1512
1353

4000 3000 2000 1500 1000 500


2. Circle the structure of the product that corresponds to the 1H NMR and IR data below. Circle
only one structure
N N
C C

N
NO2 NO2 Br Br Br
C NO2

Br
Br O Br Br
Br O Br

O OMe
O
O
OMe MeO O

1H NMR 7.22 ppm (d, J=7.9 Hz, 2H)


7.45 ppm (d, J=7.9 Hz, 2H)
2.41 ppm (s, 3H)

IR

1609
1509
2229

4000 3000 2000 1500 1000 500


3. Circle the structure of the product that corresponds to the 1H NMR and IR data below. Circle
only one structure
N N
C C

N
NO2 NO2 Br Br Br
C NO2

Br
Br O Br Br
Br O Br

O OMe
O
O
OMe MeO O

8.17 ppm (t, J=2.1 Hz, 1H)


1H NMR 7.96 (dt, J=8.0, 2.1 Hz, 1H)
7.67 (dt, J=7.7,2.1 Hz, 1H)
7.31 (dd, J=8.0, 7.7 Hz, 1H)
3.91 ppm (s, 3H)

IR

1571

1436

1729

4000 3000 2000 1500 1000 500


1. Match the following to their IR spectra
(24 points) (not all compounds have a match)

HO O

Cl

O CN
OH

b
a 2120

1585
1603
1689
3301
1500 4000 3000 2000 1500 1000 500
4000 3000 2000 1000 500

d
c
2249

1716
4000 3000 2000 1500 1000 500 4000 3000 2000 1500 1000 500
(24 points) (not all compounds have a match)
1. Match the following to their IR spectra

O
CN NO2

O O
O

b
a
1374

1670 1552

1500 4000 3000 2000 1500 1000 500


4000 3000 2000 1000 500

d
c

1776 1750
4000 3000 2000 1500 1000 500 4000 3000 2000 1500 1000 500
Name______________________________________

2. Calculate the UV maximum for the following compounds. (20 points)

O
OAc
Br

O
Name______________________________________

3. Explain how the labeled fragments are formed. Relative intensities are given in parentheses. (20 points)

180 (95)
181(100)

77 (58) N

H
MW = 181

104 (14) 182 (13)


Name______________________________________

4. The mass spectra of compounds A and B are nearly identical, except for the additional peak at 208
in the spectrum of A. Explain why, and in doing so assign the labeled peaks in the mass spectrum.
(20 points)

O
O
180
MW=208
A
152

208

O 180

MW=180

B
152
Name______________________________________

5. McLafferty rearrangements of the molecules depicted below will give rise to fragments that
can be detected by mass spectrometry. Circle the fragments that are observed.
You may need to circle more than one answer for each! (24 points)

120 121 122


D D

120 121 122


D H

O D D
120 121 122

O D H
120 121 122

O
120 121 122
D D

O
120 121 122
D H

O D D
120 121 122

O D H
120 121 122
2. C9H13NO
13 1
C NMR H NMR
138.6, s 7.40–7.22, m, 5H
129.1, d (2) 5.2 broad s, 1H (exchanges with D2O)
128.3, d (2) 3.69, dd, 1H, J = 11 and 3 Hz
126.3, d 3.45, dd, 1 H, J = 11 and 6 Hz
66.2, t 3.17, m, 1H
54.1, d 2.86, dd, 1H, J=12 and 4 Hz
40.8, t 2.58, dd, 1 HJ = 12 and 8 Hz
2.1, broad s, 2H

MS: 151 (M+, 92), 134 (3), 120 (100), 103 (22), 91 (40), 77 (12), 65 (9), 60 (90),
42 (9), 30 (4), 28 (2)
IR:

1
H NMR

J = 11 Hz
2. (continued)
To receive full credit for question 2, clearly show your rationale for elucidating the structure. In
addition, all 1H and 13C NMR chemical shifts, as well as 1H coupling constants must be assigned
and displayed in the designated blocks. This will involve drawing your final structure at least 3
times. Furthermore, assign at least 2 peaks associated with the main functional groups in the IR
spectrum. Also, assign the bolded numbers in the mass spectrum. Simply drawing the structure
of the product will get you no credit.

13
C chemical shift assignments

1
H Chemical shift assignments

1
H coupling constant assignments

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