ho o oh o o oh - university of delaware...2. (continued) to receive full credit for question 2,...
TRANSCRIPT
ab
c
d
e f
2941 17163333
1466
3341
3026
1650
1450 30341685 1617
3086
2820 2766 1703 17312966
28172716
OH O OH
O
O OH
1. Match the following to their IR spectra (30 points)
1H NMR
IR
4000 3000 2000 1500 1000 500
8.07 ppm (d, J=7.9 Hz, 2H)7.32 ppm (d, J=7.9 Hz, 2H)2.35 ppm (s, 3H)
1596
1512
1353
1. Circle the structure of the product that corresponds to the 1H NMR and IR data below. Circle
only one structure
3109
C
N
C
N
C
N
NO2 NO2NO2 Br
BrBr
Br
BrBr
O
O
O Br
BrBr
O
OMe OMeO
OMe
O
1H NMR
IR
4000 3000 2000 1500 1000 500
7.22 ppm (d, J=7.9 Hz, 2H)7.45 ppm (d, J=7.9 Hz, 2H)2.41 ppm (s, 3H)
2229
16091509
2. Circle the structure of the product that corresponds to the 1H NMR and IR data below. Circle
only one structure
C
N
C
N
C
N
NO2 NO2NO2 Br
BrBr
Br
BrBr
O
O
O Br
BrBr
O
OMe OMeO
OMe
O
1H NMR
IR
4000 3000 2000 1500 1000 500
8.17 ppm (t, J=2.1 Hz, 1H)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)
1436
1571
3. Circle the structure of the product that corresponds to the 1H NMR and IR data below. Circle
only one structure
1729
C
N
C
N
C
N
NO2 NO2NO2 Br
BrBr
Br
BrBr
O
O
O Br
BrBr
O
OMe OMeO
OMe
O
ab
c
d
33011689
1716
(24 points) (not all compounds have a match)
OHO
CN
1. Match the following to their IR spectra
O
Cl
O
OH
4000 3000 2000 1500 1000 500
1603
1585
4000 3000 2000 1500 1000 500
2120
2249
4000 3000 2000 1500 1000 500 4000 3000 2000 1500 1000 500
ab
cd
1750
(24 points) (not all compounds have a match)
4000 3000 2000 1500 1000 5004000 3000 2000 1500 1000 500
1670
4000 3000 2000 1500 1000 500 4000 3000 2000 1500 1000 500
1776
1552
1374
NO2
1. Match the following to their IR spectra
O
OOO
CN
2. Calculate the UV maximum for the following compounds. (20 points)
O
O
OAc
Br
O
Name______________________________________
180 (95)181(100)
182 (13)104 (14)
77 (58) N
H
3. Explain how the labeled fragments are formed. Relative intensities are given in parentheses. (20 points)
Name______________________________________
MW = 181
OO
A
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)
180
152
152
180
208
O
B
Name______________________________________
MW=208
MW=180
O
DD
O HD
O
D D
O HD
O
HD
O DD
O
D H
O DD
120 121 122
120 121 122
120 121 122
120 121 122
120 121 122
120 121 122
120 121 122
120 121 122
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)
Name______________________________________
2. C9H13NO 13C NMR 1H 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: 1H 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.
13C chemical shift assignments
1 H Chemical shift assignments
1 H coupling constant assignments