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