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OSE Answer Book
OSE Answer Book
OSE Answer Book
www.nd.edu/~smithgrp/structure/workbook.html
Carleton G. Collins,
Cassandra C. Shaffer,
Department of Chemistry and Biochemistry,
University of Notre Dame, IN 46556, USA
©Copyright 2020
Acknowledgement: This answer book was prepared with funding support from the
National Science Foundation (CHE 1058699) and (CHE 1708240).
1
Spectroscopic Signal/Information Comments
Technique
Problem 1
Formula C3H5BrO2, UN=1 1 double bond
Problem 2
Formula C8H14O4, UN=2 2 double bonds
2
Problem 3
Formula C9H12 UN=4 Phenyl ring
Problem 4
Formula C7H13Br UN=1 1 ring
Problem 5
Formula C5H8O, UN=2 1 ring and 1 double bond
3
1644 C=C stretch
1070, 1238 C-O stretches
Problem 6
Formula C9H13NO UN=4 Aryl ring
4
Problem 7
Formula C6H10, UN = 2 1 ring and 1 double bond
Problem 8
Formula C8H11NO, UN =4 Phenyl ring
Problem 9
Formula C10H7Br, UN=7 Naphthyl ring
5
127 (M-79) M–Br
Problem 10
Formula C14H19NO4, UN=6 1 aryl ring and 2 double bonds
6
Problem 11
Formula C6H12O2, UN=1 1 ring
3.3 H1, H2
1H NMR (ppm) 3.0 OH
1.9, 1.6 H3, H6
1.2 H4, H5
75.7 C1, C2
13C NMR (ppm) 32.8 C3, C6
24.2 C4, C5
Problem 12
Formula C7H5NO4, UN=6 1 aryl ring and 2 double bond
7
Problem 13
Formula C5H10O4, UN=1 1 double bond
Problem 14
Formula C8H6O2, UN=6 1 aryl ring and 2 double bonds
8
Problem 15
Formula C13H10O3, UN=9 2 aryl rings and 1 double bond
9
Problem 16
Formula C7H6O2, UN=5 1 aryl ring and 1 double bond
Problem 17
Formula C9H10O3, UN=5 1 aryl ring and 1 double bond
10
Problem 18
Formula C7H10O4, UN=3 2 rings and 1 double bond
Problem 19
Formula C9H7NO4, UN= 7 1 aryl ring and 3 double bonds
11
Problem 20
Formula C8H9NO2, UN=5 1 aryl ring and 1 double bond
Problem 21
Formula C9H12O3, UN=4 1 aryl ring
12
3.91 (m) H5 (diastereotopic)
3.63 (dd), 3.72 (dd) H7 (diastereotopic)
2.59 (exchanges) OH
Problem 22
Formula C9H12N2O, UN=5 1 aryl ring and 1 double bond
Problem 23
Formula C9H10O3, UN=5 1 aryl ring and 1 double bond
13
IR (cm-1) 2600-3400 COOH
3047 C(sp2)-H stretch
1718 C=O stretch (acid)
1235 C-O stretch
Problem 24
Formula C9H10O3, UN=5 1 aryl ring and 1 double bond
Problem 25
Formula C14H14O2, UN=8 2 aryl rings
14
Mass Spectrum (m/z) 214 (M+)
199 (M-15) M–CH3
171 (M-43) M–CO, CH3
128 (M-86) M–2CO, 2CH3
Problem 26
Formula C7H11BrO4, UN=2 2 double bonds
Problem 27
Formula C8H19N, UN=0 Fully saturated
15
IR (cm-1) 3410 NH stretch
2928 C(sp3)-H stretch
1461 CH2 and CH3 bend
1132 C-N stretch
Problem 28
Formula C6H12O2Cl2, UN=0 Fully saturated
Problem 29
Formula C3H7OCl, UN=0 Fully saturated
16
1H NMR (ppm) 3.59-3.65 (m) H1, H2
3.38 (s) H3
Problem 30
Formula C6H6O2, UN=4 1 aryl ring
Problem 31
Formula C6H7NO, UN=4 1 aryl ring
17
13C NMR (ppm) 157.9 C1
149.6 C3
129.2 C5
105.3 C4
103.2 C6
100.9 C2
Problem 32
Formula C7H6NF3, UN=4 1 aryl ring
18
Problem 33
Formula C6H4Cl2, UN=4 1 aryl ring
Problem 34
Formula C6H5NO3, UN=5 1 aryl ring and 1 double bond
Problem 35
Formula C6H5NO3, UN=5 1 aryl ring and 1 double bond
19
IR (cm-1) 3398 OH stretch
3114 C(sp2)-H stretch
1354, 1534 NO2 stretches
1213 C-O stretch
Problem 36
Formula C4H4N2, UN=4 1 aryl ring
20
Problem 37
Formula C6H7PO3, UN=4 1 aryl ring
Problem 38
Formula C9H8N2, UN=7 2 aryl rings
21
Problem 39
Formula C5H6O3, UN=3 1 ring and 2 double bonds
Problem 40
Formula C16H35N, UN=0 Fully saturated
Problem 41
Formula C6H12O5, UN=1 1 ring
22
60 (M-104) M–C4H8O3
Problem 42
Formula C13H9NO3, UN=10 2 aryl rings and 2 double bonds
Problem 43
Formula C7H6BrF, UN=4 1 aryl ring
23
Mass Spectrum (m/z) 188, 190 (M+, [M+2]+) Br present (1:1)
142, 144 (M-46) M–C2H3F
109 (M-79) M–Br
77 (M-111) C6H5+
Problem 44
Formula C13H10 UN=9 2 aryl rings and 1 ring
Problem 45
Formula C10H11NO2, UN=6 1 aryl ring and 1 triple bond
24
IR (cm-1) 2934 C(sp2)-H stretch
2241 C≡N stretch
1518 Aromatic C=C stretch
1025, 1262 C-O stretches (ether)
Problem 46
Formula C5H12O2, UN=0 2 double bonds or rings
25
Problem 47
Formula C6H12O3, UN=1 2 double bonds and/or rings
Problem 48
Formula C10H20O, UN=1 2 double bonds or rings
26
Problem 49
Formula C9H16O5, UN=2 2 double bonds
Problem 50
Formula C3H7OCl, UN=0 Fully saturated
27
Problem 51
Formula C8H6O3, UN=6 1 aryl ring, 1 ring, and 1 double bond
Problem 52
Formula C9H10O2, UN=5 1 aryl ring and 1 double bond
28
129.9 C4
127.8 C3
20.1 C5
Problem 53
Formula C6H8O2, UN=3 1 ring and 2 double bonds
Problem 54
Formula C5H7NO3, UN=3 1 ring and 2 double bonds
29
Problem 55
Formula C8H8O2, UN=5 1 aryl ring and 1 double bond
Problem 56
Formula C7H11NO2, UN=3 1 double bond and 1 triple bond
Problem 57
Formula C6H5O2SCl, UN=4 4 double bonds/ring (likely aromatic)
30
Mass Spectrum (m/z) 176, 178 (M+, [M+2]+) Cl present (1:3)
141 (M-35) M–Cl
77 (M-99) C6H5+
Problem 58
Formula C10H13N5O4, UN=7 1 aryl ring, 2 rings, 1 double bond
31
Problem 59
Formula C14H12O2, UN=9 2 aryl rings and 1 double bond
Problem 60
Formula C4HO3Br UN=4 1 ring and 3 double bonds
Problem 61
Formula C8H14O3, UN=2 2 double bonds
32
Mass Spectrum (m/z) 158 (M+)
103 (M-55) M–C3H3O
85 (M-73) M–OC(CH3)3
57 (M-101) C4H9+ (t-Bu cation)
Problem 62
Formula C6H11O2Br, UN=1 1 double bond
Problem 63
Formula C14H12O2, UN=9 2 aryl rings and 1 double bond
33
195 (M-17) M–OH
105 (M-107) C7H5O+
77 (M-135) C6H5+
Problem 64
Formula C10H12O, UN=5 1 aryl ring and 1 double bond
34
35