CHM-236 Organic Chemistry II
Course Description: Study of chemistry of
carbon-containing compounds continued. Structural determination and
additional reaction mechanisms and modern methods of synthesis emphasized.
Prerequisites: CHM235 and CHM235LL
Course Materials:
Announcements
Here are some more problem
sets.
Here is quiz #1. Print it out, complete it, and drop it off to
my mailbox by Tuesday, February, 9th.
Let me know right away if you
run into any downloading or printing problems.
I’ve also included relevant
problems from the McMurry text (you’ll have to scroll
down to see those.)
Problem Sets (from Smith text)
Chapter 16
Conjugation:
1, 2, 13, 14, 28, 29, 39
Resonance: 3, 6, 7, 8, 9, 11, 12,
30, 31, 32, 33, 34
Addition reactions: 15, 17, 40
Diels-Alder: 10, 18, 19, 20, 21,
22, 23, 24, 36, 37, 38, 46, 47, 48, 49, 50, 55, 56
Mechanisms: 16, 35, 41, 42, 43,
44, 45
UV/visible spectroscopy: 26, 27,
60
Other reactions: 57, 61
Chapter 17
Resonance: 1, 12, 38
Structure: 2, 24
Nomenclature: 3, 4, 5, 25, 26
Aromaticity: 8, 10,
11, 13, 14, 15, 16, 17, 18, 19, 20, 53
Huckel rule: 21, 22,
27, 28, 29, 30
Other problems: 31, 33, 34, 24,
25
Mechanisms: 36, 48, 49, 50, 51
Resonance: 38, 39
Chapter 18
Reactivity: 1, 13, 14, 17, 18
Mechanisms: 2, 3, 4, 7, 9, 11,
19, 45, 48, 49
Reactions: 5, 6, 8, 10, 35, 36
Disubstitution: 15,
16, 21, 22, 32, 33, 34
Substituents: 12,
20, 23, 41, 42, 43, 44, 46
Synthesis: 24, 37, 40, 54, 55,
56, 57
Problem Sets (from McMurry
text, Fall 2008)
Reduction/Oxidation Reactions:
Chapter 7:
13, 14, 15, 16, 20, 23a, 23d, 23e, 24a, 24b, 25a, 25b, 26a, 28, 29, 30,
31, 32, 33, 38, 40b, 40c, 43c, 44, 45
Chapter 8: 8, 9, 12, 15a, 22, 23,
24c, 25a-b, 25f, 26d, 28, 29b, 29d, 30, 31, 38a-b, 42, 45
Chapter 9: 61, 62
Chapter 10: 13, 35
Chapter 17: 7, 8, 14, 15, 35, 36,
40a, 57a, 57d
Chapter 18: 15, 40, 41, 52a, 52d
Chapter 19: 3a, 32a
Chapter 20: 26a, 26e, 49e
Radical Reactions:
Chapter 5: 2, 3, 17, 34, 37
Chapter 7: 17, 18
Chapter 9: 78
Chapter 10: 3, 4, 5, 6, 7, 19,
20, 21, 23c, 24, 28, 29, 30, 31
Chapter 16: 21, 73d
Chapter 13 (Review)
Carbon NMR: 6, 7, 8, 25, 32, 55
H1 NMR (types of H): 14, 15, 27, 31, 37
H1 NMR (shifts): 16, 17, 39
H1 NMR (signal size): 18
H1 NMR (splitting): 19, 20, 24, 40, 41
Structure elucidation: 21, 43, 44, 49, 50, 51, 52, 53,
56, 57
Chapter 14
Diene electrophilic
additions: 2, 3, 4, 17, 22, 27
Diels-Alder reaction: 7, 8, 9,
10, 18, 19, 28, 33, 34, 36, 40, 44
UV-visible spectroscopy: 16, 20,
23, 24, 31, 32, 46, 48, 49
Chapter 15
Nomenclature: 1, 2, 3, 13, 18,
19, 20, 21, 22
Resonance: 6, 11, 16, 17, 25, 26,
33, 36, 37, 39
Aromaticity: 4, 5,
7, 8, 9, 10, 12, 31, 34, 38, 41, 47
Spectroscopy: 14, 15, 42, 43, 44, 45, 46
Reactions: 30, 35, 48, 49
Chapter 16
Halogenation: 1
Nitration and sulfonation: 2, 3
Alkylation and acylation: 4, 5, 6
Substituent effects: 7, 8, 9, 10,
11, 12, 13, 14, 25, 28
Trisubstitution: 15,
16
Side chain reactions: 19
Syntheses: 21, 22, 23, 24, 26,50, 51, 52, 53, 54, , 69, 73
Structure: 26
Reactivity: 29, 30, 34, 43
Orientation effects: 31, 32, 33,
40, 41, 42, 44
Reactions: 35, 36, 47, 48
Mechanisms: 37, 45, 49, 57, 59,
64, 65, 70, 74, 75
Chapter 17
Nomenclature: 1, 2, 21, 26, 27,
29
Physical properties: 3
Acidity: 4, 5, 44
Preparation: 6, 7, 8, 9, 10, 11,
25, 35, 37, 46, 47
Reactions: 12, 24, 28, 33, 39
Mechanisms: 34, 38, 45, 48, 39,
53
Other reactions: 13, 14, 15, 16,
22, 23, 25, 30, 41, 43, 50
Syntheses: 17, 31, 32, 36, 40,
42, 49, 52, 57
Spectroscopy: 19, 20, 58, 59, 60,
61, 62, 63, 64, 65, 66
More reactions: 67, 68
Chapter 18
Nomenclature: 1, 17, 20, 24, 25
Preparation of ethers: 2, 3, 4,
5, 6
Ether reactions: 7, 8, 9, 26, 27,
31
Epoxides: 11, 12,
13, 14, 15, 21, 22, 23
Spectroscopy: 19, 53, 54, 56
Syntheses: 28, 30, 32, 52
Mechanisms: 33, 34, 35, 36, 37, 40, 41, 43
Reactions: 29
Chapter 19
Nomenclature: 1, 2, 28, 29, 30
Preparation: 3, 4, 25
Reactions: 5, 6, 7, 8, 9, 10, 11,
12, 13, 14, 15, 16, 17, 19, 20
Spectroscopy: 21, 22, 24, 59, 60,
61, 62, 63, 64, 66, 67, 68
Structure: 31
More reactions: 32, 34, 41, 48
Syntheses: 33, 36, 39, 40, 45,
46, 47, 52
Mechanisms: 38, 44
Chapter 20
Nomenclature: 1, 2, 16, 20, 21,
22
Acidity: 3, 5, 6, 8, 17, 19, 23,
24, 32, 45, 47
Preparation: 9, 18, 26
Syntheses: 10, 11, 12, 13, 25,
27, 28, 34, 35, 36, 37, 38, 39, 40, 42, 46, 48
Mechanisms: 41, 50
Spectroscopy: 14, 15, 51, 52, 53,
54, 55, 56
Reactions: 33, 43, 49
Chapter 21
Nomenclature: 1, 2, 28, 32, 33,
34
Mechanisms: 3, 7, 12, 15, 17, 30,
46, 47, 57, 58
Reactivity: 4, 5, 31
Reactions: 6, 9, 18, 19, 20, 36,
37, 38, 39, 40
Syntheses: 8, 10, 11, 13, 14, 21,
22, 29, 35, 41, 50, 52, 53, 54, 55
Spectroscopy: 26, 27, 64, 65, 66
Chapter 22
Enols: 1, 2, 3
Reactions: 4, 5, 6, 24
Acidity: 7, 8, 19, 20, 21, 22,
23, 33
Malonic esters: 11,
12, 13, 26
Acetoacetic ester:
14, 15, 27, 28
Alkylation: 17
Syntheses: 18, 29, 37, 44
Mechanisms: 25, 31, 32, 34, 35, 36, 38, 39, 40, 41
Chapter 23
Aldol condensation:
1, 2, 3, 4, 10, 23, 25, 27, 29, 31, 35
Syntheses: 7, 8, 28, 45, 46, 47,
48
Claisen condensation:
11, 12, 13, 14, 15, 38, 39
Michael reaction: 16, 17, 42, 43
Stork-enamine:
19, 20, 51
Robinson: 21, 22
Mechanisms: 30, 32, 34, 50, 53
Reactions: 37, 57
Chapter 24
Nomenclature: 1, 2, 21, 25, 26,
27, 28
Basicity: 4, 5, 6,
22, 24, 41, 42
Synthesis: 7, 9, 10, 11, 17, 18,
31, 32, 33, 34, 35, 36, 45, 49
Reactions: 14, 15, 29, 30, 37,
38, 39, 54
Spectroscopy: 20, 66, 67, 68
Mechanisms: 48, 70
Here is the link to the
problem sets for CHM 235 (Spring 2008).
The following book may be a helpful resource as you prepare for your final exam:
Preparing for Your ACS Examination in Organic Chemistry: The Official Guide
Examinations Institute / ACS / Division of Chem. Ed.
ISBN 0-9708042-1-0
http://www4.uwm.edu//chemexams/