ORGANIC CHEMISTRY 3540
TENTATIVE SYLLABUS
DR. SUNDIN
UNIVERSITY OF WISCONSIN-PLATTEVILLE
FALL, 2005
The readings and problems are from Fundamentals of Organic Chemistry,
5th Ed., by John McMurry.
DATE: READING ASSIGNMENT; PROBLEMS
- September 6 Introduction: pages xxi, 1-3. Notes
- September 7 Bonding, Isomers, Structure, and NMR Spectroscopy: pages 3-9,
418-422; page 30: # 30, 31, 32, 33, 34, 35, 37, 38, 39, 40, 26, 47, 49; page
437: # 33. Notes
- September 8 Hybridization, Molecular Shapes: pages 10-17; page 30: # 36,
41, 42, 48, 51, 58, 59, 60, 62, 63, 64, 65. Notes
- September 9 Polarity, Electronegativity, Acidity, Curved Arrow Notation:
pages 17-26; page 31: # 43, 44, 45, 46, 50, 52, 53, 54, 55, 56, 57, 61, 66. Notes
- September 12 Skeletal Structures, Functional Groups, Alkane Isomers: pages
34-40, 53-54; page 68: # 31, 32, 33, 34, 35, 36, 37, 39, 40, 41, 42, 45, 48,
51, 56, 57. Notes
- September 13 Infrared Spectroscopy: pages 406-415; page 436: # 25, 26, 30,
37, 38, 41, 42, 47a, 47b. Notes, Review.
- September 14 Discussion.
- September 15 Alkyl Groups, Alkane Nomenclature: pages 41-49; page 68: #
38, 43, 44, 47, 49, 50. Notes
- September 16 Alkane Properties, Conformations: pages 49-52; page 71: # 52,
53. Notes
- September 19 Cycloalkanes: pages 54-63; page 70: # 46, 54, 55, 58, 59, 60,
61, 62, 63, 64, 65, 67. Notes
- September 20 Discussion.
- September 21 Exam I: 7-9 pm, Ottensman 103, 105; pages
1-73, 406-415, 418-422.
- September 22 Alkenes; Structure, Nomenclature: pages 74-84; page 101: #
29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 45, 46. Notes
- September 23 Types of Organic Reactions, Mechanisms: pages 84-92; page
103: # 25, 26, 43, 46, 47. Notes
- September 26 Rates, Equilibrium, Energy: pages 92-96; page 103: # 50, 52,
53, 54, 55, 56, 57.
Notes Review.
- September 27 Markovnikov's Rule: pages 105-110; page 142: # 60, 61. Notes, Review.
- September 28 Discussion.
- September 29 Addition Reactions: pages 111-121; page 138: # 32, 33, 34,
35, 38, 39, 23, 51, 52, 53, 54, 55, 62, 63, 64. Notes
- September 30 Conjugation, Allylic Cations, Resonance: pages 122-128; page
138: # 25a, 25c, 30, 36, 47, 48, 49, 50. Notes
- October 3 Elimination Reactions, Alkynes: pages 85, 128-133; page 138: # 25b,
25d, 26, 27, 28, 29, 37, 40, 41, 42, 43, 24, 44, 45, 46, 56, 57. Notes
- October 4 Aromaticity, Aromatic Nomenclature: pages 143-149; page 172: #
26, 27, 28, 29, 50, 51, 53. Notes
- October 5 Electrophilic Aromatic Substitution: pages 149-156; page 172: #
30, 31, 37, 44, 56, 58. Notes
- October 6 Electrophilic Aromatic Reactivity: pages 156-159; page 172: #
35, 36, 40, 54, 57. Notes
- October 7 Directive Effects, Synthesis: pages 159-167; page 172: # 32, 33,
34, 23, 38, 39, 41, 42, 43, 45, 46, 47, 48, 49, 52, 55.
Notes
- October 10 Discussion.
- October 11 Chirality: pages 177-186; page 206: # 26, 27, 21, 28, 29, 30, 33, 34, 64.
Notes
- October 12 EXAM II: 7-9 pm, Ottensman 103, 105; pages 74-176.
- October 13 Configuration, Sequence Rules: pages 187-191; page 207: # 35,
36, 25, 37, 38, 39, 40, 41, 51, 54, 57, 58, 59, 61, 62, 63. Notes
- October 14 Meso Compounds, Diastereomers, Racemic Mixtures: pages 191-202;
page 208: # 42, 43, 44, 45, 46, 47, 48, 49, 50, 52, 53, 55, 56, 60. Notes
- October 17 Alkyl Halides: Nomenclature, Preparation, Reactions: pages
211-217; page 238: # 26, 27, 28, 30, 32, 36, 43, 44, 61. Notes
- October 18 Nucleophilic Substitution: pages 217-228; page 238: # 29, 31,
33, 34, 35, 38, 39, 41, 42, 46, 48, 51, 52, 57, 58, 59. Notes
- October 19 Eliminations: pages 228-233; page 239: # 37, 40, 45, 47, 49,
50, 53, 54, 55, 56, 60. Notes
- October 20 Discussion.
- October 24 Alcohols, Phenols, Ethers: Nomenclature, Hydrogen Bonding,
Acidity: pages 243-250; page 271: # 26, 27, 28, 30, 31, 47, 48, 49, 50, 51. Notes
- October 25 Preparation and Reactions of Alcohols: pages 250-258; page 272:
# 29, 32, 34, 35, 39, 40, 41, 42, 44, 53, 63. Notes
- October 26 Preparation and Reactions of Phenols, Ethers, Sulfides: pages
258-266; page 272: # 33, 34, 36, 37, 23, 38, 43, 45, 46, 52, 54, 55, 56, 57, 58, 59, 60, 61.
Notes
- October 27 Aldehydes & Ketones: Nomenclature, Properties, Reactions:
pages 276-283; page 300: # 25, 26, 27, 28, 29, 30. Notes
- October 28 Nucleophilic Additions: pages 283-300; page 301:
# 31, 32, 33, 34, 35, 38, 44, 45, 46, 50, 51, 52. Notes
- October 31 Grignard Reaction, Synthesis: pages 291-296: page 301:
# 36, 37, 39, 40, 41, 42, 43, 47, 48, 49, 53, 55. Starting from benzene
and one and two carbon compounds, synthesize: acetone
(Grignard route), acetone (alkyne
route), propionaldehyde
(Grignard route), propionaldehyde
(alkyne route), 2-methyl-2-propanol,
2-methyl-1-propanol,
2-butanol,
1-butanol,
ethyl
isopropyl ether (Grignard route), ethyl isopropyl
ether (alkyne route), acetophenone
(Friedel-Crafts route), acetophenone
(Grignard route), 1-phenyl-1-bromoethane
(Grignard route), 1-phenyl-1-bromoethane
(Friedel-Crafts route), cyclohexanone.
trans-1,2-cyclohexanediol,
p-methoxybenzaldehyde,
1,4-cyclohexanedione.
- November 1 Discussion.
- November 2 EXAM III: 7-9 pm, Boebel 217, 221; pages 176-304.
- November 3. Nuclear Magnetic Resonance Spectroscopy: pages 418-426,
430-432; page 436: # 31, 33, 23, 34, 36, 39, 40, 43, 46, 47, 49, 50, 51. Notes
- November 4 Nuclear Magnetic Resonance Spectroscopy. More C-13 Problems,
More H-1
Problems.
- November 7 Carboxylic Acids, Derivatives: Nomenclature, Acidity: pages
305-313; page 342: # 32, 33, 34, 35, 36, 37, 39, 40, 41. Notes
- November 8 Carboxylic Acids: Synthesis, Reactions; Nucleophilic Acyl
Substitution: pages 313-319; page 344: # 46, 50, 51. Notes
- November 9 Discussion.
- November 10 Acid Halides, Anhydrides, Esters: pages 320-329; page 343:
# 38, 44, 48, 52, 53, 54, 55, 56, 57, 58, 59, 60, 62, 63, 64, 65, 67. Notes
- November 11 Amides, Nitriles, Polymers: pages 329-336; page 343:
# 42, 43, 29, 45, 49, 61, 66, 69, 70.
Notes
- November 14 Tautomers, Carbonyl Alpha Substitutions: pages 347-354; page
374: # 23, 24. Notes
- November 15 Alpha Hydrogen Acidity, Enolates, Syntheses: pages 355-361;
page 374: # 25, 26, 27, 28, 29, 36, 37, 38, 44, 45, 46, 47, 54. Notes
- November 16 Condensations: pages 362-369; page 374: # 30, 31, 32,
34, 35, 39, 40, 41, 42, 43, 48, 49, 51, 52, 53. Notes
- November 17 Discussion.
- November 18 Ultraviolet Spectroscopy: pages 415-418; page 439: # 44, 52.
Notes
- November 21 Amine Nomenclature, Basicity: pages 379-386; page 402:
# 22, 23, 24, 25, 26, 27, 28, 35, 36, 37, 41, 42, 46, 47, 48. Notes
- November 22 Amine Synthesis, Reactions: pages 386-393; page 403:
# 29, 30, 31, 32, 33, 34, 38, 39, 40, 52. Notes
- November 23 Heterocycles, Alkaloids, Dyes: pages 393-397; page 404: # 43, 44, 45.
Notes
- November 28 Discussion.
- November 29 Carbohydrates, Classification, Structure of Glucose: pages
441-450; page 468: # 27, 28, 29, 46, 51, 52, 53. Notes
- November 30 EXAM IV: 7-9 pm, Ottensman 103, 105; pages 305-405, 415-440.
- December 1 Cyclic Glucose, Monosaccharides: pages 450-459; page 469:
# 30, 33, 39, 43, 44, 58. Notes
- December 2 Disaccharides, Polysaccharides: pages 459-465; page 469: # 37, 57.
Notes
- December 5 Amino Acids: pages 472-480; page 503: # 21, 31, 32, 33, 43.
Notes
- December 6 Peptides: pages 481-489; page 503: # 25, 36, 46, 48, 49, 50, 53, 54.
Notes
- December 7 Proteins: pages 490-494 page 503: # 23, 34. Notes
- December 8 Discussion.
- December 9 Enzymes: pages 494-499; page 503: # 26, 27, 41. Notes
- December 12 Nucleic Acids: pages 517-533; page 537: # 29, 30. Notes
- December 13 Lipids: pages 507-517; page 537: # 21, 23, 25. Notes
- December 14 EXAM V: 7-9 pm, Ottensman 103, 105; pages
441-539.
- December 15 Review.
- December 16 Review.
- December 21 FINAL EXAM: Wednesday, 10:00-11:50 am, Fieldhouse: ACS
Standardized. Sample
Final Exam
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