Chem 351 Tentative Lecture Schedule - Spring 2010
No |
Date | Topics |
notes | Chapter |
1 |
1/11 | Overview of redox rxns. Reduction of alkenes. | p1, p2, p3, p4, p5 | 12 |
2 |
1/13 | Reduction of alkynes. | p1, p2, p3, p4, p5 | 12 |
3 |
1/15 | Reduction of carbonyl compounds and alkyl halides. Epoxidation of alkenes. Dihydroxylation of alkenes. Ozonolysis. | p1, p2, p3, p4, p5, p6 | 12 |
4 |
1/20 | Oxidation of alcohols. Sharpless oxidation. |
p1, p2, p3, p4 | 12 |
5 |
1/22 | Radical reactions.
Halogenation. Selectivity of Br vs Cl. |
p1, p2, p3 | 15 |
6 |
1/25 | Quiz 2. Detailed analysis of Selectivity of Br vs Cl. | 15 | |
7 |
1/27 | NBS for allylic bromination. Peroxide effect on HBr additions. Lipid peroxidation. | p1, p2, p3, p4, p5 | 15 |
|
8 |
1/29 | Lipid peroxidation and antioxidants. Radical polymerization. Ozone and CFCs. Conjugation. Conjugated diene stability. |
p1, p2, p3 | 15, 16 |
9 |
2/1 | Allylic cations and radicals. 1,2 vs 1,4 addition to conjugated dienes. Resonance vs orbital descriptions of conjugated systems | p1, p2, p3, p4 | 16 |
10 |
2/3 | Huckel MO theory. Benzene and aromaticity. Benzene MOs and the Huckel rule. | p1, p2, p3, p4, p5 | 17 |
| 2/5 | Exam 1 | answers p1, p2, p3, p4 | ||
| 11 | 2/8 | Theoretical and experimental criteria for aromaticity. | p1, p2, p3, p4, p5 | 17 |
12 |
2/10 | Aromatic ions. Heteroaromatic rings. | p1, p2, p3, p4 | 17 |
13 |
2/12 | Electrophilic aromatic substitution. General mechanism. EAS specific mechanisms. Halogenation, F-C Alkylation, Nitration. Sulfonation. Proton exchange. Effects of substituents. | p1, p2, p3, p4, p5 | 18 |
14 |
2/15 | Theory of substituent effects on EAS. Resonance vs inductive effects. | 18 | |
15 |
2/19 | Orientation of EAS on disubstituted rings. Limitations of F-C alkylation. Use of F-C acylation for purposes of alkylation. | p1, p2, p3, p4 | 18 |
16 |
2/22 | More limitations of F-C reactions. Redox reactions of the benzene ring and of side chain groups. Benzylic halogenation. Synthesis. | p1, p2, p3, p4 | 18 |
| 17 | 2/24 | Nucleophilic aromatic substitution including benzene diazonium chemistry. |
p1, p2, p3, p4 | |
| 18 | 2/26 | Diazonium chemistry. Synthesis. |
p1, p2, p3 | 25.13-25.14 |
19 |
3/1 | Carboxylic Acids - naming and acidity. Amino acids. | p1, p2, p3, p4, p5, p6, p7 | 19 |
20 |
3/3 | Intro to Carbonyl Chemistry. Hydride reduction reactions. |
p1, p2, p3 | 20 |
| 3/5 | Exam 2 |
17-19, 25.13-25.14 | ||
| 21 | 3/15 | Hydride reduction reactions continued. |
p1, p2, p3, p4, p5 | 20 |
22 |
3/17 | Organometallic Chemistry. The Wurtz synthesis. Organocuprates. Alkane synthesis. Ketone synthesis. | p1, p2, p3, p4, p5, p6 | 20 |
23 |
3/19 | The Grignard synthesis. | p1, p2, p3 | 20 |
|
24 |
3/22 | Addition of amines to aldehydes and ketones: imines and enamines. | p1, p2 | 21 |
25 |
3/24 | The Wittig alkene synthesis. | p1, p2, p3 | 21 |
26 |
3/26 | Acid-catalyzed addition of water and alcohols to aldehydes and ketones. Acetals as protecting groups. | p1, p2, p3, p4, p5 | 21 |
| 27 | 3/29 | Naming of aldehydes, ketones and carboxylic acid derivatives. | p1, p2, p3, p4, p5 | 21, 22 |
| 28 | 3/31 | Reactions of carboxylic acid derivatives. | p1, p2, p3, p4, p5 | 22 |
29 |
4/5 | More reactions of carboxylic acid derivatives including saponification, polymerization, and reactions of nitriles. | p1, p2, p3, p4, p5, p6 | 22 |
30 |
4/7 | Enols and enolates as nucleophiles. Bases to use for enolate formation. Racemization/Epimerization. Halogenation. Alkylation. Kinetic vs thermodynamic enolates. | p1, p2, p3, p4, p5 | 23 |
| 4/9 | Exam 3 | 20-22 | ||
| 31 | 4/12 | The malonic ester and acetoacetic ester syntheses. Aldol reactions. | p1, p2, p3, p4 | 23 |
| 32 | 4/14 | Crossed aldol reactions and related reactions. Michael addition. Robinson annulation. | p1, p2, p3, p4 | 24 |
| 33 | 4/16 | The Claisen reaction. | p1, p2, p3 | 24 |
| 34 | 4/19 | Amines - Naming, Physical Properties, Preparation via the Gabriel synthesis and reduction of an imine. |
p1, p2, p3, p4 | 25 |
| 35 | 4/21 | Amines. Preparation via reductive amination. Reaction as bases. Alkylation of enamines. | p1, p2, p3, p4, p5 | 25, 24 |
| 36 | 4/23 | More reactions of Amines. | p1, p2, p3, p4, p5 | 25 |
| 37 | 4/26 | Carbon-Carbon Bond Forming Reactions: Lithium dialkyl cuprates for alkane synthesis. Suzuki coupling reaction. | p1, p2 | 26 |
| 38 | 4/28 | Carbon-Carbon Bond Forming Reactions: Suzuki Mechanism, Heck reaction. Carbenes and carbenoids. | p1, p2, p3, p4, p5 | 26 |
| 4/30 | Exam 4 | 23-26 | ||
| 5/5 | Final Exam |
