Chem 351 Tentative Lecture Schedule - Spring 2009
No |
Date | Topics |
notes | Chapter |
1 |
1/12 | Alkynes - Naming and Physical Properties. Alkyne addition reactions. | p1, p2 | 11 |
2 |
1/14 | More on alkyne addition reactions. | p1, p2, p3 | 11 |
3 |
1/16 | Hydroboration. Alkynide chemistry. | p1, p2, p3 | 11 |
4 |
1/21 | Overview of redox rxns. Reduction of alkenes and alkynes. Mechanism of dissolving metal reduction. | p1, p2, p3 | 12 |
5 |
1/23 | Reduction of alkyl halides. Epoxidation of alkenes. Dihydroxylation of alkenes. Ozonolysis. | 12 | |
6 |
1/26 | Use of ozonolysis for structure determination. Oxidation of alcohols. | 12 | |
7 |
1/28 | Sharpless oxidation. Radical reactions. Halogenation. | 15 | |
|
8 |
1/30 | Mechanism of
halogenation. Selectivity of Br vs Cl. |
p1, p2, p3, p4 | 15 |
9 |
2/2 | NBS for allylic bromination. Peroxide effect on HBr additions. | p1, p2, p3 | 15 |
10 |
2/4 | Radical polymerization. CFCs and ozone depletion. Lipid peroxidation. | p1, p2, p3, p4 | 15 |
| 2/6 | Exam 1 | |||
| 11 | 2/9 | Conjugation. Allylic cations and radicals. 1,2 vs 1,4 addition to conjugated dienes. | p1, p2, p3 | 16 |
12 |
2/11 | Conjugated diene stability. Resonance vs molecular orbital descriptions. | p1, p2, p3 | 16 |
13 |
2/13 | Benzene and aromaticity. Benzene MOs and the Huckel rule. | p1, p2, p3, p4 | 17 |
14 |
2/16 | No lecture - exam 1 2nd chance | ||
15 |
2/18 | Theoretical and experimental criteria for aromaticity. |
p1, p2, p3 | 17 |
16 |
2/20 | Electrophilic aromatic substitution. General mechanism. | p1, p2 | 18 |
17 |
2/23 | Electron releasing groups and electron withdrawing groups. Effects of substituents in EAS and Diels-Alder reaction. Resonance vs inductive effects. | p1, p2 | 18 |
| 18 | 2/25 | EAS specific mechanisms. Halogenation, F-C Alkylation, Nitration. | p1, p2 | 18 |
| 19 | 2/27 | Effects of substituents in EAS reactions. Orientation of EAS on disubstituted rings. Limitations of F-C alkylation. Use of F-C acylation for purposes of alkylation. | does anyone have notes they can volunteer? |
18 |
20 |
3/9 | More limitations of F-C reactions. Redox reactions of the benzene ring and of side chain groups. Benzylic halogenation. Synthesis. | p1, p2, p3 | 18 |
21 |
3/11 | Nucleophilic aromatic substitution including benzene diazonium chemistry. |
p1, p2 | 25.13-25.14 |
| 3/13 | Exam 2 |
16-18 | ||
| 22 | 3/16 | Carboxylic Acids - naming and acidity. Amino acids. |
p1, p2, p3, p4 | 19 |
23 |
3/18 | Organometallic Chemistry. The Grignard synthesis of alcohols. Organocuprates. | p1, p2, p3 | 20 |
24 |
3/20 | Intro to Carbonyl Chemistry. Hydride reduction reactions. |
p1, p2, p3 | 20 |
|
25 |
3/23 | Quiz on Lectures 22-24 | ||
26 |
3/25 | Naming aldehydes and ketones.Acid-catalyzed addition of water and alcohols to aldehydes and ketones. | 21 | |
27 |
3/27 | More on Acetals. Protecting groups. | 21 | |
| 28 | 3/30 | Addition of amines to aldehydes and ketones: imines and enamines. | p1, p2, p3 | 22 |
| 29 | 4/1 | The Wittig alkene synthesis. Ester and amide nomenclature. | p1, p2, p3, p4 | 21, 22 |
30 |
4/3 | Naming of carboxylic acid derivatives. | 22 | |
| 4/6 | Exam 3 | 19-22 | ||
|
31 |
4/8 | Reactions and preparation of carboxylic acid derivatives. SNacyl. Thionyl chloride for acyl chloride preparation.Hydrolysis of nitriles. | p1, p2, p3, p4 | 22 |
| 32 | 4/13 | Hydrazine reduction mechanism. Amide synthesis. | p1, p2 | 22 |
| 33 | 4/15 | Enols and enolates as nucleophiles. Bases to use for enolate formation. Halogenation. Alkylation. Kinetic vs thermodynamic enolate. Alkylation tricks. | p1, p2, p3, p4 | 23 |
| 34 | 4/17 | Aldol reaction. Claisen condensation. | p1, p2, p3, p4 | 24 |
| 35 | 4/20 | More on synthesis using enolates. Malonic ester and acetoacetic ester syntheses. Alkylation of enamines. | p1, p2, p3 | 24 |
| 36 | 4/22 | Aldol and Claisen related reactions. Knoevenagel condensation. | p1, p2, p3, p4 | 24 |
| 37 | 4/24 | Michael Addition. Robinson Annulation. | p1, p2 | 24 |
| 38 | 4/27 | Amines - Naming, Physical Properties, and Basicity. | p1, p2 | 25 |
| 39 | 4/29 | Preparation of Amines. Reactions of Amines - Diazonium Salts. | 25 | |
| 5/1 | Exam 4 | 22-25 | ||
| 5/4 | Final Exam | 1-30 |
