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