|
No |
Date |
Topics |
Chapter |
|
1 |
1/11 | Overview of redox rxns. Reduction of alkenes. | 12 |
|
2 |
1/13 | Reduction of alkynes.
Reduction of epoxides and alkyl halides. |
12 |
|
3 |
1/15 | Alkene and alkyne oxidations: Epoxidation and dihydroxylation of alkenes. Ozonolysis. | 12 |
|
|
1/18 | No Class - MLK Holiday |
|
|
4 |
1/20 |
Ozonolysis continued. Alcohol oxidation. Sharpless
epoxidation. |
12 |
|
5 |
1/22 | Radical reactions.
Halogenation. Selectivity of Br vs Cl. |
15 |
|
6 |
1/25 | NBS for allylic
bromination. Peroxide effect on HBr additions.
Autooxidation. |
15 |
|
7 |
1/27 | Lipid peroxidation, antioxidants, and food preservatives. Radical polymerization. Dienes. Conjugated diene stability. | 15, 16 |
|
8 |
1/29 | 1,2 vs 1,4 addition to conjugated dienes. Allylic cations and radicals. Resonance vs orbital descriptions of conjugated systems. Huckel MO theory. | 16 |
|
9 |
2/1 | Benzene and aromaticity. Benzene compound nomenclature. Benzene MOs and the Huckel rule. Theoretical and experimental criteria for aromaticity. The annulenes. | 17 |
| 10 | 2/3 | Aromatic ions; cyclopropenyl cation and cyclopentadienyl anion. Heteroaromatic rings. Naphthalene. | 17 |
| 2/5 | NMR coupling constants and
tree diagrams. |
||
| 11 |
2/8 | Exam 1 | 12, 15, 16.1-16.11, 17 |
|
12 |
2/10 | Electrophilic aromatic substitution. General mechanism. EAS specific mechanisms. Halogenation, F-C Alkylation, Nitration. Sulfonation. Proton exchange. Effects of substituents. | 18 |
|
13 |
2/12 | Theory of substituent effects on EAS. Resonance vs inductive effects. | 18 |
|
14 |
2/15 | Orientation of EAS on disubstituted rings. Limitations of F-C alkylation. Use of F-C acylation for purposes of alkylation. | 18 |
| 15 |
2/17 | Redox reactions of side chain groups. Benzylic halogenation. Benzene diazonium chemistry. Synthesis. | 18 |
|
16 |
2/19 | Nucleophilic aromatic substitution via the SNAr and benzyne mechanisms. | 18, 25.13-25.14 |
| 17 | 2/22 | Carboxylic Acids - naming, properties, preparation, and acidity. Conversion into acid chlorides. | 19, 22.10A |
| 18 | 2/24 |
Diels-Alder substituent effects and regiochemistry. |
16.12-16.14 |
|
19 |
2/26 | Diels-Alder Lab Quiz Intro to Carbonyl Chemistry. Hydride reduction reactions. |
Expt 2 and MM1 20.1-20.2a, 20.4-20.5 |
|
20 |
2/29 |
Organometallic Chemistry.
Preparation and reactions of Grignard reagents with
aldehydes, ketones, and epoxides. |
20.9-20.11, 20.14 |
| 3/2 |
Exam 2 |
16.12-16.14, 18, 19,
20.1-20.2a, 20.4-20.5, 25.13-25.14 |
|
| 20 | 3/4 |
More Grignard chemistry. Reaction with CO2. Incompatible functional groups. Protection of OH groups as TMS ethers. Protection of C=O groups as acetals. |
20.11-20.15, 21.15 |
|
21 |
3/14 |
Addition of water and alcohols to aldehydes and ketones;
hydrates, hemiacetals, and acetals. |
21.13-21.15 |
|
22 |
3/16 | Addition of amines to aldehydes and ketones: imines and enamines. Mechanism of Wolf-Kishner reduction. | 21.11-21.12 |
|
23 |
3/18 | Addition of sulfur nucleophiles to aldehydes and ketones; thioacetals. The Wittig alkene synthesis. | 21.10 |
|
24 |
3/21 | Redox reactions of aldehydes and ketones. Hydride reduction of acid chlorides and esters. Grignard reactions with acid chlorides and esters. Reaction of organocuprates with acid chlorides. | 20.7a, 20.8, 20.13, 21.8 |
|
25 |
3/23 | Anhydrides and Amides; reactions with hydride reducing agents and Grignard reagents. Carboxylic acid derivatives overall reactivity scheme. | 20.7b, 22 |
| 26 | 3/25 | Carboxylic acid derivatives overall reactivity scheme; interconversions. | 22 |
| 27 | 3/28 | Carboxylic acid derivatives overall reactivity scheme; reactions with hydride sources and organometallics. Nitrile reactions. | 22 |
|
28 |
3/30 | Amide synthesis using DCC. Naming of
carboxylic acid derivatives. Cyclic anhydrides.
Lactones, lactams, and imides. |
22 |
| 29 |
4/1 | More reactions of carboxylic acid derivatives. Polyesters. Synthesis. | 22 |
| 20 |
4/4 | Enols and enolates as nucleophiles. Bases to use for enolate formation. Racemization/Epimerization. Halogenation. | 23 |
|
31 |
4/6 | Alkylation. Kinetic vs thermodynamic enolates.The malonic ester and acetoacetic ester syntheses. | 23 |
| 32 | 4/8 | The aldol condensation. |
24 |
| 4/11 | Exam 3 | 20(except 20.15),
21, 22 |
|
| 33 | 4/13 | The Claisen condensation. Aldol and Claisen-related reactions. | 24 |
| 4/15 | No Class - Spring Break Day |
||
| 34 | 4/18 | Conjugate addition to conjugated ketones and aldehydes. Michael addition. Robinson annulation. | 20.15-20.17, 24.8-24.9 |
| 35 | 4/20 |
Amines - Naming, Physical Properties, Preparation via the Gabriel synthesis and reduction of an imine. |
25 |
| 36 | 4/22 | Amines. Preparation via reductive amination. Reaction as bases. Alkylation of enamines. | 25 |
| 37 |
4/25 |
C-C bond
forming reactions; Suzuki, Heck, and Corey-House
reactions. |
26 |
| 38 |
4/27 |
C-C bond
forming reactions; Cyclopropanation and Olefin
Metathesis. |
26 |
| 4/29 |
Exam 4 | 23-26 |
|
| 5/5 | Final Exam (8:00 AM) |