|
No |
Date |
Topics |
Chapter |
|
1 |
1/12 | Overview of redox rxns. Reduction of alkenes. | 12 |
|
2 |
1/14 | Reduction of alkynes. Reduction of epoxides and alkyl halides. Epoxidation of alkenes. | 12 |
|
3 |
1/16 | Dihydroxylation of alkenes. Ozonolysis | 12 |
|
|
1/19 | No Class |
|
|
4 |
1/21 |
Alcohol oxidation. Sharpless epoxidation. |
12 |
|
5 |
1/23 | NMR multiplets and
coupling constants. Radical reactions. Halogenation.
Selectivity of Br vs Cl. |
15 |
|
6 |
1/26 | NBS for allylic bromination.
Peroxide effect on HBr additions. Lipid peroxidation and
antioxidants. |
15 |
|
7 |
1/28 | Conjugated diene stability. Allylic cations and radicals. 1,2 vs 1,4 addition to conjugated dienes. Resonance vs orbital descriptions of conjugated systems | 16 |
|
8 |
1/30 | Huckel MO theory. Benzene and aromaticity. Benzene MOs and the Huckel rule. | 17 |
|
9 |
2/2 | Theoretical and experimental
criteria for aromaticity. The annulenes. Aromatic
ions; cyclopropenyl cation and cyclopentadienyl anion. |
17 |
| 10 | 2/4 | Heteroaromatic rings.
PAHs. Benzene compound nomenclature. |
17 |
| 2/6 | Radical polymerization,
lipid peroxidation, antioxidants, and food
preservatives. |
15 |
|
| 11 |
2/9 | Exam 1 | 12, 15, 16, 17 |
|
12 |
2/11 | Electrophilic aromatic substitution. General mechanism. EAS specific mechanisms. Halogenation, F-C Alkylation, Nitration. Sulfonation. Proton exchange. Effects of substituents. | 18 |
|
13 |
2/13 | Theory of substituent effects on EAS. Resonance vs inductive effects. | 18 |
|
14 |
2/16 | Orientation of EAS on disubstituted rings. Limitations of F-C alkylation. Use of F-C acylation for purposes of alkylation. | 18 |
| 2/18 | No Class |
||
|
15 |
2/20 | More limitations of F-C reactions. Redox reactions of the benzene ring and of side chain groups. Benzylic halogenation. Synthesis. | 18 |
| 16 | 2/23 |
Nucleophilic aromatic substitution including benzene diazonium chemistry. |
18 |
| 17 | 2/25 |
Benzene diazonium chemistry. Synthesis. |
25.13-25.14 |
|
18 |
2/27 | Carboxylic Acids - naming and acidity. Amino acids. | 19 |
|
19 |
3/2 |
Intro to Carbonyl Chemistry. Hydride reduction reactions. |
20 |
| 3/4 |
Exam 2 |
18, 19, 25.13-25.14 |
|
| 20 | 3/6 |
Organometallic Chemistry. The Grignard reaction. |
20 |
|
21 |
3/16 |
Synthesis of alcohols by Grignard route. Selective
reduction of acid chlorides and esters to aldehydes.
Silyl ether protecting groups. |
20 |
|
22 |
3/18 | The Wurtz synthesis. Organocuprates for
alkane and ketone synthesis. Physical properties and
redox reactions of aldehydes and ketones. Nucleophilc
addition mechanisms. |
20, 21 |
|
23 |
3/20 | Acid-catalyzed addition of water and alcohols to aldehydes and ketones. Acetals as protecting groups. | 21 |
|
24 |
3/23 | The Wittig alkene synthesis. | 21 |
|
25 |
3/25 | Addition of amines to aldehydes and ketones: imines and enamines. | 21 |
| 26 | 3/27 | Conjugate addition to
conjugated ketones and aldehydes. |
21 |
| 27 | 3/30 | Reactions of carboxylic acid derivatives. Overall reactivity scheme. | 21 |
|
28 |
4/1 | Fischer esterification. Cyclic
anhydrides. Amide synthesis using DCC. Nitrile
reactions. |
22 |
| 4/3 | No Class |
||
| 29 |
4/6 | Mechanism of acyl chloride formation
using thionyl chloride. Mechanism of Wolf-Kishner
reduction. Naming of carboxylic acid derivatives. |
22 |
|
30 |
4/8 | More reactions of carboxylic
acid derivatives. Transesterification. Polyesters.
Lactones, lactams, and imides. Synthesis. |
22 |
| 31 | 4/10 | Enols and enolates as nucleophiles. Bases to use for enolate formation. Racemization/Epimerization. Halogenation. | 23 |
| 4/13 | Exam 3 | 20-22 | |
| 32 | 4/15 | Alkylation. Kinetic vs thermodynamic enolates.The malonic ester and acetoacetic ester syntheses. | 23 |
| 33 | 4/17 | Aldol reactions. | 24 |
| 34 | 4/20 | Michael addition. Robinson annulation. The Claisen reaction. | 24 |
| 35 | 4/22 |
Amines - Naming, Physical Properties, Preparation via the Gabriel synthesis and reduction of an imine. |
25 |
| 36 | 4/24 | Amines. Preparation via reductive amination. Reaction as bases. Alkylation of enamines. | 25 |
| 37 |
4/27 |
C-C bond
forming reactions; Suzuki, Heck, and Corey-House
reactions. |
26 |
| 38 |
4/29 |
C-C bond
forming reactions; Cyclopropanation and Olefin
Metathesis. |
26 |
| 5/1 | Exam 4 | 23-26 |
|
| 5/7 | Final Exam |