|
No |
Date |
Topics |
Chapter |
|
1 |
1/13 | Synthesis tools. Review of reactions from Chem 350. | 12 |
|
2 |
1/15 | Multistep synthesis. Retrosynthetic analysis. | 12 |
|
3 |
1/17 | Alcohols, Phenols, Glycols. Physical properties and acidity. Methods for alcohol preparation. Hydride reduction of ketones, aldehydes. and esters. | 13 |
|
4 |
1/22 | Grignard Synthesis. | 13 |
|
5 |
1/24 | SN
and E Reactions of Alcohols. HX. Tosylation. SOCl2.
PX3. |
13 |
|
6 |
1/27 | Class
canceled. |
|
|
7 |
1/29 | Oxidation of Alcohols. Multistep Synthesis using Alcohols. Silyl ethers as protecting groups. | 13 |
|
8 |
1/31 |
Ethers and epoxides: Nomenclature, Preparation, and Reactions. | 14 |
|
9 |
2/3 | Reactions of unsymmetrical epoxides. | 14 |
|
10 |
2/5 | Crown
ethers. Thiols,
Sulfides, Disulfides, Sulfoxides, and Sulfones. |
14 |
| 11 | 2/7 | Conjugated diene stability. Resonance vs bond hybridization arguments. Electrophilic addition to conjugated dienes. Thermodynamic vs kinetic control. | 17.1-17.5 |
| 2/10 | Exam 1 | 12-14 | |
| 12 | 2/12 | Molecular orbitals of conjugated polyenes. Benzene MOs. | 17.3, 18.4 |
| 13 | 2/14 | Aromaticity. MO theory and the Huckel Rule. Theoretical criteria and experimental hallmarks of aromaticity. | 18.4-18.5 |
|
14 |
2/17 | Applying the theoretical criteria for aromaticity. The annulenes. Aromatic ions. Heteroaromatic rings. | 18.5 |
|
15 |
2/21 | Polycyclic aromatic hydrocarbons. Birch reduction, Side chain reactions of benzene rings. |
18.6-18.7 |
|
16 |
2/24 | Electrophilic aromatic substitution - general mechanism. Substituent effects. Synthesis of disubstituted benzenes. | 19 |
| 17 | 2/26 | Theory behind directing effects of
substituents in electrophilic aromatic substitution. |
19 |
| 18 | 2/28 |
Substitution on disubstituted rings. Friedel-Crafts limitations. Synthesis strategies: Friedel-Crafts acylation followed by reduction. Sulfonation as a blocking group methodology. | 19 |
|
19 |
3/3 | Other mechanisms for
nucleophilic substitution on benzene rings. The SNAr and Benzyne
mechanisms. |
19.13-19.14 |
|
20 |
3/5 | Use of diazonium chemistry for synthesis. Reduction of the nitro group. Multistep synthesis of substituted aromatics. | 19,
23.11 |
| 3/7 | Exam 2 | 17.1-5, 18, 19, 23.11 | |
| 22 |
3/19 | Pericyclic Reactions. | 17.8-17.10 |
|
23 |
3/21 | Substituent effects in Diels-Alder cycloadditions. | 17.7-17.8 |
|
24 |
3/24 | Aldehyde/Ketone reactions. Hydration
to form gem-diols. Acetal
formation. |
20 |
|
25 |
3/26 | Thioacetals and Raney Nickel
reduction. Reactions of aldehydes and ketones with amines: Imines and Enamines. Wittig synthesis. Baeyer-Villager oxidation. |
20 |
|
26 |
3/28 |
Naming of Carboxylic Acids and
Diacids. Carboxylic acid synthesis. Predicting
relative acidity. Preparation of Acyl Chlorides using Thionyl Chloride. |
21 |
| 27 | 3/31 | Reactivity of Carboxylic Acids and Carboxylic Acid Derivatives. Interconversions of CADs. Hydrolysis of CADs | 21 |
| 28 | 4/2 | More
examples of CAD reactions. Saponification. Fisher
esterification. Transesterification. Imides, lactams,
and lactones. Alternative preparations of esters. |
21 |
|
29 |
4/4 | Reactions of nitriles. | 21 |
| 30 | 4/7 | Reactions of esters, acid chlorides, and nitriles with hydride sources and organometallics. | 21 |
| 31 | 4/9 | Enolate
chemistry. Epimerization and halogenation of the alpha
carbon. |
22 |
|
|
4/11 | Exam 3. | 17.6-10, 20,
21 |
|
32 |
4/14 | Alkylation of the alpha carbon. Kinetic vs Thermodynamic Enolates. The acetoacetic ester synthesis. | 22 |
| 33 | 4/16 | Decarboxylation of beta-ketoacids.
The acetoacetic ester and malonic ester syntheses. The
aldol condensation reaction. |
22 |
| 34 | 4/21 | Reactions of Esters; the Claisen condensation. Reactions of highly stabilized enolates and enolate relatives. | 22 |
| 35 | 4/23 | Intramolecular aldols and Claisens. Michael additions. Stork enamine synthesis. | 22 |
| 36 | 4/25 | Robinson annulation. Amines - properties and basicity. | 22, 23 |
| 37 | 4/28 | Amines - synthesis and reactions. | 23 |
| 38 | 4/30 |
Reactions of Amines. | 23 |
| 5/2 | Exam 4 | 22, 23 |
|
| 5/9 | Final Exam |