| |
Date |
Topics |
Chapter |
|
1 |
1/9 | Synthesis tools. Review of reactions from Chem 350. | 12 |
|
2 |
1/11 | Multistep synthesis. Retrosynthetic analysis. | 12 |
|
3 |
1/13 | Alcohols, Phenols, Glycols. Physical properties and acidity. Methods for alcohol preparation. Hydride reduction of ketones, aldehydes. Grignard synthesis of alcohols. | 13 |
|
4 |
1/18 | Grignard retrosynthesis. Conversion of alcohols into alkyl halides. HX. Tosylation. SOCl2. PX3. Oxidation of Alcohols. | 13 |
|
5 |
1/20 | Multistep Synthesis using Alcohols. Ethers - Nomenclature, Preparation, and Reactions. Silyl ethers as protecting groups. | 13, 14 |
|
6 |
1/23 | Multistep syntheses requiring protected alcohols. | 13, 14 |
|
7 |
1/25 | Cyclic Ethers - Nomenclature, Preparation, and Reactions. Stereochemistry and regiochemistry of reactions of unsymmetrical epoxides. Use of epoxides in synthesis. | 14 |
|
8 |
1/27 | Asymmetric epoxidation.
Thiols and Sulfides. |
14.9, 14.11 |
|
9 |
1/30 |
Disulfides, Sulfoxides, and Sulfones. Dienes. Conjugated diene stability. Resonance vs bond hybridization arguments. Molecular orbital theory. | 14.11, 17.1-17.2 |
|
10 |
2/1 | Molecular orbital theory. Drawing the HOMO and LUMO of a conjugated polyene. | 17.3 |
| 2/3 | Exam 1 | 12-14 | |
| 11 | 2/6 | Electrophilic addition
to conjugated dienes. Thermodynamic vs kinetic control.
MOs for the allylic cation, radical, and anion. |
17.4-17.5 |
| 12 | 2/8 | Benzene and Aromaticity. MO theory and the Huckel Rule. Theoretical criteria and experimental hallmarks of aromaticity. | 18.4-18.5 |
| 13 | 2/10 | Applying the theoretical criteria for aromaticity. The annulenes. Aromatic ions. Heteroaromatic rings. | 18.5 |
|
14 |
2/13 | Polycyclic aromatic hydrocarbons. Birch reduction, Side chain reactions of benzene rings. |
18.6-18.7 |
|
15 |
2/15 | Substituent
effects in Diels-Alder cycloadditions. Allowed vs
forbidden cycloaddition reactions. |
17.7-17.8 |
|
16 |
2/17 | Other Pericyclic Reactions. |
17.9-17.10 |
| 17 | 2/20 | Electrophilic
aromatic substitution - general mechanism. |
19 |
| 18 | 2/22 |
Electrophilic aromatic substitution. Substituent effects. | 19 |
|
19 |
2/24 |
CLASS CANCELED:( |
|
| 20 | 2/27 |
Synthesis of disubstituted benzenes. Substitution on disubstituted rings. Friedel-Crafts limitations. Reduction of the nitro and phenone groups. Synthesis strategies. | 19 |
| 21 | 3/1 | Nucleophilic substitution on benzene rings. The SNAr and Benzyne mechanisms. Benzenediazonium salts. | 19.13-19.14, 23.11 |
| |
3/3 | Exam 2 | 17-19 |
|
22 |
3/13 | Carboxylic Acids. Naming, properties, and
reactions. |
21.1-21.5 |
|
23 |
3/15 | Aldehyde/Ketone reactions. Hydration to form gem-diols. Acetal formation. | 20 |
|
24 |
3/17 | Acetals
as protecting groups. Cyclic acetal forms of glucose.
Amylose and cellulose. |
20 |
|
25 |
3/20 |
Thioacetals and Raney Nickel reduction. Reactions of aldehydes and ketones with amines: Imines and Enamines. |
20 |
| 26 | 3/22 | Cyanohydrin formation.
Wittig synthesis. |
20 |
| 27 | 3/24 |
Julia olefination.
Imine and enamine hydrolysis. Wolf-Kishner reduction.
Baeyer-Villager Oxidation. |
20 |
|
28 |
3/27 | Reactivity of Carboxylic Acids and Carboxylic Acid Derivatives. Interconversions of CADs. Hydrolysis of CADs. | 21.6-21.12 |
| 29 | 3/29 |
More examples of CAD reactions:
Saponification. Fisher esterification.
Transesterification. Imides, lactams, and lactones. |
21.6-21.12 |
| 30 | 3/31 |
Reactions of nitriles. | 21.13 |
| 4/3 | Reactions of carboxylic acids, esters, acid chlorides, and nitriles with hydride sources and organometallics. . | 21 | |
|
31 |
4/5 | Enolate chemistry. Epimerization,
halogenation, and alkylation of the alpha carbon. |
22 |
| 32 | 4/7 | Exam 3 |
20-21 |
| 33 | 4/10 | Kinetic vs Thermodynamic Enolates. The acetoacetic ester and malonic ester syntheses. The aldol condensation reaction. | 22 |
| 34 | 4/12 | Crossed aldols and directed aldols. Variations on the aldol condensation; addition reactions of highly stabilized enolates and enolate relatives. Intramolecular aldols | 22 |
| 35 | 4/17 | Reactions of Esters; the Claisen condensation. Intramolecular Claisens. | 22 |
| 36 | 4/19 | Michael additions. Stork enamine synthesis. Robinson annulation. | 22 |
| 37 | 4/21 |
Amines - properties and basicity. | 23 |
| 38 | 4/24 |
Amines - synthesis and reactions. | 23 |
| 39 |
4/26 |
Amino
acids and proteins. |
25 |
| 4/28 |
Exam 4 |
22-23 | |
| 5/3 | Final Exam | 1-26 |