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