Chem 351 Tentative Lecture Schedule - Summer 2013
No |
Date | Topics |
Lecture Materials | Chapter |
1 |
6/17 | Synthesis. Review of reactions from Chem 350. Retrosynthetic analysis. | 12 | |
2 |
6/18 | Alcohols: Nomenclature, Physical Properties, and Reactions. Acidity of alcohols and phenols. SN and E reactions of alcohols. Oxidation of alcohols. | 13 | |
3 |
6/19 | Ways to prepare alcohols. Reduction of carbonyl compounds; NaBH4 vs LiAlH4. The Grignard synthesis. | 13 | |
4 |
6/20 | Basicity of Grignard reagents/reaction with hydroxyl groups. Ethers: Nomenclature, Physical Properties, and Reactions. Silyl ethers as protecting groups. | 13, 14 | |
5 |
6/21 | Crown ethers. Epoxides: Nomenclature, Preparation, and Reactions. Thiols and Sulfides. | 14 | |
| 6/24 | Exam 1 | 12-14 | ||
| 6 | 6/25 | Types of dienes. Stability and reactivity of conjugated dienes. Resonance vs MO explanations. Thermodynamic vs kinetic control. MO diagrams for linear polyenes. Electrocyclic reactions. | 17 | |
| 7 | 6/26 | Electrocyclic reactions. Sigmatropic shifts; the Cope and Claisen rearrangements. Cycloaddition reactions. Thermally allowed vs photochemically allowed. Benzene. Theoretical requirements for aromaticity. Experimental hallmarks of aromaticity. Anti-aromaticity. The annulenes up to 18-annulene. | 17, 18 | |
| 8 | 6/27 | Heteroaromatics. Charged aromatics. PAHs. | 18 | |
| 9 | 6/28 | Electrophilic aromatic substitution. Mechanism and substituent effects. | 19 | |
| 10 | 7/1 | Electrophilic aromatic substitution. Synthesis strategies. Nucleophilic aromatic substitution. | 19 | |
| 7/2 | Exam 2 | 17-19 | ||
| 11 | 7/3 | Aldehydes and Ketones. Naming. Nucleophilic adition mechanisms and examples. | 20 | |
| 7/4 | Independence Holiday - No Class | |||
| 12 | 7/5 | Use of acetal group as a protecting group. Nucleophilic addition of amines to aldehydes and ketones. Oximes and hydrazones. | 20 | |
| 13 | 7/8 | Carboxylic acids. Nomenclature and acid/base reactions. Substituent effects on benzoic acid acidity. Ways to prepare carboxylic acids. Carboxylic acid derivatives (CADs). Reactivity and nucleophilic substitution mechanisms. | 20, 21 | |
| 14 | 7/9 | Carboxylic acid derivatives (CADs). Preparation of acid chlorides from carboxylic acids. Interconversion of CADs. Hydrolysis of nitriles. Reduction of carboxylic acid derivatives. Grignard reactions of esters. Organocuprates. | 21 | |
| 15 | 7/10 | Saponification. Ways to prepare esters. Alpha carbon chemistry. Halogenation. Epimerization. |
21, 22 | |
| 16 | 7/11 | Exam 3 | 20-21 | |
| 7/12 | Aldol condensation. Use of LDA for enolate formation. Kinetic vs thermodynamic conditions. | 22 | ||
| 17 | 7/15 | Alkylation of the alpha position. Claisen condensations. | 22 | |
| 18 | 7/16 | Conjugate addition reactions. Synthesis. | 22 | |
| 19 | 7/17 | Amines. | 23 | |
| 20 | 7/18 | Synthetic Polymers. | 27 | |
| 7/19 | Exam 4 | 22, 23, 27 |