Chem 351 Tentative Lecture Schedule - Summer 2017
|
No |
Date |
Topics |
Chapter |
|
1 |
6/12 | Synthesis. Review of reactions from Chem 350. Retrosynthetic analysis. | 12 |
|
2 |
6/13 | Alcohols: Nomenclature, Physical Properties, and Reactions. Acidity of alcohols and phenols. SN and E reactions of alcohols. Oxidation of alcohols. | 13 |
|
3 |
6/14 | Ways to prepare
alcohols. Reduction of carbonyl compounds; NaBH4
vs LiAlH4. The Grignard synthesis. The TMS
protecting groups for alcohols. |
13 |
|
4 |
6/15 | Ethers, crown ethers, cyclic ethers.
Preparation and reactions of epoxides. Direction of
attack on unsymmetrical epoxides. |
13, 14 |
|
5 |
6/16 | Epoxide
nomenclature. Thiols, sulfides, sulfoxides, and
sulfones. |
14 |
| 6/19 | Exam 1 | 12-14 | |
| 6 | 6/20 | Types of dienes.
Stability of conjugated dienes: resonance vs MO
explanations. MO diagrams for linear polyenes. MOs of
allylic species. Benzene aromaticity and MO theory.
Cyclobutadiene and cyclooctatetraene. |
17, 18 |
| 7 | 6/21 | Addition reactions of
conjugated dienes. Pericyclic reactions. Diels-Alder cycloaddition. Using MO theory to determine symmetry allowed reactions. |
17 |
| 8 | 6/22 | Benzene. Theoretical requirements for aromaticity. Anti-aromaticity. The annulenes up to 18-annulene. Heteroaromatics. Charged aromatics. PAHs. | 18 |
| 9 | 6/23 | Electrophilic aromatic
substitution. Mechanism and substituent effects.
Synthesis of primary alkyl benzenes via
acylation/reduction. |
19 |
| 10 | 6/26 |
Electrophilic aromatic substitution.
Synthesis of polysubstituted benzenes. Reactions of
aromatic side chains. Synthesis strategies. |
19 |
| 11 |
6/27 |
Nucleophilic
aromatic substitution. Arenediazonium ions. Substituent effects in Diels-Alder reactions. |
19.13-19.14, 23.11,
17.7 |
| 6/28 |
Exam 2 |
17-19 | |
| 12 | 6/29 |
Aldehydes and Ketones. Nucleophilic
addition of water and alcohols. Use of acetal group as a
protecting group. Nucleophilic addition of amines to
aldehydes and ketones. Oximes and hydrazones. |
20 |
| 13 | 6/30 |
Mechanism of Wolf-Kishner reduction.
Wittig Synthesis. Carboxylic acids. Nomenclature and acid/base reactions. Substituent effects on benzoic acid acidity. Ways to prepare carboxylic acids. Preparation of acid chlorides from carboxylic acids. |
20, 21 |
| 14 | 7/3 | Carboxylic acid derivatives (CADs). Reactivity and nucleophilic substitution mechanisms. Interconversions of CADs. Hydrolysis of nitriles. | 21 |
| 15 | 7/4 | Independence Holiday - No Class | |
| 16 | 7/5 |
Fisher esterification. Ester preparation using
carboxylates and nucleophiles. Cyclic CADs. Polymeric
CADs. Amide formation via thermal decomposition of
ammonium carboxylates. |
21 |
| 17 | 7/6 | Practice Reactions Quiz
for Exam 3. Alpha carbon chemistry. Halogenation. |
22 |
| 18 | 7/7 | Exam 3 Alpha carbon chemistry. Alkylation using LDA. Kinetic and thermodynamic controlled enolate formation. The acetoacetic acid synthesis. |
20-21 22 |
| 7/10 | Exam 3 - retake Aldol condensation. |
22 |
|
| 19 | 7/11 | Claisen condensations. Knoevenagel, Dieckmann and other enolate-related reactions. Conjugate addition reactions. Michael addition and Robinson annulation. | 22 |
| 20 |
7/12 | Practice with Chapter 22 Reactions. Lab
clean up. |
22 |
| 21 | 7/13 | Amines: properties, synthesis, and reactions. Amino acids. Enamines as enolate equivalents. | 23 |
| 7/14 | Exam 4 | 22, 23 |