Chemistry 351, Summer 2019, Winona
State University, Dr. T. Nalli
Tentative Lecture
Schedule
|
No |
Date |
Topics |
Chapter |
|
1 |
7/8 | Radical reactions; halogenation using NBS, anti-Markovnikov HBr additions, alkene polymerization. | 11 |
|
2 |
7/9 |
Review of reactions
from Chem 350. Retrosynthetic analysis. |
12 |
|
3 |
7/10 | Alcohols and
Phenols. Physical properties and acidity. Preparation of
alcohols. Reduction of carbonyl compounds; NaBH4
vs LiAlH4. The Grignard synthesis. |
13 |
|
4 |
7/11 | Reactions of alcohols. SN, E,
and Oxidation. Ethers, crown ethers, cyclic ethers.
Silyl ether protecting groups for alcohols. |
13, 14 |
|
5 |
7/12 | Preparation and
reactions of epoxides. Direction of attack on
unsymmetrical epoxides. Epoxide nomenclature.
Thiols, sulfides, sulfoxides, and sulfones. |
14 |
| 7/15 |
Exam 1 | 11-14 | |
| 6 | 7/16 | 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. |
15, 16 |
| 7 | 7/17 |
Elimination reactions
producing conjugated dienes. Addition reactions of
conjugated dienes. Lipid peroxidation. |
15, 11.9 |
| 8 | 7/18 |
Benzene. Theoretical requirements for
aromaticity. Anti-aromaticity. The annulenes up to
18-annulene. Heteroaromatics. Charged aromatics. PAHs.
Reactions involving benzylic radicals. Side chain
oxidation. |
16 |
| 9 | 7/19 |
Electrophilic aromatic
substitution. Mechanism and substituent effects.
Synthesis of primary alkyl benzenes via
acylation/reduction. |
17 |
| 10 | 7/22 |
Electrophilic aromatic substitution.
Synthesis of polysubstituted benzenes. Reactions of
aromatic side chains. Synthesis strategies. |
17 |
| 11 |
7/23 |
Nucleophilic
aromatic substitution. Arenediazonium ions. |
17.13-17.14, 20.11 |
| 7/24 |
Exam 2 |
15-17 | |
| 12 | 7/25 |
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. |
18 |
| 13 | 7/26 |
Wittig Synthesis. Baeyer-Villiger
oxidation. Carboxylic acids. Nomenclature and acid/base reactions. Substituent effects on benzoic acid acidity. Preparation of acid chlorides from carboxylic acids. |
18, 19 |
| 14 | 7/29 | Ways to prepare carboxylic acids. Carboxylic acid derivatives (CADs). Reactivity and nucleophilic substitution mechanisms. Interconversions of CADs. Fisher esterification. Cyclic anhydrides. Amide formation via thermal decomposition of ammonium carboxylates. | 19 |
| 15 | 7/30 |
Hydrolysis of nitriles. |
19 |
| 16 | 7/31 | Practice Reactions Quiz
for Exam 3. Ester preparation using carboxylates and nucleophiles. Alpha carbon chemistry. Halogenation. Alkylation using LDA. |
19 20 |
| 17 | 8/1 |
Exam 3 |
18, 19 |
| 18 |
8/2 | Kinetic and thermodynamic controlled
enolate formation. Decarboxylation of beta-ketoacids.
The acetoacetic and malonic acid syntheses.The aldol and
Claisen condensation reactions. |
20 |
| 19 | 8/5 | Knoevenagel, Dieckmann and other enolate-related reactions. Conjugate addition reactions. Michael addition and Robinson annulation. | 20 |
| 20 |
8/6 |
Amines: properties, synthesis, and reactions. Amino acids. Enamines as enolate equivalents. | 21 |
| 8/7 |
Final Exam |
10-21 |