Chemistry 351, Spring 2020, Winona
State University, Dr. T. Nalli
Tentative
Lecture Schedule
revised 3/29/2020
Note: The chapter
readings given correspond to Klein Organic Chemistry 2nd
edition (the hard copy that you all have).
If you are using the etext available through WileyPlus
then you should subtract 1 from the listed chapter.
For example, if the reference given below is to chapter 20
then that would be chapter 19 in the etext.
| |
Date |
Topics |
Chapter |
Recording |
|
1 |
1/13 | Synthesis tools. Review of reactions from Chem 350 with emphasis on Chapter 11. | 11-12 | |
|
2 |
1/15 | Multistep synthesis. Retrosynthetic analysis. | 12 | |
|
3 |
1/17 | Alcohols,
Phenols, Glycols. Physical properties and
acidity. Reactions of alcohols: preparation of
alkyl halides. |
13.1-2, 13.9 |
|
|
4 |
1/22 | Oxidation of alcohols Methods for alcohol preparation. Hydride reduction of ketones, aldehydes. |
13.10, 13.4-13.5 | |
|
5 |
1/24 | Grignard synthesis
of alcohols. Synthesis strategies. |
13.6, 13.12 |
|
|
6 |
1/27 | Ethers - Nomenclature, Preparation, and Reactions. Silyl ethers as protecting groups. Multistep syntheses requiring protected alcohols. | 13.7, 14.1-14.6 |
|
|
7 |
1/29 | Cyclic Ethers - Nomenclature, Preparation, and Reactions. Regiochemistry of reactions of unsymmetrical epoxides. Use of epoxides in the Grignard synthesis. | 14.5, 14.6-14.10 |
|
|
8 |
1/31 | Stereochemistry of
epoxide ring opening. Bromohydrin route to epoxides.
Asymmetric epoxidation. Crown Ethers |
14.4, 14.8-14.11 |
|
|
9 |
2/3 |
Sulfur compounds. | 14.11 |
|
|
10 |
2/5 |
Dienes. Conjugated diene stability. Resonance vs bond hybridization arguments. Intro to molecular orbital theory. | 17.1-17.3 |
|
| 2/7 | Exam 1 | 11-14 | ||
| 11 | 2/10 | Drawing the HOMO
and LUMO of a conjugated polyene. Electrophilic
addition to conjugated dienes. Thermodynamic vs
kinetic control. MOs for the allylic cation. |
17.3-17.5 |
|
| 12 | 2/12 | Benzene and Aromaticity. MOs for
cyclic conjugated systems. Cyclobutadiene and
cyclooctatetraene. |
18.1-18.4 | |
| 13 | 2/14 | The Huckel Rule.
Theoretical criteria and experimental hallmarks of
aromaticity. The annulenes. Aromatic and
antiaromatic ions. |
18.1-18.5 | |
|
14 |
2/17 | Aromatic ions continued.
Cyclooctatetarene dication and sianion.
Heteroaromatic rings. Polycyclic aromatic
hydrocarbons. Buckminster Fullerene. |
18.5 | |
|
15 |
2/19 | Electrophilic
aromatic substitution - general mechanism.
Friedel-Crafts reactions. Rearrangements in F.C.
alkylation. F.C. acylation followed by reduction of
the C=O to CH2. Halogenation. Nitration. |
19.1-19.6 |
|
|
16 |
2/21 | Substituent effects in SEAr
reactions. |
19.3, 19.7-19.10 |
|
| 17 | 2/24 | Sulfonation.
Synthesis of ortho isomers. Reduction of aromatic
nitro groups. Halogenation. |
19.5-19.6, 19.11-19.12 |
|
| 18 | 2/26 |
Friedel-Crafts limitations and
synthetic implications. SEAr reactions on
disubstituted rings. Side chain reactions. Birch
reduction. |
19.4, 19.12, 18.6-18.7 | |
|
19 |
2/28 |
Birch reduction. Nucleophilic substitution on benzene rings. The SNAr and Benzyne mechanisms. Benzenediazonium salts. | 19.13-19.14, 23.11 | |
| 20 | 3/2 |
Synthesis of subsituted benzene rings
using retrosynthetic analysis/ |
19 | |
| 21 | 3/4 |
Aldehyde/Ketone properties and reactions. Nucleophilic addition of hydride and Grignard reagents. | 20.3-4, 20.9-20.10 |
|
| |
3/6 | Exam 2 | 17.1-17.5, 18-19,
23.11 |
|
| 22 |
3/30 |
Aldehyde/Ketone reactions. Hydration. Acetal formation. Acetals as protecting groups. | 20.5, 20.7, 20.8 |
Zoom
03302020 |
|
23 |
4/1 | Reactions of aldehydes and ketones
with amines: Imines and Enamines. Hydrolysis of
imines and enamines. |
20.6, 20.7 |
Zoom 04012020 |
|
24 |
4/3 | Wittig synthesis. Julia-Kocienski reaction. Baeyer-Villiger Oxidation. | 20.10-20.12 |
Zoom
04032020 ILL 04032020 |
|
25 |
4/6 |
Carboxylic Acids. Naming, properties, and reactions. Fatty Acids. | 21.1-21.5 | Zoom
04062020 ILL 04062020 |
| 26 | 4/8 |
Reactivity of Carboxylic Acids and Carboxylic Acid Derivatives. Interconversions of CADs. Hydrolysis of CADs. | 21.6-21.12 | Zoom 04082020 |
|
27 |
4/10 | More examples of CAD reactions: Saponification. Fisher esterification. Transesterification. | 21.6-21.12 |
Zoom
04102020 ILL 04102020 |
| 28 | 4/13 |
Hydrolysis of nitriles. Nitrile synthesis of carboxylic acids. Reactions of esters and acid chlorides with hydride donors and organometallics. | 21.13, 21.8-21.12 |
|
| 29 | 4/15 |
Conversion of amides to nitriles using thionyl chloride. Reactions of nitriles with hydride sources and organometallics. Nomenclature: imides, lactams, and lactones. | 21.13 | |
| 4/20 | Exam 3 |
20-21 |
||
| 30 |
4/22 | Enolate chemistry. Epimerization and halogenation of the alpha carbon. The haloform reaction. | 21.1-21.2 | |
| 31 | 4/24 | alpha-Alkylation. Kinetic vs Thermodynamic Enolates. The acetoacetic ester and malonic ester syntheses. | 22.5 | |
| 32 | 4/27 |
The aldol condensation. Crossed aldols and directed aldols. | 22.3 |
|
| 33 | 4/29 |
Variations on the aldol condensation: Addition reactions of highly stabilized enolates and enolate relatives. Intramolecular aldols. | 22.3 | |
33 |
5/1 |
Reactions of Esters; the Claisen condensation. Intramolecular Claisen. Michael additions. Stork enamine synthesis. Robinson annulation. | 22.4, 22.6-22.7 |
|
| 5/6 | Final Exam | 1-22 |