| Date |
Topics |
Chapter in Hart |
| 1/9 |
The structural theory.
Lewis and line-bond structures. Normal bonding patterns
for C, N, O, F, and H.
|
1.1-1.7 |
| 1/11 |
Drawing line-bond
structures by reference to normal valencies of elements.
Formal Charge. Resonance structures. Isomers. |
1.8-1.9, 1.11-1.13 |
| 1/13 |
Valence bond theory. Hybrid orbitals. Pi and Sigma bonds. | 1.14, 3.4-3.5, 3.19 |
| 1/18 |
Condensed and skeletal structures. Drawing
isomers. Naming of alkanes.
|
1.9-1.10, 2.1-2.4 |
| 1/20 |
More
alkane naming. Branched alkyl groups. Cycloalkanes.
|
2.4-2.5, 2.9 |
| 1/23 |
Functional
group families. Intermolecular forces. Physical
properties of alkanes - Boiling point.
|
1.18, 2.7 |
| 1/25 |
Physical properties of alkanes - Solubility. Reactions of alkanes. | 2.7, 2.12 |
| 1/27 |
Alkane
and cycloalkane conformations and stability/strain.
Cycloalkane stereoisomers. |
2.8-2.10 Liu Chap 4.1-4.2 |
| 1/30 |
Alkene
reactions. X2, H2O, and HX addition.
Markovnikov's rule. |
3.6-3.8 |
| 2/1 |
Alkenes: Naming and physical properties. Cis/trans isomers. | 3.1-3.5 |
| 2/3 |
Mechanism
of alkene addition reactions. Reaction profiles and
kinetics/thermodynamics. Dienes, Trienes, etc. Allylic
carbocations. |
3.9-3.12, 3.15a |
| 2/6 |
Exam
1 |
1-3.12 |
| 2/8 |
Alkene
Reactions: Hydroboration-Oxidation and Catalytic
Hydrogenation |
3.13-3.14 |
| 2/10 |
Alkyne
naming, properties, and reactions |
3.20-3.21 |
| 2/13 |
Benzene
- resonance and orbitals. Naming of aromatic compounds.
Electrophilic substitution - general mechanism. Alkylation. |
4.1-4.7, 4.9d |
| 2/15 |
Acylation, halogenation, sulfonation, nitration.Subsitutent effects; activators vs deactivators and o,p vs m-directors | 4.8-4.10 |
| 2/17 |
Stereochemistry.
Naming stereocenters as R or S. Properties of enantiomers.
Optical activity. |
5.3-5.6 |
| 2/20 |
More on substituent effects. Synthesis. PAHs, graphite, graphene, and bucky balls. | 4.11-4.13 |
| 2/22 |
Isomeric
relationships; constitutional vs stereoisomers.
Stereochemistry of reactions. Resolution of racemic mixtures
using acid/base reactions. |
5.10-5.12 |
| 2/24 |
E/Z designations for alkenes. IR
Spectroscopy |
5.4, 12.4 |
| 2/27 |
Exam 2 | 3-5
+ C-13 NMR |
| 3/1 |
Organic
acids and bases. Structural effects on acidity. |
Mastering
Chemistry |
| 3/3 |
Alkyl halides
and the nucleophilic substitution reaction. Stereochemistry
and kinetics of the SN1 and SN2 mechanisms. |
6.1-6.5 |
| 3/13 |
Effect
of RX structure on SN1 and SN2 rates- carbocation stability
vs steric hindrances. Solvent effects. Predicting SN1 or
SN2. |
6.4-6.6 |
| 3/15 |
The
E1 and E2 reactions. Effect of RX structure on rate. Effect
of base strength. Bulky bases, e.g., K-O-t-Bu. Predicting
mechanism, SN1/E1 or SN2 or E2. |
6.7-6.8 |
| 3/17 |
Alcohols,
phenols, diols, polyols, and ethers. Naming, properties and
acidity. |
7.1-7.6,
7.13, 8.1-8.2 |
| 3/20 |
Dehydration of alcohols. Halogenation of
alcohols using HX or PX3. |
7.7-7.10 |
| 3/22 |
Oxidation of
alcohols. Phenols as antioxidants. Thiols. |
7.12, 7.16-7.17 |
| 3/24 |
Ethers: acidity and reactions. Use as solvents. Cyclic ethers including epoxides. Epoxide reactions. | 8.3-8.9 |
| 3/27 |
No
Class |
|
| 3/29 |
Spectroscopy review. Solving an IR/NMR
puzzle. |
12 |
| 3/31 |
Exam 3 | 6-8, 12 (HNMR +
IR) + Acidity |
| 4/3 |
Aldehydes
and ketones. Naming and properties.Oxidation of aldehydes.
Nucleophilic addition reactions - hydride reductiona nd the
Grignard synthesis. |
9.1-9.5, 9.9, 9.12-9.13 |
| 4/5 |
Acid-catalyzed
carbonyl additions; acetals and imines. |
9.6-9.8, 9.10-9.11 |
| 4/7 |
Carboxylic acids; naming physical
properties and acidity. Reaction with SOCl2 to
form acid chlorides. |
10.1-10.6 |
| 4/10 |
Reactions of acid chlorides; the SNacyl
mechanism. Polyamides and polyesters. |
10.9-10.14 |
| 4/12 |
Naming
of acid chlorides, esters, and amides. Reactions of esters
and amides. |
10.17-10.21 |
| 4/17 |
Anhydrides.
Reactions of esters with Grignard reagents and hydride
sources. |
10.15-10.16, 10.19 |
| 4/21 |
Enolates; the aldol and Claisen condensation reactions. | 9.15-9.19, 10.22 |
| 4/24 |
Amines - naming an dreactions as
nucleophiles. |
11 |
| 4/26 |
Amines: basicity, preparation by reduction
of nitro groups. Diazonium chemistry. Amino acids and
polypeptides. |
11 |
| 4/28 |
Exam 4 | 9-10 |
| 5/2 |
Final Exam | cumulative |