| Date |
Topics |
Chapter in Klein |
| 8/23 |
The structural theory.
Lewis and line-bond structures. Isomers.
|
1.1-1.3 |
| 8/25 | Drawing line-bond
structures by reference to normal valencies of elements.
Formal Charge. Resonance. |
1.3-1.4 |
| 8/27 |
Condensed
and skeletal structures.
|
1.5, 1.10-1.11 |
| 8/30 |
Valence bond theory.
Hybrid orbitals. Pi and Sigma bonds.
|
1.7-1.9 |
| 9/1 |
Functional
group families. Naming alkanes and
finding isomers.
|
2.1-2.3, 4.1-4.3 |
| 9/3 |
More alkane naming.
Branched alkyl groups. Cycloalkanes.
|
4.3, 4.9 |
| 9/8 |
Drawing resonance
structures using curved arrows and pattern
recognition. Rules for judging major vs minor resonance
structures.
|
2.4, 2.7-2.12 |
| 9/10 |
Acid/base reactions.
Predicting acidity: The ARIO method.
|
3.1-3.4 |
| 9/13 |
Predicting the direction of
equilibrium. Predicting basicity. Acidic and basic functional
group families.
|
3.4-3.8 |
| 9/15 |
Intermolecular
forces and physical properties. Boiling point and water solubility.
|
1.12-1.13, 2.3 |
| 9/17 |
Cis/trans isomerism in cycloalkanes.
Drawing most stable chair conformers.
|
4.11-4.13 |
| 9/20 |
Nuclear magnetic resonance - Intro to
C-13 NMR.
|
15.1-5, 15.11-12 |
| 9/22 |
|
4.2, 4.9, 4.4-4.5 |
| 9/24 |
Isomers of C8H14. Bicycles, alkynes,
cycloalkenes, and dienes. |
4.2, 7.7, 9.2 |
| 9/27 |
Exam 1
|
1-4, 15 (C-13) |
| 9/29 |
Equilibrium
constants and free energy, enthalpy, and entropy.
Using BDEs to calculate heats of reaction. Kinetics and
collision theory.
|
6.1-6.5 |
| 10/1 |
Kinetics and collision theory. Rate laws
and reaction order. Multi-step vs
single-step mechanisms. Nucleophilic
substitution. The SN2 and SN1 mechanisms.
|
6.5-6.7 |
| 10/4 |
Transition State Theory and
the Hammond Postulate. Structural effects on rate;
steric effects (SN2) vs carbocation stability
(SN1). Stereochemistry of SN2.
|
6.6, 7.4-7.5 |
| 10/6 |
University Improvement Day - No Class
|
|
| 10/8 |
Nucleophiles and solvents. Aprotic vs protic solvents. SN2 vs SN1 stereochemistry. Neutral nucleophiles. Solvolysis.
|
7.4-7.5 |
| 10/11 |
Carbocation
rearrangements in SN1
reactions.
|
|
| 10/13 |
Properties of
enantiomers. Optical activity and specific
rotation. Optical purity and enantiomeric
excess. Chiral drugs.
|
5.4-5.7 |
| 10/15 | Chiral compounds that lack chirality centers. Resolution of racemic mixtures. Alkenes; cis/trans vs E/Z designations. | 5.9-5.11 |
| 10/18 | Alcohols as SN substrates. Protonated alcohols. Tosylates. Synthesis. | 7.12 |
| 10/20 |
The E2 reaction.
The Zaitsev rule
and effect of alkyl substitution on alkene
stability. |
7.6-7.9 |
| 10/22 | E2 stereochemistry. E2 on cyclohexyl bromides.
Anti periplanar vs syn periplanar. |
7.8 |
| 10/25 | The E1 reaction - stereochemistry and rearrangements.Bases used for E2 reactions; NaH, KO-t-Bu, DBU and DBN. | 7.9, 7.11 |
| 10/27 | Effect of RX
classification on E2 rate. Predicting the reaction, mechanism, and product. SN2, E2, or SN1/E1. |
7.11, 7.13 |
| 10/29 | Alcohol dehydration.trans-Cycloalkenes and bridgehead alkenes.The E1cB mechanism. | 7.10-7.12 |
| 11/1 | Exam 2 | 5-7, 15 (H NMR) |
| 11/3 |
Intro to alkene
addition reactions. Hydrohalogenation and X2 addition mechanisms and prediction of
stereochemistry and regiochemistry.
|
8.1-8.4, 8.9 |
| 11/5 | Acid catalyzed hydration. Synthetic methods for hydration: (a) oxymercuration-demercuration (b) hydroboration-oxidation. | 8.5-8.7 |
| 11/8 | Regiochemistry of hydroboration. Catalytic hydrogenation. | 8.7-8.8 |
| 11/10 | Alkene oxidation reactions: dihydroxylation and ozonolysis. | 8.10-8.13 |
| 11/12 |
Addition Reactions of Alkynes. HX and X2 addition.
Hydration. Keto/enol tautomerization.
|
9.6-9.8 |
| 11/15 |
Exam 3
|
8, 14 (IR) |
| 11/17 | Keto/enol tautomerization mechanism. Preparation of Alkynes. Double E2 reactions of dihalides. Deprotonation/alkylation of terminal alkynes. | 9.3-9.4 |
| 11/19 | Reactions of
Alkynes. Reduction and Ozonolysis.. |
9.5-9.7, 9.9 |
| 11/22 |
Radicals. Halogenation
of Alkanes.
|
10.1-10.5 |
| 11/29 |
Allylic bromination using NBS. Anti-Markovnikov HBr Addition - the peroxide effect.Radical polymerization. | 10.7, 10.10, 10.11 |
| 12/1 | Lipid
peroxidation. CFCs
and ozone depletion. |
10.9, 10.8 |
| 12/3 |
Exam 4 |
9-10 |
| 12/6 | Final Exam | cumulative |