| Tentative Lecture Schedule | ||||
|
No |
Date |
Topics |
Chapter in Klein |
PowerPoint or Models |
| 1 | 8/21 |
The structural theory.
Lewis and line-bond structures.
|
1 |
|
| 2 | 8/23 | Drawing line-bond
structures by reference to normal valencies of elements.
Formal Charge. Isomerism. |
1 |
|
| 3 | 8/25 |
VSEPR Theory
and Molecular Polarity.
|
1 |
|
| 4 | 8/28 |
Valence bond theory.
Hybrid orbitals. Pi and Sigma bonds. Functional group families.
|
1 |
|
| 5 | 8/30 |
Condensed
and skeletal structures. Naming
alkanes and finding isomers.
|
1, 2, 4 |
|
| 6 | 9/1 |
More alkane naming.
Branched alkyl groups. Cycloalkane isomers.
|
4 |
|
| 7 | 9/6 |
Acid/base reactions.
Predicting acidity: The ARIO method.
|
3 |
|
| 8 | 9/8 |
Predicting basicity. Predicting the direction of
equilibrium.Acidic and basic functional group
families.
|
3 |
|
| 9 | 9/11 |
Resonance theory of
bonding. Drawing resonance structures using curved
arrows and pattern recognition.
|
2 |
|
| 10 | 9/13 |
Intermolecular forces
and physical properties. Boling
point and water solubility.
|
1.12-1.13,
2.3, 4.4 |
|
| 11 | 9/15 |
Reactions of alkanes.
Combustion. Finding
some isomers of C5H8. Naming
of dienes, cycloalkenes, and bicycloalkanes.
|
4.4, 8.3, 10.2 |
|
| 12 | 9/18 | C-13 NMR. Theory and predicting number of peaks. | 16 |
PowerPoint |
| 13 | 9/20 | C-13 NMR. Peak Shifts and Intensities. DEPT
spectra. |
16 |
|
| 14 | 9/22 | Conformations and strain. | 4 |
Images of Models |
| 15 | 9/25 |
Equilibrium constants and
free energy, enthalpy, and entropy. Using BDEs to
calculate heats of reaction.
|
6 |
|
| 9/27 |
Exam 1
|
1-4, 16
(C-13) |
||
| 16 | 9/29 |
Kinetics and collision
theory. Rate laws and reaction mechanisms. The SN2 and SN1
mechanisms.
|
6 |
|
| 17 | 10/2 |
Transition State Theory and
the Hammond Postulate. Structural effects on rate;
steric effects (SN2) vs carbocation stability
(SN1). Effect of leaving group
ability. Protonated alcohols.
|
6, 7 |
|
| 18 | 10/4 |
SN2 vs SN1
Rate Effects - Effect of nucleophile
strength. Neutral nucleophiles. Aprotic vs protic
solvents.SN2 vs SN1-
Predicting which will occur.
|
7 |
|
| 19 |
10/6 |
SN2 vs SN1 - stereochemistry. Carbocation rearrangements.
|
5, 6, 7 |
|
| 20 | 10/9 |
Alcohols as
SN substrates. Tosylates.
|
|
|
| 21 | 10/11 |
Proton NMR interpretation
and unknown determination.
|
16 |
PowerPoint |
| 22 | 10/13 | Proton NMR Unknown Problems. Discerning structural relationships. |
16 5 |
|
| 23 |
10/16 |
Properties of enantiomers. Optical activity and specific rotation. Racemic mixtures. Optical purity and enantiomeric excess. Resolution of racemic mixtures. | 5 | |
| 24 | 10/18 |
Infrared Spectroscopy
|
15 |
PowerPoint |
| 25 | 10/20 | Mass spectrometry. Diisoptopic elements (Br and Cl), the nitrogen rule, types of fragmentation reactions. | 15 | PowerPoint |
| 26 | 10/23 | 1,2-Elimination of Alkyl
Halides. The E1, E2, and E1cb mechanisms. Zaitsev's rule and alkene
stability. |
8 |
|
| 10/25 |
Exam 2
|
5-7, 13.9, 15 (IR), 16 (H NMR) |
||
| 27 | 10/27 | 1,2-Elimination rate
effects and predicting the mechanism that will be
followed. SN2 vs E2 and bulky vs non-bulky strong bases. |
8 |
|
| 28 | 10/30 | Stereochemistry of E2 and
E1 reactions. |
8 |
|
| 29 | 11/1 | Alkenes;
cis/trans vs E/Z designations. Bases used for E2 reactions. |
8 |
|
| 30
|
11/3 | Alcohol dehydration. Predicting the reaction
and mechanism. SN2, E2, or SN1/E1. |
8 |
|
| 31 | 11/6 |
Addition of HX to alkenes.
Acid-catalyzed hydration. Mechanism and prediction of stereochemistry
and regiochemistry. Markovnikov's rule. X2 addition.
|
9 |
|
| 32 | 11/8 | X2 addition and halohydrin formation. Anti-Markovnikov hydration through hydroboration-oxidation. Oxymercuration/reduction. | 9 |
|
| 33 | 11/13 |
Dihydroxylation using
peracids to form epoxides. Dihydroxylation
by KMnO4 or OsO4. Ozonolysis.
Catalytic hydrogenation.
|
9 |
|
| 34 |
11/15 |
Reactions of Alkynes. HX
and X2 addition. Hydration,
Hydrogenation, Ozonolysis, Deprotonation.
|
10 |
|
| 35 | 11/17 | Exam 3 |
7-9,
15(MS) |
|
| 36 | 11/20 | Preparation of Alkynes. Multi-step Synthesis. | 10 |
|
| 37 | 11/27 |
Radicals. Radical
Chain Reactions. Halogenation of Alkanes.
|
11 |
|
| 38 | 11/29 |
HBr Addition to Alkenes. Radical
Reactions in Synthesis.
|
11 |
|
| 39 |
12/1 | Radical Reactions in Biological Systems. Polymers. | 11 | |
| |
12/4 |
Exam 4/Final Exam |
10-11/cumulative |
|