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