| Tentative
Lecture Schedule |
|
No
|
Date |
Topics
|
Chapter in Klein
|
PowerPoint or Models |
| 1 |
8/26 |
The structural theory.
Lewis and line-bond structures.
|
1
|
|
| 2 |
8/28 |
Drawing
line-bond structures by reference to
normal valencies of elements. Formal
Charge. Isomerism.
|
1
|
|
| 3 |
8/30 |
VSEPR
Theory and Molecular Polarity.
Functional
group families.
|
1
|
|
| |
9/2 |
No Class -
Labor Day Holiday
|
|
|
| 4 |
9/4 |
Valence
bond theory. Hybrid orbitals. Pi and
Sigma bonds.
|
1
|
|
| 5 |
9/6 |
Condensed
and skeletal structures. Naming
alkanes and finding isomers.
|
2,
4
|
|
| 6 |
9/9 |
Resonance theory of
bonding. Drawing resonance
structures using curved arrows and
pattern recognition.
|
2
|
|
| 7 |
9/11 |
Acid/base reactions.
Predicting acidity: The ARIO method.
|
3
|
|
| 8 |
9/13 |
Acid/base reactions.
Predicting basicity.
Predicting the direction of
equilibrium.
|
3
|
|
| 9 |
9/16 |
C-13 NMR
|
16
|
|
| 10 |
9/18 |
Intermolecular
forces and physical properties.
|
4
|
|
| 11 |
9/20 |
Finding the constitutional
isomers of C6H10.
Naming of alkynes, dienes,
cycloalkenes, and bicycloalkanes.
|
4
|
|
| 12 |
9/23 |
Processing C-13 NMR data.
Use of JEOL Delta Software.
Cis/trans isomerism.
|
4
|
|
| 13 |
9/25 |
Predicting
water solubility. Reactions of
alkanes. Heat of combustion as an
indicator of stability.
|
3
|
|
| |
9/27 |
Exam 1
|
1-4,
16
|
|
| 14 |
9/30
|
|
16
|
PowerPoint
|
| 15 |
10/2
|
More
Proton NMR. Integrations
and splitting patterns.
|
16
|
|
| 16 |
10/4 |
Equilibrium
constants and free energy,
enthalpy, and entropy. Using BDEs
to calculate heats of reaction. Kinetics
and collision theory.
|
6
|
|
| 17 |
10/7
|
Kinetics and collision
theory. Rate laws and reaction
mechanisms. The SN2 and SN1
mechanisms.
|
6
|
|
| 18 |
10/9 |
Transition State Theory and
the Hammond Postulate. Mechanisms of
nucleophilic substitution; SN2
vs SN1. Structural
effects on rate; steric effects (SN2)
vs carbocation stability (SN1).
|
6,
7
|
|
| 19 |
10/11 |
Nucleophilic substitution.
SN2 vs SN1
- reaction
stereochemistry and carbocation
rearrangements.
|
5,
6, 7
|
|
| 20 |
10/14 |
Mass spectrometry.
Diisoptopic elements, the nitrogen
rule, types of fragmentation
reactions. GC-MS.
|
15
|
PowerPoint
|
| 21 |
10/16 |
SN2 vs SN1
- Effect of
leaving group ability. Effect of
nucleophile strength. Effect of
solvent.
|
15
|
|
| 22 |
10/18 |
SN2 vs SN1
mechanism. Predicting which will
occur. SN2 reactions
in synthesis. Using
alcohols as starting materials.
Tosylates. |
7
|
|
| 23 |
10/21 |
Properties of enantiomers.
Optical activity and specific
rotation. Racemic mixtures. Optical
purity and enantiomeric
excess.
|
5
|
|
| 24 |
10/23 |
Stereochemistry. Chiral
compounds that do not contain chirality
centers. Chiral phosphines.
Alkenes;
cis/trans vs E/Z designations
|
8
|
|
| |
10/25 |
|
5-7, 15, 16
|
|
| 25 |
10/28 |
1,2-Elimination of Alkyl
Halides. The E1, E2, and E1cb
mechanisms. E2
reactions and Zaitsev's rule.
|
8
|
|
| 26 |
10/30 |
Stereochemistry of E2
reactions. |
8
|
|
| 27 |
11/1 |
Factors
that affect E2 and E1 reaction
rates. Complete comparison of the E2
and E1 mechanisms.
|
8
|
|
| 28 |
11/4 |
Bases used for E2 reactions.
Predicting the reaction and
mechanism. SN2, E2, or SN1/E1.
|
8
|
|
| 29 |
11/6 |
Addition of
HX to alkenes. Mechanism and
prediction of stereochemistry and
regiochemistry. Markovnikov's rule.
Acid-catalyzed hydration. |
9
|
|
30
|
11/8 |
X2 addition to
alkenes. Stereochemistry and
mechanism. Halohydrin formation. Anti-Markovnikov
addition of HBr - the peroxide effect.
Anti-Markovnikov
hydration through hydroboration-oxidation.
|
9
|
|
| |
11/11 |
No Class -
Veterans Day |
|
|
| 31 |
11/13 |
More
reactions of alkenes;
anti-hydroxylation,
syn-hydroxylation, catalytic
hydrogenation.
|
9
|
|
32
|
11/15 |
Reactions of
Alkynes. HX and X2 addition. |
10 |
|
| 33 |
11/18 |
Reactions of Alkynes.
Hydration and Hydrogenation.
|
10
|
|
|
11/20 |
Exam
3
|
8-9
|
|
| 34 |
11/22 |
Reactions of
Alkynes. Reduction and Oxidation
Reactions.
|
10
|
|
| 35 |
11/25 |
Preparation
of Alkynes. Multi-step Synthesis. |
10
|
|
| 36 |
12/2 |
Radicals. Radical
Chain Reactions. Halogenation of
Alkanes.
|
11
|
|
| 37 |
12/4 |
HBr Addition to Alkenes. Radical Reactions in
Synthesis.
|
11
|
|
| 38 |
12/6 |
Radical
Reactions in Biological Systems. Polymers. |
11
|
|
|
12/9
|
Exam 4 |
10-11
|
|