| Date |
Topics |
Chapter in Klein |
|
| 8/26 |
The structural theory.
Lewis and line-bond structures. Isomers.
|
1.1-1.3 |
|
| 8/28 | Drawing line-bond
structures by reference to normal valencies of elements.
Formal Charge. Resonance. |
1.3-1.4 |
|
| 8/30 |
Condensed
and skeletal structures.VSEPR Theory and
Molecular Polarity.
|
1.5, 1.10-1.11 |
|
| 9/4 |
Valence bond theory.
Hybrid orbitals. Pi and Sigma bonds.
|
1.7-1.9 |
|
| 9/6 |
Functional
group families. Naming alkanes and
finding isomers.
|
2.1-2.3, 4.1-4.3 |
|
| 9/9 |
More alkane naming and
naming of alkenes. Branched alkyl groups. Cycloalkane
isomers.
|
4.3, 4.9, 8.3 |
|
| 9/11 |
Types of carbon atoms.
Resonance theory of bonding. Drawing resonance
structures using curved arrows and pattern
recognition.
|
2.4, 2.7-2.12 |
|
| 9/13 |
Acid/base reactions.
Predicting acidity: The ARIO method.
|
3.1-3.4 |
|
| 9/16 |
Predicting
basicity. Predicting the
direction of equilibrium. Acidic and basic functional
group families.
|
3.4-3.8, 2.3 |
|
| 9/18 |
Intermolecular forces
and physical properties. Boling
point and water solubility.
|
1.12-1.13, 2.3 |
|
| 9/20 |
Reactions of alkanes.
Combustion. Finding
some isomers of C5H8. Naming
of dienes, cycloalkenes, and bicycloalkanes.
|
4.4-4.5, 8.3, 10.2 |
|
| 9/23 | C-13 NMR. Theory and predicting number of peaks. | 16.1, 16.3-16.5 |
PowerPoint |
| 9/25 | C-13 NMR. Peak Shifts and Intensities. DEPT
spectra. |
16.12-16.13 |
|
| 9/27 |
Conformations and strain. (This topic is
covered primarily in the molecular modeling labs) |
4.6-4.14 |
Ring
Strain Models |
| 9/30 |
Introduction to mass spectrometry.
|
15.8-15.13 | PowerPoint |
| 10/2 |
Exam 1
|
1-4, 8.3, 10.2, 16 (C-13) |
|
| 10/4 |
Equilibrium constants
and free energy, enthalpy, and entropy. Using BDEs
to calculate heats of reaction.
Kinetics and collision theory.
Rate laws and reaction order.
|
6.1-6.8 |
|
| 10/7 |
More on
collision theory. Multi-step vs single-step reactions.
Kinetics and reaction mechanisms. Nucleophilic substitution. The SN2 and SN1 mechanisms.
|
6.5-6.7 |
|
| 10/9 |
Transition State Theory and
the Hammond Postulate. Structural effects on rate;
steric effects (SN2) vs carbocation stability
(SN1).
|
6.6, 7.4-7.5 | |
| 10/11 |
Effect of leaving group
ability. Effect of nucleophile
strength. Neutral nucleophiles. Aprotic vs protic solvents.
|
7.4-7.5 |
|
| 10/14 |
Properties of
enantiomers. Optical activity and specific
rotation. Optical purity and enantiomeric
excess. Chiral drugs.
|
|
|
| 10/16 |
Nucleophiles and solvents. SN2 vs SN1 stereochemistry.
|
7.4-7.5 |
|
| 10/18 | Chiral compounds that lack chirality centers. Carbocation rearrangements in SN1 reactions. | 6.11 |
|
| 10/21 | Alcohols as SN substrates. Protonated alcohols. Tosylates. Synthesis. | 7.6-7.9 | |
| 10/23 |
Alkenes; cis/trans vs E/Z designations. Elimination reactions of Alkyl Halides. The E1, E2, and E1cb mechanisms. | 8.1-8.4 | |
| 10/25 | E1 and E2
reactions. The Zaitsev
rule and effect of alkyl substitution on alkene
stability. Alcohols as E1/E2 reactants -
dehydration. |
8.5-8.11 |
|
| 10/28 | E1 and E2 rate effects. Predicting which elimination mechanism will be followed. E1 and E2 Stereochemistry. | 8.7, 8.9 |
|
| 10/30 | Bases used for E2 reactions; NaH vs KO-t-Bu. DBU and DBN. Predicting the reaction and mechanism. SN2, E2, SN1, or E1. | 8.12-8.14 | |
| 11/1 | Exam 2 |
5-8, 15 (MS) |
|
| 11/4 |
Intro to alkene
addition reactions. Hydrohalogenation and X2 addition mechanisms and prediction of
stereochemistry and regiochemistry.
|
9.1-9.3, 9.8 | |
| 11/6 | Acid catalyzed hydration. Synthetic methods for hydration: (a) oxymercuration-demercuration (b) hydroboration-oxidation. | 9.4-9.6 |
|
| 11/8 | Mechanism and stereochemistry of alkene
hydroboration. Synthesis strategies. |
9.6 |
|
| 11/13 | Dihydroxylation by KMnO4 or OsO4. Catalytic hydrogenation. | 9.9-9.10 |
|
| 11/15 | Ozonolysis.
Synthesis. |
9.7, 9.11 |
|
| 11/18 |
Exam 3
|
9, 16 (H NMR) | |
| 11/20 |
Preparation of Alkynes. Double E2 reactions of
dihalides. Deprotonation/alkylation of terminal alkynes.
Reactions of Alkynes. HX
addition and X2 addition.
|
10.3-10.4, 10.10, 10.6, 10.8 |
|
| 11/22 | Reactions of Alkynes. Hydration, Hydroboration. Keto/enol tautomerization. | 10.7 |
|
| 11/25 | Reactions of
Alkynes. Hydrogenation,
Ozonolysis.
|
10.5, 10.9 |
|
| 12/2 |
Radicals. Radical
Chain Reactions. Halogenation of Alkanes. NBS.
|
11.1-11.6 |
|
| 12/4 |
HBr Addition to Alkenes. Radical
Reactions in Synthesis.
|
11.10, 11.13 |
PowerPoint |
| 12/6 | Radical Reactions in Biological Systems. Polymers. | 11.9, 11.11 |
|
| 12/9 |
Exam 4 Final Exam |
10-11/cumulative
including a combined spectroscopy problem |
|