| Tentative Lecture Schedule | ||
| Date |
Topics |
Chapter in Karty |
| 8/21 |
The structural theory. Lewis structures.
|
1.1-1.5 |
| 8/23 | Drawing structures by reference to normal
valencies of elements. Formal Charge. Isomers. Resonance
structures. |
1.6,1.9, 1.10 |
| 8/25 |
Condensed and skeletal
structures. Forms of carbon. Common types of resonance
structures; allylic, aromatic, and carbonyl. Functional
group families.
|
1.10-1.13 |
| 8/28 |
Naming alkanes and finding isomers.
Cycloalkanes.
|
A.1-A.2, A.4 |
| 8/30 |
Naming of branched alkyl groups. Valence
bond theory. Hybrid orbitals. Pi and Sigma bonds.
|
A4-A.5, app E.1 3.1-3.9 |
| 9/1 |
VBT continued: cis/trans isomers, alkynes
and allenes, hybridization effects on effective
electronegativity and bond
lengths. Also see this reference.
MO Theory. (Leah4Sci.com explains this well in this video.) |
3.5, 3.7, 3.9, 3.10 |
| 9/6 |
Acid/base reactions.Using pKa values to
Predicting the direction of equilibrium. Predicting
acidity from structure: The CARDIN-al method.
|
6 |
| 9/8 |
Drawing most stable conformers. Resonance
and Inductive Effects on Acidity. Acidic and basic
functional group families.
|
4.1-4.8, 6.2, 6.6 |
| 9/11 |
Nuclear magnetic resonance - C-13 NMR
theory and interpretation
|
17.1-17.3, 17.5, 17.12 |
| 9/13 |
C-13 NMR interpretation; # of
peaks, shift, and peak intensity.
Intermolecular forces and physical properties.
Boiling point and water solubility.
|
17.12, 2.4-2.8 |
| 9/15 | Predicting
relative base strengths. Combustion and "Ring"
strain. Models |
6, 4.1-4.9 |
| 9/18 |
Exam 1
|
1-4, 6, C-13 NMR |
| 9/20 | Equilibrium reactions. Energy diagrams. Enthalpy, entropy, and free energy. Reaction rates and collision theory. | 6.3, 8.4 |
| 9/22 | Kinetics.
Predicted rate laws for elementary reactions. Stepwise
reactions. Nucleophilic substitution reactions. The SN1
and SN2 mechanisms. |
8.4, 8.1, 7.2, 9.6 |
| 9/25 |
Leaving groups and nucleophiles in SN
reactions. The tosylate leaving group. Neutral
nucleophiles - solvolysis. Master
Organic Chemistry.
|
9.3-9.6 |
| 9/27 |
More on solvolysis. Solvent effects in SN reactions. Naming of ethers, alkenes, alkynes, alcohols, thiols, and amines. | 9.7, A.6, B.1, D.2 |
| 9/29 |
Stereochemistry
of SN reactions. |
8.5 |
| 10/2 | Carbocation
rearrangements. SN2 vs SN1 for synthesis. Properties of
enantiomers; specific rotation. |
7.7, 8.6, 5.12 |
| 10/4 | Resolution
of racemic mixtures. Enantiomeric excess and optical purity.
Chiral atoms other than carbon. Chiral compounds that do not possess
chiral centers. |
5.13-5.14 |
| 10/6 | Elimination
reactions. The E1 and E2 mechanisms. Zaitsev's rule.
Stereochemistry |
7.5, 8.2, 8.5 |
| 10/9 | Effect of R group on E rates.
Cis/trans/E/Z isomerism in alkenes. Competition between SN2,
E2, SN1 and E1 mechanisms. |
3.7, 9 |
| 10/11 | More on E2 elimination stereochemistry. More on SN2, E2, SN1 and E1competitions. | 9 |
| 10/13 | Replacement
of the hydroxyl group of an alcohol: (1) Reaction with HX
(2) Tosylation followed by SN reaction. |
MOC
Ref |
| 10/16 | Exam 2 | 5, 7, 8, 9 |
| 10/18 |
Synthesis
- terminology and principles. Reaction of ROH with PX3.
The Williamson ether synthesis. |
10.1-10.5 |
| 10/20 | Diazomethane for RCOOMe synthesis. Epoxides as SN substrates. Synthesis of epoxides by SN chemistry. | 10.6, 10.8-10.9 |
| 10/23 | Synthesis of
alkenes, thioethers, and alkynes. Double elimination
reactions of dihalides. |
10.5,
10.12, 11.1 |
| 10/25 | Carbon nucleophiles + epoxides. Alkylation of alpha carbons. | 11.1-11.5 |
| 10/27 | Solving IR/NMR
unknowns |
16-17 |
| 10/30 | Proposing a
molecular formula based on a mass spectrum. Thermodynamic vs
kinetic enolate formation. Reactions of organometallics with
epoxides. |
15.5, 7.1b, 11.2-11.3 |
| 11/1 | The
Hammond Postulate. Amines and quaternary ammonium salts from
alkyl halides. Hofmann elimination. |
9.3a, 10.10-10.11 |
| 11/3 | Epoxide naming. The Twelve Principles of
Green Chemistry |
11.6 |
| 11/6 | Exam 3 | 10.1-10.9, 10.12, 11, 16, 17 |
| 11/8 | Electrophilic addition (EA) to alkenes. HX addition and Markovnikov's rule. Acid catalyzed hydration. | 12.1-12.6 |
| 11/10 | No
class for Veterans Day |
|
| 11/13 |
EA reactions of dienes. 1,2 vs
1,4 addition. HX additions to alkynes.
|
12.9-12.10, 12.7 |
| 11/15 | Hydration of alkynes. Keto-enol tautomerism. Use of EA reactions in synthesis. Epoxidation using peroxycarboxylic acids. | 7.10, 12.8, 12.11, 13.1, 13.3 |
| 11/17 | Carbenes and cyclopropanation. X2 addition to alkenes. Bromohydrin formation. | 13.2, 13.4 |
| 11/20 | Synthetic
tools" Oxymercuration/reduction. Hydroboration/oxidation. |
13.5, 13.6 |
| 11/27 |
Alkyne additions. Synthesis. |
13.7, 13.8 |
| 11/29 | Catalytic hydrogenation of alkenes and
alkynes. Synthesis. |
13.9 |
| 12/1 |
Exam 4 |
12-13, 15 |
| 12/6 | Final Exam | cumulative |