| Date |
Lecture Topic |
Readings
(Chapters from Wade) |
Problems (from Wade) |
| Wed, Jan 23 |
Course Introduction |
- |
- |
| Fri, Jan 25 |
Valence Electrons, Bonds, and
Drawing Organic Molecules |
Chap. 1.1-1.9 |
Chap. 1:
1-10, 14-19, 21, 23-32, 34-47 |
|
Special: 8 AM, Mon, Jan 28 |
Workshop 1: Drawing Organic Molecules
Workshop 2: Valency and Formal
Charges |
Workshop 1 Solutions
Workshop 2 Solutions |
|
| Mon, Jan 28 |
Resonance Structures;
Lewis Acids and Bases |
Chap. 1.10-1.14 |
|
| Wed, Jan 30 |
Relative Acidity and
Basicity
In-Class Exercise: Organic Acids
and Bases |
In-Class Solutions |
|
8 AM,
Fri, Feb 1 |
Workshop 3: Charge and Resonance
Workshop 4:
Mechanisms of Lewis Acids and Bases
Workshop 5: Ranking Acids and Bases |
Workshop 3 Solutions
Workshop 4 Solutions
Workshop 5 Solutions |
|
| Fri, Feb 1 |
Molecular Orbital Mixing |
Chap. 2.1-2.3 |
Chap. 2:
1-11, 14-16, 19-22, 26-37, 40, 42-44 |
| Mon, Feb 4 |
Hybridization and
the Shapes of Molecules
In-Class Exercise:
Wedge/Dash-Bond Drawings |
Chap. 2.4-2.8
In-Class Solutions
ChemDraw and
Chem3D |
|
| Wed, Feb 6 |
Isomers;
Polarity and Intermolecular
Forces |
Chap. 2.9-2.14 |
|
8 AM,
Fri, Feb 8 |
Workshop 6: Hybridization and
Molecular Shape
Workshop 7: Molecular Orbitals |
Workshop 6 Solutions
Workshop 7 Solutions |
|
| Fri, Feb 8 |
Linear Alkanes: Structures and Conformations
In-Class
Exercise: Newman Projections |
Chap. 3.1-3.8
In-Class Solutions |
Chap. 3:
11-13, 16, 18-29, 31, 33, 42-46 |
| Mon, Feb 11 |
Cycloalkanes |
Chap. 3.9-3.16 |
|
| Wed, Feb 13 |
Substituents on Cycloalkanes
In-Class
Exercise: Disubstituted Cyclohexane Conformers |
In-Class
Solutions |
|
8 AM,
Fri, Feb 15 |
Workshop 8: Cyclohexane Conformers,
and Sweetness
Workshop 9: Fused Rings in Steroids |
Workshop 8 Solutions
Workshop 9 Solutions |
|
| Fri, Feb 15 |
Chirality and Chiral
Centers |
Chap. 5.1-5.3 |
Chap. 5:
1-24, 26-31, 35-39 |
|
Mon, Feb 18 |
Exam 1 (Covers Chapters
1-3)
Last Name A-M: SciCB 125
Last Name N-Z: Anderson 310 |
|
|
| Wed, Feb 20 |
Cahn-Ingold-Prelog Nomenclature, Diastereomers,
Meso Compounds
In-Class Exercise: Cahn-Ingold-Prelog
Assignments |
Chap. 5.4-5.11
In-Class Solutions |
|
8 AM,
Fri, Feb 22 |
Workshop 10:
Assigning (R) and (S) Stereochemistry
Workshop 11: Enantiomers,
Diastereomers, and Meth |
Workshop 10 Solutions
Workshop 11 Solutions |
|
| Fri, Feb 22 |
Racemates, Optical
Activity,
Separating Enantiomers and Diastereomers |
Chap. 5.12-5.16 |
|
| Mon, Feb 25 |
2nd-Order Nucleophilic
Substitution (SN2): Mechanism, Transition States, Energetics
In-Class Exercise: SN2
Mechanisms |
Chap. 6.1-6.12
In-Class Solutions |
Chap. 6:
11-40, 44-62, 69, 72-75(b-d) |
| Wed, Feb 27 |
2nd-Order Nucleophilic
Substitution (SN2): Ranking Nucleophiles and Leaving Groups, Hammond's Postulate |
|
|
8 AM,
Fri, Feb 29 |
Workshop 12:
Chemotherapeutic Alkylating Agents
Workshop 13: Multistep Reaction
Mechanisms |
Workshop 12 Solutions
Workshop 13 Solutions |
|
| Fri, Feb 29 |
1st-Order Nucleophilic
Substitution (SN1); Multistep Mechanisms and Rate-Limiting Steps
In-Class Exercise:
Proton-Mediated SN1 Mechanisms |
Chap. 6.13-6.16
In-Class Solutions |
|
| Mon, Mar 3 |
1st- and 2nd-Order Elimination
(E1 & E2)
In-Class Exercise:
Stereoselectivity of E2 |
Chap. 6.17-6.21
In-Class Solutions |
|
| Wed, Mar 5 |
Alkene Stability,
Preference in E1/E2
In-Class Exercise: E2 Reactions
with Multiple Products
Comparison of SN1, SN2, E1, and E2 Reactivities |
Chap. 7.1-7.11
In-Class Solutions |
Chap. 7:
9-10, 13-19, 24-25, 28-29, 33, 38, 40b, 40c, 41-48, 53-56 |
8 AM,
Fri, Mar 7 |
Workshop 14: Predicting Reaction Outcomes
Workshop 15: Drawing Potential Energy Diagrams |
Workshop 14 Solutions
Workshop 15 Solutions |
|
| Fri, Mar 7 |
Finishing Off
Substitution and Elimination |
|
|
|
Mon, Mar 10 |
Exam 2 (Covers Chapters
5-7)
Last Name A-M: SciCB 125
Last Name N-Z: Anderson 310 |
|
|
| Wed, Mar 12 |
Radical Halogenation:
Mechanism, Energetics |
Chap. 4.1-4.16 |
Chap. 4:
1-4, 9-10, 14-21, 23-32, 35-37, 39-50, 53-55 |
8 AM,
Fri, Mar 14 |
Workshop 16: Unpaired Electron Pushing |
Workshop 16 Solutions |
|
| Fri, Mar 14 |
Radical Halogenation:
Selectivity
In-Class Exercise: Planning
Multistep Organic Syntheses |
In-Class Solutions |
|
| Mon,
Mar 17 |
Holiday. |
|
|
| Wed,
Mar 19 |
Holiday. |
|
|
| Fri,
Mar 21 |
Holiday. |
|
|
| Mon, Mar 24 |
Electrophilic
Addition to Alkenes: Hydrohalogenation and Hydration (Adding HX and H2O) |
Chap. 8.1-8.7 |
Chap. 8:
1-43, 47-68, 70 |
| Wed, Mar 26 |
Electrophilic
Addition to Alkenes: Halogenation, Halohydrins and Epoxides |
Chap. 8.8-8.11 |
|
8 AM,
Fri, Mar 28 |
Workshop 17:
More Multistep Organic Synthesis
Workshop 18: Diastereoselectivity in Organic Synthesis
Workshop 19: Diverted Alkene Addition Mechanisms |
Workshop 17 Solutions
Workshop 18 Solutions
Workshop 19 Solutions |
|
| Fri, Mar 28 |
Alkene Hydrogenation, Hydroxylation, and Cleavage, and a Tale of Fat
In-Class
Exercise: Choosing Between Multiple Synthetic Routes |
Chap. 8.12-8.15
In-Class Solutions |
|
| Mon, Mar 31 |
Alkynes: Acidity,
Synthesis via Acetylides |
Chap. 9.1-9.7 |
Chap. 9:
1, 5-7, 13-24, 25c, 30, 32-34, 36-40, 42 |
| Wed, Apr 2 |
Alkynes: Reactions
In-Class
Exercise: Alkynes in Synthesis |
Chap. 9.9-9.10
In-Class Solutions |
|
8 AM,
Fri, Apr 4 |
Workshop 20: Interfering Functional Groups
Workshop 21: Retrosynthetic
Analysis |
Workshop 20 Solutions
Workshop 21 Solutions |
|
| Fri, Apr 4 |
Alcohols: Properties and
Acidity |
Chap. 10.1-10.6 |
Chap. 10:
7-27, 35, 37-49, 51 |
|
Mon, Apr 7 |
Exam 3 (Covers Chapters
4,8,9)
Last Name A-M: SciCB 125
Last Name N-Z: Anderson 310 |
|
|
| Wed, Apr 9 |
Alcohols: Synthesis by
Organometallic Carbonyl Addition |
Chap. 10.7-10.10 |
|
8 AM,
Fri, Apr 11 |
Workshop 22:
Alcohols from Alkylmetal Reagents |
Workshop 22 Solutions |
|
| Fri, Apr 11 |
Oxidation and Reduction: Reduction of
Carbonyls with Hydride Reagents
In-Class Exercise: Multistep
Synthesis with Organometallic Additions to Carbonyls |
Chap. 10.11-10.12
In-Class Solutions |
|
| Mon, Apr 14 |
Oxidation and Reduction:
Oxidation of Alcohols
In-Class Exercise: Oxidizing and
Reducing Agent Worksheet |
Chap. 11.1-11.4
In-Class Solutions |
Chap. 11:
1-3, 5-6, 9-13, 15-29, 31-38, 40-49, 51-58, 60-63 |
| Wed, Apr 16 |
Tosylates as Good
Leaving Groups; Conversion of Alcohols |
Chap. 11.5-11.14 |
|
8 AM,
Fri,
Apr 18 |
Workshop 23: Diagnostic Tests Based on Oxidation and Reduction
Workshop 24: Mechanisms with Nucleophilic Attack on
Carbonyls |
Workshop 23 Solutions
Workshop 24
Solutions |
|
| Fri,
Apr 18 |
Principles of NMR Spectroscopy |
Chap. 13.1-13.4 |
Chap. 13:
1-27, 34-40, 43-45 |
| Mon, Apr 21 |
Principles of NMR,
Continued |
|
|
| Wed, Apr 23 |
NMR Spectroscopy:
Chemical Shift; Integrals
In-Class Exercise:
Using NMR to Analyze a Typical Chemical Reaction |
Chap. 13.5-13.7
In-Class Solutions |
|
8 AM,
Fri, Apr 25 |
Workshop 25: Functional Group Interconversion with
Tosylates
Workshop 26:
Equivalent and Inequivalent Nuclei |
Workshop 25 Solutions
Workshop 26 Solutions |
|
| Fri, Apr 25 |
NMR Spectroscopy:
Splitting Patterns
In-Class Exercise: Splitting
Patterns in NMR |
Chap. 13.8-13.10
In-Class Solutions |
|
| Mon, Apr 28 |
13C NMR;
Magnetic Resonance Imaging |
Chap. 13.12-13.14 |
|
| Wed, Apr 30 |
Infrared Spectroscopy |
Chap. 12.1-12.12 |
Chap. 12:
2-7, 14-16, 19-21, 25 |
8 AM,
Fri, May 2 |
Workshop 27: Complex Splitting Patterns
in NMR
Workshop 28: Structure
Determination with NMR |
Workshop 27 Solutions
Workshop 28 Solutions |
|
| Fri, May 2 |
Mass Spectrometry:
Principle, Exact Mass Determination |
Chap. 12.13-12.16 |
|
|
Mon, May 5 |
Exam 4 (Covers Chapters
10,11,13)
Last Name A-M: SciCB 125
Last Name N-Z: Anderson 310 |
|
|
| Wed, May 7 |
Mass Spectrometry:
Fragmentation, Applications |
|
|
8 AM,
Fri, May 9 |
Workshop 29: Using IR, MS
and NMR Data for Structure
Elucidation |
Workshop 29 Solutions |
|
| Fri, May 9 |
|
|
|
Fri, May 16
(1:30 - 3:30 pm) |
Final Exam (all-inclusive)
Last Name A-M: SciCB 125
Last Name N-Z: SciCB 175 |
|
|