| Date |
Lecture Topic |
Readings
(Chapters from Wade) |
Problems
(from Wade, 8th ed.) |
| Wed, Sep 4 |
Course
Introduction; Valence Electrons |
Chap. 1.1-1.9 |
Chap.
1:
1-11, 14-19, 21, 23-32, 34-52 |
| Fri, Sep 6 |
Bonds, and Drawing Organic Molecules |
|
|
| Mon, Sep 9 |
Resonance
Structures; Hybridization
and the Shapes of Molecules |
|
Chap.
2:
1-11, 14-16, 19-22, 25-37, 40, 42-44 |
Workshop,
Tues, Sep 10 |
Workshop
1: Drawing Organic Molecules
Workshop 2: Valency and
Formal Charges
|
Workshop 1
Solutions
Workshop 2
Solutions
|
|
| Wed, Sep 11 |
Molecular
Orbital Mixing
In-Class Exercise:
Wedge/Dash-Bond Drawings |
Chap. 1.10-1.14
In-Class
Solutions
ChemDraw and Chem3D
|
|
| Fri, Sep 13 |
Lewis Acids and Bases; Relative
Acidity and Basicity
In-Class Exercise:
Acid-Base Reactions and "Electron Pushing"
At-Home Exercise:
The Pharmacology of Organic Acids and Bases |
Chap. 2.1-2.3
In-Class
Solutions
At-Home
Solutions
|
Chap.
2:
1-11, 14-16, 19-22, 25-37, 40, 42-44 |
Honors Tutor
Session
Middlebrook Hall,
9th Floor Study Lounge
6:00 - 8:00 pm |
|
|
|
| Mon, Sep 16 |
Organic Functional Groups;
Molecular Polarity; Intermolecular Forces (Handouts from Sep 13)
|
Chap. 2.4-2.8
|
|
Workshop,
Tues, Sep 17 |
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
|
|
| Wed, Sep 18 |
Naming Organic Molecules
(Handouts from Sep 13)
|
Chap. 2.9-2.14 |
|
| Fri, Sep 20 |
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, 42-48 |
| Mon, Sep 23 |
Cycloalkanes |
Chap. 3.9-3.16 |
|
Workshop,
Tues, Sep 24 |
Workshop
6: Hybridization and Molecular Shape
Workshop 7: Molecular
Orbitals
|
Workshop 6
Solutions
Workshop 7
Solutions
|
|
| Wed, Sep 25 |
Substituents
on Cycloalkanes
In-Class Exercise:
Disubstituted Cyclohexane Conformers
|
In-Class
Solutions
|
|
| Fri, Sep 27 |
Chirality
and Chiral Centers |
Chap. 5.1-5.3 |
Chap.
5:
1-24, 26, 28-31, 35 |
| Mon, Sep 30 |
Cahn-Ingold-Prelog
Nomenclature, Diastereomers, Meso Compounds
In-Class Exercise:
Cahn-Ingold-Prelog Assignments
|
Chap. 5.4-5.11
In-Class
Solutions
|
|
Workshop,
Tues, Oct 1 |
Workshop
8: Cyclohexane Conformers, and Sweetness
Workshop 9: Fused Rings in
Steroids
|
Workshop 8
Solutions
Workshop 9
Solutions
|
|
|
Wed, Oct
2 |
Exam
1
(Covers Chapters 1-3) |
|
|
| Fri, Oct 4 |
Racemates,
Optical Activity, Separating Enantiomers and Diastereomers (Handouts from Sep
30) |
Chap. 5.12-5.16 |
|
| Mon, Oct 7 |
2nd-Order
Nucleophilic Substitution (SN2): Mechanism,
Transition States, Energetics
In-Class Exercise: SN2
Mechanisms
|
Chap. 6.1-6.12
In-Class
Solutions
|
Chap.
6:
1, 5, 7, 11-40, 44-62, 66, 68-69, 71-74(b-d) |
Workshop,
Tues, Oct 8 |
Workshop 10: Achiral or Chiral?
Workshop 11:
Assigning (R) and (S)
Stereochemistry
Workshop 12: Enantiomers,
Diastereomers, and Meth
|
Workshop 10
Solutions
Workshop 11
Solutions
Workshop 12 Solutions
|
|
| Wed, Oct 9 |
2nd-Order
Nucleophilic Substitution (SN2): Ranking
Nucleophiles and Leaving Groups, Hammond's Postulate |
|
|
| Fri, Oct 11 |
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, Oct 14 |
1st-
and 2nd-Order Elimination (E1 & E2)
In-Class Exercise:
Stereoselectivity of E2
|
Chap. 6.17-6.21
In-Class
Solutions
|
|
Workshop,
Tues, Oct 15 |
Workshop 13:
Chemotherapeutic Alkylating Agents
Workshop 14: Multistep
Reaction Mechanisms
|
Workshop 13
Solutions
Workshop 14
Solutions
|
|
| Wed, Oct 16 |
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, 38-39, 40b, 40c, 41-48, 53-57 |
| Fri, Oct 18 |
Finishing Off Substitution and Elimination
(notes from Wed)
At-Home Exercise:
Mechanism Practice Problems
|
At-Home
Solutions
|
|
| Mon, Oct 21 |
Radical
Halogenation: Mechanism, Energetics
|
Chap. 4.1-4.16 |
Chap.
4:
1-4, 9-10, 14-21, 23-32, 35-37, 39-50, 53-57 |
Workshop,
Tues, Oct 22 |
Workshop 15: Predicting
Reaction Outcomes
Workshop 16: Drawing
Potential Energy Diagrams
|
Workshop 15
Solutions
Workshop 16
Solutions
|
|
Wed,
Oct 23
|
Exam
2
(Covers Chapters 5-7)
|
|
|
| Fri, Oct 25 |
Radical
Halogenation: Selectivity
In-Class Exercise:
Planning Multistep Organic Syntheses
|
In-Class
Solutions
|
|
| Mon, Oct 28 |
Electrophilic
Addition to Alkenes: Hydrohalogenation and Hydration (Adding HX and H2O) |
Chap. 8.1-8.7 |
Chap.
8:
1-24, 29-39, 45, 47a-n, 47p-q, 48-50, 56-70, 72 |
Workshop,
Tues, Oct 29 |
Workshop 17: Unpaired
Electron Pushing |
Workshop 17
Solutions |
|
| Wed, Oct 30 |
Electrophilic
Addition to Alkenes: Halogenation, Halohydrins and Epoxides |
Chap. 8.8-8.11 |
|
| Fri, Nov 1 |
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, Nov 4 |
Alkynes:
Acidity, Synthesis via Acetylides |
Chap. 9.1-9.7 |
Chap.
9:
1, 5-25, 30-34, 35a-c, 36-42 |
Workshop,
Tues, Nov 5 |
Workshop 18: More
Multistep Organic Synthesis
Workshop 19: Diverted Alkene Addition Mechanisms
|
Workshop 18
Solutions
Workshop 19
Solutions
|
|
| Wed, Nov 6 |
Alkynes:
Reactions (Handouts from Nov 4)
In-Class Exercise:
Alkynes in Synthesis
|
Chap. 9.9-9.10
In-Class
Solutions
|
|
| Fri, Nov 8 |
Alcohols:
Properties and Acidity |
Chap. 10.1-10.6 |
Chap.
10:
7-27, 35, 37-49, 51-52 |
| Mon, Nov 11 |
Alcohols:
Synthesis by Organometallic Carbonyl Addition |
Chap. 10.7-10.10 |
|
Workshop,
Tues, Nov 12 |
Workshop 20: Diastereoselectivity in Organic Synthesis
Workshop 21: Interfering
Functional Groups
Workshop 22: Retrosynthetic Analysis
|
Workshop 20
Solutions
Workshop 21
Solutions
Workshop 22
Solutions
|
|
Wed,
Nov 13
|
Exam
3
(Covers Chapters 4,8,9)
|
|
|
| Fri, Nov 15 |
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, Nov 18 |
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, 18-27, 31, 33-38, 40-49, 51-58, 60-65 |
Workshop,
Tues, Nov 19 |
Workshop 23: Alcohols
from Alkylmetal Reagents |
Workshop 23
Solutions |
|
| Wed, Nov 20 |
Tosylates
as Good Leaving Groups; Conversion of Alcohols |
Chap. 11.5-11.14 |
|
| Fri, Nov 22 |
Principles
of NMR Spectroscopy |
Chap. 13.1-13.4 |
Chap.
13:
1-27, 34-40, 43-45 |
| Mon, Nov 25 |
NMR
Spectroscopy: Chemical Shift, Integrals In-Class Exercise: Using
NMR to Analyze a Typical Chemical Reaction
|
Chap. 13.5-13.7
In-Class
Solutions
|
|
Workshop,
Tues, Nov 26 |
Workshop 24: Diagnostic
Tests Based on Oxidation and Reduction
Workshop 25: Mechanisms
with Nucleophilic Attack on Carbonyls
Workshop 26: Functional
Group Interconversion with Tosylates
|
Workshop 24
Solutions
Workshop 25
Solutions
Workshop 26 Solutions
|
|
| Wed, Nov 27 |
NMR Spectroscopy: Splitting
Patterns (Handouts from 11/25)
In-Class Exercise:
Splitting Patterns in NMR |
Chap. 13.8-13.14
In-Class Solutions |
|
| Fri, Nov 29 |
Holiday. |
|
|
| Mon, Dec 2 |
NMR Spectroscopy: 13C
NMR; Infrared
Spectroscopy In-Class Exercise: 13C
NMR Analysis |
Chap. 12.1-12.12
In-Class Solutions |
Chap.
12:
2-7, 14-16, 19-21, 25 |
Workshop,
Tues, Dec 3 |
Workshop 27: Equivalent
and Inequivalent Nuclei
Workshop 28: Structure
Determination with NMR
|
Workshop 27
Solutions
Workshop 28
Solutions
|
|
| Wed, Dec 4 |
Mass
Spectrometry: Basic Principles, Fragmentation
In-Class Exercise:
Interpreting IR Spectra
|
In-Class
Solutions |
|
| Fri, Dec 6 |
Mass
Spectrometry: Exact Mass Determination, Isotope Patterns |
Chap. 12.13
|
|
Workshop,
Fri, Dec 6
Appleby 3
3:00-4:00 pm |
Workshop 29: Complex
Splitting Patterns in NMR
Workshop 30: Using IR, MS and NMR Data for
Structure Determination |
Workshop 29
Solutions
Workshop 30
Solutions
|
|
|
Mon, Dec 9 |
Exam 4
(Covers Chapters 10,11,13)
|
|
|
| Wed, Dec 11 |
Mass Spectrometry: Whatever we
didn't get to on 12/6 |
|
|
Mon,
Dec 16
(10:30 am - 12:30 pm) |
Final
Exam (all-inclusive) |
|
|