| Date |
Lecture Topic |
Readings
(Chapters from Smith) |
Problems (from Smith, 4th ed.) |
Problems
(from Smith, 3rd ed.) |
| Mon, Jun 13 |
Course
Introduction;
Conjugated Alkenes: Thermochemistry, Molecular Orbitals |
Chap. 16.1-16.9, 16.15; 27.2 |
Chap.
16: 1-10, 12-27, 30-36, 38-64, 67-74
|
Chap.
16: 1-3, 7, 12-35, 40-62
|
| Tues, Jun 14 |
Absorption Spectroscopy; Allyl Intermediates; 1,2- and 1,4-Addition of Dienes
In-Class Exercise:
Molecular Orbital Diagrams of Conjugated Systems
In-Class Exercise: Allylic Carbocations
and Electron Pushing |
Chap. 16.10-16.14
In-Class Solutions
In-Class Solutions |
|
|
| Wed, Jun 15 |
Kinetic vs. Thermodynamic Control; The Diels-Alder Reaction
In-Class
Exercise: Regio- and Stereochemistry in the Diels-Alder Reaction |
In-Class Solutions |
|
|
Workshop,
Thurs, Jun 16
7:00-7:50 AM
Smith 111 |
Workshop 1:
Structure Determination by UV/Vis Spectroscopy
Workshop 2:
Molecular Orbitals and Reactivity
Workshop 3: Reversible Diels-Alder
Reactions
|
Workshop 1 Solutions
Workshop
2 Solutions
Workshop 3
Solutions
|
|
|
| Thurs, Jun 16 |
Aromatic Molecules |
Chap. 17.1-17.11 |
Chap. 17: 1, 8-22, 26-27,
31-52, 59-67 |
Chap. 17: 1-2, 9, 11-26, 28,
32-53, 61-65 |
| Mon, Jun 20 |
Electrophilic Aromatic
Substitution; Directing Groups |
Chap. 18.1-18.4, 18.6-18.9 |
Chap. 18: 1-17, 19-33, 36-70,
75-80 |
Chap. 18: 2-26, 30-69, 75-78 |
Workshop,
Tues, Jun 21
7:00-7:50 AM
Smith 111 |
Workshop 4: Aromatic, or Not?
Workshop 5: Aromatic
Ions in Acid-Base Reactions
Workshop 6: Electrophilic Aromatic
Substitution in Aspirin Manufacture |
Workshop 4 Solutions
Workshop 5 Solutions
Workshop 6 Solutions |
|
|
| Tues, Jun 21 |
Friedel-Crafts
Alkylation and Acylation; Oxidation and Reduction of Aromatic Molecules;
The Sandmeyer Reaction
In-Class Exercise: Electrophilic
Aromatic Substitution Mechanisms
In-Class Exercise: Predicting Products
From Electrophilic Aromatic Substitution |
Chap. 18.5, 18.10-18.14;
25.13-25.15
In-Class Solutions
In-Class Solutions |
|
|
| Wed, Jun 22 |
Carboxylic Acids;
Addition Chemistry of the Carbonyl Group
In-Class Exercise: Multistep Synthesis of Aromatic Molecules |
Chap. 19.1-19.14
In-Class Solutions |
Chap. 19: 10-20, 23-25,
33-55, 63-73 |
Chap. 19: 12-20, 22, 24-25,
34-41, |
Workshop,
Thurs, Jun 23
7:00-7:50 AM
Smith 111 |
Workshop 7:
Synthesizing
Complex Aromatic Products
Workshop 8: Electrophilic Aromatic
Substitution in the Thyroid
|
Workshop 7 Solutions
Workshop 8 Solutions |
|
|
| Thurs, Jun 23 |
Organometallic Reagents
and Addition to Carbonyls |
Chap. 20.1-20.2, 20.9-20.11 |
Chap. 20: 1-71, 78-84 |
Chap. 20: 1-73, 80-81, 83 |
Mon, Jun 27
(8:00 am -
8:50 am) |
Exam
1
(Covers Chapters 16-19,
25.13-25.15) |
|
|
|
Mon, Jun 27(8:55 am -
9:15 am) |
Organometallic Addition to
α,β-Unsaturated
Carbonyls and Epoxides |
Chap. 20.13-20.16
|
|
|
Workshop,
Tues, Jun 28
7:00-7:50 AM
Smith 111 |
POSTPONED. |
|
|
|
| Tues, Jun 28 |
Hydride Addition to Carbonyl
Groups
In-Class Exercise:
Multistep Synthesis with Organometallic Additions to Carbonyls |
Chap. 20.3-20.8
In-Class
Solutions |
|
|
| Wed, Jun 29 |
Acetals
and Ketals; Protecting Groups; The Wittig Reaction |
Chap. 21.1-21.17 |
Chap. 21: 1-2, 9, 11-38, 45-79,
86-92 |
Chap. 21: 1-2, 12-41, 42-81,
89-93 |
Workshop,
Thurs, Jun 30
7:00-7:50 AM
Smith 111 |
Workshop 9: Alcohols
from Alkylmetal Reagents
Workshop 10: Mechanisms
with Nucleophilic Attack on Carbonyls |
Workshop 9 Solutions
Workshop 10 Solutions
|
|
|
| Thurs, Jun 30 |
Imines, Enamines, and
Derivatives |
|
|
|
| Mon, Jul 4 |
|
|
|
|
Workshop,
Tues, Jul 5
7:00-7:50 AM
Smith 111 |
Workshop 11:
Protecting Groups in Organic Synthesis
Workshop 12: Sugars as Hemiketals
|
Workshop 11 Solutions
Workshop 12 Solutions
|
|
|
| Tues, Jul 5 |
Equilibrium Reactions to
Carboxylic Acid Derivatives, Mechanisms
In-Class Exercise: Electron
Pushing in Carboxylic Acid Derivative Exchange |
Chap. 22.1-22.7
In-Class Solutions |
Chap. 22: 1-3, 9-36, 42-78,
86-91 |
Chap. 22: 1-3, 9-40, 43-81,
89-91 |
| Wed, Jul 6 |
Activating Carboxylic Acids: Acyl Halides,
Anhydrides, and Carbodiimide Coupling |
Chap. 22.8-22.12 |
|
|
Workshop,
Thurs, Jul 7
7:00-7:50 AM
Smith 111 |
Workshop 13:
Mechanisms of Macrolactonization
Workshop 14: Carboxylic Acids as
Synthetic Intermediates |
Workshop 13
Solutions
Workshop 14 Solutions |
|
|
| Thurs, Jul 7 |
Reactions of Amides,
Esters, and Nitriles; Enolate Stability; Enolate Protonation, Halogenation,
and Alkylation |
Chap. 22.13-22.18;
Chap. 23.1-23.8 |
Chap. 23:
1-20, 32-72, 74-78 |
Chap. 23:
1-20, 30-46, 54-56 |
Mon, Jul 11
(8:00 am -
8:50 am) |
Exam
2
(Covers Chapters 20-22) |
|
|
|
Mon, Jul 11(8:55 am -
9:15 am) |
Stereoselective Enolate
Additions |
|
|
|
Workshop,
Tues, Jul 12
7:00-7:50 AM
Smith 111 |
POSTPONED. |
|
|
|
| Tues, Jul 12 |
Aldol and Claisen Condensations
In-Class Exercise: Planning Aldol
Reactions |
Chap. 24.1-24.9
In-Class
Solutions |
Chap. 24:
1-13, 15-25, 28-75 |
Chap. 24:
1-71 |
| Wed, Jul 13 |
Michael Addition in Carbonyl
Condensation; Robinson Annulation
In-Class Exercise: Planning Claisen
Reactions
At-Home Exercise: The Robinson Annulation in Steroid Synthesis |
In-Class
Solutions
At-Home
Solutions |
|
|
Workshop,
Thurs, Jul 14
7:00-7:50 AM
Smith 111 |
Workshop 15:
Asymmetric Induction via Chiral Enamines
Workshop 16: Synthesis with Enolates
|
Workshop 15
Solutions
Workshop 16 Solutions |
|
|
| Thurs, Jul 14 |
Amines |
Chap. 25.1-25.12 |
Chap. 25:
1-3, 8-38, 46-82, 86-90 |
Chap. 25:
1-4, 10-40, 44-84, 88-90 |
| Mon, Jul 18 |
Carbon-Carbon Coupling Methods;
Olefin Metathesis |
Chap. 26.1-26.6 |
Chap. 26:
1-54 |
Chap. 26:
1-50 |
Workshop,
Tues, Jul 19
7:00-7:50 AM
Smith 111 |
Workshop 17: Aldol
and Claisen Mechanisms
Workshop 18: More Synthesis with Enolates
Workshop 19: Synthesizing Complex
Amines |
Workshop 17 Solutions
Workshop 18 Solutions
Workshop 19 Solutions |
|
|
| Tues, Jul 19 |
Pericyclic Reactions |
Chap. 27.3-27.6 |
Chap. 27:
2-25, 28-59 |
|
| Wed, Jul 20 |
Carbohydrates |
|
|
|
Thurs, Jul 21
(8:00 am -
8:50 am) |
Exam
3
(Covers Chapters 23-26) |
|
|
|
Thurs, Jul 21
(8:55 am -
9:15 am) |
Glycosides
In-Class Exercise: Drawing
Cyclic Monosaccharides |
Chap. 28.1-28.8, 28.12
In-Class
Solutions |
Chap. 28:
1-18, 29-49, 58-60, 68-71, 76-78 |
Chap. 27:
1-24, 30-63, 69-78 |
| Mon, Jul 25 |
Oligo- and Polysaccharides;
Introduction to Nucleic Acids |
|
|
|
Workshop,
Tues, Jul 26
7:00-7:50 AM
Smith 111 |
Workshop 20: Drawing More Cyclic Monosaccharides
Workshop 21: Mechanisms
of Glycolysis |
Workshop 20 Solutions
Workshop 21 Solutions |
|
|
| Tues, Jul 26 |
Nucleic Acids, cont. |
Chap. 28.13-28.14 |
|
|
| Wed, Jul 27 |
Amino Acids |
Chap. 29.1, 29.5-8 |
Chap. 29:
1-3, 13-24, 29-39, 53-69 |
Chap. 28:
1-3, 13-24, 29-38, 62-69 |
Workshop,
Thurs, Jul 28
7:00-7:50 AM
Smith 111 |
Workshop 22: Solid-Phase Synthesis
of Oligosaccharides Workshop 23:
Catalyzing Transphosphoesterification
Workshop 24: Fmoc
Chemistry in Peptide Synthesis
Workshop 25: Analyzing Non-Standard Amino
Acids |
Workshop 22
Solutions
Workshop
23 Solutions
Workshop 24 Solutions
Workshop 25
Solutions |
|
|
| Thurs, Jul 28 |
Isoelectric Point; Peptide Synthesis |
|
|
|
| Mon, Aug 1 |
Polymers: Introduction and
Characterization |
Chap. 31.1-9 |
Chap. 31:
1-62 |
Chap. 30:
1-58 |
Tues, Aug 2
(8:00 am -
8:50 am) |
Exam
4
(Covers Chapters 27-29) |
|
|
|
Tues, Aug 2
(8:55 am-
9:15 am) |
Polymerization Techniques,
cont.; Co-Polymerization |
|
|
|
Workshop,
Wed, Aug 3
7:00-7:50 AM
Smith 111 |
Workshop 26: Regiochemistry in Butadiene Polymerization
Workshop 27: Bisphenol A Polycarbonate,
and the Alternatives |
Workshop 26 Solutions
Workshop 27
Solutions |
|
|
| Wed, Aug 3 |
|
|
|
|
Thurs,
Aug 4
(8:00 am -
9:15 am) |
Final Exam
(Comprehensive;
Covers Chapters 16-29, 31) |
|
|
|