Course Schedule

Chemistry 2301

Organic Chemistry I

[Syllabus] [Course Schedule] [Exams] [Gradescale] [Moodle]

Lecture Schedule

Download items individually from the calendar below. Solutions to Workshops and In-Class Exercises will be posted after the material has been covered in class (usually by the afternoon of the scheduled date).

Date	Lecture Topic	Readings (Chapters from Smith)	Problems (from Smith, 4th ed.)	Problems (from Smith, 3rd ed.)
Tues, Sep 8	Course Introduction; Valence Electrons and Bonds	Chap. 1.1	Chap. 1: 1-90	Chap. 1: 1-22, 23-91 (except parts dealing with bond strength)
Thurs, Sep 10	Drawing Organic Molecules; Bond Polarity; Resonance Structures	Chap. 1.2-1.5, 1.7, 1.11-1.12
Tues, Sep 15	Hybridization and the Shapes of Molecules	Chap. 1.6, 1.8
Thurs, Sep 17	More on Molecular Shapes; Isomers; Electron Pushing in Acid-Base Reactions In-Class Exercise: Wedge/Dash-Bond Drawings	Chap. 1.9-1.10, 2.1-2.2 In-Class Solutions ChemDraw and Chem3D	Chap. 2: 2-6, 8-28, 32-63, 67-77	Chap. 2: 2, 4-7, 9-22, 24-74
Workshop, Fri, Sep 18 2:30-4:00 PM Appleby 3	Workshop 1: Drawing Organic Molecules Workshop 2: Valency and Formal Charges Workshop 3: Hybridization and Molecular Shape Workshop 4: Charge and Resonance	Workshop 1 Solutions Workshop 2 Solutions Workshop 3 Solutions Workshop 4 Solutions
Tues, Sep 22	Relative Acidity and Basicity; Organic Functional Groups; Intermolecular Forces and Solubility In-Class Exercise: Acid-Base Reactions and "Electron Pushing" At-Home Exercise: The Pharmacology of Organic Acids and Bases	Chap. 2.3-2.8, 3.1-3.8 In-Class Solutions At-Home Solutions	Chap. 3: 1-5, 10-11, 21-30, 38-46	Chap. 3: 19-22
Thurs, Sep 24	Linear Alkanes: Structures and Conformations In-Class Exercise: Newman Projections	Chap. 4.1-4.10 In-Class Solutions KhanAcademy Lectures on Organic Nomenclature	Chap. 4: 1-8, 16-31, 34-38, 47-76	Chap. 4: 1-9, 18-31, 36-39, 47-68, 75-78
Workshop, Fri, Sep 25 2:30-4:00 PM Appleby 3	Workshop 5: Mechanisms of Lewis Acids and Bases Workshop 6: Ranking Acids and Bases	Workshop 5 Solutions Workshop 6 Solutions
Tues, Sep 29	Cycloalkane Conformations; Drawing Cyclohexanes	Chap. 4.11-4.15
Thurs, Oct 1	Mono- and Di-substituted Cycloalkanes In-Class Exercise: Disubstituted Cyclohexane Conformers	In-Class Solutions
Workshop, Fri, Oct 2 2:30-4:00 PM Appleby 3	Workshop 7: Newman Projections and Potential Energy Diagrams Workshop 8: Cyclohexane Conformers, and Sweetness	Workshop 7 Solutions Workshop 8 Solutions
Tues, Oct 6 (9:45 am - 10:35 am) *A-Ma:* Smith 100 *Mc-Ng:* Mondale 65 *Ni-Ro:* Blegen 110 *Ru-Sk: Blegen 140 Sn-U:* Blegen 240 *V-Z:* Blegen 145	Exam 1 (Covers Chapters 1-4)
Tues, Oct 6 (10:45 am - 11:00 am)	Stereogenic Centers; Cahn-Ingold-Prelog Nomenclature In-Class Exercise: Cahn-Ingold-Prelog Assignments	Chap. 5.1-5.6 In-Class Solutions	Chap. 5: 2-26, 33-63, 66-72	Chap. 5: 2-28, 34-63, 67-71
Thurs, Oct 8	Meso Compounds; Racemates; Optical Activity; Diastereomers	Chap. 5.1-5.13
Workshop, Fri, Oct 9 2:30-4:00 PM Appleby 3	Workshop 9: Achiral or Chiral? Workshop 10: Assigning (R) and (S) Stereochemistry	Workshop 9 Solutions Workshop 10 Solutions
Tues, Oct 13	2nd-Order Nucleophilic Substitution (S_N2): Mechanism, Transition States, Energetics In-Class Exercise: S_N2 Mechanisms	Chap. 7.1-7.6; 6.1, 6.5-6.7, 6.9 In-Class Solutions	Chap. 7: 1-3, 7-41, 49-87	Chap. 7: 1-3, 7, 9-43, 49-88
Thurs, Oct 15	2nd-Order Nucleophilic Substitution (S_N2): Ranking Nucleophiles and Leaving Groups, Hammond's Postulate	Chap. 7.7-7.12
Workshop, Fri, Oct 16 2:30-4:00 PM Appleby 3	Workshop 11: Enantiomers, Diastereomers, and Meth Workshop 12: S_N2 Chemistry: Causing Cancer, and Curing It	Workshop 11 Solutions Workshop 12 Solutions
Tues, Oct 20	1st-Order Nucleophilic Substitution (S_N1); Multistep Mechanisms and Rate-Limiting Steps	Chap. 7.13-7.19, 6.2-6.3, 6.8, 9.11	Chap. 6: 1-3, 7-22, 26-30, 35-57	Chap. 6: 1-4, 8-26, 28-31, 38-59
Thurs, Oct 22	Drawing Multi-step Mechanisms (no handout) In-Class Exercise: Proton-Mediated S_N1 Mechanisms	In-Class Solutions
Workshop, Fri, Oct 23 2:30-4:00 PM Appleby 3	Workshop 13: Multistep Reaction Mechanisms	Workshop 13 Solutions
Tues, Oct 27	1st- and 2nd-Order Elimination (E1 & E2) In-Class Exercise: Stereoselectivity of E2	Chap. 8.1-8.11, 9.8-9.9 In-Class Solutions	Chap. 8: 1-70	Chap. 8: 1-68
Thurs, Oct 29	Alkene Stability, Preference in E1/E2 In-Class Exercise: E2 Reactions with Multiple Products At-Home Exercise: Mechanism Practice Problems	In-Class Solutions At-Home Solutions
Workshop, Fri, Oct 30 2:30-4:00 PM Appleby 3	Workshop 14: Predicting Reaction Outcomes Workshop 15: Drawing Potential Energy Diagrams	Workshop 14 Solutions Workshop 15 Solutions
Tues, Nov 3 (9:45 am - 10:35 am) *A-Da, Mc-Z:* Smith 100 *De-Go:* Mondale 65 *Gr-He:* Blegen 110 *Hi-Ka: Blegen 140 Ke-Le:* Blegen 240 *Li-Ma*: Blegen 145	Exam 2 (Covers Chapters 5-8, 9.8-9.9, 9.11)
Tues, Nov 3 (10:45 am - 11:00 am)	Alcohols and Ethers; Conversion of Alcohols; Tosylates as Good Leaving Groups	Chap. 9.1-9.7, 9.10, 9.12-9.14	Chap. 9: 1-2, 9-34, 38, 46-83	Chap. 9: 1-2, 10, 12-38, 47-73, 75-84
Thurs, Nov 5	Electrophilic Addition to Alkenes: Hydrohalogenation and Hydration (Adding HX and H₂O) In-Class Exercise: Planning Multistep Organic Syntheses	Chap. 10.1-10.12 In-Class Solutions	Chap. 10: 1-3, 6-7, 12-33, 37-38, 41-42, 50-77	Chap. 10: 1, 6, 13-35, 52-79
Tues, Nov 10	Electrophilic Addition to Alkenes: Halogenation, Halohydrins, Hydroboration	Chap. 10.13-10.18
Thurs, Nov 12	Synthesis and Reactivity of Epoxides; Hydrogenation, Dihydroxylation of Alkenes	Chap. 9.15-9.17; 12.3-12.4;12.8-12.9
Workshop, Fri, Nov 13 2:30-4:00 PM Appleby 3	Workshop 16: Diverted Alkene Addition Mechanisms Workshop 17: More Multistep Organic Synthesis	Workshop 16 Solutions Workshop 17 Solutions
Tues, Nov 17	Alkynes In-Class Exercise: Alkynes in Synthesis	Chap. 11.1-11.12 In-Class Solutions	Chap. 11: 1, 6-23, 26-68	Chap. 11: 1, 3, 7-25, 29-69
Thurs, Nov 19	Oxidation and Reduction of C-O Bonds; Introduction to Radicals	Chap. 12.1-12.2; 12.5-12.7; 12.10-12.15	Chap. 12: 1-81	Chap. 12: 1-77
Workshop, Fri, Nov 20 2:30-4:00 PM Appleby 3	Workshop 18: Diastereoselectivity in Organic Synthesis Workshop 19: Interfering Functional Groups	Workshop 18 Solutions Workshop 19 Solutions
Tues, Nov 24 (9:45 am - 10:35 am) *De-Ro:* Smith 100 *A-Da, Ru-Z:* Willey 175	Exam 3 (Covers Chapters 9-12)
Tues, Nov 24 (10:25 am - 10:45 am)	Radical Halogenation: Selectivity	Chap. 15.1-15.13	Chap. 15: 1-29, 32-71, 79-81	Chap. 15: 1-29, 32-71, 79-81
Thurs, Nov 26	Holiday.
Tues, Dec 1	Principles of NMR Spectroscopy; Chemical Shift	Chap. 14.1-14.11	Chap. 14: 1-79	Chap. 14: 1-74
Thurs, Dec 3	NMR Spectroscopy: Integrals and Splitting Patterns In-Class Exercise: Splitting Patterns in NMR	In-Class Solutions
Workshop, Fri, Dec 4 2:30-4:00 PM Appleby 3	Workshop 20: Diagnostic Tests Based on Oxidation and Reduction Workshop 21: Unpaired Electron Pushing Workshop 22: Equivalent and Inequivalent Nuclei	Workshop 20 Solutions Workshop 21 Solutions Workshop 22 Solutions
Tues, Dec 8	¹³C NMR; Infrared Spectroscopy In-Class Exercise: ¹³C NMR Analysis	Chap. 13.1-13.8 In-Class Solutions	Chap. 13: 1-58	Chap. 13: 1-54
Thurs, Dec 10	Mass Spectrometry: Basic Principles; Fragmentation
Workshop, Fri, Dec 11 2:30-4:00 PM Appleby 3	Workshop 23: Complex Splitting Patterns in NMR Workshop 24: Structure Determination with NMR Workshop 25: IR Spectroscopy and MS Fragmentation Patterns Workshop 26: Using IR, MS and NMR Data for Structure Elucidation	Workshop 23 Solutions Workshop 24 Solutions Workshop 25 Solutions Workshop 26 Solutions
Tues, Dec 15 (9:45 am - 10:35 am) *A-Ha, Ru-Z:* Smith 100 *He-Ro:* Willey 175	Exam 4 (Covers Chapters 13-15)
Tues, Dec 15 (10:25 am - 10:45 am)	Mass Spectrometry: Analyzing Complex Mixtures; Exact Mass Determination, Isotope Patterns
Mon, Dec 21 (1:30 pm - 3:30 pm) *Br-Ro:* Smith 100 *A-Bo, Ru-Z:* Fraser 101	Final Exam (Covers Chapters 1-15)