Chem 2301: Organic Chemistry I, section 002 (9:15 MWF)
Fall Semester, 2009
Instructor: Tim Soderberg
Office: Sci 1320
Phone: 589-6331
email: soderbt
Go to Tim Soderberg's web site
Go to UMM Chemistry Discipline website
Textbook: Organic Chemistry (5th edition) by Paula Bruice. Copies of the Study Guide for the text will be on reserve in the library, or you may opt to purchase your own copy (these are not on sale in the campus bookstore, so you'll need to go through Amazon.com or another source).
It is highly recommended that you also purchase a molecular model set, although these won't be used until a few weeks into the course.
Two other books are totally optional: "Pushing Electrons - a Guide for Students of Organic Chemistry" by Daniel Weeks, and "Organic Chemistry as a Second Language" by David Klein - we won't use these in class, but some students find it helpful for self-study.
Note: both the 8:00 and the 9:15 sections of Chem 2301 (O-chem I) will be taught using the Paula Bruice textbook, covering the same chapters. In the spring of 2010, however, the 9:15 section of Chem 2302 (O-chem II) will switch to a textbook that I have written, which emphasizes biological organic chemistry instead of taking the traditional approach in which the focus is on laboratory/synthetic organic chemistry. The 8:00 section of Chem 2302, taught by professor Carpenter, will continue using the Bruice text. Students from both fall 2301sections may register for either section of 2302 in the spring.
Students who register for the 9:15 section of Chem 2302 in the spring will need to purchase another text in January- this will be a bound printout produced by the UMM duplicating services, and should cost less than $25 (this represents copying/binding costs only). Professor Carpenter and I will try to figure out a convenient system by which this year's students can opt to sell their used copies of the Bruice text (it's expensive!) to next year's students, in order to keep everyone's textbook costs to a minimum.
Click here to downoad the course syllabus (PDF)
Course announcements:
Exam III, covering chapters 6, 7, and 12, is scheduled for Friday, December 4.
Download powerpoint slides of my lecture notes (very bare-bones - mainly just figures from the text and a few key points about them)
Chapter 12 slides (to print this out for lecture, I recommend that you print as 'handouts', with two slides per page)
Useful links:
Database of IR, MS, and NMR spectra
Jmol (for visualizing protein structures)
IUPAC nomenclature - all the details you might ever need to know!
Ongoing class summary:
Monday, Nov 23: Mass spectrometry (12.1 - 12.5)
Next class: A few more cool examples of the use of MS. Start chapter 8: Nucleophilic substitution reactions (section 8.1 - 8.4).
Friday, Nov, 20: A few final examples of Diels-Alder stereoselectivity. UV-visible spectroscopy (section 12.16-12.20). Intro to mass spectrometry (12.1)
Wednesday, Nov 18: Finish discussion of IR spectroscopy. More on the Diels-Alder reaction (7.12): regioselectivity, s-cis and s-trans conformations and cyclopentadiene as a Diels-Ader reactant, fused ring endo vs exo products (stereoselectivity).
Monday, Nov 16: Intro to spectroscopy in general, IR spectroscopy (skipping ahead a little for lab) Sections 12.6 - 12.15
Friday, Nov 13: 1,2 vs 1,4 addition (7.10), thermodynamic vs kinetic control (7.11), the Diels-Alder reaction (7.12).
Wednesday, Nov 11: The MO picture of conjugated pi bonds (7.8), resonance/conjugation effects on acidity and basicity (7.9).
Monday, Nov 9: Evaluating the stability/importance of difference resonance contributors (7.5), resonance and stability (7.6 - 7, the MO picture of isolated pi bonds (7.8).
Friday, Nov 6: Interlude for lab: the mechanism and logistics of an alcohol dehydration reaction. Back to Chapter 7: rules for drawing resonance structures; benzene, carbocations, amides (7.1-7.4)
Wednesday, Nov 4: Designing a synthesis (6.11, 6.12). Start chapter 7: resonance (7.1 - 7.4)
Monday, Nov 2: Return exam, go over in class
Friday, Oct 29: Start chapter 6: Reactions of alkynes - sections 6.5 - 6.10 (read sections 6.1-6.4 on your own, no lecture on this)
Wednesday, Oct 28: Exam II (Bruice chapters 3, 4, 5)
Monday, Oct 26: Review for Exam II, go through practice exam.
Friday, Oct 23: Stereochemistry of halogen addition/halohydrin formation, hydroboration oxidation, catalytic hydrogenation.
Wednesday, Oct 21: hydroboration/oxidation, catalytic hydrogenation, relative stabilites of alkenes (sections 4.10 - 4.12). Back to chapter 5: start the stereochemistry of alkene additions (sections 5.18, 5.19) Stereochemistry of HBr addition.
Monday, Oct 19: Fall break, no class
Friday, Oct 16: addition of Br2 and Cl2, oxymercuration-reduction, addition of peroxyacids (epoxide formation) (sections 4.7 - 4.9)
Wednesday, Oct 14: Hammond postulate (4.3), regiochemistry of electrophilic additions (4.4), acid-catalyzed addition of water/alcohols (4.5), carbocation rearrangements (4.6).
Monday, Oct 12: a little more on Fischer projections, Haworth projections (just for your interest, not in text until Chapter 21) absolute configuration of glyceraldehyde (5.15). Start chapter 4 (reactions of alkenes: review of electrophilic addition of HBr (4.1), carbocation stability (4.2), Hammond postulate (4.3).
Friday, Oct 9: Epimers, naming chiral compounds (5.13), meso compounds (5.12), Fischer projections.
Wednesday, Oct 7: Optical activity (5.8-5.9), enantiomeric excess (5.10), molecules with more than one asymmetric center (5.11).
Monday, Oct 5: Review of Friday's material, the R/S naming system, how proteins recognize stereochemistry.
Friday, Oct 2: Wrap-up chapter 3, start chapter 5: chirality, asymmetric centers, stereocenters enantiomers, (sections 5.1-5.6).
Wednesday, Sept 30: Return exam I, go over in class.
Note: After finishing chapter 3, we will be skipping to chapter 5, then coming back to cover chapter 4 later (exam II will still cover chapters 3, 4, and 5). This is so that we are able to cover the stereochemistry material in time to do the molecular modelling lab in Chem 2311. I will start lecturing on chapter 5 on Friday, Oct 2. We will not cover sections 5.18, 5.19, and 5.20 until after we cover chapter 4.
Monday, Sept 28: Continuing chapter 3: Thermodymamics and kinetics, using an energy diagram to describe a reaction, curved arrows to illustrate the addition of HBr to an alkene (3.6 - 3.8)
Friday, Sept 25: Exam I (Bruice chapter 1, 2)
Wednesday, Sept 23: Review for Exam I
Monday, Sept 21: Start chapter 3 (alkenes). Degree of unsaturation (3.1). Read 3.2 (nomenclature of alkenes) on your own - no lecture on this topic, but you are responsible for it on exam II. Review structure, bonding of alkenes (3.3), cis/trans isomerism (3.4, 3.5)
Friday, Sept 18: conformations of cycloalkanes (2.11-2.14).
Wednesday, Sept 16: solubility (2.9), biological applications of solubility concepts, conformations of straight-chain alkanes (2.10)
Monday, Sept 14: Boiling point/melting point/(2.9), examples relating to biology.
Friday, Sept 11: More on the resonance effect on acidity (1.22) buffers (1.24-25), Lewis acids (1.26). Starting chapter 2: intromolecular forces (8.9). Read section 2.1-2.8 (basic structure/nomenclature info) on your own, not covered in lecture (but feel free to ask questions in class!)
Wednesday, Sept. 9: structural effects on acidity (1.20-23)
Friday, Sept 4: Modeling of allene, overview of functional groups (table on inside back cover of Bruice text). pKa (1.17), organic acids (1.18) predicting Keq of acid-base reactions (1.19)
Wednesday, Sept. 2: sp hybrid orbitals and the bonding in ethyne (1.9), more examples of describing bonding with hydbrid orbital theory (1.10-1.14), molecular dipole moments (1.15), starting acids/ bases (1.16)
Monday, August 31: Line structures (not in text - see announcements for practice problems), atomic orbitals (1.5), molecular orbitals (1.6), hybrid orbitals: sp3 and methane (1.7), sp2 and ethane (1.8)
sp hybrid orbitals and the bonding in ethyne (1.9), more examples of describing bonding with hydbrid orbital theory (1.10-1.14), molecular dipole moments (1.15), acids/ bases and pKa (1.16-1.19)
Friday, August 28: Electron configuration (1.2), ionic and covalent bonding (1.3), drawing structures (1.4)
Wednesday, August 26: Introduction to the course, going through the syllabus. Start chapter 1: What is organic chemistry? Review of atoms, orbitals (section 1.1, 1.2)