CH 241: Organic Chemistry

Syllabus and Course Information - Fall 2001

Formula I: Two "best" hour exam scores + one half of remaining hour exam score + final exam score + lab score.

Formula II: All three hour exam scores + two-thirds of final exam score + lab score.

• Atoms, molecules, bonding, polar and nonpolar molecules, intermolecular forces, solubilities, Lewis structures, preliminary ideas of resonance, arrow formalism, acids and bases.

• Introduction to orbitals, molecular orbital description of bonding, hybridization, structure of methane.

• Alkanes- conformational analysis, structural isomerism and nomenclature, alkyl groups.

• Alkenes- structure and bonding, nomenclature, E-Z notation, hydrogenation, relative stabilities. Alkynes- structure and bonding, relative stabilities, double and triple bonds in rings.

• Dienes and the allyl system, conjugation, introduction to the concept of aromaticity. UV spectroscopy.

• Stereochemistry- chirality, enantiomerism, R-S notation, diastereomerism, optical resolution.

• Ring systems- strain, stereochemistry of cyclohexane, conformational analysis of cyclohexane and its substituted derivatives, bicyclic and polycyclic compounds.

• Nuclear Magnetic Resonance (NMR) spectroscopy.

• Infrared (IR) spectroscopy.

• Alkyl halides, substitution reactions of alkyl halides- SN 2 and SN 1 mechanisms. Elimination reactions- E1 and E2 mechanisms.

• Overview of substitution and elimination reactions, oxidation of alcohols, rates and equilibria, syntheses.

• Acids and bases revisited. Additions to alkenes- mechanism of hydrogen halide additions, regiochemistry, resonance effects, carbocation stabilities, addition of other unsymmetrical reagents, hydroboration, dimerization and polymerization of alkenes.

• Carbocation rearrangements, addition of halogens to alkenes, oxymercuration, epoxidation and chemistry of oxiranes, cyclopropanation, carbenes, ozonolysis, alkene oxidations with permanganate and osmium tetroxide, addition reactions of alkynes.

• Please stay current with the material. The course is highly cumulative. Ideas introduced early on will be used to develop other concepts later. Thus, letting things slide is unwise, as the material begins to accumulate relentlessly. As the semester progresses and other demands on your time increase, playing catch-up will be harder to do. Furthermore, it is possible, indeed likely, that many of the concepts in the course will become clear only after you have had a chance to ponder them for a while. This period of reflection is critical and hence the need for time. So try not to learn everything at once. Even a half-hour of regular study each day is likely to be more useful to you than any all-night, caffeine-powered cramathons.

• Write, write, write. I cannot overemphasize the importance of writing in this course. Simply listening to me lecture, reading your text, or watching ³cool² graphics flash by the screen is not enough. Sometimes it is all too easy to lull yourself into thinking that you understand the material. You will notice, however, that expressing your ideas clearly in writing (which is what you will have to do in the exams anyway) requires a higher level of mastery. To reach that level you must practice writing. Also, donıt try to work problems in your head. Write them out. Having the material written out in front of you often provides clues to solutions that you might not ³see² otherwise. So, please! Trust me on this. Write, write, write. Honest!

• Network with your classmates. Obviously this advice is not going to work for everyone since some people prefer to study alone. Thatıs okay. Nevertheless, if you can, try studying with a partner or in groups. You will be astonished at the insight that you gain when you have to explain something to others. Besides, if each member of the group agrees to work a few problems, then the group as a whole will be able to work a large number of problems. Working as many problems as you can will greatly aid your understanding of the material. It is important, however, for all members of the group to be good citizens. One reason for the breakdown of group study is that one or two people do all the work and the rest just piggy-back. Donıt let that happen.

• Make the most of the resources available to you. We are here to help you learn. So come talk to us. Itıs crazy not to take advantage of what we might have to offer by way of assistance. Office hours, help sessions, and personal; appointments are all excellent forums to ask questions. If the course does not seem to be going well, please get help right away. Our chances of rescuing you are better the more lead time we have.

• Stay involved and keep a positive attitude. Perseverance will be an important key to success. Yes, it is a hard course but, no, it is not impossible. It can, in fact, be a lot of fun if you give it a chance. No kidding. Try it.