Course Expectations--and Tips for Success

• You understand the structure of organic molecules: hybridization and geometry of carbon and other atoms; drawing correct Lewis structures (including lone pairs); use of the bond-line structure notation and filling in implied valences.
• You have a fairly sophisticated understanding of bonding: localized sigma bonds; delocalized pi bonding; uso of MO theory, including the chemical significance of the HOMO, LUMO and (for radicals) the SOMO. You can qualitatively rank the energies of different electron pairs in the molecule.
• You can correctly write and interpret resonance structures, and translate a set of resonance forms to a qualitative MO description of bonding.
• You understand the definitions used to describe aspects of organic stereochemistry: R/S stereogenic centers; E/Z double bonds; cis vs. trans in several instances; identification of chirality in all cases.
• You understand the parallels and differences between Lewis bases and nucleophiles.
• You understand the parallels and differences between Lewis acids and electrophiles.
• You understand how to recognize and predict the reactions of common nucleophiles.
• You understand how to recognize and predict the reactions of common electrophiles.
• You understand the definition of pKa for Brønsted acids, and know the pK_a of H₃O⁺, H₂O, acetylene, ethene, and methane.
• You have a working knowledge of IR, NMR and mass spectrometry and can use spectroscopic data to identify simple organic compounds.

This course is going to cover a large number of chemical reactions (close to 150!). While memorization of reactions is a necessary element of learning this material, memorization alone will be insufficient to earn the highest grade. The material will be presented in a way to help you organize your approach. The "functional group" organization will take advantage of the fact that many transformations of a particular functional group will share elements of mechanism. This should allow you to more easily digest the rather large amount of material.

While you are free to take any approach to the course that works for you, I have the following recommendations.

• Come to class and take notes. The vast majority of students need this experience of writing down reactions as a start to the pattern recognition and memorization process.
• Read the textbook, and work the in-chapter problems as you go. Ideally, you will come to class having read ahead a bit so you know what's coming; this gives you the opportunity to ask questions in class on issues you don't fully understand.
• Work the assigned problems. Many of these will appear in the graded Sapling homework, but there are limits to how much we can ask in those exercises. Ideally, you should spend a little time every day working problems, rather than digging through everything once a week (or worse, just before an exam!). Most importantly: make sure you understand how to get the correct answer if your first attempt differs from that in the Study Guide!
• Take advantage of office hours--bring in questions; even if you don't know where to start, pick a problem that you can't work and ask about it.
• After an exam, compare your answers to the exam key. Make certain you understand the difference between how you approached a question, and how I expected you to analyze it.
• Remember that Organic Chemistry is a cumulative subject: everything we talk about relies on concepts we developed earlier. If you don't understand a piece, it'll come back to haunt you--make sure you get it straight.
• Never wait to ask for help!