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Chemistry 203: Organic Chemistry

Course Level: 
Second Year
Academic Year: 
2014/2015

Instructor: Marco A. Ciufolini, A331 Chem-Phys Building.
Office Hours: by appointment only. Please e-mail me ( ) to arrange a meeting. Sporadic drop-ins OK.
Course website: http://groups.chem.ubc.ca/chem203/Chem_203.html
TextbookOrganic Chemistry, Fifth Edition, by Brown, Foote, Iverson, and Anslyn; Brooks-Cole, 2008, available at the UBC Bookstore
Other Useful Materials:
• Molecular Model Set: you are strongly advised to obtain a set of inexpensive molecular models. These will greatly facilitate your study of organic chemistry.
• Study Guide and Solutions Manual for Brown, Foote and Iverson
You are encouraged to consult other introductory organic chemistry textbooks [available at the Barber Learning Center (QD 251.2)] to supplement classroom notes and to access additional problems related to the C203 curriculum.

Prerequisites: CHEM 203 is an advanced university course, and it assumes that you are thoroughly familiar with fundamental concepts of introductory chemistry. You should thoroughly review the following material:
Structure & Bonding : single and multiple bonds, σ and π bonding, VSEPR, electronegativity, polarized bonds, formal charges, oxidation states
Elementary organic chemistry: alkanes and their nomenclature, conformational analysis, eclipsed and staggered conformers of ethane, syn, gauche, and anti conformers of n-butane, conformations of cyclohexane.
Stereochemistry: molecular chirality, stereogenic (sometimes improperly described as"asymmetric") carbons, R and S notation, stereoisomers (enantiomers, diastereomers), meso forms.

The first three chapters of the CHEM 203 textbook provide an excellent overview of the above concepts. You are responsible for doing a thorough review of the material covered in these chapters, which will not be discussed in class. Working out all the problems will greatly assist you in learning.
Chapter 1 Covalent Bonding and Shapes of Molecules. All sections. This chapter contains basic information about structure, bonding, resonance, and functional groups (subject matter that Chemistry 203 students have encountered before).
Chapter 2 Alkanes and Cycloalkanes. All sections except 2.4B and 2.7B. Essentially all of the material presented in this chapter was covered in first-year chemistry.
Chapter 3 Stereoisomerism and Chirality. All sections except 3.8B,C. Essentially all of the material presented in this chapter was covered in first-year chemistry, especially: (a) stereoisomers (b) enantiomers (c) chirality (d) chirality centers (e) stereogenic centers (f) optical activity (g) specific rotation (h) R and convention for designation of configuration of chirality centers (i) diastereomers (j) meso compounds (k) racemic compounds and their resolution into two enantiomers (l) Fischer projections.

First-year chemistry courses briefly introduced the following concepts, which are central to CHEM 203:
Thermodynamics: Changes in enthalpy (ΔH) and free energy (ΔG); relationship between ΔG° and equilibrium constant fora reaction (Gibbs equation): ΔG° = – n RT ln (Keq
Kinetics: reaction rates, rate law, order of a reaction, activation barrier, activation energy, Arrhenius equation.
Acid-base equilibria: dissociation constant (Ka and pKa) A portion of this material will be discussed in some depth in CHEM 203, but you are expected to thoroughly review pertinent notes from first year courses.

The Language of Organic Chemistry: Like any other area of human endeavoring, organic chemistry requires a language of its own to express complex, subtle concepts in a clear and concise fashion. Of course, all new terms introduced in class will be clearly defined and their use will be thoroughly exemplified, but you may find it useful to review organic chemical terminology by consulting the glossary of terms at the end of the textbook (G.1-G.14). There, you will find definitions of many terms used in organic chemistry.