Organic Chemistry

After graduating from the Girls' Latin School in Boston, Paula Bruice earned an A.B. from Mount Holyoke College and a Ph.D. in chemistry from the University of Virginia. She then received an NIH postdoctoral fellowship for study in the Department of Biochemistry at the University of Virginia Medical School and held a postdoctoral appointment in the Department of Pharmacology at Yale Medical School. Paula has been a member of the faculty at the University of California, Santa Barbara since 1972, where she has received the Associated Students Teacher of the Year Award, the Academic Senate Distinguished Teaching Award, two Mortar Board Professor of the Year Awards, and the UCSB Alumni Association Teaching Award.

• PART 1: AN INTRODUCTION TO THE STUDY OF ORGANIC CHEMISTRY 1. Remembering General Chemistry: Electronic Structure and Bonding2. Acids and Bases: Central to Understanding Organic ChemistryTUTORIAL: Acids and Bases3. An Introduction to Organic Compounds: Nomenclature, Physical Properties, and StructurePART 2: ELECTROPHILIC ADDITION REACTIONS, STEREOCHEMISTRY, AND ELECTRON DELOCALIZATION TUTORIAL: Using Molecular Models4. Isomers: The Arrangement of Atoms in SpaceTUTORIAL: Interconverting Structural Representations5. Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and KineticsTUTORIAL: Drawing Curved Arrows6. The Reactions of Alkenes • The Stereochemistry of Addition Reactions7. The Reactions of Alkynes • An Introduction to Multistep Synthesis8. Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction the Reactions of BenzeneTUTORIAL: Drawing Resonance ContributorsPART 3: SUBSTITUTION AND ELIMINATION REACTIONS 9. Substitution and Elimination Reactions of Alkyl Halides10. Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds11. Organometallic Compounds12. RadicalsTUTORIAL: Drawing Curved Arrows in Radical SystemsPART 4: IDENTIFICATION OF ORGANIC COMPOUNDS 13. Mass Spectrometry; Infrared Spectroscopy; and UV/Vis Spectroscopy14. NMR SpectroscopyPART 5: CARBONYL COMPOUNDS 15. Reactions of Carboxylic Acids and Carboxylic Acid Derivatives16. Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives17. Reactions at the α-CarbonTUTORIAL: Synthesis and Retrosynthetic AnalysisPART 6: AROMATIC COMPOUNDS 18. Reactions of Benzene And Substituted Benzenes19. More About Amines • Reactions of Heterocyclic CompoundsPART 7: BIOORGANIC COMPOUNDS 20. The Organic Chemistry Of Carbohydrates21. Amino Acids, Peptides, and Proteins22. Catalysis in Organic Reactions and in Enzymatic Reactions23. The Organic Chemistry of the Coenzymes, Compounds Derived from Vitamins24. The Organic Chemistry of the Metabolic Pathways25. The Organic Chemistry of Lipids26. The Chemistry of the Nucleic AcidsPART 8: SPECIAL TOPICS IN ORGANIC CHEMISTRY 27. Synthetic Polymers28. Pericyclic ReactionsAppendices I. pKa ValuesII. KineticsIII. Summary of Methods Used to Synthesize a Particular Functional GroupIV. Summary of Methods Employed to Form Carbon-Carbon BondsV. Spectroscopy TablesVI. Physical Properties of Organic CompoundsVII. Answers to Selected Problems