Student Study Guide and Solutions Manual for Organic Chemistry

About our author 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 ONE: An Introduction to the Study of Organic Chemistry

1. Remembering General Chemistry: Electronic Structure and Bonding

2. Acids and Bases: Central to Understanding Organic Chemistry

TUTORIAL: Acids and Bases

3. An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure

PART TWO: Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization

TUTORIAL: Using Molecular Models

4. Isomers: The Arrangement of Atoms in Space

TUTORIAL: Interconverting Structural Representations

5. Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics

TUTORIAL: Drawing Curved Arrows

6. The Reactions of Alkenes • The Stereochemistry of Addition Reactions

7. The Reactions of Alkynes • An Introduction to Multistep Synthesis

8. Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction the Reactions of Benzene

TUTORIAL: Drawing Resonance Contributors

PART THREE: Substitution and Elimination Reactions

9. Substitution and Elimination Reactions of Alkyl Halides

10. Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds

11. Organometallic Compounds

12. Radicals

TUTORIAL: Drawing Curved Arrows in Radical Systems

PART FOUR: Identification of Organic Compounds

13. Mass Spectrometry; Infrared Spectroscopy; and UV/Vis Spectroscopy

14. NMR Spectroscopy

PART FIVE: Carbonyl Compounds

15. Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

16. Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives

17. Reactions at the α-Carbon

TUTORIAL: Synthesis and Retrosynthetic Analysis

PART SIX: Aromatic Compounds

18. Reactions of Benzene And Substituted Benzenes

19. More About Amines • Reactions of Heterocyclic Compounds

PART SEVEN: Bioorganic Compounds

20. The Organic Chemistry Of Carbohydrates

21. Amino Acids, Peptides, and Proteins

22. Catalysis in Organic Reactions and in Enzymatic Reactions

23. The Organic Chemistry of the Coenzymes, Compounds Derived from Vitamins

24. The Organic Chemistry of the Metabolic Pathways

25. The Organic Chemistry of Lipids

26. The Chemistry of the Nucleic Acids

PART EIGHT: Special Topics in Organic Chemistry

27. Synthetic Polymers

28. Pericyclic Reactions

Appendix I pKa Values

Appendix II Kinetics

Appendix III Summary of Methods Used to Synthesize a Particular Functional Group

Appendix IV Summary of Methods Employed to Form Carbon-Carbon Bonds

Appendix V Spectroscopy Tables

Appendix VI Physical Properties of Organic Compounds

Appendix VII Answers to Selected Problems