Student Solutions Manual for Organic Chemistry

About our authors L.G. “Skip” Wade received his B.A. from Rice in 1969 and then went on to Harvard University, where he did research with Professor James D. White. While at Harvard, he served as the Head Teaching Fellow for the organic laboratories and was strongly influenced by the teaching methods of two master educators, Professors Leonard K. Nash and Frank H. Westheimer. After completing his Ph.D. at Harvard in 1974, Dr. Wade joined the chemistry faculty at Colorado State University. Over the course of fifteen years at Colorado State, Dr. Wade taught organic chemistry to thousands of students working toward careers in all areas of biology, chemistry, human medicine, veterinary medicine, and environmental studies. He also authored research papers in organic synthesis and in chemical education, as well as eleven books reviewing current research in organic synthesis. Since 1989, Dr. Wade has been a chemistry professor at Whitman College, where he teaches organic chemistry and pursues interests in organic synthesis and forensic chemistry. Dr. Wade received the A.E. Lange Award for Distinguished Science Teaching at Whitman in 1993. Jan Simek was born to humble coal-mining parents who taught him to appreciate the importance of carbon at a very early age. At age 14, he was inspired to pursue a career teaching chemistry by his high school chemistry teacher, Joe Plaskas. Under the guidance of Professor Kurt Kaufman at Kalamazoo College, Dr. Simek began lab work in synthesis of natural products that turned into research in hop extracts for the Kalamazoo Spice Extraction Company. After receiving a master’s degree from Stanford University, Dr. Simek worked in the pharmaceutical industry, synthesizing compounds designed to control diabetes and atherosclerosis, and assisted in the isolation of anti-cancer antibiotics from natural sources. Returning to Stanford University, Dr. Simek completed his Ph.D. with the legendary Professor Carl Djerassi, who developed the first synthesis of steroidal oral contraceptives. Dr. Simek’s 35-year teaching career was spent primarily at California Polytechnic State University, San Luis Obispo, where he received the university’s Distinguished Teaching Award. Other teaching experiences include Albion College, the University of Colorado at Boulder, Kalamazoo College, and the University of California at Berkeley. In addition to his pharmaceutical research, he has industrial experience investigating dyes, surfactants, and liquid crystals, and he continues to consult for the biotechnology industry. Although his outside interests include free climbing in Yosemite, performing in a reggae band, and parasailing over the Pacific, as close as he gets to any of those is tending his backyard garden with his wife Judy.

1. Structure and Bonding

2. Acids and Bases: Functional Groups

3. Structure and Stereochemistry of Alkanes

4. The Study of Chemical Reactions

5. Stereochemistry

6. Alkyl Halides. Nucleophilic Substitution

7. Structure and Synthesis of Alkenes; Elimination

8: Reactions of Alkenes

9. Alkynes

10. Structure and Synthesis of Alcohols

11. Reactions of Alcohols

12. Infrared Spectroscopy and Mass Spectrometry

13. Nuclear Magnetic Resonance Spectroscopy

14. Ethers, Epoxides and Thioethers

15. Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

16. Aromatic Compounds

17. Reactions of Aromatic Compounds

18. Ketones and Aldehydes

19. Amines

20. Carboxylic Acids

21. Carboxylic Acid Derivatives

22. Condensations and Alpha Substitutions of Carbonyl Compounds

23. Carbohydrates and Nucleic Acids

24. Amino Acids, Peptides, and Proteins

25. Lipids

26. Polymers