Organic Chemistry

David Klein is a Senior Lecturer in the Department of Chemistry at Johns Hopkins University where he has taught organic chemistry since 1999. Having worked with thousands of students, he has intense first-hand knowledge of how they learn and the difficulties they encounter. He received his bachelor's degree in chemistry from Johns Hopkins University and his PhD from the University of California at Los Angeles under the supervision of Professor Orville Chapman. Motivated by his experiences teaching organic chemistry as a graduate student at UCLA, David wrote Organic Chemistry as a Second Language (John Wiley & Sons, 2004, updated 2nd edition published in 2008), which has become a highly valued student study resource. David has received numerous teaching awards at both UCLA and Johns Hopkins for his unique, skill-building approach to organic chemistry instruction. David is married with five children, and he enjoys skiing, scuba diving, and Tae Kwon Do.

1 A Review of General Chemistry: Electrons, Bonds, and Molecular Properties 1

2 Molecular Representations 49

3 Acids and Bases 93

4 Alkanes and Cycloalkanes 132

5 Stereoisomerism 181

6 Chemical Reactivity and Mechanisms 226

7 Alkyl Halides: Nucleophilic Substitution and Elimination Reactions 271

8 Addition Reactions of Alkenes 343

9 Alkynes 400

10 Radical Reactions 435

11 Synthesis 479

12 Alcohols and Phenols 505

13 Ethers and Epoxides; Thiols and Sulfides 556

14 Infrared Spectroscopy and Mass Spectrometry 602

15 Nuclear Magnetic Resonance Spectroscopy 649

16 Conjugated Pi Systems and Pericyclic Reactions 701

17 Aromatic Compounds 751

18 Aromatic Substitution Reactions 790

19 Aldehydes and Ketones 844

20 Carboxylic Acids and Their Derivatives 898

21 Alpha Carbon Chemistry: Enols and Enolates 954

22 Amines 1008

23 Introduction to Organometallic Compounds 1054

24 Carbohydrates 1107

25 Amino Acids, Peptides, and Proteins 1147

26 Lipids 1190

27 Synthetic Polymers 1227