Organic Chemistry As a Second Language: Second Semester Topics

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.

Chapter 1 Aromaticity 1.1 Introduction to Aromatic Compounds 1.2 Nomenclature of Aromatic Compounds 1.3 Criteria for Aromaticity 1.4 Lone Pairs Chapter 2 IR Spectroscopy 2.1 Vibrational Excitation 2.2 IR Spectra 2.3 Wavenumber 2.4 Signal Intensity 2.5 Signal Shape 2.6 Analyzing an IR Spectrum Chapter 3 NMR Spectroscopy 3.1 Chemical Equivalence 3.2 Chemical Shift (Benchmark Values) 3.3 Integration 3.4 Multiplicity 3.5 Pattern Recognition 3.6 Complex Splitting 3.7 No Splitting 3.8 Hydrogen Deficiency Index (Degrees of Unsaturation) 3.9 Analyzing a Proton NMR Spectrum 3.10 13C NMR Spectroscopy Chapter 4 Electrophilic Aromatic Substitution 4.1 Halogenation and the Role of Lewis Acids 4.2 Nitration 4.3 Friedel-Crafts Alkylation and Acylation 4.4 Sulfonation 4.5 Activation and Deactivation 4.6 Directing Effects 4.7 Identifying Activators and Deactivators 4.8 Predicting and Exploiting Steric Effects 4.9 Synthesis Strategies Chapter 5 Nucleophilic Aromatic Substitution 5.1 Criteria for Nucleophilic Aromatic Substitution 5.2 SNAr Mechanism 5.3 Elimination-Addition 5.4 Mechanism Strategies Chapter 6 Ketones and Aldehydes 6.1 Preparation of Ketones and Aldehydes 6.2 Stability and Reactivity of CO Bonds 6.3 H-Nucleophiles 6.4 O-Nucleophiles 6.5 S-Nucleophiles 6.6 N-Nucleophiles 6.7 C-Nucleophiles 6.8 Some Important Exceptions to the Rule 6.9 How to Approach Synthesis Problems Chapter 7 Carboxylic Acid Derivatives 7.1 Reactivity of Carboxylic Acid Derivatives 7.2 General Rules 7.3 Acid Halides 7.4 Acid Anhydrides 7.5 Esters 7.6 Amides and Nitriles 7.7 Synthesis Problems Chapter 8 Enols and Enolates 8.1 Alpha Protons 8.2 Keto-Enol Tautomerism 8.3 Reactions Involving Enols 8.4 Making Enolates 8.5 Haloform Reaction 8.6 Alkylation of Enolates 8.7 Aldol Reactions 8.8 Claisen Condensation 8.9 Decarboxylation 8.10 Michael Reactions Chapter 9 Amines 9.1 Nucleophilicity and Basicity of Amines 9.2 Preparation of Amines through SN2 Reactions 9.3 Preparation of Amines through Reductive Amination 9.4 Acylation of Amines 9.5 Reactions of Amines with Nitrous Acid 9.6 Aromatic Diazonium Salts Chapter 10 Diels-Alder Reactions 10.1 Introduction and Mechanism 10.2 The Dienophile 10.3 The Diene 10.4 Other Pericyclic Reactions Answer Key Index