[Annotatie]: Organic Chemistry II as a Second Languagehelps students understand the fundamental principles and themes of mechanisms, so students can predict reactions--even ones that they have never seen before.[Inhoudsopgave]: CHAPTER 1IR SPECTROSCOPY1 1.1 Vibrational Excitation2 1.2 IR Spectra3 1.3 Wavenumber4 1.4 Signal Intensity9 1.5 Signal Shape11 1.6 Analyzing an IR Spectrum19 CHAPTER 2NMR SPECTROSCOPY26 2.1 Chemical Equivalence26 2.2 Chemical Shift (Benchmark Values)30 2.3 Integration35 2.4 Multiplicity39 2.5 Pattern Recognition41 2.6 Complex Splitting43 2.7 No Splitting44 2.8 Hydrogen Deficiency Index (Degrees of Unsaturation)46 2.9 Analyzing a Proton NMR Spectrum49 2.10 13C NMR Spectroscopy53 CHAPTER 3ELECTROPHILIC AROMATIC SUBSTITUTION56 3.1 Halogenation and the Role of Lewis Acids57 3.2 Nitration61 3.3 Friedel-Crafts Alkylation and Acylation64 3.4 Sulfonation72 3.5 Activation and Deactivation76 3.6 Directing Effects78 3.7 Identifying Activators and Deactivators88 3.8 Predicting and Exploiting Steric Effects98 3.9 Synthesis Strategies106 CHAPTER 4NUCLEOPHILIC AROMATIC SUBSTITUTION112 4.1 Criteria for Nucleophilic Aromatic Substitution112 4.2 SNAr Mechanism115 4.3 Elimination-Addition121 4.4 Mechanism Strategies126 CHAPTER 5KETONES AND ALDEHYDES129 5.1 Preparation of Ketones and Aldehydes129 5.2 Stability and Reactivity of C¨O Bonds133 5.3 H-Nucleophiles135 5.4 O-Nucleophiles140 5.5 S-Nucleophiles153 5.6 N-Nucleophiles155 5.7 C-Nucleophiles165 5.8 Some Important Exceptions to the Rule175 5.9 How to Approach Synthesis Problems180 CHAPTER 6CARBOXYLIC ACID DERIVATIVES187 6.1 Reactivity of Carboxylic Acid Derivatives187 6.2 General Rules188 6.3 Acid Halides192 6.4 Acid Anhydrides201 6.5 Esters203 6.6 Amides and Nitriles213 6.7 Synthesis Problems222 CHAPTER 7ENOLS AND ENOLATES231 7.1 Alpha Protons231 7.2 Keto-Enol Tautomerism233 7.3 Reactions Involving Enols238 7.4 Making Enolates241 7.5 Haloform Reaction244 7.6 Alkylation of Enolates247 7.7 Aldol Reactions252 7.8 Claisen Condensation259 7.9 Decarboxylation266 7.10 Michael Reactions273 CHAPTER 8AMINES281 8.1 Nucleophilicity and Basicity of Amines281 8.2 Preparation of Amines through SN2 Reactions283 8.3 Preparation of Amines through Reductive Amination287 8.4 Acylation of Amines291 8.5 Reactions of Amines with Nitrous Acid295 8.6 Aromatic Diazonium Salts298 Answer Key301 Index345
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