DETAILED CONTENTS 9.7 Alkylation and Acylation of Aromatic Rings:The Friedel-Crafts Reaction 331 98 Substituent Effects in Electrophilic Substitutions 336 Nucleophilic Aromatic Substitution 344 9.10 Oxidation and Reduction of Aromatic Compounds4 9.1n An Introduction to Organic Synthesis:Polysubstituted Benzenes349 Summary 355 Summary of Reactions 356 Lagniappe-Aspirin,NSAIDs,and COX-2 Inhibitors 357 Exercises 359 10 Structure Determination:Mass Spectrometry, Infrared Spectroscopy,and Ultraviolet Spectroscopy 367 10.1 Mass Spectrometry of Small Molecules:Magnetic-Sector Instruments 368 Interpreting Mass Spectra36 Mass Spectrometry of Some Common Functional Groups 373 10.4 Mass Spectrometry in Biological Chemistry:Time-of-Flight(TOF) Instruments 376 10.5 Spectroscopy and the Electromagnetic Spectrum 377 10.6 Infrared Spectroscopy 380 107 Interpreting Infrared Spectra 381 Infrared Spectra of Some Common Functional Groups 384 Ultraviolet Spectroscopy 389 10.10 Interpreting Ultraviolet Spectra:The Effect of Conjugation 391 10.11 Conjugation,Color,and the Chemistry of Vision39 Summary 394 Lagniappe-Chromatography:Purifying Organic Compounds 395 Exercises 3% 11 Structure Determination:Nuclear Magnetic Resonance Spectroscopy 404 11.1 Nuclear Magnetic Resonance Spectroscopy 405 11.2 The Nature of NMR Absorptions 406 11.3 Chemical Shifts 409 11.4 1NMR Spectroscopy Signal Averaging and FT-NMR 1.5 Characteristics of 13C NMR Spectroscopy 412 11.6 DEPT 13C NMR Spectroscopy 415 111 Uses of 13C NMR Spectroscopy 417 x detailed contents 9.7 Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction 331 9.8 Substituent Effects in Electrophilic Substitutions 336 9.9 Nucleophilic Aromatic Substitution 344 9.10 Oxidation and Reduction of Aromatic Compounds 347 9.11 An Introduction to Organic Synthesis: Polysubstituted Benzenes 349 Summary 355 Summary of Reactions 356 Lagniappe—Aspirin, NSAIDs, and COX-2 Inhibitors 357 Exercises 359 Structure Determination: Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet Spectroscopy 367 10.1 Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments 368 10.2 Interpreting Mass Spectra 369 10.3 Mass Spectrometry of Some Common Functional Groups 373 10.4 Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments 376 10.5 Spectroscopy and the Electromagnetic Spectrum 377 10.6 Infrared Spectroscopy 380 10.7 Interpreting Infrared Spectra 381 10.8 Infrared Spectra of Some Common Functional Groups 384 10.9 Ultraviolet Spectroscopy 389 10.10 Interpreting Ultraviolet Spectra: The Effect of Conjugation 391 10.11 Conjugation, Color, and the Chemistry of Vision 392 Summary 394 Lagniappe—Chromatography: Purifying Organic Compounds 395 Exercises 396 Structure Determination: Nuclear Magnetic Resonance Spectroscopy 404 11.1 Nuclear Magnetic Resonance Spectroscopy 405 11.2 The Nature of NMR Absorptions 406 11.3 Chemical Shifts 409 11.4 13C NMR Spectroscopy: Signal Averaging and FT–NMR 411 11.5 Characteristics of 13C NMR Spectroscopy 412 11.6 DEPT 13C NMR Spectroscopy 415 11.7 Uses of 13C NMR Spectroscopy 417 10 11 39144_ FM_i-xxiv.indd x 8/26/09 10:48:50 AM