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iv Contents Chapter 9 Further Reactions of Alcohols and the Chemistry of Ethers 164 Solutions to Problems 171 Chapter 10 Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure 192 Solutions to Problems 196 Chapter 11 Alkenes; Infrared Spectroscopy and Mass Spectrometry 216 Solutions to Problems 219 Chapter 12 Reactions of Alkenes 237 Solutions to Problems 243 Chapter 13 Alkynes: The Carbon-Carbon Triple Bond 267 Solutions to Problems 269 Chapter 14 Delocalized Pi Systems: Investigation by Ultraviolet and Visible Spectroscopy 280 Solutions to Problems 283 Chapter 15 Benzene and Aromaticity: Electrophilic Aromatic Substitution 300 Solutions to Problems 302 Chapter 16 Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity 316 Solutions to Problems 317 Chapter 17 Aldehydes and Ketones: The Carbonyl Group 330 Solutions to Problems 334 Chapter 18 Enols, Enolates, and the Aldol Condensation: α, ß-Unsaturated Aldehydes and Ketones 350 Solutions to Problems 353 Chapter 19 Carboxylic Acids 371 Solutions to Problems 374

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