CHAPTER 7AMINES.pptVIP

CHAPTER 7. AMINES Objective: * Determine the names using structures and structures using names, and * Describe and explain the properties, preparation methods and reactions of amines. 6.1. Structure 6.5 basicity of Amines (Continued) 6.2. Nomenclature Read #19-2, pg 871 6.3. Physical properties Read #19-4, pg 875 6.4. Spectroscopy Read #19-9, pg 884 6.5 Basicity of Amines Basicity of Amines (Continued) General reaction: Ionization in water: B + H2O --- BH(+) + OH(-) Measurement of Basicity: Kb = [BH(+)][OH(-)] / [B] Values of Kb: small and hard to measure Remedy: use pKb = - logKb = Kb = 10-pKb Examples: Methylamine Kb = 4.3E-4 pKb = 3.36 Aniline 4.0E-10 9.40 Pyridine 1.8E-9 8.75 More info: #19-5, pg 877 Usually available in tables: Ka, pKa of conjugate acid. 6.6. Preparation a. Reduction of azides and nitriles. Substrates: azides, and nitriles. Reaction site: C or N bound to N through multiple bonds Reagents: sources of H(-) or H(.). Role: add H’s to N (azides) or to CΞN bond (nitriles). Most commonly used: * LiAlH4 in ether, followed by H2O * H2 on Pt. Products: primary amines. Reduction of azides and nitriles (General pathway) Reduction of azides and nitriles (Examples) Reduction of azides and nitriles (Exercises) Answer Questions 19-30 a b, pg 917 b. Reduction of Nitro Compounds Substrates: nitro compounds. Reaction sites: N. Reaction property: electrophilic Reagents: sources of H(.). Most common: * H2 with a catalyst * Acids with active (easily reduced) metals. Examples: Zn, Sn, … Role: add H’s to N. Products: Primary amines Reduction of Nitro Compounds (Illustrations) Reduction of Nitro Compounds (Exercises) Answer Questions 19-31 a, b c, pg 918 c. Gabriel Synthesis. Substrates: Alkyl halides. Reaction site: C linked to the halogen. Reactive property: electrophilic Reagents: * sources of N. Reactive property: nucleophilic. Most common: Potassium Phthalimide. The N replaces the halogen on the reaction site. Result: a neutral phthalimide. * B