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CHAPTER 10 Properties and Preparation of Alcohols 1 2 Physical Properties of Alcohols Solubility in Water Alcohols with ≥6 C’s are water insoluble Table of Ka Values Properties of Alcohols: Acidity 6 Alcohols react with Alkali Metals like Na and K to produce alkoxide ions and hydrogen gas © 2013 Pearson Education, Inc. Chapter 10 7 Synthesis of Alcohols (Review) • Nucleophilic substitution (usually SN2) of alkyl halide. • Alkene Addition: – Water in acid solution (suffers from rearrangements). – Oxymercuration–demercuration. – Hydroboration–oxidation. Synthesis of Vicinal Diols (Review) Vicinal diols: • Syn hydroxylation of alkenes. – Osmium tetroxide, hydrogen peroxide. – Cold, dilute, basic potassium permanganate. • Anti hydroxylation of alkenes. – Peroxyacids followed by hydrolysis. Grignard Reactions to produce Alcohols To form a Grignard, an alkyl halide is treated with Mg metal. Alkyl halides, aryl halides and vinyl halides are all reactive. Grignard Reagents create nucleophilic carbon