Alcohols and Phenols: Nomenclature, Properties, Preparation, Reactions, and Spectroscopy -, Study notes of Organic Chemistry

Download Alcohols and Phenols: Nomenclature, Properties, Preparation, Reactions, and Spectroscopy - and more Study notes Organic Chemistry in PDF only on Docsity! SCB CH232 summer 2009 Chapter 17 Lecture Outline "Alcohols & Phenols" (problems: 26, 29, 30-33, 34-36, 37, 39, 40, 41, 43-44, 46-48, 50, 52-53, 55, 57, 61, 64b, 65) I. Nomenclature II. General Properties A. hydrogen bonding, boiling point B. acid/base reactions III. Preparation of Alcohols A. alkene hydration (review ch 7.4-7.5) 1. oxymercuration-reduction to give Markovnikov hydration 2. hydroboration-oxidation to give anti-Markovnikov hydration B. alkene di-hydroxylation to form 1,2-diols (review ch 7.8) 1. syn di-hydroxylation with OsO4 2. anti di-hydroxylation via epoxidation/ hydrolysis C. carbonyl group reduction (nucleophilic addition to the carbonyl) 1. hydride addition to aldehydes and ketones by NaB H4 and LiAlH4 2. hydride addition to esters and carboxylic acids by LiAlH4 D. Grignard reagent chemistry (nucleophilic addition to the carbonyl) 1. formation of Grignard reagents (review ch 10.7) 2. addition to aldehydes, ketones, esters, and CO2 IV. Reactions of Alcohols A. ROH deprotonation to form alkoxide anions B. ROH dehydration to form alkenes C. ROH conversion to RX (review ch 10.6) or ROTs (review ch 11.1, 11.3) D. ROH oxidation to carbonyl compounds 1. 1˚ alcohols to aldehydes 2. 1˚ alcohols to carboxylic acids 3. 2˚ alcohols to ketones E. ROH protection by silylation V. Phenols - preparation and uses VI. Spectroscopy of Alcohols and Phenols Key Concepts and Learning Objectives • be able to name simple alcohols and phenols • know pKa's of water, ethanol, and phenol and how substituents on these structures would affect acidity and be able to rationalize why one alcohol is a stronger or weaker acid than another • know reactions (including stereochemistry and regiochemistry) to make alcohols from alkenes (3), alcohols from hydride and Grignard reagent addition to carbonyl compounds (10), and diols from alkenes (2) • know alcohol transformations to make alkenes (2), alkyl halides (3), tosylates (1), aldehydes (1), ketones (2), carboxylic acids (1), and silyl ethers (1) • know how phenol is made from cumene and how phenol is oxidized to p-benzoquinone • know the quinone/hydroquinone redox couple • be able to recognize an alcohol from its IR and NMR spectral data • beable to use the reactions of this chapter in the synthesis of organic molecules