Chapter 11 Notes - 12/11/2010 Nomenclature"...

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12/11/2010 1 Chapter 11 Alcohols and Ethers Chapter 11 2 Nomenclature Nomenclature of Alcohols (Sec. 4.3F) Nomenclature of Ethers Common Names The groups attached to the oxygen are listed in alphabetical order IUPAC Ethers are named as having an alkoxyl substituent on the main chain Chapter 11 3 Cyclic ethers can be named using the prefx oxa- Three-membered ring ethers are called epoxides OR oxiranes; UNLIKE OTHER ETHERS, THEY ARE REACTIVE Four-membered ring ethers are called oxetanes Five-membered ring ethers are o±ten called ±urans Four-membered ring ethers are o±ten called pyrans This nomenclature relates to sugars: FURANoses, PYRANoses O Tetrahydropyran (Oxacyclohexane) OH OH O H O O H α -D-ribo FURAN ose OH OH OH O H O O H α -D-gluco PYRAN ose Chapter 11 4 Physical Properties of Alcohols and Ethers Ether boiling points are roughly comparable to hydrocarbons of the same molecular weight Molecules of ethers cannot hydrogen bond to each other Alcohols have considerably higher boiling points Molecules of alcohols hydrogen bond to each other Both alcohols and ethers can hydrogen bond to water and have similar solubilities in water Diethyl ether and 1-butanol have solubilites of about 8 g per 100 mL in water
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12/11/2010 2 Chapter 11 5 Synthesis of Alcohols from Alkenes Acid-Catalyzed Hydration of Alkenes This is a reversible reaction with Markovnikov regioselectivity •Hydration: addition of water (forwards) favoured by: Excess H 2 O Low temperature •Dehydration of alcohol: elimination of water (backwards) favoured by absence of H 2 O: Use conc. H 2 SO 4 High temperature Chapter 11 6 Hydroboration-Oxidation This addition reaction occurs with anti-Markovnikov regiochemistry and syn stereochemistry Chapter 11 7 Alcohols as Acids and Bases Alcohols have acidities and basicities similar to water
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Chapter 11 Notes - 12/11/2010 Nomenclature"...

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