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ForClassChapter 11afterclass - Chapter 11 Alcohols and...

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Chapter 11 Alcohols and Ethers 1
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Nomenclature of Ethers Common Names: alkyl1 alkyl2 ether, in alphabetical order 2 IUPAC names: alkoxy substituents on the main chain
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Cyclic Ethers Cyclic ethers are formally named by the “Replacement approach”: parent ring with prefix oxa- indicating one ring carbon is replaced by oxygen. Three membered ring ethers: common names are epoxides, oxiranes, with the simplest one is ethylene oxide. Four-membered ring ethers can be called oxetanes The simplest five-membered ring ether is a common organic solvent tetrahydrofuran (THF) Oxacyclopentane Or tetrahydrofuran (THF) 1,4-dioxacyclohexane (1,4-dioxane) O O 3
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Physical Properties of Alcohols and Ethers • Ether molecules cannot hydrogen bond to each other, and so their boiling points resemble those of hydrocarbons: 35°C for diethylether, 36°C for pentane, while 1-butanol boils at 118°C Alcohols and ethers can hydrogen-bond to water and thus have similar solubilities: about 8g diethyl ether or 1-butanol dissolve in 100 mL in water 4 OH OH OH O H OH OH OH OH Ethylene glycol Glycerol Benzyl alcohol Allyl alcohol Phenol http://s4.hubimg.com/u/1084 303_f248.jpg http://www.savannahgoa.com/product.php?i=10
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Synthesis of Alcohols from Alkenes Acid-Catalyzed Hydration of Alkenes (reversible, Markovnikov) Hydroboration-Oxidation (syn addition, anti-Markovnikov regiochemistry) 5
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Alcohols as Acids and Bases Alcohols have acidities and basicities similar to water Hindered alcohols such as tert -butanol are less acidic ( higher pKa values) Conj. acid H 3 O + CH 3 CH 2 OH 2 + Conj. base HO - CH 3 CH 2 O - Alcohols are stronger acids than terminal alkynes and 1°or 2°amines.
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