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Created by Ch. 11 - 1 Chapter 11 Alcohols & Ethers
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Ch. 11 - 2 OH OH OH 1. v Alcohols have a  hydroxyl  (–OH) group bonded to a  saturated  carbon atom (sp3  hybridized) 1o 2o 3o Ethanol 2-Propanol (isopropyl alcohol) 2-Methyl- 2-propanol ( tert -butyl alcohol)
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Ch. 11 - 3 v Phenols Compounds that have a hydroxyl  group attached  directly  to a  benzene ring OH Phenol OH 4-Methylphenol OH 2-Chlorophenol Cl H 3 C
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Ch. 11 - 4 v Ethers The oxygen atom of an ether is  bonded to two carbon atoms Diethyl ether tert -Butyl methyl ether Divinyl ether O O CH 3 O O Ethyl phenyl ether
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Ch. 11 - 5 1A. Nomenclature of Alcohols v Rules of naming alcohols Identify the longest carbon chain that includes the carbon to which the – OH group is attached Use the lowest number for the carbon to which the –OH group is  attached Alcohol as parent (suffix) t ending with “ ol
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Ch. 11 - 6 v Examples OH OH OH OH 2-Propanol (isopropyl alcohol) 1,2,3-Butanetriol
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Ch. 11 - 7 v Example OH OH 1 2 3 4 5 6 7 OH 1 2 5 4 3 6 7 8 or wrong 3-Propyl-2-heptan ol
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Ch. 11 - 8 1B. Nomenclature of Ethers v Rules of naming ethers Similar to those with alkyl halides t CH3O– Methoxy t CH3CH2O– Ethoxy v Example O Ethoxy ethane (diethyl ether)
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Ch. 11 - 9 v Cyclic ethers Oxacyclopropane or oxirane (ethylene oxide) O O O O O Oxacyclobutane or oxetane Oxacyclopentane (tetrahydrofuran or THF) 1,4-Dioxacyclohexane (1,4-dioxane)
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Ch. 11 - 10 2. Physical Properties of Alcohols and Ethers v Ethers have boiling points that are roughly comparable with those of  hydrocarbons of the same molecular weight (MW) v Alcohols have much higher boiling points than comparable ethers or  hydrocarbons
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Ch. 11 - 11 v For example O Diethyl ether (MW = 74) b.p. = 34.6 o C Pentane (MW = 72) b.p. = 36 o C OH 1-Butanol (MW = 74) b.p. =  117.7 o C v Alcohol molecules can associate with each other through  hydrogen bonding whereas those of ethers and hydrocarbons cannot
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Ch. 11 - 12 v Water solubility of ethers and alcohols Both ethers and alcohols are able to  form hydrogen bonds with water Ethers have solubilities in water that are  similar to those of alcohols of the same  molecular weight and that are very  different from those of hydrocarbons The solubility of alcohols in water  gradually decreases as the hydrocarbon  portion of the molecule lengthens; long- chain alcohols are more “alkane-like”  and are, therefore, less like water
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Ch. 11 - 13 4. Synthesis of Alcohols from Alkenes v Acid-catalyzed Hydration of Alkenes C C H H 2 O C C OH H C C O H H H C C H H H 2 O H 2 O
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v Acid-Catalyzed Hydration of Alkenes Markovnikov regioselectivity
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This note was uploaded on 01/16/2012 for the course PSYCH 373 taught by Professor Marthafaircloth during the Spring '09 term at Campbell.

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ch11.pptx - Chapter11 Alcohols&Ethers Createdby

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