sol11ch11.pdf - Chapter 11 Alcohols Ethers Table of...

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Chapter 11 Alcohols & Ethers
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Table of Contents 1. Structure & Nomenclature 2. Physical Properties of Alcohols and Ethers 3. Important Alcohols & Ethers 4. Synthesis of Alcohols from Alkenes 5. Reactions of Alcohols 6. Alcohols as Acids 7. Conversion of Alcohols into Alkyl Halides 8. Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides 9. Alkyl Halides from the Reaction of Alcohols with PBr 3 or SOCl 2 10. Tosylates, Mesylates, and Triflates: Leaving Group Derivatives of Alcohols 11. Synthesis of Ethers 12. Reactions of Ethers 13. Epoxides 14. Reactions of Epoxides 15. Anti 1,2-Dihydroxylation of Alkenes via Epoxides 16. Crown Ethers 17. Summary of Reactions of Alkenes, Alcohols, and Ethers
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In this chapter we will consider: v The structures, properties, and nomenclature of common alcohols and ethers v Key molecules that contain such groups v The reactivity of alcohols, ethers, and a special group of ethers known as epoxides
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OH OH OH 1. Structure & Nomenclature v Alcohols have a hydroxyl (–OH) group bonded to a saturated carbon atom (sp 3 hybridized) 1 o 2 o 3 o Ethanol 2-Propanol (isopropyl alcohol) 2-Methyl- 2-propanol ( tert -butyl alcohol)
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OH OH OH 2-Propenol (allyl alcohol) 2-Propynol (propargyl alcohol) Benzyl alcohol
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v Phenols Compounds that have a hydroxyl group attached directly to a benzene ring
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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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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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v Examples OH OH OH OH 2-Propanol (isopropyl alcohol) 1,2,3-Butanetriol
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v Example OH 3-Propyl-2-heptan ol
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1B. Nomenclature of Ethers v Rules of naming ethers Similar to those with alkyl halides t CH 3 O– Methoxy t CH 3 CH 2 O– Ethoxy v Example O Ethoxy ethane (diethyl ether)
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v Cyclic ethers
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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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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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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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v Physical Properties of Ethers Dimethyl ether
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