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chapter11 - Organic Chemistry William H Brown Christopher S...

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11- 11-1 Organic Organic Chemistry Chemistry William H. Brown William H. Brown Christopher S. Foote Christopher S. Foote Brent L. Iverson Brent L. Iverson
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11- 11-2 Ethers & Ethers & Epoxides Epoxides Chapter 11 Chapter 11
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11- 11-3 Structure Structure The functional group of an ether is an oxygen atom bonded to two carbon atoms in dialkyl ethers, oxygen is sp 3 hybridized with bond angles of approximately 109.5°. in dimethyl ether, the C-O-C bond angle is 110.3° H H O H C H H H C
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11- 11-4 Structure Structure in other ethers, the ether oxygen is bonded to an sp 2 hybridized carbon in ethyl vinyl ether, for example, the ether oxygen is bonded to one sp 3 hybridized carbon and one sp 2 hybridized carbon CH 3 CH 2 -O-CH=CH 2 Ethoxyethene (Ethyl vinyl ether)
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11- 11-5 Nomenclature: ethers Nomenclature: ethers IUPAC: the longest carbon chain is the parent name the OR group as an alkoxy substituent Common names: name the groups bonded to oxygen in alphabetical order followed by the word ether ether 2-Methoxy-2- methylpropane ( tert- Butyl methyl ether) Ethoxyethane (Diethyl ether) CH 3 CH 3 CH 3 CH 2 OCH 2 CH 3 CH 3 OCCH 3 trans- 2-Ethoxy- cyclohexanol OCH 2 CH 3 OH
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11- 11-6 Nomenclature: ethers Nomenclature: ethers Although cyclic ethers have IUPAC names, their common names are more widely used IUPAC: prefix ox- ox- shows oxygen in the ring the suffixes - irane irane , - etane etane , - olane olane , and - ane ane show three, four, five, and six atoms in a saturated ring Oxirane (Ethylene oxide) Oxolane (Tetrahydrofuran) Oxane (Tetrahydropyran) 1,4-Dioxane O O 1 2 3 O O O O Oxetane
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11- 11-7 Physical Properties Physical Properties Although ethers are polar compounds, only weak dipole-dipole attractive forces exist between their molecules in the pure liquid state
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11- 11-8 Physical Properties Physical Properties Boiling points of ethers are lower than alcohols of comparable MW close to those of hydrocarbons of comparable MW Ethers are hydrogen bond acceptors they are more soluble in H 2 O than are hydrocarbons
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11- 11-9 Preparation of Ethers Preparation of Ethers Williamson ether synthesis: Williamson ether synthesis: S N 2 displacement of halide, tosylate, or mesylate by alkoxide ion 2-Methoxypropane (Isopropyl methyl ether) Iodomethane (Methyl iodide) Sodium isopropoxide + + CH 3 CH 3 CH 3 I CH 3 CHO - Na + CH 3 CHOCH 3 Na + I - S N 2
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11- 10 10 Preparation of Ethers Preparation of Ethers yields are highest with methyl and 1° halides, lower with 2° halides (competing β -elimination) reaction fails with 3° halides ( β -elimination only) CH 3 CH 3 CH 3 CO K + CH 3 Br S N 2 CH 3 CH 3 CH 3 COCH 3 K + Br - + + Potassium tert- butoxide Bromomethane (Methyl bromide) 2-Methoxy-2-methylpropane ( tert- Butyl methyl ether) CH 3 CH 3 CH 3 CBr CH 3 O - Na + E2 CH 3 CH 3 C=CH 2 CH 3 OH Na + Br - + + + 2-Bromo-2- methylpropane Sodium methoxide 2-Methylpropene
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11- 11 11 Preparation of Ethers Preparation of Ethers Acid-catalyzed dehydration of alcohols diethyl ether and several other ethers are made on an
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