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Overview

An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).

Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols. Ethers are considered good solvents because of their ability to form hydrogen bonds with other molecules, combined with the London Dispersion forces between the alkyl groups bonded to oxygen. Ethers have high volatility and can quickly evaporate during the isolation of reaction products.

Table 1. Comparison of Boiling Points of Ethers, Alcohols, and Hydrocarbons

Name Structural Formula Molecular weight (g/mol) bp (°C)
Dimethyl ether Figure1 46 −25
Ethanol Figure1 46 78
Propane Figure1 44 −42
Diethyl ether Figure1 74 35
1-Butanol Figure1 74 118
Pentane Figure1 72 36

Теги

EtherDipole MomentPolarityC O BondsBoiling PointsAlcoholsHydrocarbonsWater solubleHydrogen Bond AcceptorsHydrogen Bond DonorsSolubility In WaterGood SolventsLondon Dispersion ForcesAlkyl GroupsVolatilityEvaporateIsolation Of Reaction Products

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11.2 : Physical Properties of Ethers

Ethers, Epoxides, Sulfides

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11.1 : Structure and Nomenclature of Ethers

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11.3 : Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

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11.4 : Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

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11.5 : Ethers to Alkyl Halides: Acidic Cleavage

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11.6 : Autoxidation of Ethers to Peroxides and Hydroperoxides

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11.7 : Crown Ethers

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11.8 : Structure and Nomenclature of Epoxides

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11.9 : Preparation of Epoxides

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11.10 : Sharpless Epoxidation

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11.11 : Acid-Catalyzed Ring-Opening of Epoxides

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11.12 : Base-Catalyzed Ring-Opening of Epoxides

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11.13 : Structure and Nomenclature of Thiols and Sulfides

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11.14 : Preparation and Reactions of Thiols

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11.15 : Preparation and Reactions of Sulfides

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