Ch 14 - Ethers, Epoxides, and Sulfides

Ch 14 Ethers, - E th ers E poxi d es a nd S u lfides l S-crown-6 with K s olvated 14 or aryl(benzene ring groups Like alcohols ethers are related

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14 Ethers, ±poxides, and SulfIde² Ethers are compounds of Formula R - 0 -R', where R and R± may be aLkyl groups or aryl (benzene ring) groups. ²Ike alcohoLs, ethers are reLated to water³ with a´kyl groups replacing the hydrogen atomsµ ¶n an aLcoho·¸ one hydrogen atom of water Is replaced by an alkyL group¹ ¶n an ether, both hydrogens are repLaced by alkyl groupsµ The two alkyL groups are the same in a symmetrical ether and diºerent in an un- symmetricaL ether. H»O¼H water Examples of ±therS diethyl ether (a symmetrIcaL ether) R-O-H alcoho± R»O»R½ eTheR < l 0-CH¾ meThyl phenyL ether (an unsyMmetrica² ether³ Q TetrahydrofUran ´a symmetrµcal, cyclµc eThe¶) As wIth other Functional groups³ we wILL discuss how ethers are formed and how they reactµ Ethers (other than epoxides) are relatively unreactive¿ however, and they are not frequently used as synthetIc intermediatesµ Because they are stable with many types of reagents³ ethers are commonly used as soLvents for organic reactionsµ ¶n thIs chapter, we consIder the propertIes of ethers and how these propertIes make ethers such vaLuabLe soLvents for organIc reactionsµ Àhe most Important commercIal ether Is diethyl ether³ often caLLed "ethyl ether³Á or simply "etherÂÁ Ether is a good soLvent For reactIons and extractions³ and it is used as a volatile startIng fluid for dIesel and gasoline engines¹ Ether was used as a surgicaL anesthetIc For over a hundred years (starting in 1842), but it Is hIghly ÃÄammabÅe³ and patIents oFten vomited as they regained consciousness¹ SeveraL compounds that are less fÆammable and more easIly tolerated are now In use, Including nItrous oxide ( N20 ) and halothane ² 3 »CHCLBr ) ¹ 14-2A Structure an d PolaRity o f Et h ers ²ike water³ ethers have a bent structure³ with an ³p 3 hybrid oxygen atom gIving a nearÈ Ly tetrahedral bond angLeµ ¶n water, the non bonding electrons compress the H »0 - H bond angle to 1É4¹5°Ê but in a typIcaL ether, the bulk oF the alkyl groups enlarges the LS-Crown-6 w·¸h K+ so¹vated 14-1 Introduction 14-2 Physical Properties of Ethers 623
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