[理学]Chapter 11醇、醚.pptVIP

Chapt 11 Alcohols and Ethers Structure and Nomencalture Alcohols: -OH is attached to a saturated carbon atom. Enols: -OH is attached to an unsaturated carbon atom. Nomenclature of Ethers IUPAC substitutive names are used for more complicated ethers and for compounds with more than one ether linkage. Ethers are named as alkoxyalkanes, alkoxyalkenes, and alkoxyarenes. Cyclic ethers can be names in several ways. Physical Properties of Alcohols Alcohols have much higher b.p. than comparable ethers or hydrocarbons. ------H-bond Physical Properties Ethers Ethers have similar boiling points that are comparable with those of hydrocarbons of the same molecular weight. -----The b.p. of diethyl ether (MW = 74) is 34.60C; that of pentane (MW = 74) is 36 0C. Ethers are able to form hydrogen bonds with compounds such as water. Synthesis of Alcohols from Alkenes Acid-Catalyzed Hydration of Alkenes: Alcohols from Alkenes through  Oxymercuration-Demercuration Complete within 20 s to 10 min at rt or below Oxymercuration-demercuration is highly regioselective. Hydroboration（硼氢化反应）: Carried out by using the boron hydride (B2H6) called diborane. The Stereochemistry of Hydroboration----a syn addition The net result of hydroboration-oxidation is an anti-Markovnikov addition of water to a double bond. The Stereochemistry of Hydroboration The overall result is the syn addition of –H and –OH. Protonolysis of Organoboranes Reactions of Alcohols The oxygen atom of an alcohol polarizes both the C–O bond and the O–H bond: Alcohols can react with protonated alcohols to afford ethers. ?as nucleophiles Alcohols as Acids Alcohols have acidities similar to that of water. * Methanol is a slightly stronger acid than water Conversion of Alcohols into Mesylates and Tosylatess Alcohols react with sulfonyl chlorides to form sulfonates. ? no change of configuration Mesylates and Tosylates in SN2 Reactions : Alkyl sulfonates are frequently used as substrates for nuc