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1、Chap 7 Alcohols, Phenols, Ethers1Section 1 Alcohols. Structure,Classification and NomenclaturealiphaticalcoholCH3OHalicyclicalcoholaromaticalcohol OH hydroxyl2primaryalcoholCH3CH2OHsecondaryalcohol(CH3)2CHOHtertiaryalcohol(CH3)3COHmonobasicalcoholCH3CH2OHpolybasicalcoholCH2OHCH2OHCH2OHCHOHCH2OH(glyc
2、ol)(glycerol)3Alcoholarenamedsystemicallybydroppingthefinal“e”oftheparenthydrocarbonandaddingthesuffix“ol.”Thefunctionalgroup,OH(hydroxyl),isgiventhelowestnumberpossible,takingprecedenceoverothergroupsinthemolecule.Thelongestcarbonchainisidentifiedandthesubstituentsnumberedappropriately.4methanoleth
3、anolbenzyl alcohol(benzalcohol)2-propanol(isopropyl alcohol)2-methyl-2-propanol(tert-butyl alcohol)53-chloro-4-fluoro-2-pentanolglycerol(glycerin)64-methyl-4-hexene-2-olnot3-methyl-2-hexene-5-ol 3-methylcyclopentanol7. Preparation of Alcohol1. From alkeneTheelementsofwatercanbeaddedtothealkenesinthe
4、presenceofacid(thecommononeissulfuricacid.)TheadditionisMarkovnikovs addition.82. From alkyl halidesDisplacementofprimary or secondaryhalidesbyhydroxideleadstoalcohol.Buttertiaryhalidesareseldomusedduetotheeliminationreactioncomplicatetheprocessandlowertheyield.93. From carbonyl compoundsReductionof
5、aldehydesorketonesbyhydrogenleadstoprimary or secondary alcohols.10AldehydesorketonesreactwithGrignard reagentscangetsecondary or tertiary alcohols.11Insimilarfashionmagnesiumreducethecarbon-halogenbondsofalkylhalides.Halidereactivityincreasesintheorder:Cl Br HBr HClTheactivities of R-OHis:Allyl or
6、benzyl tertiary secondary primary25Whenalcoholsreactwithhalogenacids,sometimeswillcause rearrangementduetotheproduceofcarbocations(carbocationstendtorearrangementtomakethemmorestable.)2627Toavoidrearrangement,wecanusethionyl chloride(SOCl2)orphosphorus trihalides(PX3)toinsteadofhalogenacids(HX.)28Hy
7、drochloric acid/dry zinc chloride which is calledLucas reagent.29BecausetheChlorohydrocarbonsareindissolvableinhydrochloricacid,ifthealcoholreactswithLucasreagent,youwillseethereaction solution divide into tow layers or the solution become turbidness.Sowecanusethisreagenttodistin-guishprimary,second
8、aryandtertiaryalcohols.301)TertiaryalcoholsreactwithLucasreagentatonceandreleaseheat.2)SecondaryalcoholsreactwithLucasreagentwithin5minutesandnoobviousheatrelease.3)PrimaryalcoholsdonotreactwithLucasreagentatroomtemperatureevenafteronehour.31(2) DehydrationA.intermolecular140(ether)2conc. H2SO4 is c
9、oncentrated sulfuric acid.32B.intramolecular170(ethylene)TheintramoleculardehydrationofalcoholisSaytzeff elimination.ThemechanismisE1reaction,sotherateis:tertiary secondary primary33major productminor product34Whatweconcernaboutistheintramoleculardehydration.Sowhenwedohomeworkortestpaper,alwaysgivet
10、heintramolecular dehydrationproductsinthedehydrationreactionofalcoholsunlesswepointoutthereactionisintermolecularreaction.35(3) React with inorganic oxacid (esterification)nitrous acidnitric acidThesetwoproductsarefamousangiomyocardiac(medicinesforheartandbloodvessel.)amyl nitritetrinitroglycerin36A
11、scanio Sobrero 索布雷罗索布雷罗 Alfred Noble 诺贝尔诺贝尔371998年诺贝尔医学奖年诺贝尔医学奖Nitroglycerinwassynthesizedin1846,andwasfirstusedtotreatanginalattacksin1879.LouisJ.Ignarro 伊格纳罗伊格纳罗FeridMurad 慕拉德慕拉德RobertF.Furchgott弗奇戈特弗奇戈特 38coordinate bondphosphoric acidsulfuric acid39Theaboveacidshavetwoorthreehydroxyls,sotheycanr
12、eactwithtwoorthreemoleculesofalcohol.(dimethyl sulfate)40phosphatidate (磷脂磷脂)41phosphatidylcholine (磷脂磷脂酰胆碱，卵磷脂胆碱，卵磷脂)42nucleotides of DNAnucleotides of RNA433. Oxidation reaction44 Collins reagent (chromium trioxide in pyridine) 454. React with cupric hydroxide and periodic acidThesaltisblue color,
13、soyoucanusethisreactiontodistinguish1,2-glycols.46Whena1,2-diolisoxidizedbyperiodicacid(HIO4)itiscleavedtoapairofcarbonylcompound.47 The general reactionA specific example48Ester of periodic acidThe intermediate breaks down to form the two carbonyl compounds.49acetaldehydeformaldehydeformic acidacetone50
