上海交通大学试卷(B卷)

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1、上海交通大学试卷（B卷）2006至2007年第1学期班级号：____________________学号：__________________姓名：_________课程名称：OrganicChemistryII(Jan.26，2007)Youhave120minutestoanswerallofthefollowing10questions.Thetotalvalueofthemis100points.GoodLuck!1.(5points)Inyourmind,whatarethefiveke

2、ypointsyoulearnedinorganicchemistry?Why?(10points)Whatarethedifferencesbetweenarylhalidesandalkylhalidesinthesubstitutionreactions?Why?RX:SN1andSN2ArX:SNAraddition-eliminationElimination–addition:BengyneEliminationadditionExplaination:a)b)sp2C-Xshorte

3、randstrongerresonance(10points)Howaboutthereactionofphenolwithconcentratedsulfuricacid?Explainitsmechanismandperformanceindetail.AnswerMachanism:electrophilicaromaticsubstitutiona)b)c)a)(10points)Whatarethenamedreactionsasfollows?(Giveexamples)(a)TheD

4、iels-Alderreaction(b)TheFriedel-Craftsalkylation(c)TheClaisencondensation(d)TheMichaeladdition(11points)Whatisaldolreaction?Giveitsmechanismsinthepresenceofacidandbaserespectively?AnswerAcid:Base(a)(b)(c)(10points)Outlinearoutetopreparethefollowingcom

5、poundfrombenzeneandotherneededreagents:Answer(10points)Preparationofthefollowingcompoundfromethylene.Answer(9points)Givethreedifferentmethodsforconvertingcarbonylgroupsofaldehydesandketonesto–CH2-groups.answera)TheClemmensenReductionb)c)Wolff-Kishnerr

6、eduction(15points)Explainthefollowingitemsusingexamples:(a)Markovnikovadditionvsanti-Markovnikovaddition(b)Zaitevrulevs.Hofmannrule(c)OxidationvsreductionAnswera)MarkovnikovadditionAnti-Markovnikovadditionb)ZaitevruleToformthemorestablealkeneHofmannru

7、lesToformtheleastsubstitutedalkenec)Oxidation:toincreaseitsoxygencontent(decreaseitsHcontent)oritscontentofanyelementmoreelectronegativethancabon.Reduction:theoppositeofoxidation(10points)DescribetheimpotanceandlimitationsofGrinardreagentsinorganicsyn

8、thesis.AnswerLimitations:sensitivetoH2Oand–OH,-NH2,-NHR,-COOH,-SO3H,-SH,-CH(acid)and