大学课程-有机化学反应总结.ppt

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烃,醋酸,H,2,，,Pd/C,1,、顺式加氢,2,、反式加溴,3,、马氏规则：,H,+,主要加到含氢多的碳上。,CH,3,CH=CH,2,+Br,2,(H,2,O)CH,3,-CH-CH,2,|,|,HO,Br,过氧化物 或 光照,CH,3,CH=CH,2,+HBr CH,3,CH,2,CH,2,Br,4,、反马氏加,HBr,5,、,间接水合,异丙醇,6,、,硼烷,反马氏加水,CH,3,CH,2,CH,2,OH,CH,3,CH=CH,2,B,2,H,6,H,2,O,2,，,HO,-,H,2,O,RCCH,1)B,2,H,6,2)H,2,O,2,/OH,RCH,2,CHO,7,、烯丙位卤代,7,、烯丙位卤代,大家有疑问的，可以询问和交流,可以互相讨论下，但要小声点,CH,3,CO,3,H,8,、,烯烃环氧化,9,、烯烃被,KMnO,4,氧化,冷稀，中性或碱性,KMnO,4,KMnO,4,+,CH,3,COOH,10,、,烯烃臭氧化,(CH,3,),2,C=CH,2,O,3,H,2,O,Zn,(CH,3,),2,C=O +CH,2,O,炔 烃,1、炔钠与碳链增长,CH,3,C,CNa+C,2,H,5,Br,CH,3,C,CC,2,H,5,+,Na,Br,R-C,C-R,Lindlar,催化剂,顺式加成,2,、催化氢化,Lindlar,催化剂：,Pd-CaCO,3,/PbAc,2,、Pd-BaSO,4,/喹啉,R-C,C-R,Na,NH,3,(l),反式加成,3,、与卤素加成,HC,CH,Cl,2,Cl,2,FeCl,3,FeCl,3,C,HCl,2,-CHCl,2,CH,2,=CH-CH,2,-C,CH,CH,2,BrCHBr-CH,2,-C,CH,Br,2,(1mol),马氏规则,4,、与,HX,加成,5,、与,H,2,O,加成,CH,CH+HOCH,3,CH,2,=CHOCH,3,KOH,加热，加压,6,、与甲醇加成,7,氧化反应,RCOOH+RCOOH,KMnO,4,二 烯 烃,1,、加成反应,1,2,加成,1,4,加成,2,、狄尔斯,-,阿尔德反应,+,脂 环 烃,小环环烷烃,(,n,=3,，,4,),活泼，易开环,1,、催化加氢时，氢总是从不含取代基的一端加入，如：,2,、,与,HX/X,2,加成时，,在含氢最多与含氢最少的位置断键,Br,2,CH,3,CHBrCH,2,CH,2,Br,H,总是加在含氢多的碳原子上（马氏规则）,3,、取代反应,4,、,环烷烃常温下与不与高锰酸钾、臭氧反应,。,5,、环烯烃反应（等同于烯烃的反应）,苯 环,1,、,苯环卤代、硝化,2,、,占位反应,3,、,傅,-克烷基化反应,C,6,H,6,+CH,2,=CH,2,AlCl,3,C,6,H,5,CH,2,CH,3,C,6,H,6,+CH,3,CH,2,OH,C,6,H,5,CH,2,CH,3,H,2,SO,4,+CH,3,CH,2,CH,2,Cl,AlCl,3,4,、傅,-,克酰基化反应,5,、,合成直链烷基苯,6,、氯甲基化反应,HCHO,，,HCl(,浓,),ZnCl,2,60,o,C,7,、,侧链,烃基的氧化,多 环 芳 烃,X,2,1,、取代反应,2,、取代反应,3,、氧化,1,4-,萘醌,卤 代 烃,1,、取代,【,X,Cl,，,Br,】,CH,2,CH,CHCl,Cl,NaOH/H,2,O,CH,2,CH,CHCl,OH,例：,醇解,R-X,为一,级卤代烃,（仲、叔卤代烷主要发生消除反应生成烯烃）,腈解,R-X+NaCN R-CN,醇,例,1,：关于,CH,3,CH,2,OC(CH,3,),3,合成路线的选择,CH,3,CH,2,Br+NaOC(CH,3,),3,CH,3,CH,2,OC(CH,3,),3,CH,3,CH,2,ONa+BrC(CH,3,),3,叔卤代烷主要发生消除,例,2,：关于苯甲醚,合成路线的选择,卤苯中,C-Cl,很稳定,CH,2,CH,CHCl,Cl,NaOH/H,2,O,CH,2,CH,CHCl,OH,例：,与,AgNO,3,醇溶液反应,2,、消去反应,一般来说，,H,从含,H,少的碳原子上脱去：,反式消除,优先得共轭烯烃,邻二、偕二卤代烷得到炔烃,CH,3,CH,CH,CH,2,Cl,KOH/,乙醇,CH,2,CH,CH,CH,2,3,、与金属钠反应,2Na,2,醇、醚、酚,1.,醇与卤化磷、氯化亚砜反应,3,ROH +PBr,3,3RBr +H,3,PO,4,ROH +PX,5,RX +HX +POX,3,2CH,3,OH+2 HOSO,2,OH (,硫酸,),2 CH,3,OSO,2,OH,CH,3,OSO,2,OCH,3,硫酸二甲酯,减压蒸餾,-H,2,SO,4,2,、硫酸二甲酯,3,、消去反应,75%H,2,SO,4,用氧化铝作脱水时，一般不发生重排。,360,O,C,140,O,C,4,、,PCC,氧化,氯铬酸吡啶,5,、环氧,乙烷,环氧乙烷是张力很大的环,因此化学性质较活泼。发生开环反应。,6.,卤代,7,、,酚与,酸酐,或,酰氯反应,或者用：,CH,3,COCl,酚比芳烃容易进行傅,-,克反应。且以对位产物为主。,8,、烷基化和酰基化反应,8.,酚的氧化反应,醛、酮,1.,加,HCN,-,羟基腈,2,、与炔化钠加成,3,、与氨及其衍生物加成,亚胺,4,醛酮的,-H,卤代,单卤代,Br,2,H,2,O,也可写成：,NaOX,完全卤代,CH,3,CHO,HCCl,3,+HCOONa,Cl,2,/NaOH,卤仿反应,Br,2,/NaOH,5,、羟醛缩合反应,6,、还原成醇,7.,还原成亚甲基,-CH,2,-,NH,2,-NH,2,NaOH,(HOCH,2,CH,2,),2,O,8.,歧化反应,不含,-H,的醛在浓碱下歧化,+,HCHO,+HCOO,浓碱,甲,醛总是被氧化,羧酸及其衍生物,1,、,酰卤的生成,2,、酸酐的生成,高沸点的羧酸酐常,用乙酸酐作脱水剂,乙酸酐,混合酸酐：酰卤与羧酸盐一起共热制备,某些二元酸，只需加热即可分子内脱水生成五元环或六元环 的酸酐。如：,3,、酯的生成,4,、,酰胺的生成,200,5,、脱羧反应（失去,CO,2,）,a,、,羧酸的,-,碳上连有较强吸电基,时，易脱羧；,b,、,-,位为羰基时，,易脱羧。,6.-,氢的卤代反应,羧基卤代一般要在少量红磷存在下进行。,BrCH,2,COOH,CH,3,COOH,Br,2,P,7,、脱水反应,-,羟基酸,:,生成六元环交酯,-,羟基酸,:,生成,，,-,不饱和羧酸,-,或,-,羟基酸,:,五元或六元环内酯,8,、水解,9,、,酰氯、酸酐,都是常用的酰基化试剂,10,、羧基的还原反应,11,、金属氢化物,(LiAlH,4,),还原羧酸衍生物,RCOCl,1)LiAlH,4,2)H,3,O,+,RCH,2,OH,12,、还原反应,1,）催化氢化,2,）罗森门德还原法,13,、,Hofmann,降解反应,有机含氮化合物,1,、硝基,还原,2.,硝基,对芳卤的影响,NO,2,使邻、对位,Cl,的反应活性增大。,3,、胺的制备方法,4,、季铵盐和季铵碱,（,AgOH,）,主要产物：取代基少的烯烃,5.,水解,腈类化合物在酸或碱催化下很容易水解成羧酸。,6.,加氢还原,腈通过,催化加氢、,LiAlH,4,还原,等可以制备伯胺,R-NH,2,7,、重氮基被卤素，氰基取代的反应,(1),还原反应,8,、保留氮的反应,(2),偶合反应,杂 环 化 合 物,1,、加氢,2,、亲电取代反应,取代反应一般发生在,位，若,有基团存在，则进入,位,重要衍生物,呋喃甲醛,3,、,吡啶环的亲电取代反应,（,性质与硝基苯相似,）,