有機(jī)化學(xué)Chapter3.Alkenes烯烴

1、Chapter 3 Alkenes3.1 Alkene Nomenclature3.2 Structure of Alkenes3.3 Isomerism in Alkenes 3.3.1 Stereo-isomerism in Alkenes 3.3.2 Naming Stereoisomeric Alkenes 1. Naming by term Cis-trans 2. Naming by the E, Z Notational System 3.4 Reactions of Alkenes 3.4.1 Electrophilic Addition of Alkenes(烯烴親電加成）烯

2、烴親電加成） (1) Addition of Hydrogen Halides to Alkenes （烯烴與鹵化氫加成）（烯烴與鹵化氫加成） Orientation of electrophilic addition （親電加成的方向）（親電加成的方向） Mechanism of the Reaction（反應(yīng)機(jī)理）（反應(yīng)機(jī)理） The stability of carbocations （碳正離子的穩(wěn)定性）（碳正離子的穩(wěn)定性） Carbocation Rearrangements （碳正離子的重排）碳正離子的重排） Peroxide effect（過(guò)氧化物效應(yīng)（過(guò)氧化物效應(yīng)）(2) Add

3、ition of Sulfuric acid to Alkenes （烯烴與硫酸加成）（烯烴與硫酸加成）(3) Acid-catalyzed Hydration of Alkenes (酸催化的烯烴水合反應(yīng)酸催化的烯烴水合反應(yīng))(4) Hydroboration-Oxidation of alkenes （硼氫化（硼氫化-氧化反應(yīng)）氧化反應(yīng)）(5) Addition of Halogen to Alkenes（與鹵素加成與鹵素加成） (6) Conversion of Alkenes to Vicinal Halohydrin (鄰鹵代醇鄰鹵代醇) 3.4.2 Hydrogenation of

4、 Alkenes (烯烴的氫化反應(yīng)）烯烴的氫化反應(yīng)） Heat of hydrogenation（氫化熱）（氫化熱） Stabilities of alkenes（烯烴的穩(wěn)定性）（烯烴的穩(wěn)定性） Mechanism of alkenes hydrogenation （烯烴加氫的反應(yīng)機(jī)理）（烯烴加氫的反應(yīng)機(jī)理） Stereochemistry of Alkenes hydrogenation (烯烴加氫的立體化學(xué)烯烴加氫的立體化學(xué)) Heterogeneous reaction （異相反應(yīng)）（異相反應(yīng)） 3.4.3 Oxidation of Alkenes（烯烴的氧化）（烯烴的氧化） (1) E

5、poxidation of alkenes（烯烴的環(huán)氧化）（烯烴的環(huán)氧化） (2) Hydroxylation of alkenes（烯烴的羥基化）（烯烴的羥基化） (3) Oxidative cleavage of alkenes: （烯烴氧化斷鍵）（烯烴氧化斷鍵） (A) Ozonolysis of alkenes（烯烴的臭氧化烯烴的臭氧化） (B) With KMnO4 solution （烯烴的高錳酸鉀氧化）（烯烴的高錳酸鉀氧化） 3.4.4 Reaction of Alkenes with Alkenes: Polymerization（聚合反應(yīng)）（聚合反應(yīng)）Alkenes: (Ol

6、efin) Hydrocarbon containing carbon-carbondouble bondThe site of reactions The functional group（反應(yīng)部位）（反應(yīng)部位） （官能團(tuán)）（官能團(tuán)）AliphatichydrocarbonsSaturated(飽和烴飽和烴)Unsaturated(不飽和烴不飽和烴)AlkanescycloalkanesAlkenesAlkynesCCRHRRP74Isobutylene（異丁烯）（異丁烯）CCH2H3CH3CHCH3CH3CH3- Pinene（ - 蒎烯）蒎烯）3.1 Nomenclature of Al

7、kenesIUPAC Names:1. Give the base name by selecting the longest continuous carbon chain including the double bond . -ene （某烯）（某烯）2. Number: Give the double- bond carbons the lower number. 3. The location of substituents like alkanes.4. When C number is over 10: 稱某碳烯稱某碳烯CH3(CH2)3CHCH(CH2)4CH35-Undece

8、ne5-十一碳烯十一碳烯CCCH3CH2CH3CH2CH2HH2-Ethyl-1-penteneCH3CH34,4-DimethylcyclohepteneAlkenyl groups（烯基）（烯基）:Vinyl （乙烯基）（乙烯基）Allyl (Allylic group)（烯丙基）（烯丙基）CH3CHCHCH2CHCH2CHCH2Propenyl（丙烯基）（丙烯基）CH2CCH3Isopropenyl（異丙烯基）（異丙烯基）CH2Methenecyclohexane（亞甲基亞甲基環(huán)己烷）環(huán)己烷）P773.2 Structure of AlkenesStructure of Ethylene

9、:sp2 Hybrid orbitalsP13, 1.9C:Ground state2p2s1sPromotionof electronExcitated state2p2s1ssp2-hybridized state1s2psp2Hybri-dizationAn sp2 orbital1/3 s orbital2/3 p orbital Three equivalent sp2 hybrid orbitals lie in a plane at angle of 120to one another.Geometric structure of C atom with sp2-hybrid:

10、Planar triangle(平面三角平面三角) A single unhybridized p orbital perpendicular to the sp2 plane. The formation of C-C bond: 2p-2p side by side overlap. The formation of C-H bond : sp2-1s overlap.One C-C bond and 4 C-H bond are coplanar.The formation of C-C bond: 2p-2p side by side overlap. In the molecule

11、of Ethylene :The formation of C _ Cbond: sp2 _ sp2 overlapp orbital overlapHHHH- bondp orbitaloverlapCCbondbondCarbon-carbon double bondModels of Ethylene分子的不飽和度分子的不飽和度(Degree of unsaturation)只含碳、氫、氧、氮以及單價(jià)鹵素的計(jì)算公式：只含碳、氫、氧、氮以及單價(jià)鹵素的計(jì)算公式： C1(XN)/2 其中，其中，C 代表碳原子的數(shù)目，代表碳原子的數(shù)目，X代表氫和鹵素原子的代表氫和鹵素原子的總數(shù)，總數(shù)，N 代表氮

12、原子的數(shù)目，氧和其他二價(jià)原子對(duì)代表氮原子的數(shù)目，氧和其他二價(jià)原子對(duì)不飽和度計(jì)算沒(méi)有貢獻(xiàn)，故不需要考慮氧原子數(shù)。不飽和度計(jì)算沒(méi)有貢獻(xiàn)，故不需要考慮氧原子數(shù)。這種方法只適用于含碳、氫、單價(jià)鹵素、氮和氧的這種方法只適用于含碳、氫、單價(jià)鹵素、氮和氧的化合物。化合物。 補(bǔ)充理解說(shuō)明：補(bǔ)充理解說(shuō)明： (1）若有機(jī)物為含氧化合物，因?yàn)檠鯙槎r(jià)，）若有機(jī)物為含氧化合物，因?yàn)檠鯙槎r(jià)，C=O與與C=C“等效等效”，所以在進(jìn)行不飽和度計(jì)算時(shí)可不考，所以在進(jìn)行不飽和度計(jì)算時(shí)可不考慮氧原子。慮氧原子。 如如CH2=CH2、CH3CHO、CH3COOH的不飽和度的不飽和度為為1。 2）有機(jī)物分子中的鹵素原子取代基，可視

13、作氫原）有機(jī)物分子中的鹵素原子取代基，可視作氫原子計(jì)算不飽和度子計(jì)算不飽和度。 如：如：C2H3Cl的的為為1，其他基團(tuán)如，其他基團(tuán)如-NH2、-SO3H等都等都視為氫原子。視為氫原子。 (3）有機(jī)物分子中含有）有機(jī)物分子中含有N、P等三價(jià)原子時(shí)，每增加等三價(jià)原子時(shí)，每增加1個(gè)三價(jià)原子，則等效為減少個(gè)三價(jià)原子，則等效為減少1個(gè)氫原子。個(gè)氫原子。 如，如，CH3NH2的不飽和度的不飽和度=0。 (4）C=C， C=N 碳碳雙鍵的不飽和度碳碳雙鍵的不飽和度=1；碳碳叁；碳碳叁鍵鍵 ，CN的不飽和度的不飽和度=2, 環(huán)狀化合物的不飽和環(huán)狀化合物的不飽和度度=1 。 不飽和度計(jì)算的用途不飽和度計(jì)算的用

14、途先寫(xiě)出分子式，然后根據(jù)分子式計(jì)算不飽和度，來(lái)先寫(xiě)出分子式，然后根據(jù)分子式計(jì)算不飽和度，來(lái)推測(cè)分子中可能的雙鍵，三鍵或者環(huán)的個(gè)數(shù)。推測(cè)分子中可能的雙鍵，三鍵或者環(huán)的個(gè)數(shù)。3.3 Isomerism in Alkenes3.3.1 Stereo-isomerism in AlkenesCCHHHCH2CH3CCHCH3HCH3CCH3CHHCH3CCH3CHHCH31-Butene2-Methylpropylene Isobutenecis-2-Butene trans-2-ButeneConstitutional isomers(I)(III) (IV)(II)(I)(II)(III)(IV)

15、Stereoisomers(III)(IV)Cis-trans isomersThe different spacialarrangement of atoms or atomic groups.cis-2-Butenetrans-2-ButeneRotation aboutC-C double bondis restricted ConfigurationPhysical properties:m.p; b.p3.3.2 Naming Stereoisomeric Alkenes1. Naming by term Cis-trans The same atoms oratomic group

16、son the same sideson the opposite sidesof the double bond.Prefixcis-trans-2. Naming by the E, Z Notational systemTo disubstitutedAlkenes:CCHCH2CH2CH3H3CCH3CCClHBrCH2CH3E, Z Notational systembase on an Sequence Rule （次序規(guī)則）（次序規(guī)則） Cahn-Ingold-Prelog priority Rule Considering each of the double-bonded c

17、arbon, identify the two atoms directly attached and rank them according to atomic number.CCClHBrCH2CH3Br Cl, C HLowpriorityHighpriorityE configuration: the high-priority groups are on the opposite sides of the double-bond(E)-1-Bromo-1-chloro-1-butene(E)-1-氯氯-1-溴溴-1-丁丁烯烯LowpriorityHighpriorityZ confi

18、guration: the high-priority groups are on the same sides of the double-bond2. When two atoms directly attached to the double bond are identical, look at the second, third,or fourth atoms away from the double-bonded carbons until the first difference is found. CCHCH2CH2CH3H3CCH3(Z)-3-methyl-2-hexene(

19、Z)-3-甲基甲基-2-己己烯烯CHHHCCHHHHHCCH3HHOH ZCC+ BrBrCCBr BrOrganic Reactions:The broken of original bonds,the formation of new bonds.Starting material（原料）（原料）Substrate（底物）（底物）Reagent（試劑）（試劑） ProductReactants A covalent bond may break in two way:A BA + BHomolytic bond break(Radical)(均裂均裂)A BA + BHeterolytic

20、 bond break(Polar)(異裂異裂)CCl4solventCCCH3.4 Reactional sites of alkene:The bond is active and is readily attacked bysome reagents. Additionreaction- H is easily lost3.4.1. Electrophilic Addition of Alkenes（親電加成反應(yīng)）（親電加成反應(yīng)） CC electrons lie above and below the plane ofdouble bond, so - bonded electrons

21、 are exposed (裸露裸露).- bond The bond is attacked by electron-seeking reagentsElectrophile （親電試劑）（親電試劑）An reaction rule:Electronegative species+Electropositivespecies(1) Addition of Hydrogen Halides (鹵化氫鹵化氫) to Alkenes CC+ HXCCHXAlkane halide Halogen Halide Halo 鹵素鹵素 鹵化物鹵化物 取代基取代基 Fluorine Fluoride Fl

22、uoro Chlorine Chloride Chloro Bromine Bromide Bromo Iodine Iodide Iodo+ HClCH3CHCHCH3CH3CH2CHCH3Cl 2-Butene 2-Chlorobutane Orientation of electrophilic addition: Markovnikovs RuleCH3CHCH2+ HBrCH3CH CH2HBr+CH3CH CH2HBrAddition to an unsymmetricallysubstituted alkenes: Markovnikovs Rule: In the additi

23、on of HX to an alkene, the H attaches to the carbon with fewer alkyl groups and X attaches to the carbon with more alkyl groups.(80%)(20%)Vladimir Vassilyevich Markovnikov1838-1904 Mechanism of the Reaction:Step 1.R2CCR2+ HXR2CCR2H+ XThe formation of the carbocation (正碳離子正碳離子)Reactive intermediateSt

24、ep 2. The formation of the carbocation is the rate-determining step.R2CCR2H+XR2CCR2HXslowfastH3CCH3CH3C+H3CCH3HC+HCH3HC+CH3+ The stability of carbocations: The one reason that stabilize a carbocation:the electron-donating effect of alkyl groups.The structure of carbocations:+CRRR120The positively ch

25、argecarbon atom is sp2-hybridized,The p orbital is vacant.The carbocation is trigonal plane.Tertiary(3 ) Secondary(2 ) primary(1 ) MethylThe Structure and Stability of CarbocationCRRR+120 osp2 hybrid, 120 o, empty p orbitalC+GC+GABStability: A BThe Effect of HyperconjugationCHH+CHHHCH+CHHHCHHHCHCHHH

26、CHH bondThe trivalent carbon is sp2-hybridized and has a vacant p orbital extending perpendicular to the plane of the carbon and three attached groups.- p - p -For StabilityCH3CHCH3CH3CH3CCH3CH3+CH3CH2+The Structure and Stability of Carbon RadicalCH3CHCH3CH3CH3CCH3CH3CH3CH2 BThe Effect of Hyperconju

27、gation for Carbon RadicalCHHCHHHCHCHHHCHHHCHCHHCHH bond Regioselectivity (區(qū)域選擇區(qū)域選擇 性性) of the reaction The reaction that can proceed in morethan one direction, but actually in whichone direction is preferred.Regiospecific (區(qū)域?qū)Ｒ坏膮^(qū)域?qū)Ｒ坏? A more highly substituted carbocation ismore stable than a less h

28、ighly substituted one.+CH3CH2+ The electron-donating or electron-withdraw effect of a group that is transmitted through bond.Inductive effect(誘導(dǎo)效應(yīng)誘導(dǎo)效應(yīng)) of substituents:CCH2CH3CH3H+CCH2CH3CH3+HExplanation for “Markovnikovs rule”CCH2 + HClCH3CH3Cl-CCH2CH3CH3HClCl-CCH2CH3CH3HCl(I)(II)The stabilities of

29、 carbocation:(I) (II)Electrophilic addition to an unsymmetri-cally substituted alkene give the more highly substituted carbocation.CH3CHCH3CH CH2H Carbocation Rearrangements (重排重排)(40%) (60%)HClCl-(I)(II)Cl-Stabilities of C+:Tertiary SecondaryHydride-shiftCH3CHCH3CHCH2HCl(CH3)2CHCHCH3Cl+ (CH3)2CCH2C

30、H3Cl0CH3CCH3CH2CH2HProblem:Propose a mechanism to account for the followingresult:+ HBrCH2CH3Br Reactivity:HI HBr HCl HFBased on the ability to proton-donating of HX Alkenes? Peroxide effect (過(guò)氧化物效應(yīng)過(guò)氧化物效應(yīng)) An unsymmetric alkene reacts with HBr in the present of a peroxide (R-O-O-R), theAnti-Markovni

31、kov addition occurs.H2CCHCH2CH3+ HBrR-O-O-RBrCH2CH2CH2CH3(95%)Free-radicaladdition（過(guò)氧化乙酰）（過(guò)氧化乙酰） （過(guò)氧化苯甲（過(guò)氧化苯甲 酰）酰）CH3CC OOPhCC OCPhOOOOCCH3OThe Mechanism for Anti-Markovnikov Addition of Alkenes OOOOOOH BrOOH+BrH2CHCCH2CH3BrH2CCHH2CCH3H BrBrH2CCH2H2CCH3+BrOOOOOOH BrOOH+BrCH2HCCH2H3CH2CCHH2CCH3H Br+B

32、rBrBrStability:BrH2CCHH2CCH3H2CCHH2CCH3Br orWhy?Route 1Route 2(2) Addition of Sulfuric acid to AlkenesCH3CH2CH+ HOSOOHOColdCH3CHCH3HSO4CH3CHCH3OSO3HH2OHeatCH3CHCH3OHCold ConcentratedH2SO4Alkyl hydrogenSulfate(硫酸氫酯硫酸氫酯)Hydration (水合反應(yīng)水合反應(yīng))MeCHCH2+H-OSO3HMeHCCH3+-OSO3HOSO3HOHH+OH2+-H+MeMeOHMechanism:(

33、3) Acid-catalyzed Hydration of Alkenes (酸催化的烯烴水合反應(yīng)酸催化的烯烴水合反應(yīng))(4) Hydroboration-Oxidation(硼氫化硼氫化-氧化氧化) of alkenes The method for preparation of the alcohols from anti-Markov. Addition.The hydroxyl group was added on lesssubstituted carbon.CH3(CH2)7CHCH2CH3(CH2)7CH2CH2OHOrganoboranes(有機(jī)硼烷有機(jī)硼烷)Herbert

34、Charles BrownGot the 1979 Nobel prizeMajor method to prepare alcohols in industryCC+HHHHH2OH2SO4(Cat.)250 CCH3CH2OHCatalyst:Dilute H2SO4,H3PO4 He discovered the hydroborationreaction (addition of diborane to alkenes) and developed the multi-faceted and synthetically useful chemistry of the resulting

35、 organo-boranes. In this photo, Professor Brown holds a model of 9-borabicyclo3.3.1nonane (9-BBN),prepared by adding borane to1,5-cyclooctadiene and itself a stable, useful hydroborating reagent. This work is summarized in Browns book Organic Synthesis via Boranes (1975). Brown contri-buted to many

36、other areas of organicchemistry, among which were selective reducing agents, steric effects (in displacement, elimination and acid-base reactions), and directive effects in electrophilic aromatic substitution (the + constant). Brown is perhaps the mostprolific organic chemist of the 20th century. He

37、 is best known for his work in organoboron chemistry, for which he shared (with G. Wittig) the 1979 Nobel Prize in Chemistry. (5) Hydroboration- Oxidation(硼氫化反應(yīng)硼氫化反應(yīng)):CC+BHCCHBorganoboraneCH3CHCH2(CH3CH2CH2)2BHborane+-H3C CHCH2H BH2H3CHCCH2HBH2OrganoboranesSteric hindranceCH3CHCH2(CH3CH2CH2)3BH2O2,

38、OH-, 25- 30 oCOH3CH2CCH2OHFeature of hydroboration-oxidation:1. Regioselectivity: following Markov. Rule.2. Stereochemistry:Syn-addition （順式加成）（順式加成） : Two atoms or groups add to the sameface of a double bond.B3+OOHH(H2O2)BOOHH-H+BOOHBOOHO-1, 2 shiftrepeatOBOOHB(OH)3H+OHHtrans-2-Methylcyclo-pentanol

39、3. Non rearrangementSyn-additionAnti-addition （反式加成）（反式加成） : Two atoms or groups add to the opposite faces of a double bond.CC+ BrBrCCBrBrThe stereoselectivity of Hydroboration-Oxidation:Problem: What products would you obtain from reaction of 1-ethylcyclopentene with BH3,followed by H2O2,OH-? CH3+

40、1/2 B2H6HH2BCH3HH2O2OHHHOCH3H(6) Solvomercuration/reduction(溶劑溶劑汞化汞化/還原反應(yīng)：羥汞化還原反應(yīng)：羥汞化-脫汞反應(yīng)）脫汞反應(yīng)）1) Hg(OAc)2/ THF-H2O2) NaBH4/NaOH/H2OOHH1) Hg(OAc)2/ THF-H2O2) NaBH4/NaOH/H2OOHHgOAcOHHABCMechanism:RHgOAcOAc-CH3COO-RHgOH2+BHHHNaHOAc-H+-CH3COO-ROHHgHROHROHHgHROHHRHg OAcH2O(7) Addition of Halogen to Alk

41、enes(CH3)2CHCHCHCH3+ Br2CCl4(CH3)2CHCHCHCH3BrBr0Vicinal dihalide(鄰二鹵代物鄰二鹵代物)Solvents: CH2Cl2,CHCl3, Acetic acidIdentification for C=C.Reagents: Cl2, Br2.Mechanism of the reaction:BrBr CCBr + BrCCStep1.CCBrBrCCBrBrStep2.Bromo-anionattacks from sideopposite.Step 1 is the rate- determining step.Bromoni

42、um ion ( 型離子型離子)Step 1.Step 2. Stereochemistry of halogen additionAnti-additionBrBrBrHHBrBrH BrH(8) Conversion of Alkenes to Vicinal Halohydrin(鄰鹵代醇鄰鹵代醇)- HalohydrinCC+CCXX2 + H2OOH+ HXAddition of halogen in aqueous solution.Mechanism of the reaction:CH3CH2CHCl2H2OCH3CH2ClCHCH3CH2CHClOHFeatures of t

43、he reaction: Following Markov. Rule, equal to the addition of one mole of HO-Cl+(次氯酸次氯酸)2. Anti-addition3.4.2 Hydrogenation of Alkenes+ heatCatalyst: Pt(platinum),Pd(palladium), Ni(nickle)CC+ H2CatalystCCHHr.tFeatures of the reaction:1. An exothermic reaction（放熱反應(yīng)）（放熱反應(yīng)）Broken: bond, H-H bondFormati

44、on: 2 C-H bond Heat of hydrogenation:The heat evolved on hydrogenation of one mole. of an alkene. The higher is the heat of hydrogenation,the less stable is the alkene.The heat of hydrogenation is relative to the stability of alkenes.Stability of alkenes:CH2CH2 RCHCH2 RCHCHR R2CCHR R2CCR2Cis- Trans-

45、Mechanism of alkene hydrogenation2. The role of the metal catalystVery slowly without catalyst.Changing the reaction path to lower activation energy （活化能）（活化能）. The addition of hydrogen to alkene is catalytic hydrogenation （催化氫化）（催化氫化）.3. Stereochemistry of Alkene hydrogenationAlkene hydrogenation:

46、syn-addition （順式加成）（順式加成）CatalystHydrogen absorbedon catalyst surfaceComplex of alkeneto catalystMechanism of alkene hydrogenationInsertion of hydrogeninto C=CAlkaneproductRegeneratedcatalystH2HHC CH HC CHHC CH H+CCH4. Heterogeneous reaction （異相反（異相反 應(yīng)）應(yīng)）Solvent （溶劑）：（溶劑）： ethanol, hexane or acetic

47、acid.To dissolve a alkene Metal: solid The reaction occurs at the interface of two phase.CH3CH3H2, PtCH3CH3HHCH3COOHHomogeneous(均相）均相） 3.4.3 Oxidation of Alkenes(1) Epoxidation of Alkenes (環(huán)氧化反應(yīng)環(huán)氧化反應(yīng))CC+ RCOOOHCC+ORCOOHPeroxy acid(過(guò)氧酸過(guò)氧酸)Epoxide(環(huán)氧化物環(huán)氧化物)Sharpless, K. B.got the 2001 Nobel prize.Mech

48、anism:Reagent: CH3COOOHPeroxyacetic acid(過(guò)氧乙酸過(guò)氧乙酸)R1R3R2R4+OOArHOK. Barry Sharpless, Ph.D. Organic/Inorganic ChemistThe Scripps Research Institute/chem/sharpless/cv.html(2) Hydroxylation(羥基化反應(yīng)羥基化反應(yīng)) of alkenes: Alkenes react with potassium perman-ganate or Osmium tetraoxide in b

49、asic solution to form 1,2-diols (glycol)(二醇二醇).Cyclohexenecis-cyclohexanediol(37%)syn stereochemistry.+ KMnO4NaOHH2OOHOHHHCH3CHCH2(1) OsO4, pyridine(2) Na2SO3/H2OCH3CHCH2OHOHCold solution of NaOH: Lower temperarue 10 oC(3) Oxidative cleavage of alkenes:(A) Ozonolysis of Alkenes (臭氧化反應(yīng)臭氧化反應(yīng))O3(ozone)

50、Reducing agent: ZnMechanism :R1R2R3R3O3R1R2R3R4OOOH2O/ZnR1R2O+R3R4OMechanism: RRRRRRRROOORROOOOCH2Cl2or MeOH+RROOO OOORRRRR1RR1RMnOOOO-R1RR1RMnOOOO-(VII)R1RR1RMnOOOO-(V)NaOH/H2OR1RR1ROHOHR1RR1RMnOO-OO(V)R1RR1RMnOO-OO(V)-OHR1RR1RMnOOHOO(V)H2ONaOH/H2O-MnO3-MnO4- + MnO2MnO3-Identification to the struct

51、ure of a alkeneCCH3CH3CHCH31) O32) H2O, ZnCCH3CH3O + OCCH3H2-Methyl-2-butene Acetone Acetaldehyde(B) With KMnO4 solutionIn hot OH- solution, neutral or acidic solution:Isopropylidene-cyclohexene (異亞丙基環(huán)己烯異亞丙基環(huán)己烯)Cyclohexa-none(環(huán)己酮環(huán)己酮)AcetoneCH3CH2CHCH CH2CH3+ KM nO4H2OCH3CH2CHCOCH3+ CO2OH(45% )CCH3CH3+ KMnO4H2OO + OCH3CH33.4.5 Reaction of Alkenes with Alkenes: Polymerizationn CH2CH2200, 200MPaO2 or peroxide CH2CH2( )nPolyethylene(聚乙烯聚乙烯)Ethylene: monomersPoly