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有機化學雙語版+Review+1.ppt

'有機化學雙語版+Review+1.ppt'
A Review of “Organic Chemistry”in First TermPart A Some Important Concepts and Structure1. Different kinds of Organic Compounds.Saturated Compd.AlkanesCycloalkanesAlkyl halidesAlcoholsUnsaturated Compd.AlkenesAlkynesDieneArenesReactive intermediatesAlkylAllylicBenzyl CarbocationsRadicalsC atomsHybrizationGeometric structure2. Formation of Chemical bonds.C–C σbondC–HσbondC=C double bondsTriple bondsStructure3. Bilingual nomenclature. 4. IsomersConstitutionalStereoisomersConformersStereoisomersConfigurational isomersEnatiomers(R,S)DiatereomersMeso-isomersRacemic mixtureChiralAchiral Optical Symetric Unsymetric Mole.cis-transIsomers:(Z),(E)OpticalactivitySymetric elementsNewman Fischer ProjectionsChair conformation5. AromaticityReso-naceformProblem 1 The structure of Comp. A is representedby the constitution shown:(a) How many of the optical isomers?(b) Write the Fischer projections of the optical isomers and give the IUPAC names.(c) Sight down the C3–C4 bond, and draw the most stable Newman projection formulas of the optical isomers .(d) Identify the relationship of these optical isomers.6. Organic acids and bases7. Substitutent effects Problem 2 Write a structural formula for the most stable conformation of the each of the following compounds:(a) cis-Cyclohexadiol.(b) trans-4-tert-Butyl-1-methylcyclohexane.(c)Give the stable conformer. Part B. Organic Reactions Radical ReactionsHalogenation of alkanes. α- Halogenation of alkenes. Reactions of NBS.d. Anti-Markovnikov addition: (HBr–ROOR)2. Nucleophilic SubstitutionsSubstrates Nucleophilea. Alkyl halidesb. Alcohols:HX, PX3, SOCl2TSCl or MsClROTsI -3. Elimination4. Electrophilic additonsSubstrates ElectrophilesAlkenesAlkynesConjugated dienesHX, X2, X2+H2O, H+/H2O (HgSO4/H2SO4/H2O)B2H6/H2O2–OH -,1,2-adddition1,4-additioncycloaddition5. Aromatic ElectrophilicsubstitutionsHalogenationNitrationSufonationFriedel-Crafts reactions6. HydrogenationsAlkenesDienesH2 / Pd,Ni…AlkynesAlkanescis-AlkenesH2Pd,Ni…Na or LiLiq. NH3H2Lindlar-Pdor P-2 Catalysttrans-Alkenes7. OxidationsAlkenesAldehydesor KetonesAlkynesCarboxylAcids Alkylbenzens:Na2Cr2O7/H+Benzoic acidPart C. Organic SynthesisOrganic SynthesisThe transformation of functional groupsb. The change of C skeletonc. The shift of functional groupsPart D. Mechanism of Organic ReactionsThe formation of a carbocationSN1 ReactionsE1 ReactionsRearrange-mentAromatic ElectrophilicsubstitutionAddition of HX to alkenes b. The halonium ion:Addition of X2 to a alkeneSN2 ReactionsE2 ReactionsTransition Statesc. BimolecularReactionsTable 1 Over summary of SN1,SN2, E1 and E2 reactionsRCH2XCH3XR2CHXR3CXMethyl 1° 2° 3°GivesSN2reac-tionsGaves mainly SN2,except with a hind-ered-strong base[e.g.,(CH3)3CO-] and then gives mainly E2Gaves mainly SN2,with weak base(e.g.,I-,CN -, N3-,RCO2-)and mainly E2With strongerbases(e.g.,RO -)Bimolecular reactionly SN1/E1 or E2In solvolysis give SN1/E1,and at lowtemperature SN1is favored and gavesmainly E2with strongerbases(e.g.,RO -)Part E. Stereoselectivity of Reactions1. Catalytic hydrogenations of alkynes:H2 / Lindlar-PdSyn-additionP-2 catalystLi or Na / Liq. NH3:2. Addition of X2 to Alkenes:Anti-addition3. Hydroboration-Oxidation of alkenes:Syn-addition4. Epoxidation of Alkenes:Syn-addition5. SN2 Reactions:Inversion of configurationRetention of configuration6. E2 Reaction:Anti-EliminationSN1 reaction:racemization Anti-additionPart F. Regioselectivity of Reactions1. Electrophilic addiitons of alkenes: Markovnikov’s rule2. Addition of HBr to a alkene in the presence of ROOR:Anti-Markovnikov’s rule3. Elimination:Zaitsev’s rule4. Aromatic electrophilic substitution of substituted benzenes: Directing effect of substituents on aromatic ringPart G. Identification of Organic Compounds1. Ozonolysis of alkenes and alkynes.3. Additions of Br2 to Alkenes.2. Oxidations of Alkenes by KMnO4.4. Reactions of Terminal alkynes with Ag(NH3)NO3 or Cu(NH3)Cl.5. Reactions of conjugated dienes with maleic anhydride. ……6. Oxidations of alkylbenzenes to benzoic acidIsobutyl iodide tert-Butyl chloride2.1.Racemization3.(R)-sec-Butyl alcohol(S)-sec-Butyl azide(R)- (R)-(S)-SN2 ReactionProblems to Chapter 8P2467.22 (d)1-Bromo-2-ethylpentane2- 乙基-1-溴戊烷3-Bromomethylhexane7.29 (a) SN2Rate<p-π conjugation(c) also.Electronic effect7.30(c)(f)7.32SN1:SN2:Steric hindrancecrowding7.34(a)(b)(c)SN27.35Ch.P196Racemic-formsRetention Inversion SN17.48(a)E1SN1(b)7.49E27.50(Z)-2,3-Diphenyl-2-butene7.51(a)(b)7.52(2R,3S)-2-Bromo-3-phenylbutane(Z)-2-Phenyl-2-butene7.53(E)7.55SN17.58AYou should comprehend well the meaning of the following reactions : 1.Hydroboration-Oxidation of alkenes.2. Diels-Alder Cycloaddition Reaction.3. Friedel-Crafts Alkylation of Arene.4.SN2 Reaction. 5.The Williamson Synthesis of Ethers.
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review+1 有機化學 review 雙語
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