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1(freeradicalinitiator)Cl22ClBr22BrhvhvCl2Br22electrophilicreagentpdHClBrRCH2CH3CONO2SO3HSO3BF3AlCl3Lewisacid3nucleophilicreagentOHHSCNNH2RCH2RORSPhORCOOXH2OROHRORNH3RNH2Lewisbase4CH3ONa+CH3BrCH3OCH3+NaBrNaCH3CH3OBrCH3OCH3O()SN2E2HSN1E1(activeintermediate)1carbonfreeradicalSP2PPCCHHHCHHCHHHCHHCH2CHCH2CH2CH3(CH3)3C(CH3)2CHCH3CH22carbocationSP2P12PPCCHHHCHHCHHHCHHCH3(CH3)3C(CH3)2CHCH3CH2CH2CHCH2CH2SN1E13SP3SP2PPCCHHHCHHCHHHCH2CHCH2CH23R2R1RCH34carbeneCHBr3OHHCBrBrBrBrCBr2CH2transitionstateT.SSN2CHBrHHOH+CHHHHOBrHOCHHH+BrT.S12SP3SP2P341T.S2T.S1015T.S3T.S1H2SN1E134563(1)(2)(3)P32373(1)(2)(3)P56582(1)(-)(2)P1251262(1)(2)P5053SN21(1),T.S(2)(3)P186194SN12(1)(2)(3)P186194E21(1)T.S(2)P194198E12(1)(2)(3)P1931941(1)(2)SN1E12(1)(2)P401404()(I)(Introduction)(C)(Conjugation)(I)(+I)CH3BrCH3CH2PPCH2CHCHCH2CH2CHClOHCH2CHCHHHCHHCHHHOHOHCH3SO3HCH3SO3HHHHHHHHHHHHH-p-(1)(2)(3),CH3CHCHCHCH2CH3CH2CH2CH2Cl1234564n+27rearrangement111,2CH3CHHCH2CH3CHCH321,2CH3CCH3CH2CH3CCH2CH3CH3CH331,2C6H5CC6H5CH2C6H5CCH2C6H5OHOHHC6H5CCH2C6H5OC6H5CCH2C6H5OHCH3CCOHCH3CH3OHCH3HCH3CCOHCH3CH3OH2CH3H2OCH3CCOHCH3CH3CH3CH3CCOHCH3CH3CH3HCH3CCOCH3CH3CH3()ArRH4CHCH3CH3HH2OCHCH3OHCHCH3OH2ClCH3Cl5CH3CHCHCH2ClClCH3CHCHCH2CH3CHCHCH2OHCH3CHCHCH2OHCH3CHCHOHCH2211,3CH3CCHH2OHgSO4,H2SO4CH3CCH2OHCH3CCH3O2ONH2OHNOHH2SO4NOH2H2ON1,2NH2ONOH2HNOH1,3NHO1CCOOHOHH3CH2CH3OHHHOHC2H52HHHHHHHHHHHH4COOHCH3OHH5(conformation)(1)(2)(3)eee7(1)(2)(3)1D/LDLCHOOHHCH2OHCHOOHHCH2OHD(+)L()DLdl2Z/EZECH3CCHClC2H5CH3CCHC2H5Cl(Z)32(E)323/CH3CCHCH3HCH3CCHHCH322CH3HCH3HCH3HHCH31,41,44R/SRSCadcbCadbcRSR/S12COOHSO3HCOORCOXCNCHOCOOH()OH()SHNH2ORCCCC(RXNO2)3ON(CH3)2NH2OHOCH3NHCOCH3ROCOCH3C6H5FClBrINH3NO2CNSO3HCOOHCHOCOCH3COOCH3CONH2H2CCCH3CH3H2CHCCH2CH2CH3CH2OHCH3OCH3CH2CHOHCH3CHOCH2CHCH2CH3CH3CHCHCH312341256n2n2n7(2R,3R)12170(2S,3S)12170(2R,3S)0146dl02061,3CH3COCH2COOC2H5CH3COHCHCOOC2H5CH3CH2NOOCH3CHNOHOCH2CHNH2CH3CHNHHNCONCOH1112142HCHOCH3CHORCHOC6H5CHOCH3COCH3RCOCH3C6H5COCH3C6H5COC6H532H2OHXNH3123SN1SN2SN2SN1CH34H2/NiNa+C2H5OHFe+HClNaBH4LiAlH4/512123624-CH3CH1NaOHNaOHNaOH2NaNO2+HClOH