alkanealkyl halide alkene alcohol etheraldehydeketonealkyne acetal/hemiacetalimine/enaminecarboxylic acidacyl chlorideanhydrideester amide nitrileMajor function group transformationoxidationreduction±H2O; ±HXamine(CH3)2CHCH2CH38O25CO2+6H2O+ROH+HXRX+H2O(SN1/SN2)ROH+SOCl2RCl+SO2+HCl3ROH+PBr33RBr+H3PO3RH+X2RX+HX(free radical)Chapter 4HOHH++H2OH X+B-+HB+X-(E1)(E2)Chapter 5H2/PdHHChapter 6HBrBrH2OorROHOH or ORH2SO4(AdE2, carbocation)(AdE2, carbocation)BrBrBr2HOBrBr2H2OHOH1) BH32) H2O2,OH-+OOOHO+OHO1) O32) (CH3)2SorZn/H2OHO OChapter 8RCH2XNu:-(SN2)RCHXNu:-/base(SN2/E2)R(SN1/E1)RCXNu:-/baseRR(E2, or SN1/E1)SOClOROH+pyridineSOORO(ROTs)CHCXtBuO-(E2)HBrhor peroxideCH2Br(free radical)HHBr Br2NaNH2CCH3C CH3CCH3CH1) NaNH22) RCH2XCCH3C CH2RCCH3C CH32H2/PdCCH3C CH3H2Lindlar'scatalystCCH3C CH3Na0NH3CCH3CH2Br2H3CBr BrBrBrHCCH3CH2HClH3C CH3Cl ClCCH3CHH3C CH3H2SO4HgSO4H2OOCH3OH+CCNaH3CCH3ONa+CCHH3C(AdE2, bromonium ion)(AdE2, bromonium ion)Chapter 9H3C CH3OH3C CH2OHChapter 10XNu:-Nu+Nu(SN1, SN2, SN2')NBSCCl4,heatBr(free radical)HClClCl+Br2BrBr+OOO+OOOHHheatBrBr(hydrogenation)(hydroboration-oxidation)(AdE2)(epoxidation)(AdE2)(ozonolysis)(Diels-Alder)Chapter 14BrMgetherMgBrBrLipentaneLi+LiBrMgBrH2OH+Mg(OH)BrMgBr1)O2) H3O+OHCuLi2+Brether+CHI2Zn(Cu)etherChapter 15O1) CH3CH2MgBr2) H3O+OHO1) CH3CH2Li2) H3O+OHO1)2) H3O+OHHC CNaO1) NaBH42) H3O+OHO1) LiAlH42) H3O+OHChapters 11/12Na2Cr2O7or KMnO4H2O, heatOOHNa/NH3(l)CH3OHNBS/CCl4heatBrFe (cat.)heatPh+Br2BrheatPh+HNO3NO2H2SO4heat+SO3SO3HH2SO4heatPh+AlCl3(cat.)ClheatPh+AlCl3(cat.)ClOOheat+AlCl3(cat.)OOOOOZn(Hg)HClOH2NNH2KOHNO2NaOCH3CH3OHNO2ClOChapter 162OHH+O+H2OI2/CH3CH2OHIOONa+BrOOHBrNaOH/H2OOCl+SNaSOOH+H2SO4OOHS+CH3ISI-S+NaIO4SOOH2/PtethanolOHOHOH(CH3)3COOHOsO4(cat.)tBuOH, O H-OHK2Cr2O7H2SO4/H2OOHOOHPCC or PDCHOCH2Cl2OH1) DMSO/(COCl)2HO2) (CH3CH2)3NOHOH+HIO4HOHOSHHSO2/FeCl3SS(Birch reduction)(radical)(radical)(SEAr)(benzenium ion)(Friedel-Crafts)(carbocation)(acylium ion)ClemmensenWolff-Kishner(nitronium ion)(SN2Ar or Ad-E, Meisenheimer complex)(Grignard)(SN2)(Gilman)(Simmons-Smith)(N-Ad)(AdN2)(hydrogenation)(dihydroxylation)(Swern)(SN2)(AdN2)(AdN2)(AdN2)(AdE2)(Williamson ether synthesis)(SN2)(SN2)(SN2orSN1)(SN2)Chapter 17O1) NaCN2) H3O+CNOHO+H2OH3O+HO OHOHHOO+H3O+OOO+CH3NH2NOHOOHH3O+O+HNNOH-N+H2OO+H2NNH2NNH2O+Ph3PCH2+Ph3POHO1) K2Cr2O72) H3O+OHOPh3P+CH3BrPh3PCH3BrPh3PCH3Br+NaCH2SOCH3Ph3PCH2+SOMgBr1) CO22) H3O+OHOChapter 18Br+NaCNCN+NaBrCNH2O/H2SO4heatOOHOOH+OHH3O+(cat.)OO+H2OOHHOOOO+H2OH3O+(cat.)OOHOheatO+CO2Chapter 19reactivity sequence of acyl compounds:OClOOO OOOOHONH2generalized equation:OX+Nu-ONu+X-examples:OCl+OHOO+H2OOO O+NH2HOOHNOROHO+SOCl2RClOSO2+HCl+O+OOOHOO+OHOOO+NaOHOONa+OHOO+2CH3MgBrOH2) H3O+OO+ LiAlH4OH2) H3O+NH2OP4O10heatH3CCNCN1) KOH/H2O/heat2) H3O+OOHCN+CH3MgBr2) H3O+ONHO+LiAlH42) H3O+NHCN+LiAlH42) H3O+NH2mechanism?reactive intermediate?regioselectivity?stereoselectivity?intramolecular vs intermolecular?nucleophile? electrophile?oxidation? reduction?name reaction?How to apply them in multistep synthesis?(AdN2)(AdN2)(E-Ad)(Ad-E)(Ad-E)(Ad-E)(phosphonium salt)(ylide)(Wittig)(AdN2)(SN2)(Ad-E)(Ad-E)(Ad-E)(decarboxylation)(6-membered-ringtransition state)(Ad-E)(Ad-E)(Baeyer-Villiger)(Ad-E)(Ad-E)(Ad-E)(Ad-E)(AdN2)(Ad-E)(AdN2)Chapter 20 (new C-C bonds are bolded)OOH-+O-+H2OLiN+OOOOLi+HNHOPh2xKOH/H2OHOPhOHPhheatHOPhPh+H2O(aldol condensation)OO ONa2CO3,H2Oheat+H2O(intramolecular aldol)PhOH+ONaOH, H2OheatPhO(mixed aldol)OO2x1) NaOCH2CH32) H3O+O OO+CH3CH2OH(Claisen condensation)OOOO1) NaOCH32) H3O+OOO+CH3OH(Dieckmann cyclization)PhOO+OO 1) NaOCH32) H3O+PhOOO+CH3OH(mixed Claisen)PhOBr1) LDA2)PhOOO OOO O1) CH3CH2ONaCH3CH2OHethyl acetoacetate1) NaOH2) H3O+3) heatOO OO OO OO O1) CH3CH2ONaCH3CH2OH2) CH3I1) NaOH2) H3O+3) heatHOOO OO OO OO O1) CH3CH2ONaCH3CH2OH2) BrCH2CH2Br1) NaOH2) H3O+3) heatHOOOacid or baseOHOHOH++O+Br2H3O+(cat.)OBr+HBrO+3Br2NaOH, H2OONaO+HCBr3+3NaBrHO+MgBr2) H3O+OH(1,2-addition)HO+2) H3O+KCNHONC(1,4-addition; conjugate addition)OOO+KOHCH3OHOOOKOHheatOO+H2OO+LiCu(CH3)21) diethyl ether2) H2OO(1,4-addition)(LDA)2) CH3Imalonic ester(enolization; tautomerization)(haloform reaction)(Michael addition)(Robinson
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