FSU CHM 2210 - Major function group transformation

Unformatted text preview:

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


View Full Document

FSU CHM 2210 - Major function group transformation

Download Major function group transformation
Our administrator received your request to download this document. We will send you the file to your email shortly.
Loading Unlocking...
Login

Join to view Major function group transformation and access 3M+ class-specific study document.

or
We will never post anything without your permission.
Don't have an account?
Sign Up

Join to view Major function group transformation 2 2 and access 3M+ class-specific study document.

or

By creating an account you agree to our Privacy Policy and Terms Of Use

Already a member?