Major cid 3 function cid 3 group cid 3 transformation anhydride acyl cid 3 chloride carboxylic cid 3 acid ester amide nitrile alkyne ketone aldehyde acetal hemiacetal imine enamine r e d u c t i o n o x i d a t i o n alkyl cid 3 halide alkene alcohol ether amine alkane H2O cid 3 HX CH3OH H3C C CNa CH3ONa H3C C CH CH3 2CHCH2CH3 8O2 5CO2 6H2O 1 BH3 2 H2O2 OH OH H hydroboration oxidation AdE2 H3C C C CH3 H2 Lindlar s catalyst O OH O 1 O3 O O epoxidation AdE2 OH 2Br2 Br Br H3C C C H H3C Br H Br O O ozonolysis H 2HCl Cl Cl H3C C C H H3C CH3 Chapter 4 ROH HX RX H2O SN1 SN2 ROH SOCl2 RCl SO2 HCl 3ROH PBr3 3RBr H3PO3 RH X2 RX HX free radical Chapter 5 H OH H H2O E1 H X B HB X E2 Chapter 6 H2 Pd H H HBr Br hydrogenation ROH AdE2 carbocation 2 CH3 2S or Zn H2O Chapter 8 Nu R CH2 X SN2 R CH X R Nu base SN2 E2 SN1 E1 Nu base R C X E2 or SN1 E1 Chapter 10 Nu OR ROTs X O S O E2 R R Cl O S O pyridine tBuO X C C H Chapter 9 H Br Br H 2 NaNH2 1 NaNH2 2 RCH2X 2H2 Pd Na0 NH3 HBr CH2Br h or peroxide free radical H2O or ROH OH or OR AdE2 carbocation H2SO4 Br2 Br Br Br HO Br2 H2O AdE2 bromonium ion H3C C C CH3 AdE2 bromonium ion H3C C C CH3 H3C C C CH3 H3C C C H H3C C C CH2R H2SO4 HgSO4 H2O H3C C C H OH O O H3C CH3 H3C CH2 H3C CH3 Nu Nu SN1 SN2 SN2 NBS CCl4 heat Br free radical HCl Cl Br2 Br Br Br heat O O O Diels Alder O Cl Br O H H O Chapters 11 12 Chapter 14 Na2Cr2O7 or KMnO4 H2O heat O OH Na NH3 l CH3OH Birch reduction radical NBS CCl4 heat radical Br Br2 Fe cat heat Ph Br SEAr benzenium ion HNO3 Ph NO2 nitronium ion H2SO4 heat H2SO4 heat MgBr Grignard Li LiBr H Mg OH Br Mg ether Li Br Br pentane H2O MgBr MgBr O 1 2 H3O CuLi 2 CHI2 ether Br Zn Cu ether dihydroxylation CH3 3COOH OsO4 cat tBuOH OH OH OH K2Cr2O7 H2SO4 H2O PCC or PDC CH2Cl2 OH OH O OH O H O OH SN2 Gilman Simmons Smith OH 1 DMSO COCl 2 2 CH3CH2 3N OH OH HIO4 O H HS SH O2 FeCl3 S S Swern H H O O 1 CH3CH2MgBr OH Chapter 16 H N Ad 2 OH O H2O SN2 SO3 SO3H Chapter 15 AlCl3 cat heat Ph Friedel Crafts carbocation 2 H3O Cl O AlCl3 cat O Ph acylium ion Cl heat O O AlCl3 cat O O 1 CH3CH2Li 2 H3O O 1 HC CNa 2 H3O Clemmensen O 1 NaBH4 OH O heat O Zn Hg HCl O H2NNH2 KOH 2 H3O 2 H3O ethanol I2 CH3CH2OH ONa Br I O AdE2 O O SN2 Williamson ether synthesis AdN2 NaOH H2O OH Br Cl SNa AdN2 OH OH AdN2 AdN2 S SN2 OH SN2 or SN1 Wolff Kishner O 1 LiAlH4 OH OH O H2SO4 O Cl NO2 NaOCH3 CH3OH O SN2Ar or Ad E Meisenheimer complex NO2 O H2 Pt OH hydrogenation S CH3I S I SN2 S NaIO4 O S Chapter 17 Chapter 18 O 1 NaCN OH 2 H3O CN AdN2 H3O HO OH AdN2 H2O OH HO OH H3O O OH H3O OO E Ad MgBr 1 CO2 2 H3O Br NaCN SN2 CN H2O H2SO4 heat O SOCl2 O OH AdN2 R OH O R Cl SO2 HCl Ad E O O O O H O O Baeyer Villiger Ad E OH O 2 CH3MgBr OH Ad E 2 H3O CN NaBr O Ad E OH O O O O OH H3O cat O H2O Ad E O 2 H3O LiAlH4 OH Ad E OH OH O H3O cat O CH3NH2 N Ad E HO O H2O Ad E H3C C N H N N OH Ad E O O heat O OH CO2 decarboxylation 6 membered ring transition state 1 KOH H2O heat O O O O O Cl O O OH NH2 LiAlH4 N H2O Chapter 19 O H2NNH2 NH2 N Ad E reactivity sequence of acyl compounds O O O O O O Ph3P CH3Br Ph3P CH3Br phosphonium salt generalized equation Ph3P CH3Br NaCH2SOCH3 Ph3P CH2 ylide O S O Ph3P CH2 O 1 K2Cr2O7 O H 2 H3O OH Nu X Ad E O X O examples O Nu O Cl OH Ph3P O Wittig O O O NH2 O O NaOH H2O H N O O O HO O OH ONa O O NH2 CN P4O10 heat 2 H3O CN CH3MgBr 2 H3O 2 H3O O N H CN LiAlH4 2 H3O Ad E OH O N H AdN2 Ad E NH2 AdN2 mechanism reactive intermediate regioselectivity stereoselectivity intramolecular vs intermolecular nucleophile electrophile oxidation reduction name reaction How to apply them in multistep synthesis Chapter 20 new C C bonds are bolded O H2O O OH Li N LDA 2 x Ph heat Ph O O H O H Ph heat OLi O H N OH O H Ph O KOH H2O Ph H2O aldol condensation O O O O Na2CO3 H2O Ph O NaOH H2O heat Ph 1 NaOCH2CH3 O O O 2 H3O O H O 2 x O O O O 1 NaOCH3 2 H3O O H2O intramolecular aldol O mixed aldol CH3CH2OH O Claisen condensation O O CH3OH O Dieckmann cyclization O O 1 NaOCH3 O O Ph O O 2 H3O Ph O CH3OH mixed Claisen O 1 LDA O Ph 2 Br Ph O O 1 CH3CH2ONa CH3CH2OH O O O ethyl acetoacetate 2 CH3I 1 NaOH 2 H3O 3 heat O O O O O O malonic ester 1 CH3CH2ONa CH3CH2OH 2 CH3I O O O O 1 NaOH 2 H3O 3 heat O HO O O 1 CH3CH2ONa CH3CH2OH O 2 BrCH2CH2Br O O O O 1 NaOH 2 H3O 3 heat O HO acid or base OH OH OH enolization tautomerization O O Br2 H3O cat HBr Br O 3 Br2 NaOH H2O O HCBr3 3 NaBr ONa haloform reaction MgBr 1 2 addition 2 H3O OH 2 H3O O KCN 1 4 addition conjugate addition NC O H O O KOH CH3OH O KOH heat H2O O Michael addition Robinson annulation O O LiCu CH3 2 1 diethyl ether 2 H2O 1 4 addition O O H O O H O