1 Summary of reactions

Step 1 H2SO4 EAdd Step 2 H2O warm hydrolysis KOH aqueous heat under reflux NuSub Br2, Cl2 UV light Fr Sub KOH aqueous heat under reflux Nu Sub 1 o amine alkane halogenoalkane alkene alcohol aldehyde ketone carboxylic acid diol dihalogenoalkane Br2, Cl2 room temp EAdd HBr, HCl room temp EAdd KOH alcoholic heat under reflux Elimination conc. H2SO4 or conc. H3PO4 Elimination, dehydration If primary Na2Cr2O7/H+ heat and distill partial ox If secondary Na2Cr2O7/H+ heat oxidation (If primary) Na2Cr2O7/H+ heat under reflux + excess oxidising agent Oxidation nitrile KCN in ethanol/ water mixture heat under reflux NuSub poly(alkene) high pressure catalyst Acyl chloride/ acid anhydride ester Primary amide secondary amide hydroxynitrile H2O room temp Nu add/elim Alcohol room temp Nu add/elim NH3 room temp Nu add/elim 1 o amine room temp Nu add/elim Acyl chloride room temp Nu add/elim NaBH4 Red Nu Add NaBH4 Red Nu Add LiAlH4 in ether reduction Alcohol + H2SO4 heat esterification Caboxylic acid + H2SO4 heat esterification NaCN + H2SO4 Nu Add 2 o amine 3 o amine Quaternary salt haloalkane NuSub Esters and amides can be hydrolysed by NaOH and acids 3. Alcoholic NH3 heat under pressure NuSub. conc nitric acid + conc sulphuric acid Electrophilic substitution C O CH3 acyl chloride in the presence of anhydrous aluminium chloride catalyst Electrophilic substitution NH2 Sn and HCl reduction NH C O CH3 CH3COCl Nucleophilic add-el CH O CH3 H NaBH4 Red Nu Add NH CH3 CH3Cl Nu sub C O CH3 H NaCN + H2SO4 CN Nu Add C OH CH3 CH2 NH2 LiAlH4 reduction Aromatic synthetic routes H3C CH O C O CH3 CH3CO2H + H2SO4 heat esterification