4 Organic synthesis

Br2, Cl2 UV light Free radical Substitution amine alkane haloalkane alkene alcohol aldehyde ketone carboxylic acid dihaloalkane Br2, Cl2 room temp Electrophilic addition HBr ,HCl room temp Electrophilic addition If primary heat gently and distill partial oxidation If secondary heat under reflux oxidation Na2Cr2O7/H+ heat under reflux + excess oxidising agent Oxidation poly(alkene) high pressure Catalyst polymerization KOH aqueous heat under reflux Nucleophilic substitution H2, Nickel Catalyst addition/reduction NaBr/H2SO4 Heat under reflux substitution hydroxynitrile HCN + KCN Nucleophilic addition Acyl chloride ester Primary amide secondary amide H2O room temp Alcohol room temp NH3 room temp 1 o amine Alcohol + H2SO4 room temp heat esterification Esters and amides can be hydrolysed by NaOH and acids SOCl2 Acyl chloride room temp Nu add/elim 2 o amine 3 o amine haloalkane NuSub Na2Cr2O7/H+ NaBH4 Reduction NaBH4 Reduction nitrile Acid hydrolysis Heat with HCl H2O (g) Catalyst: Conc H3PO4 conc. H2SO4 or conc. H3PO4 Elimination, dehydration Caboxylic acid + H2SO4 heat esterification H2/nickel catalyst Reduction CN– and ethanol Nucleophilic substitution 6. Alcoholic NH3 heat under pressure Nucleophilic substitution. conc nitric acid + conc sulphuric acid Electrophilic substitution C O CH3 acyl chloride in the presence of anhydrous aluminium chloride catalyst Electrophilic substitution Sn and HCl NH2 reduction NH C O CH3 CH3COCl CH O CH3 H NaBH4 Red Nu Add NH CH3 CH3Cl Nu sub C O CH3 H CN NaCN + H2SO4 Nu Add A. Aromatic synthetic routes H3C CH O C O CH3 CH3CO2H + H2SO4 heat esterification N Goalby chemrevise.org Br Br2 FeBr3 Electrophilic substitution CH2CH3 chloroalkane and anhydrous AlC3 catalyst. Hydrogen Nickel catalyst