organic synthesis

• Alcoholic NH3


  Nucleophilic substitution
• Br2, Cl2


  • Free radical substitution
• Organic compounds


  • amine
  • alkane
  • haloalkane
  • alkene
  • alcohol
  • ketone
  • aldehyde
  • carboxylic acid
  • dihaloalkane
• Br2, Cl2


  Electrophilic addition
• HBr, HCl


  Electrophilic addition
• Oxidation of alcohols


  1. If primary: heat gently and distill (partial oxidation)

  2. If secondary: heat under reflux (oxidation)

  3. Na2Cr2O7/H+, heat under reflux + excess oxidising agent (Oxidation)
• Polymerisation


  High pressure, Catalyst
• Nucleophilic substitution


  1. KOH aqueous, heat under reflux

  2. NaBr/H2SO4, Heat under reflux
• Addition/reduction


  H2, Nickel Catalyst
• Nucleophilic addition


  HCN + KCN
• Acyl chloride


  Ester, Primary amide, Secondary amide
• Esterification


  Alcohol + H2SO4, heat
• Hydrolysis of esters and amides

  NaOH and acids
• Nucleophilic addition-elimination


  SOCl2, room temp
• Nucleophilic substitution


  2o amine, 3o amine, haloalkane
• Reduction


  Na2Cr2O7/H+, NaBH4
• Acid hydrolysis


  Heat with HCl, H2O (g), Catalyst: Conc H3PO4 or conc. H2SO4
• Elimination, dehydration


  Carboxylic acid + H2SO4, heat
• Reduction


  H2/nickel catalyst
• Nucleophilic substitution


  CN- and ethanol
• Electrophilic substitution


  Conc nitric acid + conc sulfuric acid
• Electrophilic substitution


  Acyl chloride in the presence of anhydrous aluminium chloride catalyst
• Reduction


  Sn and HCl
• Nucleophilic addition


  NaBH4
• Nucleophilic substitution


  CH3Cl
• Nucleophilic addition


  NaCN + H2SO4
• Esterification


  CH3CO2H + H2SO4, heat
• Electrophilic substitution


  Br2, FeBr3
• Hydrogen, Nickel catalyst


  Reduction
• Distillation


  Separation technique to separate an organic product from its reacting mixture
• Reflux


  Used when heating organic reaction mixtures for long periods, condenser prevents organic vapours from escaping
• Anti-bumping granules are added to the flask in both distillation and reflux to prevent vigorous, uneven boiling by making small bubbles form instead of large bubbles
• Recrystallisation


  1. Step 1: Dissolve impure compound in minimum volume of hot solvent

  2. Step 2: Hot filter solution through (fluted) filter paper quickly

  3. Step 3: Cool the filtered solution by inserting beaker in ice

  4. Step 4: Suction filtrate with a buchner flask to separate out crystals

  5. Step 5: Wash the crystals with distilled water

  6. Step 6: Dry the crystals between absorbent paper
• Purifying an organic liquid

  Put distillate of impure product into a separating funnel, wash with sodium hydrogencarbonate solution or saturated sodium chloride solution, dry with drying agent, decant liquid into distillation flask, distill to collect pure product
• Melting point can be used to test the purity of a sample - a sharp melting point indicates high purity
• Boiling point can be used to determine the purity of a liquid, but is less accurate than melting point