C31 organic synthesis + analysis

• to convert from alkane to halogenoalkane:

  • add bromine or chlorine
  • conditions = UV light
  • mechanism is free-radical substitution
• to convert from halogenoalkane to primary amine:

  • add alcoholic NH3
  • conditions = heat, pressure
  • mechanism is nucleophilic substitution
• to convert from halogenoalkane to nitrile:

  • add alcoholic/aqueous KCN
  • conditions = heat, reflux
  • mechanism is nucleophilic substitution
• to convert from nitrile to primary amine:

  • add LiAlH4
  • conditions = in ether
  • mechanism is reduction
• to convert from primary amine to secondary amide:

  • add acyl chloride
  • conditions = room temperature
  • mechanism is addition-elimination
• to convert from primary amine to secondary amine:

  • add alcoholic NH3
  • conditions = heat, pressure
  • mechanism is nucleophilic substitution
• to convert from secondary amine to tertiary amine:

  • add alcoholic NH3
  • conditions = heat, pressure
  • mechanism is nucleophilic substitution
• to convert from tertiary amine to quaternary ammonium salt:

  • add alcoholic NH3
  • conditions = heat, pressure
  • mechanism is nucleophilic substitution
• to convert from acyl chloride to secondary amide:

  • add primary amine
  • conditions = room temp
  • mechanism is addition-elimination
• to convert from acid anhydride to secondary amide:

  • add primary amine
  • conditions = room temperature
  • mechanism is addition-elimination
• to convert from acyl chloride to primary amide:

  • add NH3
  • conditions = room temperature
  • mechanism is addition-elimination
• to convert from acid anhydride to primary amide:

  • add NH3
  • conditions = room temperature
  • mechanism is addition-elimination
• to convert from acyl chloride to ester:

  • add alcohol
  • conditions = room temperature
  • mechanism is addition-elimination
• to convert from acid anhydride to ester:

  • add alcohol
  • conditions = room temperature
  • mechanism is addition-elimination
• to convert from acyl chloride to carboxylic acid:

  • add water
  • conditions = room temperature
  • mechanism is addition-elimination
• to convert from acid anhydride to carboxylic acid:

  • add water
  • conditions = room temperature
  • mechanism is addition-elimination
• to convert from carboxylic acid to ester:

  • add alcohol and H2SO4
  • conditions = heat
  • mechanism is esterification
• to convert from aldehyde to carboxylic acid:

  • add excess acidified potassium dichromate
  • conditions = heat, reflux
  • mechanism is oxidation
• to convert from alcohol to aldehyde:

  • add acidified potassium dichromate
  • conditions = heat, distillation
  • mechanism is partial oxidation
• to convert from alcohol to ketone:

  • add acidified potassium dichromate
  • conditions = heat
  • mechanism is oxidation
• to convert from ketone to alcohol:

  • add NaBH4
  • mechanism is reduction or nucleophilic addition
• to convert from alcohol to ester:

  • add carboxylic acid + H2SO4
  • conditions = heat
  • mechanism is esterification
• to convert from alcohol to alkene:

  • add concentrated H2SO4 or H3PO4
  • mechanism is elimination, dehydration
• to convert from alkene to alcohol:

  • add H2SO4
  • mechanism is electrophilic addition
  • add H2O
  • conditions = heat
  • mechanism is hydrolysis
• to convert from alkene to polyalkene:

  • conditions = high pressure, catalyst
  • mechanism is addition polymerisation
• to convert from alkene to halogenoalkane:

  • add HBr or HCl
  • conditions = room temperature
  • mechanism is electrophilic addition
• to convert from halogenoalkane to alkene:

  • add alcoholic KOH
  • conditions = heat, reflux
  • mechanism = elimination
• to convert from alkene to dihalogenoalkane:

  • add bromine or chlorine
  • conditions = room temperature
  • mechanism is electrophilic addition
• to convert from dihalogenoalkane to diol:

  • add aqueous KOH
  • conditions = heat, reflux
  • mechanism is nucleophilic substitution
• to convert from halogenoalkane to alcohol:

  • add aqueous KOH
  • conditions = heat, reflux
  • mechanism is nucleophilic substitution
• to convert from ketone to hydroxynitrile:

  • add NaCN and H2SO4
  • mechanism is nucleophilic addition
• to convert from aldehyde to hydroxynitrile:

  • add NaCN and H2SO4
  • mechanism is nucleophilic addition
• to convert from alcohol to halogenoalkane:

  • add hydrogen halide
  • conditions = room temperature
  • or
  • add sodium halide and concentrated H2SO4
  • conditions = heat, reflux
  • mechanism is substitution
• to convert from alcohol to carboxylic acid:

  • add acidified potassium dichromate
  • conditions = heat, reflux
  • mechanism is oxidation
• to convert from carboxylic acid to alcohol:

  • add LiAlH4
  • conditions = in ether
  • mechanism is reduction
• to convert from aldehyde to alcohol:

  • add aqueous NaBH4
  • conditions = heat
  • or
  • add LiAlH4
  • conditions = in ether
  • mechanism is reduction
• to convert from nitrile to carboxylic acid:

  • add dilute acid or dilute alkali
  • conditions = heat, reflux
  • mechanism is acid-base hydrolysis
• to convert from nitrile to amide:

  • add H2O and an acid/base catalyst
  • mechanism is hydration
• to convert from amide to nitrile:

  • add P4O10
  • conditions = heat, reflux
  • mechanism is dehydration
• to convert from nitrile to amine:

  • add LiAlH4
  • conditions = in ether
  • mechanism is reduction