organic synthesis

• Alcoholic NH3

  1. heat under pressure

  2. NuSub
• Step 1 H2SO4

  EAdd
• Step 2 H2O warm

  1. hydrolysis

  2. KOH aqueous

  3. heat under reflux

  4. NuSub
• Br2, Cl2


  1. UV light

  2. Fr Sub
• KOH aqueous

  1. heat under reflux

  2. Nu Sub
• Organic compounds

  • 1o amine
  • alkane
  • halogenoalkane
  • alkene
  • alcohol
  • ketone
  • aldehyde
  • carboxylic acid
  • diol
  • dihalogenoalkane
• Br2, Cl2

  1. room temp

  2. EAdd
• HBr, HCl


  1. room temp

  2. EAdd
• KOH alcoholic

  1. heat under reflux

  2. Elimination
• conc. H2SO4 or conc. H3PO4

  Elimination, dehydration
• If primary Na2Cr2O7/H+


  1. heat and distill

  2. partial ox
• If secondary Na2Cr2O7/H+

  1. heat

  2. oxidation
• If primary Na2Cr2O7/H+

  1. heat under reflux + excess oxidising agent

  2. Oxidation
• KCN in ethanol/water mixture

  1. heat under reflux

  2. NuSub
• high pressure catalyst

  poly(alkene)
• Acyl chloride/acid anhydride

  ester
• Primary

  amide
• Secondary

  amide
• H2O


  1. room temp

  2. Nu add/elim

  3. hydroxynitrile
• Alcohol

  1. room temp

  2. Nu add/elim
• NH3

  1. room temp

  2. Nu add/elim

  3. 1o amine
• Acyl chloride

  1. room temp

  2. Nu add/elim
• NaBH4


  Red Nu Add
• LiAlH4 in ether


  reduction
• Alcohol + H2SO4


  1. heat

  2. esterification
• Carboxylic acid + H2SO4

  1. heat

  2. esterification
• NaCN + H2SO4


  Nu Add
• Nitrogen compounds


  • 2o amine
  • 3o amine
  • Quaternary salt
• halogenoalkane


  NuSub
• Esters and amides can be hydrolysed by NaOH and acids
• Chemists aim to design processes that do not require a solvent and that use non-hazardous starting materials
• Chemists aim to design production methods with fewer steps that have a high percentage atom economy
• Distillation


  Separate an organic product from its reacting mixture
• Reaction: primary alcohol aldehyde

  1. Reagent: potassium dichromate (VI) solution and dilute sulfuric acid

  2. Conditions: use a limited amount of dichromate and warm gently and distil out the aldehyde as it forms
• Reaction: primary alcohol carboxylic acid

  1. Reagent: potassium dichromate(VI) solution and dilute sulfuric acid

  2. Conditions: use an excess of dichromate, and heat under reflux
• Reflux is used when heating organic reaction mixtures for long periods
• Never seal the end of the condenser as the build up of gas pressure could cause the apparatus to explode
• Anti-bumping granules are added to the flask in both distillation and reflux to prevent vigorous, uneven boiling
• Electric heaters are often used to heat organic chemicals as they are normally highly flammable