synthetic routes

• alcohol to haloalkane:

  • substitution of alcohols
  • electrophilic addition
  • uses a hydrogen halide made in situ
• alkene to haloalkane:

  • electrophilic substitution
  • hydrogen halide
• alcohol to alkene:

  • reflux
  • catalyst ( H3PO4/ H2SO4)
• alkene to alcohol:

  • hydrolysis reaction
  • water
  • concentrated H2SO4
  • 200°C
• alkene to alkane:

  • hydrogenation
  • 150°C
  • nickel catalyst
  • hydrogen
• alkane to haloalkane:

  • halogen
  • uv light
  • free radical substitution
• haloalkane to alcohol:

  • nucleophilic substitution
  • hydroxide ion
  • NaOH
  • reflux
• alcohol to carboxylic acid:

  • use primary alcohol
  • oxidising agent
  • reflux
  • K2Cr2O7/H+
  • oxidation of alcohols
• alcohol to aldehyde:

  • oxidising agent
  • primary alcohol
  • distillation
  • K2Cr2O7/H2SO4
  • oxidation of alcohols
• alcohol to ketone:

  • secondary alcohol
  • oxidising agents
  • distillation
  • K2Cr2O7/H2SO4
  • oxidation of alcohols
• ketone to alcohol:

  • reducing agent
  • nucleophilic addition
• carbonyl to hydroxy-nitrile:

  • use HCN
  • allows us to alter the length of the carbon chain
  • nucleophilic addition
• carboxylic acid + alcohol -> ester + water

  (H2SO4)
• ester + water -> carboxylic acid + alcohol

  (H+)
• ester + water -> carboxylate salt + alcohol

  (OH-)
• carboxylic acid + thionyl chloride (SOCl2) -> acyl chloride + SO2 (g) + HCl (g) (anhydrous)
• acyl chloride + alcohol -> ester
• acyl chloride + water -> carboxylic acid + HCl
• acyl chloride + NH3 -> primary amide + HCl
• what type of reaction is acyl chloride and water 


  nucleophilic addition-elimination
• amine + H+ -> amine salt
• amine + haloalkane -> primary amine + HCl

  • nucleophilic substitution
• haloalkane + NaCN -> nitrile
• haloalkane + NH3 / ethanol -> amine
• nitrile + H2 / Ni -> amine
• nitrile to amine is a reduction reaction
• hydroxynitrile + H2 / Ni -> amine
• ketone + NaCN (aq) / H+ (aq) -> hydroxynitrile
• aldehyde + NaCN (aq) / H+ (aq) -> hydroxynitrile
• aldehyde + K2Cr2O7 / H2SO4 and reflux -> carboxylic acid
• hydroxynitrile or nitrile + H2O / HCl and heat -> carboxylic acid
• nitrile to carboxylic acid is hydrolysis
• alcohol + carboxylic acid / conc H2SO4 or acid anhydride -> ester
• aldehyde to hydroxynitrile is nucleophilic addition
• alcohol to ester is esterification
• carboxylic acid + alcohol / conc H2SO4 -> ester
• carboxylic acid to ester is esterification
• ester + dilute acid, heat -> carboxylic acid
• ester to carboxylic acid is hydrolysis
• ester + OH- and heat -> carboxylate