3.14 Organic Synthesis

• Alcohol to Alkene

  Elimination

  Conc H2SO4

  180 degrees Celsius
• Alkene to alcohol

  Electrophilic addition

  Conc H3PO4

  High T

  High P
• Alkene to alkylhydrogensulphate

  Electrophilic addition

  Conc H2SO4
• Alkylhydrogensulphate to alcohol

  Hydrolysis

  Water and warm
• Alkene to alkane

  Electrophilic addition

  H2,Ni catalyst
• Alkane to haloalkane

  Free radical substitution

  Halogen (X2)

  UV light
• Alkene to haloalkane

  Electrophilic addition

  HX(e.g.HBr)
• Haloalkane to alkene

  Elimination

  KOH (ethanol)

  Hot
• Haloalkane to alcohol

  Nucleophilic substitution

  NaOH(aq) warm
• Haloalkane to nitrile

  Nucleophilic substitution

  KCN (ethanol)

  Reflux
• Haloalkane to amine

  Nucleophilic substitution

  NH3

  Heat
• Secondary alcohol to ketone

  Oxidation

  K2Cr2O7

  H2SO4

  Heat under reflux
• Primary alcohol to aldehyde

  Oxidation

  K2Cr2O7

  H2SO4

  Distillation
• Aldehyde to carboxylic acid

  Oxidation

  K2Cr2O7

  H2SO4

  Reflux/

  Tollens reagent/

  Fehlings solution
• Carboxylic acid to ester

  Esterification

  Alcohol

  Conc H2SO4
• Ketone to 2-hydroxynitrile


  Nucleophilic addition

  HCN
• Aldehyde to 2-hydroxynitrile


  Nucleophilic addition

  HCN
• Ketone to alcohol

  Reduction

  NaBH4(aq)
• Aldehyde to alcohol

  Reduction

  NaBH4(aq)
• Alcohol to ester

  Esterification

  Carboxylic acid, conc H2SO4/

  Acyl chloride/

  Acid anhydride
• Nitrile to amine

  Reduction

  LiAlH4
• Amine to amide


  Addition elimination

  Acyl chloride/

  Acid anhydride
• Benzene to cyclohexane

  Reduction

  H2, Ni catalyst, 150 degrees celsius
• Benzene to nitrobenzene

  Electrophilic substitution (nitration)

  Conc H2SO4, Conc HNO3, 50 degrees Celsius
• Nitrobenzene to phenylamine

  Reduction

  Sn catalyst, conc HCl then NaOH
• Phenylamine to Benzanamide

  Addition elimination

  (Acylation)

  Acyl chloride/ acid anhydride
• Benzene to phenylmethanone

  Acyl chloride/acid anhydride

  AlCl3 catalyst
• Phenylmethanone to phenylmethanol

  Reduction

  NaBH4(aq)