Organic Synthesis

• Alkane to Halogenoalkane

  X2 and UV light

  Free Radical Substitution
• Halogenoalkane to Alkane

  H2/Ni catalyst

  Nucleophilic Sub
• Halogenoalkane to Alkene

  Hot KOH or NaOH in ethanolic solution

  Elimination
• Alkene to Halogenoalkane

  HX or X2

  Electrophilic Addition
• Alkene to Alcohol

  H2O as steam, acid catalyst - H2SO4

  Electrophilic Addition
• Alcohol to Alkene

  Excess conc H2SO4

  Elimination
• Halogenoalkane to Nitrile

  KCN in ethanol

  Reflux

  Nucleophilic Sub
• Halogenoalkane to Amine

  Excess conc NH3 in ethanol

  Heat & pressure

  Nucleophilic Sub
• Halogenoalkane to Nitrile

  KCN in ethanol, reflux

  Nucleophilic Sub
• Alkene to Alcohol

  H2O (g), heat

  Acid catalyst - H2SO4

  Electrophilic Addition
• Alcohol to Alkene

  Conc H2SO4

  Elimination
• Alcohol to Aldehyde/Ketone

  K2Cr2O7 /H+

  Elimination
• Aldehyde/Ketone to Alcohol

  NaBH4 in water with methanol (sodium borohyride as reducing agent)

  Reduction
• Aldehyde/Ketone to Hydroxynitrile

  KCN & H2SO4

  Heat & distillation

  Nucleophilic Addition?
• Nitrile to Primary Amine

  LiAlH4, dry ether, room temp, dilute H2SO4

  Reduction
• Alcohol to Carboxylic Acid

  Excess K2Cr2O7/ H+ (dilute H2SO4)

  Reflux

  Oxidation
• Aldehyde/Ketone to Carboxylic Acid

  Excess K2Cr2O7 / H+ (dilute H2SO4)

  Reflux

  Oxidation
• Carboxylic Acid to Ester

  Alcohol, conc H2SO4 catalyst

  Oxidation of Alcohol

  Esterfication
• Ester to Alcohol

  Reflux, H2O, acid or base catalyst

  Hydrolysis
• Amide to Nitrile

  P4O10, heat, distillation

  Amide is dehydrated
• Nitrile to Amide

  H2O, acid/base catalyst
• Nitrile to Carboxylic Acid

  H2O, dilute HCl, reflux

  Nitriles are hydrolysed
• Acid Chloride to Ester

  ROH, room temp

  Nucleophilic Addition-Elimination
• Acid chloride to Carboxylic Acid

  H2O

  Nucleophilic Addition-Elimination
• Acid Chloride to Amide

  Conc NH3, room temp

  Nucleophilic Addition-Elimination