Organic synthesis

• Organic to Organic


  Name of reaction:

  Reactants:

  Conditions:

  Other products:
• Alkane to Haloalkane

  Radical substitution

  Halogen (X2)

  UV light

  produces HX(g)

  May produce further substitutions
• Alkene to Alkane

  Electrophilic addition (hydrogenation)

  H2

  Ni catalyst, 423K
• Alkene to Alcohol

  Electrophilic addition (hydration)

  Steam

  acid catalyst, heat
• Alkene to Dihaloalkane

  Electrophilic addition

  Halogen (X2)
• Alkene to Haloalkane

  Electrophilic addition

  Hydrogen Halide (HX)
• Haloalkane to Alcohol

  Nucleophilic substitution (hydrolysis)

  NaOH

  Reflux

  product: NaX
• Alcohol to Aldehyde

  Oxidation

  Acidified potassium dichromate (2H+/Cr2O72-) [O]

  Distillation

  Primary alcohol
• Haloalkane to Secondary Amine

  Nucleophilic substitution

  1. Ammonia (in ethanol) -> R-ammonium salt

  2. alkali (eg. NaOH) -> Amine

  
  

  Continuous for primary > secondary > tertiary > quaternary
• Nitrobenzene to Phenylamine

  Reduction

  1. Tin and concentrated HCl (reducing agents) -> phenyl ammonium

  2. Excess NaOH -> phenylamine
• Haloalkane to Primary Amine

  Nucleophilic substitution

  1. excess Ammonia (in ethanol) -> R-ammonium salt

  2. alkali (eg. NaOH) -> Amine
• Alcohol to Carboxylic acid

  Oxidation

  Excess Acidified potassium dichromate (2H+/Cr2O72-) [O]

  Reflux

  Primary alcohol
• Alcohol to Ketone

  Oxidation

  Acidified potassium dichromate (2H+/Cr2O72-) [O]

  Reflux

  Secondary alcohol
• Aldehyde to Carboxylic acid

  Oxidation

  Acidified potassium dichromate (2H+/Cr2O72-) [O]

  Reflux
• Alcohol to Alkene

  Elimination (dehydration)

  Concentrated acid catalyst

  Reflux

  Produces water
• Alcohol to Haloalkane

  Nucleophilic substitution

  Sodium Halide

  H2SO4
• Alcohol to Ester

  Condensation (esterification)

  Carboxylic acid

  Concentrated H2SO4 catalyst

  Reflux
• Carboxylic acid to Ester

  Condensation (esterification)

  Alcohol

  Concentrated H2SO4 catalyst

  Reflux
• Amino acid to Ester

  Esterification

  Alcohol, H+

  Concentrated H2SO4 catalyst

  Heat

  Produces basic amine group (NH3+ on ester)
• Benzene to Halobenzene

  Bromination/ Chlorination (electrophilic substitution)

  Halogen (X2)

  AlX3 or FeX3 catalyst (halogen carrier catalyst)

  RTP
• Benzene to Nitrobenzene

  Nitration (electrophilic substitution)

  HNO3

  H2SO4 catalyst, heat

  can do multiple substitutions
• Benzene to Alkyl benzene

  Alkylation (electrophilic substitution)

  Haloalkane (XR)

  AlX3 catalyst (halogen carrier catalyst)

  RTP
• Benzene to Acylated benzene

  Acylation (electrophilic substitution)

  XCOR

  AlX3 catalyst (halogen carrier catalyst)

  RTP
• Phenol to Phenoxide salt

  Neutralisation

  NaOH

  Na Phenoxide
• Carboxylic acid to Aldehyde

  Reduction (Addition)

  (NaBH4) reducing agent [H]

  Water catalyst
• Carboxylic acid to Alcohol

  Reduction (Addition)

  (NaBH4) reducing agent [H]

  Water catalyst
• Aldehyde to alcohol

  Reduction (Addition)

  (NaBH4) reducing agent [H]

  Water catalyst
• Ketone to alcohol

  Reduction (Addition)

  (NaBH4) reducing agent [H]

  Water catalyst
• Aldehyde to Hydroxynitrile

  Nucleophilic addition

  YCN (Y = Na/H/K)

  Acid catalyst
• Ketone to Hydroxynitrile

  Nucleophilic addition

  YCN (Y = Na/H/K)

  Acid catalyst
• Nitrile to Amine

  Reduction

  H2

  Nickel catalyst
• Acyl chloride to Carboxylic acid

  HydrolysisH2ORTP?HCl gas
• Acid anhydride to Carboxylic acid

  Hydrolysis

  H2O
• Ester to Carboxylic acid

  Acid Hydrolysis

  Water

  -> carboxylic acid + alcohol
• Ester to Alcohol

  Acid/ Alkali Hydrolysis

  Acid (Water) -> alcohol + carboxylic acid

  Alkali (Y-OH) -> alcohol + carboxylate salt
• Ester to Carboxylate salt

  Hydrolysis

  Alkali (Y-OH) -> alcohol + carboxylate salt
• Amide to Carboxylic acid

  Hydrolysis
• Nitrile to Carboxylic acid

  Hydrolysis

  dilute HCl (H2O+HCl)

  Heat
• Haloalkane to Nitrile

  Nucleophilic substitution

  NaCN/KCN in ethanol
• Aldehyde to Nitrile

  Nucleophilic addition

  NaCN and H2SO4

  H2O to add H to O:

  Hydroxynitrile produced