Organic synthesis

Alkene → Haloalkane

Alkene → Haloalkane

• ELECTROPHILIC ADDITION

  • HX / X2

  • 20ºC

Alkene → Alkane

• HYDROGENATION (ADDITION)

  • H2

  • Ni catalyst

  • 150ºC

Alkene → Alcohol

• HYDRATION (ELECTROPHILIC ADDITION)

  • Steam

  • H3PO4

  • 300ºC

  • 60atm

Haloalkane → Alkene

• ELIMINATION

  • KOH in ethanol

  • Heat under reflux

Alcohol → Alkene

• ELIMINATION (DEHYDRATION)

  • Conc. H2SO4

  • Heat

Alkane → Haloalkane

• FREE RADICAL SUBSTITUTION

  • X2

  • UV light

Haloalkane → Alcohol

• NUCLEOPHILIC SUBSTITUTION

  • Warm aq. NaOH

  • Reflux

Alcohol → Haloalkane

• NUCLEOPHILIC SUBSTITUTION

  • NaX

  • H2SO4

  • 20ºC

Haloalkane → 1º amine

• NUCLEOPHILIC SUBSTITUTION

  • NH3 in ethanol

  • Heat

Haloalkane → Nitrile

• NUCLEOPHILIC SUBSTITUTION

  • KCN in ethanol

  • Reflux

Alcohol → Aldehyde

• OXIDATION

  • 1º alcohol

  • H2SO4 + K2Cr2O7

  • Distillation

Alcohol → Aldehyde → Carboxylic acid

• OXIDATION

  • 1º alcohol

  • H2SO4 + K2Cr2O7

  • Reflux

Alcohol → Ketone

• OXIDATION

  • 2º alcohol

  • K2Cr2O7

  • Reflux

Aldehyde → Alcohol

• REDUCTION

  • NaBH4 in methanol + water

Carboxylic acid → Aldehyde → Alcohol

• REDUCTION

  • NaBH4 in methanol + water

Ketone → Alcohol

• REDUCTION

  • NaBH4 in methanol + water

Nitrile/Hydroxynitrile → Amine

• REDUCTION

  • H2

  • Ni catalyst

  • High T + P

Aldehyde/Ketone → Hydroxynitrile

• NUCLEOPHILIC ADDITION

  • aq. KCN + H2SO4

  • 20ºC

Carboxylic acid → Acyl chloride

• NUCLEOPHILIC ADDITION-ELIMINATION

  • SOCl2

Acyl chloride → Carboxylic acid

• NUCLEOPHILIC ADDITION-ELIMINATION

  • H2O

  • 20ºC

Acyl chloride → 1º amide

• NUCLEOPHILIC ADDITION-ELIMINATION

  • NH3

  • 20ºC

Acyl chloride → 2º amide

• NUCLEOPHILIC ADDITION-ELIMINATION

  • 1º amine

  • 20ºC

Acyl chloride → Ester

• NUCLEOPHILIC ADDITION-ELIMINATION

  • Alcohol

  • 20ºC

Carboxylic acid → Ester

• ESTERIFICATION

  • Alcohol

  • conc. H2SO4

  • Heat

Ester → Carboxylic acid

• HYDROLYSIS

  • Dil. H2SO4

  • Reflux

Ester → Carboxylate ion

• HYDROLYSIS

  • Dil. NaOH

  • Reflux