Transcript Organic synthesis revision

Organic Synthesis (aliphatic compounds)
ALKENE
KETONE
2-HYDROXYNITRILE
(CYANOHYDRIN)
ALCOHOL
ALDEHYDE
CARBOXYLIC
ACID
ALKANE
HALOGENOALKANE
NITRILE
AMINE
AMIDE
ESTER
ACYL
CHLORIDE
ALKENE → ALCOHOL
• COLD CONC. SULFURIC ACID
• THEN ADD WATER
• Electrophilic addition (hydration)
ALCOHOL → ALKENE
• CONC SULFURIC ACID
• Heat under reflux
• OR
• Al2O3
• 300 °C
• Elimination (dehydration)
ALKENE → ALKANE
• HYDROGEN
• Heat
• Nickel catalyst
• Addition (hydrogenation)
ALKENE → HALOGENOALKANE
• HYDROGEN HALIDE, e.g. HBr
• Room temperature
• Electrophilic addition
HALOGENOALKANE→ ALKENE
• POTASSIUM HYDROXIDE
(ethanolic)
• Elimination
HALOGENOALKANE→ ALCOHOL
• POTASSIUM HYDROXIDE
(aqueous)
• Heat under reflux
• Nucleophilic Substitution
HALOGENOALKANE→ AMINE
• CONC. AMMONIA (aqueous)
• Heat
• Nucleophilic Substitution
HALOGENOALKANE→ NITRILE
• POTASSIUM CYANIDE
• ETHANOL (SOLVENT)
Or
• LITHIUM ALUMINIUM TETRAHYDIDE
• DRY ETHER (SOLVENT)
• Then add water
• Nucleophilic Substitution
KETONE → ALCOHOL
• LITHIUM ALUMINIUM TETRAHYDIDE
• DRY ETHER (SOLVENT)
• Then add water
OR
• SODIUM BORON TETRAHYDRIDE
• METHANOL / ETHANOL / WATER (SOLVENT)
• Reduction
• ALSO GRIGNARD REAGENTS
SECONDARY ALCOHOL → KETONE
• POTASSIUM DICHROMATE (VI)
• DILUTE SULFURIC ACID (to
acidify)
• Heat under reflux
• Oxidation
ALDEHYDE → CARBOXYLIC ACID
• POTASSIUM DICHROMATE (VI)
• CONCENTRATED SULFURIC ACID (to
acidify)
• Heat under reflux
• Oxidation
PRIMARY ALCOHOL → ALDEHYDE
• POTASSIUM DICHROMATE (VI)
• DILUTE SULFURIC ACID (to
acidify)
• Distillation
• Oxidation
PRIMARY ALCOHOL → CARBOXYLIC ACID
• POTASSIUM DICHROMATE (VI) Excess
• SULFURIC ACID Concentrated
• Heat under reflux
• Oxidation
KETONE → 2-HYDROXYNITRILE
• POTASSIUM CYANIDE
• DILUTE SULFURIC ACID
- React to produce hydrogen
cyanide
• Nucleophilic Addition
ALDEHYDE → 2-HYDROXYNITRILE
• POTASSIUM CYANIDE
• DILUTE SULFURIC ACID
- React to produce hydrogen
cyanide
• Nucleophilic Addition
ALDEHYDE → PRIMARY ALCOHOL
• LITHIUM ALUMINIUM TETRAHYDIDE
• DRY ETHER (SOLVENT)
Or
• SODIUM BORON TETRAHYDRIDE
• METHANOL / ETHANOL / WATER (SOLVENT)
• Reduction
• ALSO GRIGNARD REAGENTS
CARBOXYLIC ACID → ALDEHYDE
• LITHIUM ALUMINIUM TETRAHYDIDE
• DRY ETHER (SOLVENT)
Or
• SODIUM BORON TETRAHYDRIDE
• METHANOL / ETHANOL / WATER
(SOLVENT)
• Reduction
CARBOXYLIC ACID → PRIMARY ALCOHOL
• LITHIUM ALUMINIUM TETRAHYDIDE
• DRY ETHER (SOLVENT)
Or
• SODIUM BORON TETRAHYDRIDE
• METHANOL / ETHANOL / WATER
(SOLVENT)
• Reduction
NITRILE → AMINE
• LITHIUM ALUMINIUM TETRAHYDIDE
• DRY ETHER (SOLVENT)
• THEN ADD WATER
Or
• SODIUM BORON TETRAHYDRIDE
• METHANOL / ETHANOL / WATER (SOLVENT)
• Reduction
NITRILE → CARBOXYLIC ACID
• DILUTE HYDROCHLORIC ACID
• Heat under reflux
• Hydrolysis
CARBOXYLIC ACID → ESTER
• ALCOHOL
• CONC. SULFURIC ACID (catalyst)
• Condensation Reaction
ALCOHOL→ ESTER
• CARBOXYLIC ACID
• CONC. SULFURIC ACID (catalyst)
• Condensation Reaction
ALKANE→ HALOGENO ALKANE
• HALOGEN
• UV light
• Free Radical Substitution
CARBOXYLIC ACID → ACYL CHLORIDE
• SCl2O (or PCl3, PCl5)
• Heat under reflux
• Nucleophilic substitution reaction
HALOGENOALKANE → ALCOHOL
• KOH or NaOH (aqueous)
• Heat under reflux
• Nucleophilic substitution
– SN2 for 1° and 2° halogenoalkanes
– SN1 for 3° halogenoalkanes
ALCOHOL → HALOGENOALKANE
• SODIUM HALIDE (solid) e.g. NaBr
OR
• PHOSPOROUS HALIDE e.g. PCl3
• CONC. SULPHURIC ACID (catalyst)
• Reflux
• Nucleophilic substitution reaction
ACYL CHLORIDE → ESTER
• ALCOHOL
• Condensation reaction
AMIDE → AMINE
• LiAlH4
• Reduction
AMIDE → NITRILE
• P2O5
• Distillation
• Elimination