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Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOL HALOGENOALKANE AMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDE NITRILE AMIDE CARBOXYLIC ACID ESTER ACYL CHLORIDE

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Page 1: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

Organic Synthesis (aliphatic compounds)

ALKENE ALKANE

KETONE ALCOHOL HALOGENOALKANE AMINE

2-HYDROXYNITRILE(CYANOHYDRIN)

ALDEHYDE NITRILE AMIDE

CARBOXYLICACID ESTER

ACYLCHLORIDE

Page 2: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

ALKENE → ALCOHOL

• COLD CONC. SULFURIC ACID

• THEN ADD WATER

• Electrophilic addition (hydration)

Page 3: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

ALCOHOL → ALKENE

• CONC SULFURIC ACID• Heat under reflux

• OR

• Al2O3 • 300 °C

• Elimination (dehydration)

Page 4: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

ALKENE → ALKANE

• HYDROGEN

• Heat

• Nickel catalyst

• Addition (hydrogenation)

Page 5: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

ALKENE → HALOGENOALKANE

• HYDROGEN HALIDE, e.g. HBr

• Room temperature

• Electrophilic addition

Page 6: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

HALOGENOALKANE→ ALKENE

• POTASSIUM HYDROXIDE (ethanolic)

• Elimination

Page 7: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

HALOGENOALKANE→ ALCOHOL

• POTASSIUM HYDROXIDE (aqueous)

• Heat under reflux

• Nucleophilic Substitution

Page 8: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

HALOGENOALKANE→ AMINE

• CONC. AMMONIA (aqueous)

• Heat

• Nucleophilic Substitution

Page 9: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

HALOGENOALKANE→ NITRILE

• POTASSIUM CYANIDE• ETHANOL (SOLVENT)

Or

• LITHIUM ALUMINIUM TETRAHYDIDE• DRY ETHER (SOLVENT)• Then add water

• Nucleophilic Substitution

Page 10: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

KETONE → ALCOHOL

• LITHIUM ALUMINIUM TETRAHYDIDE• DRY ETHER (SOLVENT)• Then add water OR

• SODIUM BORON TETRAHYDRIDE• METHANOL / ETHANOL / WATER (SOLVENT)

• Reduction

• ALSO GRIGNARD REAGENTS

Page 11: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

SECONDARY ALCOHOL → KETONE

• POTASSIUM DICHROMATE (VI)

• DILUTE SULFURIC ACID (to acidify)

• Heat under reflux

• Oxidation

Page 12: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

ALDEHYDE → CARBOXYLIC ACID

• POTASSIUM DICHROMATE (VI)

• CONCENTRATED SULFURIC ACID (to acidify)

• Heat under reflux

• Oxidation

Page 13: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

PRIMARY ALCOHOL → ALDEHYDE

• POTASSIUM DICHROMATE (VI)

• DILUTE SULFURIC ACID (to acidify)

• Distillation

• Oxidation

Page 14: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

PRIMARY ALCOHOL → CARBOXYLIC ACID

• POTASSIUM DICHROMATE (VI) Excess

• SULFURIC ACID Concentrated

• Heat under reflux

• Oxidation

Page 15: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

KETONE → 2-HYDROXYNITRILE

• POTASSIUM CYANIDE

• DILUTE SULFURIC ACID

- React to produce hydrogen cyanide

• Nucleophilic Addition

Page 16: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

ALDEHYDE → 2-HYDROXYNITRILE

• POTASSIUM CYANIDE

• DILUTE SULFURIC ACID

- React to produce hydrogen cyanide

• Nucleophilic Addition

Page 17: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

ALDEHYDE → PRIMARY ALCOHOL

• LITHIUM ALUMINIUM TETRAHYDIDE• DRY ETHER (SOLVENT)

Or

• SODIUM BORON TETRAHYDRIDE• METHANOL / ETHANOL / WATER

(SOLVENT)

• Reduction

• ALSO GRIGNARD REAGENTS

Page 18: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

CARBOXYLIC ACID → ALDEHYDE

• LITHIUM ALUMINIUM TETRAHYDIDE• DRY ETHER (SOLVENT)

Or

• SODIUM BORON TETRAHYDRIDE• METHANOL / ETHANOL / WATER

(SOLVENT)

• Reduction

Page 19: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

CARBOXYLIC ACID → PRIMARY ALCOHOL

• LITHIUM ALUMINIUM TETRAHYDIDE• DRY ETHER (SOLVENT) Or

• SODIUM BORON TETRAHYDRIDE• METHANOL / ETHANOL / WATER

(SOLVENT)

• Reduction

Page 20: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

NITRILE → AMINE

• LITHIUM ALUMINIUM TETRAHYDIDE• DRY ETHER (SOLVENT)• THEN ADD WATER Or

• SODIUM BORON TETRAHYDRIDE• METHANOL / ETHANOL / WATER

(SOLVENT)

• Reduction

Page 21: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

NITRILE → CARBOXYLIC ACID

• DILUTE HYDROCHLORIC ACID• Heat under reflux • Hydrolysis

Page 22: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

CARBOXYLIC ACID → ESTER

• ALCOHOL

• CONC. SULFURIC ACID (catalyst)

• Condensation Reaction

Page 23: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

ALCOHOL→ ESTER

• CARBOXYLIC ACID

• CONC. SULFURIC ACID (catalyst)

• Condensation Reaction

Page 24: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

ALKANE→ HALOGENO ALKANE

• HALOGEN

• UV light

• Free Radical Substitution

Page 25: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

CARBOXYLIC ACID → ACYL CHLORIDE

• SCl2O (or PCl3, PCl5)

• Heat under reflux

• Nucleophilic substitution reaction

Page 26: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

HALOGENOALKANE → ALCOHOL

• KOH or NaOH (aqueous)

• Heat under reflux

• Nucleophilic substitution– SN2 for 1° and 2° halogenoalkanes

– SN1 for 3° halogenoalkanes

Page 27: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

ALCOHOL → HALOGENOALKANE

• SODIUM HALIDE (solid) e.g. NaBr

OR

• PHOSPOROUS HALIDE e.g. PCl3

• CONC. SULPHURIC ACID (catalyst)• Reflux

• Nucleophilic substitution reaction

Page 28: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

ACYL CHLORIDE → ESTER

• ALCOHOL

• Condensation reaction

Page 29: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

AMIDE → AMINE

• LiAlH4

• Reduction

Page 30: Organic Synthesis (aliphatic compounds) ALKENE ALKANE KETONE ALCOHOLHALOGENOALKANEAMINE 2-HYDROXYNITRILE (CYANOHYDRIN) ALDEHYDENITRILEAMIDE CARBOXYLIC

AMIDE → NITRILE

• P2O5

• Distillation

• Elimination