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Organic Synthesis (aliphatic compounds)

Organic Synthesis (aliphatic compounds). ALKENE. ALKANE. KETONE. ALCOHOL. HALOGENOALKANE. AMINE. ALDEHYDE. NITRILE. AMIDE. 2-HYDROXYNITRILE (CYANOHYDRIN). CARBOXYLIC ACID. ESTER. ACYL CHLORIDE. ALKENE → ALCOHOL. COLD CONC. SULFURIC ACID THEN ADD WATER

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Organic Synthesis (aliphatic compounds)

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

  2. ALKENE → ALCOHOL • COLD CONC. SULFURIC ACID • THEN ADD WATER • Electrophilic addition (hydration)

  3. ALCOHOL → ALKENE • CONC SULFURIC ACID • Heat under reflux • OR • Al2O3 • 300 °C • Elimination (dehydration)

  4. ALKENE → ALKANE • HYDROGEN • Heat • Nickel catalyst • Addition (hydrogenation)

  5. ALKENE → HALOGENOALKANE • HYDROGEN HALIDE, e.g. HBr • Room temperature • Electrophilic addition

  6. HALOGENOALKANE→ ALKENE • POTASSIUM HYDROXIDE (ethanolic) • Elimination

  7. HALOGENOALKANE→ ALCOHOL • POTASSIUM HYDROXIDE (aqueous) • Heat under reflux • Nucleophilic Substitution

  8. HALOGENOALKANE→ AMINE • CONC. AMMONIA (aqueous) • Heat • Nucleophilic Substitution

  9. HALOGENOALKANE→ NITRILE • POTASSIUM CYANIDE • ETHANOL (SOLVENT) Or • LITHIUM ALUMINIUM TETRAHYDIDE • DRY ETHER (SOLVENT) • Then add water • Nucleophilic Substitution

  10. KETONE → ALCOHOL • LITHIUM ALUMINIUM TETRAHYDIDE • DRY ETHER (SOLVENT) • Then add water OR • SODIUM BORON TETRAHYDRIDE • METHANOL / ETHANOL / WATER (SOLVENT) • Reduction • ALSO GRIGNARD REAGENTS

  11. SECONDARY ALCOHOL → KETONE • POTASSIUM DICHROMATE (VI) • DILUTE SULFURIC ACID (to acidify) • Heat under reflux • Oxidation

  12. ALDEHYDE → CARBOXYLIC ACID • POTASSIUM DICHROMATE (VI) • CONCENTRATED SULFURIC ACID (to acidify) • Heat under reflux • Oxidation

  13. PRIMARY ALCOHOL → ALDEHYDE • POTASSIUM DICHROMATE (VI) • DILUTE SULFURIC ACID (to acidify) • Distillation • Oxidation

  14. PRIMARY ALCOHOL → CARBOXYLIC ACID • POTASSIUM DICHROMATE (VI) Excess • SULFURIC ACID Concentrated • Heat under reflux • Oxidation

  15. KETONE → 2-HYDROXYNITRILE • POTASSIUM CYANIDE • DILUTE SULFURIC ACID - React to produce hydrogen cyanide • Nucleophilic Addition

  16. ALDEHYDE → 2-HYDROXYNITRILE • POTASSIUM CYANIDE • DILUTE SULFURIC ACID - React to produce hydrogen cyanide • Nucleophilic Addition

  17. ALDEHYDE → PRIMARY ALCOHOL • LITHIUM ALUMINIUM TETRAHYDIDE • DRY ETHER (SOLVENT) Or • SODIUM BORON TETRAHYDRIDE • METHANOL / ETHANOL / WATER (SOLVENT) • Reduction • ALSO GRIGNARD REAGENTS

  18. CARBOXYLIC ACID → ALDEHYDE • LITHIUM ALUMINIUM TETRAHYDIDE • DRY ETHER (SOLVENT) Or • SODIUM BORON TETRAHYDRIDE • METHANOL / ETHANOL / WATER (SOLVENT) • Reduction

  19. CARBOXYLIC ACID → PRIMARY ALCOHOL • LITHIUM ALUMINIUM TETRAHYDIDE • DRY ETHER (SOLVENT) Or • SODIUM BORON TETRAHYDRIDE • METHANOL / ETHANOL / WATER (SOLVENT) • Reduction

  20. NITRILE → AMINE • LITHIUM ALUMINIUM TETRAHYDIDE • DRY ETHER (SOLVENT) • THEN ADD WATER Or • SODIUM BORON TETRAHYDRIDE • METHANOL / ETHANOL / WATER (SOLVENT) • Reduction

  21. NITRILE → CARBOXYLIC ACID • DILUTE HYDROCHLORIC ACID • Heat under reflux • Hydrolysis

  22. CARBOXYLIC ACID → ESTER • ALCOHOL • CONC. SULFURIC ACID (catalyst) • Condensation Reaction

  23. ALCOHOL→ ESTER • CARBOXYLIC ACID • CONC. SULFURIC ACID (catalyst) • Condensation Reaction

  24. ALKANE→ HALOGENO ALKANE • HALOGEN • UV light • Free Radical Substitution

  25. CARBOXYLIC ACID → ACYL CHLORIDE • SCl2O (or PCl3, PCl5) • Heat under reflux • Nucleophilic substitution reaction

  26. HALOGENOALKANE → ALCOHOL • KOH or NaOH(aqueous) • Heat under reflux • Nucleophilic substitution • SN2 for 1° and 2° halogenoalkanes • SN1 for 3° halogenoalkanes

  27. ALCOHOL → HALOGENOALKANE • SODIUM HALIDE (solid) e.g. NaBr OR • PHOSPOROUS HALIDE e.g. PCl3 • CONC. SULPHURIC ACID (catalyst) • Reflux • Nucleophilic substitution reaction

  28. ACYL CHLORIDE → ESTER • ALCOHOL • Condensation reaction

  29. AMIDE → AMINE • LiAlH4 • Reduction

  30. AMIDE → NITRILE • P2O5 • Distillation • Elimination

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