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
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