Organic Chem Identification Reactions

1. Alkanes
a. No identification (Free radical Substitution is not)

2. Alkenes
a. Addition of bromine liquid/ dissolved in CCl4 Decolourisation of reddish-brown bromine b. Total bond cleavage with acidified KMnO4; Reflux Decolourisation of purple MnO4-

3. Benzene
a. Halogenation with bromine liquid and anhydrous AlCl3, at room temperature Decolourisation of reddish-brown bromine

4. Alkylbenzene
a. Halogenation with bromine liquid and anhydrous AlCl3, at room temperature Decolourisation of reddish-brown bromine

5. Alcohols
a. Halogenation with PCl5, cold White fumes of HCl produced b. Tri-iodomethane/ Iodoform test with alkaline I2(aq), heat Yellow precipitate formed (For alcohol with CH3 substituent)

6. Phenol
a. Halogenation with PCl5, cold White fumes of HCl produced b. Neutral Iron(III) chloride solution at room temperature Violet coloration c. Bromine water at room temperature o Decolourisation of reddish-brown bromine and white precipitate of 2,4,6-tribromophenol

7. Aldehydes
a. Oxidation with Acidified K2Cr2O7, heat Orange solution of Cr2O72- turns green b. Oxidation with Acidified KMnO4, heat Decolourisation of purple MnO4c. Tollens Reagent, heat Formation of silver mirror For comparison with ketone d. Fehlings solution Formation of reddish-brown precipitate For comparison with ketone e. 2,4-dinitrophenylhydrazine (Bradys Reagent), room temperature Formation of bright orange precipitate For comparison with non-carbonyl compounds f. Tri-iodomethane/ Iodoform test with alkaline I2(aq), heat Yellow precipitate formed (For carbonyl compounds with CH3 substituent) Done by Nickolas Teo Jia Ming, CG 12/11

8. Ketone
a. Oxidation with Acidified K2Cr2O7, heat Orange solution of Cr2O72- turns green b. Oxidation with Acidified KMnO4, heat Decolourisation of purple MnO4c. 2,4-dinitrophenylhydrazine (Bradys Reagent), room temperature Formation of bright orange precipitate For comparison with non-carbonyl compounds d. Tri-iodomethane/ Iodoform test with alkaline I2(aq), heat Yellow precipitate formed (For carbonyl compounds with CH3 substituent)

9. Benzaldehyde
a. Oxidation with Acidified K2Cr2O7, heat Orange solution of Cr2O72- turns green b. Oxidation with Acidified KMnO4, heat Decolourisation of purple MnO4c. Tollens Reagent, heat Formation of silver mirror d. Does not react with Fehlings solution For comparison with other aliphatic carbonyl compounds e. 2,4-dinitrophenylhydrazine (Bradys Reagent), room temperature Formation of bright orange precipitate For comparison with non-carbonyl compounds

10. Phenylethanone
a. Oxidation with Acidified K2Cr2O7, heat Orange solution of Cr2O72- turns green b. 2,4-dinitrophenylhydrazine (Bradys Reagent), room temperature Formation of bright orange precipitate For comparison with non-carbonyl compounds c. Tri-iodomethane/ Iodoform test with alkaline I2(aq), heat Yellow precipitate formed (already has CH3 substituent)

11. Carboxylic acid

a. Halogenation with PCl5, cold White fumes of HCl produced b. Reaction with metal carbonate at room temperature Effervescence of a colourless odourless gas (CO2)

12. Acyl chloride

a. No identification

13. Ester
a. No identification

14. Amide
a. Alkaline hydrolysis NH3 gas evolved for unsubstituted amide For comparison with amine Done by Nickolas Teo Jia Ming, CG 12/11

15. Amine
a. No identification

16. Phenylamine
a. Aqueous bromine at room temperature o Decolourisation of reddish-brown bromine and white precipitate of 2,4,6-tribromophenol b. Sodium chlorate(I) solution at room temperature Violet colouration

17.Halogenoalkane
a. Formation of ester with Silver(I) salt of carboxylic acid in alcohol; Reflux White precipitate o If chloroalkane Pale yellow precipitate o If bromoalkane Yellow precipitate o If iodoalkane

Done by Nickolas Teo Jia Ming, CG 12/11