1. Identify an Unknown
Type of compound:
Aldehyde
Alcohol
Amine
Ketone

2. Procedure 1. Physical Properties Melting point or boiling point
2. Functional Group
Infrared spectrum
NMR Spectrum
Solubility
Classification Tests
3. Solid Derivative

3. Measure boiling point of liquids
Distill your unknown and note the boiling point
If can’t distill or not enough sample use this technique.

4. Functional Group - No Yes Alcohol Amine Aldehyde Ketone NMR + Yes No
Carbonyl Group ( cm-1)? No
Yes
Alcohol Amine
Aldehyde Ketone
Broad OH in IR
NMR - +
Yes No
Alcohol
Aldehyde
Ketone
Amine (Basic?)
cm-1
Yes No
Primary or Secondary
Tertiary

5. 2,4-dinitrophenylhydrazine test
Aldehyde or ketone

6. 2,4-dinitrophenylhydrazone+

7. Mechanism

8. Iodoform Test
Reagent: NaOH and I2 (NaOI)

9. Iodoform Test

11. Ceric Nitrate Test for Alcohols
(NH4)2Ce(NO3)6 + ROH
(NH4)2Ce(NO3)5OR
+ HNO3

12. Amines
1. Odor
2. If not soluble in water they may dissolve in dilute aqueous acid (HCl).
3. Water solutions of amines are basic to litmus.

13. Hinsberg Test for Amines
Benzenesulfonyl Chloride

14. Hinsberg Test for Amines
Primary: Soluble. PPT if add HCl
Secondary: Insoluble
Tertiary: Tends not to react

15. Derivatives Aldehydes and Ketones 1. 2,4-dinitrophenylhydrazone
2. Semicarbazone

16. Alcohol Derivative
3,5-dinitrobenzoyl
chloride
3,5-dinitrobenzoate

17. Amine Derivatives Benzamide Benzoyl Chloride Benzenesulfonyl Chloride
Primary and Secondary Amines
Benzamide
Benzoyl Chloride
Benzenesulfonyl Chloride
Benzenesulfamide

18. Sample Unknown
B.p. = o
DNP = o

19. Data table

20. Acetophenone

21. Sample Unknown
B.p. = o
3,5-dinitrobenzoate = o

22. Data table

23. i-PrOH

24. Sample Unknown
B.p = 106o
3,5-dinitrobenzoate 85o

25. Data Table

26. Isobutyl alcohol

27. Sample Unknown
B.p. = 160o
3,5-dinitrobenzoate: o

28. Data Table

29. cyclohexanol
cyclohexanol

30. Sample Unknown
B.p. = o
2,4-DNP = o

31. Data Tables

32. cyclohexanone
cyclohexanone

33. B.p. = o
Benzenesulfonamide o
Benzamide o

35. aniline