1. Unknown #2
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

4. Functional Group - No Yes Alcohol Amine Aldehyde Ketone CrO3 + Yes No
Carbonyl Group ( cm-1)? No
Yes
Alcohol Amine
Aldehyde Ketone
Broad OH in IR
CrO3 - +
Yes No
Alcohol
Aldehyde
Ketone
Amine (Basic?)
cm-1
Yes No
Primary or Secondary
Tertiary

5. Chromic Acid Test
CrO3/H2SO4 in acetone
Cr3+
H2CrO4
green
red

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

7. 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.

8. Benzenesulfonyl Chloride
Hinsberg Test for Amines
Benzenesulfonyl Chloride

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

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

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

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

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

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

19. B.p = 106o
3,5-dinitrobenzoate 85o

22. B.p. = 160o
3,5-dinitrobenzoate: o

24. cyclohexanol

25. B.p. = o
2,4-DNP = o

27. cyclohexanone

28. B.p. = o
Benzenesulfonamide o
Benzamide o

30. aniline