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

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

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

4. Carbonyl Group (1650 - 1725 cm -1 )? Yes No Aldehyde Ketone NMR Aldehyde Ketone + - Alcohol Amine Broad OH in IR Yes No Alcohol Amine (Basic?) 3700 - 4000 cm -1 Yes Primary or Secondary No Tertiary Functional Group

5. Aldehyde or ketone 2,4-dinitrophenylhydrazine test

6. + 2,4-dinitrophenylhydrazone

7. DNP Mechanism

8. Reagent: NaOH and I 2 (NaOI) Iodoform Test

11. (NH 4 ) 2 Ce(NO 3 ) 6 + ROH (NH 4 ) 2 Ce(NO 3 ) 5 OR + HNO 3 Ceric Nitrate Test for Alcohols

12. 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. Amines

13. Benzenesulfonyl Chloride Hinsberg Test for Amines

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

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

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

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

18. B.p. =198-200 o DNP = 231-235 o Sample Unknown

19. Table

20. Structure of Unknown

21. Sample Unknown B.p. = 80 - 85 o 3,5-dinitrobenzoate = 119 - 121 o

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

27. B.p. = 160 o 3,5-dinitrobenzoate: 108-110 o

29. cyclohexanol

30. B.p. = 155-157 o 2,4-DNP = 158 - 160 o

32. cyclohexanone

33. B.p. = 180 -183 o Benzenesulfonamide 110 - 112 o Benzamide 160 - 163 o

35. aniline