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

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Presentation on theme: "Identify an Unknown Type of compound: Aldehyde Alcohol Amine Ketone."— Presentation transcript:

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

10

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

34

35 aniline


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