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Type of compound:

Identify an Unknown. Type of compound:. Aldehyde Alcohol Amine Ketone. Procedure. 1. Physical Properties. Melting point or boiling point. 2. Functional Group. Infrared spectrum NMR Spectrum Solubility Classification Tests. 3. Solid Derivative. Measure boiling point of liquids.

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  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

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

  5. 2,4-dinitrophenylhydrazine test Aldehyde or ketone

  6. 2,4-dinitrophenylhydrazone +

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

  8. Iodoform Test

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

  10. 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.

  11. Hinsberg Test for Amines Benzenesulfonyl Chloride

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

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

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

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

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

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

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

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

  20. cyclohexanol

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

  22. cyclohexanone

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

  24. aniline

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