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Identify an Unknown

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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Identify an Unknown

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

  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. DNP Mechanism

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

  9. Iodoform Test

  10. 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-dinitrobenzoate 3,5-dinitrobenzoyl chloride

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

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

  19. Table

  20. Structure of Unknown

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

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

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

  24. cyclohexanol

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

  26. cyclohexanone

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

  28. aniline

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