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Identify an Unknown

Learn how to identify unknown compounds including aldehydes, alcohols, amines, and ketones using physical properties, infrared and NMR spectra, solubility, classification tests, and derivative measurements.

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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. Mechanism

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

  9. Iodoform Test

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

  11. 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.

  12. Hinsberg Test for Amines Benzenesulfonyl Chloride

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

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

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

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

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

  18. Data table

  19. Acetophenone

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

  21. Data table

  22. i-PrOH

  23. Sample Unknown B.p = 106o 3,5-dinitrobenzoate 85o

  24. Data Table

  25. Isobutyl alcohol

  26. Sample Unknown B.p. = 160o 3,5-dinitrobenzoate: 108-110o

  27. Data Table

  28. cyclohexanol cyclohexanol

  29. Sample Unknown B.p. = 155-157o 2,4-DNP = 158 - 160o

  30. Data Tables

  31. cyclohexanone cyclohexanone

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

  33. aniline

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