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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 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 Distill your unknown and note the boiling point If can’t distill or not enough sample use this technique.
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
2,4-dinitrophenylhydrazine test Aldehyde or ketone
Iodoform Test Reagent: NaOH and I2 (NaOI)
Ceric Nitrate Test for Alcohols (NH4)2Ce(NO3)6 + ROH (NH4)2Ce(NO3)5OR + HNO3
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.
Hinsberg Test for Amines Benzenesulfonyl Chloride
Hinsberg Test for Amines Primary: Soluble. PPT if add HCl Secondary: Insoluble Tertiary: Tends not to react
Derivatives Aldehydes and Ketones 1. 2,4-dinitrophenylhydrazone 2. Semicarbazone
Alcohol Derivative 3,5-dinitrobenzoate 3,5-dinitrobenzoyl chloride
Amine Derivatives Primary and Secondary Amines Benzamide Benzoyl Chloride Benzenesulfonyl Chloride Benzenesulfamide
Sample Unknown B.p. =198-200o DNP = 231-235o
Sample Unknown B.p. = 80 - 85o 3,5-dinitrobenzoate = 119 - 121o
B.p = 106o 3,5-dinitrobenzoate 85o
B.p. = 160o 3,5-dinitrobenzoate: 108-110o
B.p. = 155-157o 2,4-DNP = 158 - 160o
B.p. = 180 -183o Benzenesulfonamide 110 - 112o Benzamide 160 - 163o