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

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Presentation transcript:

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

2,4-dinitrophenylhydrazine test Aldehyde or ketone

2,4-dinitrophenylhydrazone +

Mechanism

Iodoform Test Reagent: NaOH and I2 (NaOI)

Iodoform Test

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-dinitrobenzoyl chloride 3,5-dinitrobenzoate

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

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

Data table

Acetophenone

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

Data table

i-PrOH

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

Data Table

Isobutyl alcohol

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

Data Table

cyclohexanol cyclohexanol

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

Data Tables

cyclohexanone cyclohexanone

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

aniline