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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
Identify an Unknown

Type of compound:

Aldehyde

Alcohol

Amine

Ketone

procedure
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
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
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

iodoform test
Iodoform Test

Reagent: NaOH and I2 (NaOI)

ceric nitrate test for alcohols
Ceric Nitrate Test for Alcohols

(NH4)2Ce(NO3)6 + ROH

(NH4)2Ce(NO3)5OR

+ HNO3

amines
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
Hinsberg Test for Amines

Benzenesulfonyl Chloride

hinsberg test for amines1
Hinsberg Test for Amines

Primary: Soluble. PPT if add HCl

Secondary: Insoluble

Tertiary: Tends not to react

derivatives
Derivatives

Aldehydes and Ketones

1. 2,4-dinitrophenylhydrazone

2. Semicarbazone

alcohol derivative
Alcohol Derivative

3,5-dinitrobenzoate

3,5-dinitrobenzoyl

chloride

amine derivatives
Amine Derivatives

Primary and Secondary Amines

Benzamide

Benzoyl Chloride

Benzenesulfonyl Chloride

Benzenesulfamide

sample unknown
Sample Unknown

B.p. =198-200o

DNP = 231-235o

sample unknown1
Sample Unknown

B.p. = 80 - 85o

3,5-dinitrobenzoate = 119 - 121o

sample unknown2
Sample Unknown

B.p = 106o

3,5-dinitrobenzoate 85o

sample unknown3
Sample Unknown

B.p. = 160o

3,5-dinitrobenzoate: 108-110o

cyclohexanol
cyclohexanol

cyclohexanol

sample unknown4
Sample Unknown

B.p. = 155-157o

2,4-DNP = 158 - 160o

cyclohexanone
cyclohexanone

cyclohexanone

slide33

B.p. = 180 -183o

Benzenesulfonamide 110 - 112o

Benzamide 160 - 163o