CHEM 036 Fall 2006

Experiment #4: Acid/Base Extraction

Acid/base is an extremely useful separation technique in organic chemistry. Using simple acid/base
reactions, several different classes of organic molecules can be separated from one another. This procedure
is most easily visualized using the flow chart for acid/base extraction on the following page.
In this experiment you will be randomly assigned a mixture containing two components; an acid, a base, or
a neutral component. The goal will be to separate the mixture by acid/base extraction, recrystallize the
solid compounds and identify them based on solubility and melting point determination. You will be given
approximately 2 g of the mixture and use the miniscale procedure described in the text.

Objectives:
1.

Separate the two compounds of your unknown mixture.

2.

Purify the unknowns by recrystallization.

3.

Analyze and identify the compounds by melting point determination.

Helpful Hints:
1.

Do not throw anything away until you have collected all the compounds.

2.

Always label your beakers, flasks, test tubes, etc.

3.

Be clear which layer is which; water vs. organic.

4.

If you create an emulsion, be patient.

5.

Drying agents do not need to be weighed out exactly. Add enough drying agent to cover the
bottom and swirl the flask. When the drying agent flows freely, the solvent is dry.

6.

Do not add drying agent to the water layer!

7.

Do not forget to vent your separatory funnel.

CHEM 036 Fall 2006

Acid/Base Extraction Separation Scheme

Unknown Mixture (three components)
O
RCOH

RNH2

RH

acid

base

neutral
CH 2 Cl2

H2 O Layer

5 % N aO H

CH2 C l2 Layer

RNH2

RCONa
concd. HCl

RH

5 % HCl
H2O Layer

CH2 C l2 Layer
evaporate

RCOH
SOLID ACID

RNH3 C l

5 % NaOH

RN H2
SOLID BASE

RH
SOLID N EUTRAL

Extraction Unknowns
Fall 2006
NAME

MP (C)

STRUCTURE
O

p-anisic acid

OH

182-185

CH 3O

216-218

anthracene
O

benzoic acid

OH

biphenyl

121-123

69-72

camphor

175-177
sublimes
O

NH2

4-chloroaniline

69-72

Cl

2-chlorobenzoic acid

OH

138-140

Cl
O
H

trans-cinnamic acid

C
C

OH

133-134

OCH 3

1,4 -dimethoxybenzene

56-60
CH 3O

O
O

ethyl-4-aminobenzoate
H 2N

88-90

Extraction Unknowns
Fall 2006
fluorene

114-116

naphthalene

80-82
sublimes

NH2

4-nitroaniline

149-151

O 2N
OH

phthalic acid

O
O

OH

salicylic acid

205 d
v. water soluble

OH
O

OH

158-160

trans-stilbene

122-124

C
H

CH3 O

o-toluic acid

OH

103-105

m-toluic acid

H 3C

OH

NH2

p-toluidine
H 3C

108-110

41-46