Extractions - University of Illinois Archives Archives/1505050... · If K = 1.0, a = 10 grams, S2 =...
Transcript of Extractions - University of Illinois Archives Archives/1505050... · If K = 1.0, a = 10 grams, S2 =...
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Extractions
Mixture of benzoic acid, anthracene, andp-nitroaniline
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COHO
NH2
NO2
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Mixture of methylene chloride and water
Density of CH2Cl2 is 1.33 g/mL
CH2Cl2
H2O
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If we dissolve NaCl in this mixturewhich phase has the highest saltconcentration?
Salts concentrate inthe water layer
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If we dissolve benzoic acid in thismixture in which phase would itconcentrate?
Neutral organiccompounds concentrate inthe organic phase
Salts
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Salts in water phase
Neutral organiccompounds in theorganic phase
Water
CH2Cl2
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COOH + Na OH COO Na
Benzoic Acid Sodium Benzoate
Treatment of benzoic acid withsodium hydroxide converts itinto the salt, sodium benzoate.
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COOH + Na OH COO Na
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NH3 + HCl NH4+ Cl-
Base Acid Salt
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NH2O2N + HCl NH3O2N Cl
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Use separatory funnel for separations.
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Shake to be surephases equilibrate
Hold stopperand stopcock
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benzoic Acid
p-nitroaniline
anthracene
HCl CH2Cl2
NH3O2N ClBenzoic acid
Anthracene
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benzoic Acid
anthracene
NaOH CH2Cl2
COO Na anthracene
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NH3O2N Cl COO Na
NH2O2N
NaOH
COOH
Filterwashdryweigh
HCl
Filterwashdryweigh
Dryfilterevaporate
weigh
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Addition of acid tothe sodiumbenzoate solutioncauses benzoic acidto precipitate.
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The benzoic acid isfiltered, washed,and dried.
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Weigh the benzoicacid and measure itsmelting point.
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NH2O2NNH3O2N ClNaOH
Cool to complete precipitation
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Dry the methylene chloride solutionof anthracene with a small amountof sodium sulfate.
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Remove the drying agent by filtrationthrough a fluted filter paper.
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Evaporate themethylene chlorideon a steam bath.
Use an invertedfunnel connected tothe vacuum line tocollect the vapor.
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Weigh your products and measuretheir melting points.
Put your samples in labeled vialsand give them to your TA.
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10 g t-butyl alcohol100 mL ether100 mL water
Partition Coefficients
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2.2 = x g / 200 mL
( 10 - x)g /100 mL
x = 8.1 grams
10 grams t-butyl alcohol
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Which is better?
Extract once with 200 mL or twice with 100 mL?
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If K = 1.0, a = 10 grams, S2 = 100 mL
Extract once with 200 mL yields 6.7 grams
Extract once with 100 mL yields 5.0 gramsSecond extraction with 100 mL yields 2.5 gramsTotal 2 extractions with 100 mL = 7.5 grams
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Grams extracted vs. number of extractionsfor K = 1, 2 and 4