NAME: Celene.S.

Mohammed ID#2017071049
LAB TITLE: Acid- Base Solvent Extraction DATE: 08/09/17
LAB PARTNER(S): Krysta Jagan, Suma Alexander, Sarah- Joy De Francois

Abstract

The technique used in this lab was solvent extraction. A mixture consisting of a carboxylic acid,
phenol, and a neutral substance were separated from an ether solution. The carboxylic acid
(salicylic acid) was ionized with a weak base (Sodium Hydroxide) and drained and the
phenol(naphthalene) was treated with a strong acid (concentrated HCl) to allow ionization and
drain aqueous layer. The layer of aqueous solution was extracted and remaining was the neutral
compound(acetanilide) in the ether solvent. The three separated substances were allowed to cool
so crystallization can occur for identification and the solids were weighed. The results stated that

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the aqueous acid extract had the greatest percentage yield of 43.3%, the aqueous extract had a
percentage yield of 41.1% and the ether solvent had a percentage yield of 24.0%.

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Hypothesis
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A neutral compound can be obtained via acid-base solvent extraction of an organic solution since
all the remaining compounds can be ionized and drained from the solution.
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Introduction
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Acid-base solvent extraction can be used in separating neutral, basic, and acidic organic
substances by maintaining the pH of the aqueous layer. Extraction is a process whereby a
substance can be separated from other substances based on their solubility’s in a liquid. The
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technique of solvent extraction is always carried out in a separatory funnel and the solvent layers
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are mixed by shaking the separatory funnel and allowing the layers to reform and settle. The
bottom layer which is usually the aqueous layer and is drained through the stopcock leaving
behind the top layer which is usually the organic layer.
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In acid base extraction, a solvent such as an ether is mixed with an aqueous solution of a
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different pH. Liquids that combine to create a homogeneous liquid phase are called miscible and
this means that the two substances are equally soluble in all proportions however, majority of the
organic liquids used as solvents in organic chemistry are not soluble in water; because the
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organic solvent is not soluble in water, it separates into a separate phase of two distinct layers
and this is known as immiscible. Two immiscible solvents are required for solvent extraction,
one being polar (aqueous) and the other non-polar so when the two immiscible solvents are
placed into the separatory funnel, two liquid layers are formed. The denser solvent is always at
the bottom layer of the separatory funnel so they can be drained off. The ether solvent will
precipitate out of the molecule as soon as it is ionized and will dissolve into the aqueous layer.

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 The aqueous layer can then be removed and the pure substance can be obtained through
crystallization.
The process of extraction is usually done if one of two things is desired: 1. the isolation of
dissolved substances from solutions or solid mixtures or 2. for the removal of unwanted soluble
impurities from mixtures and this process is called washing. The distribution or partition law
says that if a substance is added to a system of two liquid layers, consisting of two immiscible or
relatively miscible parts, then that substance will distribute itself amongst the two layers for the
ratio of the concentration in one solvent to the concentration in the second solvent to remain
constant at constant temperature. At the point of equilibrium, the partition coefficient is shown
by the equation:
K = concentration in solvent A / concentration in solvent B, where the constant K is the
distribution or partition coefficient. The distribution coefficient can be assumed approximately
equal to the ratio of the solubility’s in the two solvents.

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Procedure

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Refer to: CHEM 241 Lab Manual, Lab #1 Acid- Base Solvent Extraction, pg. 7.
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Flow Chart
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Add solution to
separatory funnel Extract ethyl acetate Chill combined
Dissolve 2 grams of followed by 25mL of 3M layer by adding 25mL aqueous layers and
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NaOH. Shake of 3M NaOH neutralise slowly

solid mixture into 20 solution. Combine
vigourously then with concentrated
mL of ethyl acetate.
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remove stopper. Allow aqueous layers into HCl until just acidic.
layers to separate then same beaker. Save this for step 7
drain the aqueous layer.
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Isolate solid from step4 by vacuum Add 10mL of fresh ethyl

Evaporate ethyl acetate filtration then wash solid with a little acetate to separatory
from organic layer using cold water. Let solid dry in open area funnel. Remove water
hotplate.Allow sample to
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and determine its weight. Repeat traces with anhydrous

cool so that the organic this step on the aqueous acid extract sodium sulfate. Separate
neutral compound using 3M NaOH then allow it to dry liquid from solid using
crystallizes and weigh. and weight it filter tip pipette.

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 Pre-Lab Questions
1. Suppose solute A has a distribution coefficient of 1.0 between water and diethyl ether.
Demonstrate that if 100 mL of a solution of 5.0 g of A in water were extracted with
two 25-mL portions of ether, a smaller amount of A would remain in the water than if
the solution were extracted with one 50 mL portion of ether.
START
5.0g of compound A in 100mL of water:
5.0−x g
( )
C2 50 mL diethyl ether
K=1.0= C1 = x g
( − )
100 mL H 2 O

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( 5.0−x ) (100)

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1.0=

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50 x

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50x= 500-100x
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150x= 500
Therefore, x= 3.33 g of compound A remains in water.
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FINISH
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So, the amount remaining in the diethyl ether layer is given by:
5.0 g- 3.33g=1.67g
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1.67 g compound A remained in 150 ml diethyl ether

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3.33 g compound A remained in 100 mL water

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2. Consider the following solvent pairs. If mixed together, which pairs would form two
layers? If they form two layers, which solvent would be on top? Find the densities for
each of these solvents in the CRC Handbook.
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a. hexanes and water

Hexane is insoluble in water so it forms two layers since hexane has a density of 0.6548 g/mL
and water has a density of 1 g/mL. Hence, hexane floats atop the layer of water.

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 b. water and methylene chloride
Methylene Chloride is 1.3 g/mL and water is 1g/mL, they would form two layers with the top
being water and the bottom being methylene chloride.
c. hexanes and methylene chloride
These compounds are miscible so it mixes together and no layers are formed. Hexane has a
density of 0.659 g/mL and methylene chloride is 1.3g/mL.
d. methanol and hexanes
They would form two layers with hexane being on top of methanol. This is because hexane has a
density of 0.659 g/mL and methanol has a density of 0.791 g/mL
e. ethanol and water
Ethanol and water are miscible so they mix. Ethanol has a density of 0.789 g/mL and water has a

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density of 1g/mL.

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f. acetone and toluene

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Two layers would be formed with acetone being on top and toluene below. Acetone has a density

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of 0.791 g/mL and toluene has a density of 0.87 g/mL.
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3. If you are uncertain as to which layer in the separatory funnel is aqueous when extracting
an aqueous solution with an organic solvent, how could you settle the issue?
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A drop of water can be added to small sample of both layers (aqueous and organic) and if the
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drop dissolves in the water, that said layer is the aqueous layer. However, if the drop does not
dissolve then, that layer is the organic layer.
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4. Indicate whether each of the following statements is true (T) or false (F).
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____(a) Benzoic acid and p-nitroaniline form water-soluble salts, whereas naphthalene does not
____(b) Carboxylic acids and phenols containing six or more carbon atoms per molecule are
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more soluble in dichloromethane than in water

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____(c) Carboxylic acids containing six or more carbon atoms per molecule are more soluble in
3 M sodium hydroxide than in dichloromethane
____(d) Naphthalene is more soluble in dichloromethane than is sodium benzoate.
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 5. Devise and draw a flow diagram for the separation of CH3CH2CH2Br, (CH3CH2CH2)3N,
and CH3CH2CO2H.

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 Results/Observations
Table 1 showing results obtained for the aqueous base extraction.
Description Mass of Mass of Product yield Colour Observations
product product after (%) change
before(g) (g)
Data 1 0.667 0.274 41.1% Organic layer 2 layers
was light formed with
pink and a layer of
aqueous layer effervescence
was at the top,
translucent. exothermic

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reaction;

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cloudy

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precipitate.

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Table 2 showing results obtained for the aqueous acid extraction.
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Description Mass of Mass of Product yield Colour Observations
product product (%) change
before (g) after(g)
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Data 2 0.667 0.289 43.3% Organic layer 2 layers

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was pink and formed with

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aqueous layer some

was effervescence,
translucent. endothermic
reaction.
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Table 3 showing results obtained for the ethyl acetate extraction

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Description Mass of Mass of Product yield Colour Observations

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product product after (%) change

before(g) (g)
Data 3 0.667 0.160 24.0% Dark pink Clumping
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organic layer occurred due

above clear to the
aqueous presence of
layer. water.
Organic
substance

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 became more
concentrated.

Calculations:
Data 3:
1.To find mass of product after (g):
Mass of flask & salt(g)- Mass of flask= Mass of salt(g)
78.43g - 78.27g = 0.16g
2. Product Yield (%):
Final Mass (actual recovery )
X 100
A

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0.16
X 100

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0.667
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24%
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Discussion
In this lab, a mixture of three solids was separated to their individual components by extraction,
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based upon their acid-base properties .The hypothesis was accepted since a neutral compound
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can be obtained via acid-base solvent extraction of an organic solution since all of the remaining
compounds can be ionized and drained from the solution .The acid (salicylic acid) reacted with
NaOH to give a salt that moved from the organic phase to aqueous phase and thus was able to be
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removed from the mixture. The base(phenol-naphthalene) reacted with concentrated HCl to give
its salt which moved from the organic phase to the aqueous phase. The component remaining in
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the organic phase was the neutral compound( acetanilide). Both the acid and base extracts were
neutralized to give back the solids of salicylic acid and naphthalene.
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According to the data recorded in table 1, the aqueous base extract had a mass of 0.274 g after
and a product yield of 41.1% while the data recorded in table 2 showed that the aqueous had a
mass of 0.289 g after and a product yield of 43.3%. Table 3 results showed that the product
weighed 0.18g after and had a product yield of 24%. It can be concluded from these results that
three solids of equal amounts were not obtained and this was due to the errors encountered while
doing the lab.

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 One source of error encountered upon doing this lab was loss of solid mixture while putting it
into the conical hence, it affected results since mass was lost. Another source of error was the
loose cork our group had so while shaking, some solution was lost and this could have also
affected the final weight obtained in each table. The last source of error and most common in
solvent extraction is the fact that the very last drop of aqueous layer is not able to get out the
separatory funnel because there will always be some transfer of organic layer into the conical
flask. If these sources of error weren’t present the mass of the products after would have been
more and in turn the product yield would have been greater. If I were to repeat this experiment to
achieve better precision I would repeat the procedure at least twice and take an average of the
values.

Conclusion
Upon completing this lab, I can safely say that the hypothesis is accepted since a neutral

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compound can be obtained by the process of acid-base solvent extraction of an organic solution

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where all the remaining compounds can be ionized and drained from the solution. The process of

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washing and venting stood out to me most while doing this lab and I have gained a better

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knowledge on acid-base chemistry.

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References
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Bettelheim,, F. and Landesberg, J. (2012). Laboratory Experiments for Introduction to General,

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Organic and Biochemistry. [online] Google Books. Available at: https://books.google.tt/books?

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id=peMJAAAAQBAJ&pg=PA299&lpg=PA299&dq=An+unknown+compound,
+believed+to+be+a+hydrocarbon,+showed+the+following+behaviour:
+it+burned+with+a+yellow+sooty+flame;
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+no+heat+or+colour+appeared+when+sulphuric+acid+was+added;
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+permanganate+solution+remained+purple;
+the+red+colour+of+bromine+was+lost+only+after+a+catalyst+was+added.&source=bl&ots=A
P0J8tffQA&sig=OS86MnVm8OOA7Q09mMoZGeYStbU&hl=en&sa=X&ved=0ahUKEwj2---
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M7qXWAhVG0WMKHdvcDg4Q6AEIMzAC#v=onepage&q&f=false [Accessed 15 Sep. 2017].

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Bruice, P. (1941.). Organic chemistry. 7th ed. Harlow, Essex: Pearson Education 2014, pp.51-53.
Lewis, E. and Berry, M. (2006). AS and A level chemistry. Harlow, Essex: Pearson Education,
pp.572-597.
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