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Lab Report
Experiment 2#
Abstract#
# For this experiment, we intended to examine the various acids and bases and how their
properties are related to solubility. In learning this, we are afforded the opportunity to better
understand how we can isolate and purify products of a reaction. To achieve this, we tested
various acids and bases with various solutions and under various conditions to examine the
affect on the compound in question. We found that non-polar solvents will only dissolve other
non-polar solvents, similarly polar solvents will only dissolve other polar solvents. Next, the data
seemed to indicate that, although alcohols are miscible with water, a longer sequence of
carbons attached to the alcohol limit its solubility. In exploring temperature dependency, we
found that at room temperature, our solute did not fully dissolve, however, as the temperature
warmed, it did in fact dissolve. Furthermore, as this solution cooled, solid crystals reformed.
This indicates that as temperature increases, solubility increases. To test for acid solubility, we
mixed an acid with different solutions and found that when mixed with a base an acid-base
reaction occurs, when mixed with an acid no result occurred, and that it is able to interact and
dissolve when mixed with an ether. In testing for the solubility of bases, we found that a base
will dissolve if mixed with a non-polar acid only; a polar acid limits the solubility of a base.
Finally, in testing for acid-base solubility, we found that solubility does occur between our acid-
base solution and diisobutylamine up until the point the solution becomes too saturated, at
#
Jackie Molstad 2
Introduction:#
# By completing this experiment, we are able to understand the properties of acids and
bases that allow for solubility. And in knowing this, we are able to isolate and purify the products
of reactions, which is beneficial in the handling, studying and clean-up of chemicals not only in
the lab but in every day life. My lab partner and I performed seven experiments focused
towards an understanding of a specific property of acids and bases. We tested solute miscibility
with a non-polar and polar solution as well as water solubility of alcohols. We also tested for
temperature dependance in solubility, and the solubility of an acid, a base and an acid-base
mixture. #
# It is important to understand the types of bonds that hold atoms together. Non-polar
covalent bonds occur when electrons are shared equally. Two atoms of differing
electronegativity will not share electrons equally, but the more electronegative atom will attract
the electron more, creating a polar covalent bond. The difference in electronegativity among the
two atoms participating in a polar covalent bond causes the bond to undergo a dipole moment;
a measurement of the size of the charge and distance between them. These can be of varying
strength, and give rise to the various properties observed in a given molecule and governs how
they will interact with other molecules. An ionic bond occurs when the electrostatic attraction
between two ions oppositely charged, where one atom looses an electron and the other gains
weak attraction when an instantaneous dipole or charge occurs in an atom or molecule and the
force affects nearby atoms or molecules. This has an effect on the physical properties of
molecules. For example, while ionization potential decreases down the columns of the periodic
higher melting and boiling points as the size of the atom increases. A temporary dipole can
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occur in a non-polar atom or molecule. This occurs when the non-polar molecules get close to
each other, the bonding electron from one atom repels the neighboring electron (Pedersen,
Myers 33-35). #
hydrogen bonding; a covalent bond between hydrogen with nitrogen, oxygen or fluorine. In
order for a hydrogen bond to form, the atoms must be much different with respect to
electronegativity and the atom bonding to hydrogen must have lone pairs to be able to share
electrons. When a hydrogen bond forms, the electronegative atom has a partial negative
charge and the hydrogen atom has a partial positive charge (Pedersen, Myers 33-35). #
# #
#
Part I: Solute Miscibility with a Non-polar Solvent
Table 1 # #
#
# Table 1 illustrates the data we gathered for this experiment. We added 1 mL of hexane
to six dry reaction tubes along with five drops of each solution to one reaction tube. #
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Hexane is a non-polar substance, an alkane that interacts with molecules through induced
dipole-induced dipole interactions. Therefore, only non-polar solutions are able to dissolve in it.
Diethyl ether is non-polar and therefore is miscible with hexane. And while dichloromethane has
a polar region, it has a large enough non-polar region to allow it to be miscible with hexane.
Ethanol, ethyl acetate, acetone and water are all polar molecules and they are immiscible with
hexane. #
#
Part II: Solute Miscibility with a Polar Solvent#
Table 2
# #
# Table 2 illustrates the data collected from this experiment. We placed 1 mL of water to
six reaction tubes and added five drops of each solution in one of the reaction tubes. Since
water is a polar substance, only polar substances are able to dissolve in it. Water is able to form
hydrogen bonds, a strong dipole-dipole interaction. Diethyl ether and toluene are non-polar
molecules that are immiscible with water. And, as stated above, while dichloromethane has a
polar region, the polarity is not strong enough to dissolve in water. Acetone, ethyl acetate and
ethane are all polar molecules, and they are miscible with water. #
#
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Table 3
# #
water into four reaction tubes, each with five drops of one of the alcohols listed. Ethanol and 1-
propanol were miscible with water while 1-butanol and 1-pentanol were not. This indicates that
although alcohols are miscible with water, the solubility is reduced in larger alcohols. As the non
polar region on the alcohol increases in number of carbons, therefore becomes longer, the
intermolecular forces between the non-polar molecules overcome the dipole-induced dipole
moment. However, a smaller carbon chain alcohol can interact with water through dipole-dipole
forces between the hydrogen and oxygen bonds in water and alcohol. #
#
Part IV: Temperature Dependence of Solubility#
Table 4
Observation
Benzoic Acid and Water Clear, some dissolved, some solid crystals remain
# Table 4 marks the data received from this experiment. We measured 0.051 grams of
benzoic acid into one reaction tube. We then added 1 mL of water to each along with a boiling
stick. We mixed this vigorously and recorded our observations in the first row. Then, we heated
this mixture using a sand bath until the water began to boil. We then recorded our observation
in the second row. Finally, we allowed the solution to cool to room temperature and left
undisturbed where we then recorded our observation in the third and final row. This solution
was saved and used to perform Part VII. At the beginning room temperature, the benzoic acid
did not fully dissolve, maintaining a solid state. This is because the non-polar region is unable
to interact with the polar dipole-dipole interactions in water. However, after heating it, the
remaining crystals did dissolve because the heat disrupted the intermolecular forces between
the benzoic acid and the surrounding molecules. The benzoic acid was then able to form
interactions with water via induced dipole-induced dipole reactions. After cooling the solution,
solids formed, indicating benzoic acid regained its induced dipole-induced dipole intermolecular
#
Part V: The Solubility of an Acid#
Table 5
Observation Result
- cooled and 10 drops of 6M " thick, crystal appearance, cloudy reformation of crystals
HCl added
- ether separated onto " white crystals remain on glass dissolved crystals remain after
watch glass evaporation occurs
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#
# Table 5 illustrates the data we collected from this experiment. We measured 0.055
grams of benzoic acid to five reaction tubes. We then added 1 mL of water to each reaction tube
as well as one of the listed solutions. We then thoroughly stirred our mixtures and recorded our
observation. Then, the solution with 6M NaOH was cooled then 10 drops of 6M HCl and
recorded our observation. Finally, to the reaction tube with diethyl ether, we pipetted to mix the
two layers, removed as much of the ether as possible and added it to a watch glass. This was
done in the fume hood to allow evaporation of the ether. We then recorded our observations. #
# Benzoic acid is immiscible with water, however when NaOH or NH4OH is added, the
ions create ion-ion interactions. The intermolecular force between the ion and the dipole allows
benzoic acid to dissolve. Adding HCl has no effect on benzoic acid because they are both
acidic solutions, however, adding HCl to a cooled test tube with NaOH and benzoic acid causes
the benzoic crystals to reform. This is because HCl is a strong acid that replaces the benzoic
acid in the acid-base reaction with NaOH. NaHCO3 dissolves the benzoic acid and gas forms.
Benzoic acid dissolves in the diethyl ether with a layer floating on top. When added to the
watch glass, the ether group evaporates and only benzoic acid is left behind as a layer of white
solid.
#
Part VI: Solubility of Bases:#
Table 6
Observation Result
# Table 6 marks the data received from this experiment. We mixed 5 drops of
diisobutylamine in three reaction tubes along with 2.5 mL of water in each. Additionally, we
added one of the following solutions and recorded our observations. Diisobutylamine is
immiscible with water because of the difference in polarities, so two distinct layers form. The
reaction between NaOH was weak because both substances are bases. HCl reacts well with
diisobutylamine because it is a strong acid and is able to dissociated into ions, disrupting the
intermolecular forces with water. Diethyl ether can interact with diisobutylamine via induced
dipole-induced dipole interactions, but not completely strong enough to disrupt dipole-dipole
#
Part VII: Solubility of an Acid-Base Mixture#
Table 7#
Results
# #
# Table 7 describes the data received from this experiment. We used the saved benzoic
acid solution from Part IV, to which we added three drops of diisobutylamine, stirred the mixture
and recorded our observations. We then added three more drops of diisobutylamine, stirred the
mixture and recorded our observations. Finally, we added three more drops of diisobutylamine,
stirred the mixture and recorded our observations. Diisobutylamine and benzoic acid are unable
to disrupt the dipole-dipole interactions in water alone, however when mixed, an acid-base
reaction occurs where the ions are able to form induced dipole interactions with water. As more
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diisobutylamine is added, benzoic acid becomes the limiting reactant and is completely
consumed in the reactions, resulting in insolubility in excess, forming two distinct layers. #
#
Conclusion:#
# The solubility of various acids and bases is dependent upon the polarity of the
molecules, and thus the bond that forms between them. Temperature also plays a role in
solubility, specifically, a higher temperature is able to disrupt the intermolecular forces that hold
molecules together, allowing solubility to occur. When mixed, acids and bases result in a
product that is able to interact with water, a polar substance, even if the reactants are non-polar.
To further this examination of acids and bases, I would like to better understand temperature’s
role. I would like to know at what temperature these solutions are starting the dissolving
process. Then, we could compare that to the electronegativity of the molecules to get an
Predictions:#
disrupt the intermolecular forces between the water molecules. Should form two distinct
layers. #
- dibromomethane in water will be insoluble. Since bromide is less electronegative than Cl, the
overall polarity is lower and therefore will not disrupt the intermolecular forces between the
water molecule. #
- methanol in water will be soluble. The dipole-dipole interactions in a small alcohol hydroxyl
- 1,4-butanediol in water will be soluble. Even though there is an alkane chain, the two
Experimental Section: #
Refer to the lab manual Understanding the Principles of Organic Chemistry: A Laboratory
#
References:#
(2015, November 3) What is an Induced Dipole Attraction? London Dispersion Forces and Van #
(2017, August 19) Acids and Bases Chemistry - Basic Introduction. The Organic Chemistry #
#
Post-Lab Questions:"
water
ethyl acetate#
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2. benzoic acid#
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hexane #
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3. a) #
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b) The two layers form because the limiting reagent is benzoic acid. benzoic acid will dissolve in
water along with dipentylamine but the dipentylamine would be left over. So the two layers form. #
5. b) a saturated solution of sodium bicarbonate would not dissolve benzoic acid because there
is a limiting agent in a saturated solution and all the reactants will be used up to prevent the