Jackie Molstad 1

Lab Report 


Experiment 2#

Investigating Solubility and Acid-Base Reactions #

Lab Partner: Eduardo Hernandez#

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

which point the acid-base solution will not dissolve. #

#
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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

the lost electron (Pedersen, Myers 32-33). #

# An induced dipole attraction can be observed in molecules. Induced dipoles occur as a

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

table, polarizability increases. Polarizability prevails ionization potential, which manifests as

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). #

# Dipole-dipole interactions are a permanent dipole experienced by a polar covalent bond.

These interactions are temperature dependent. A special type of dipole-dipole interaction is

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). #

# #

Results and Discussion:#

#
Part I: Solute Miscibility with a Non-polar Solvent

Solute Observation Result

diethyl ether clear, no layers, no swirling disolved

ethyl acetate some clouding not dissolved

acetone clear not dissolved

ethanol clear not dissolved

dichloromethane some swirling disolved

water two distinct layers not dissolved

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

Solute Observation Result

diethyl ether two distinct layers not dissolved

ethyl acetate no layers, some swirling dissolved

dichloromethane no swirling, two layers not dissolved

acetone clear, no layers dissolved

ethanol clear, no layers dissolved

toluene two distinct layers not dissolved

# #

# 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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Part III: Water Solubility of Alcohols #

Table 3

Alcohol Observation Result

ethanol cloudy and swirly dissolved

1-propanol cloudy and swirly dissolved

1-butanol two distinct layers not dissolved

1-pentanol two distinct layers not dissolved

# #

# Table 3 highlights the data we collected during this experiment. We placed 1 mL of

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

Heated in Sand Bath Completely dissolved, no crystals remain, clear

solution

Cooled to Room Temp white and foggy

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# 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

forces between the non-polar regions. 


#
Part V: The Solubility of an Acid#

Table 5

Observation Result

10 drops 6M NaOH clear dissolved

- cooled and 10 drops of 6M " thick, crystal appearance, cloudy reformation of crystals
HCl added

10 drops 6M NH4OH clear dissolved

10 drops 10% NaHCO3 bubbles, clear dissolved

5 drops 6 M HCL gloopy, some bubbles dissolved

20 drops diethyl ether clear dissolved

- 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

5 drops of 6M NaOH two distinct layers, some bubbles slightly dissolved

formed

10 drops of 6M HCl clear, swirling dissolved

25 drops of diethyl ether two distinct layers not dissolved

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# 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

interactions in water, resulting in the formation of two distinct layers. #

#
Part VII: Solubility of an Acid-Base Mixture#

Table 7#

Results

3 drops of diisobutylamine started to clear right away

additoinal 3 drops of diisobutylamine even clearer, swirling occurs

additional 3 drops of diisobutylamine two distinct layers form

# #

# 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

understanding of how electronegativity relates to the temperature at which it begins to dissolve. #

Predictions:#

- 1,2-dichloroethane in hexane will be soluble since both contain non-polar regions.#

- 1,2-dichloroethane in water will be insoluble. 1,2-dichloroethane is not polar enough to

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

group means that methanol will be able to react with water. #

- 1,4-butanediol in water will be soluble. Even though there is an alkane chain, the two

hydroxyl groups form dipole-dipole interactions with water. #

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Experimental Section: #

Refer to the lab manual Understanding the Principles of Organic Chemistry: A Laboratory

Course pages 214-218. #

#
References:#

Pedersen; Myers. Understanding the Principals of Organic Chemistry: A laboratory Course; #

# Brooks/Cole, Cengage Learning: Belmont, CA. pg. 31-85, 214-218#

(2015, November 3) What is an Induced Dipole Attraction? London Dispersion Forces and Van #

# der Waal Forces. Math & Science 2024. YouTube. YouTube.#

(2017, August 19) Acids and Bases Chemistry - Basic Introduction. The Organic Chemistry #

# Tutor. YouTube. YouTube.#

#
Post-Lab Questions:"

1. a) polar, protic: likely to participate in reactions, able to hydrogen bond


water 


b) polar, aprotic: solvents that cannot participate in hydrogen bonding


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. #

4. a) water-acetone: miscible. Water-ethanol: immiscible, ethanol on top. Water-diethyl ether:

immiscible, diethyl ether on top. Water-dichloromethane: immiscible, water on top. Water-ethyl

acetate: immiscible, ethyl acetate on top. Hexane-acetone: miscible. Hexane-toluene:

immiscible, hexane on top. #

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

making of the product.