Identification of Unknown Organic Acid

Shubh Patel
Chemistry 1211K Lab- Spring 2022

Dr. Laroui

F31

4-25-2022

P6291413-FS-22
 Abstract

The overall purpose of this CHEM 1211K laboratory class was to experiment and

identify the unknown organic acid which was provided by our lab professor. Each student was

given a unique unknown organic acid which we performed various experiments to discover key

characteristics of our individual unknown organic acid. Throughout this laboratory, we

performed a total of seven various experiments that related to our acid and implied various

laboratory techniques. Additionally, we had learned topics from the lecture which corresponded

to the individual lab experiment which can be implied conceptually as well. Furthermore, we had

learned different types of mathematical concepts which we had solved for collecting accurate

data towards our experiments. Before identifying the unknown acid, it is very crucial to analyze

the characteristics of the acid and the way it should be treated. The first experiment,

“Recrystallization Of An Unknown Solid”, taught us how to dissolve compounds in a procedure

that purified a sample through recrystallization. The solubility and melting point experiments

were utilized to determine the specific melting point of the unknown organic acid. Additionally,

the solubility experiment had also identified the specific percentage of ethanol and percentage of

water that was needed which would help dissolve the unknown organic acid. Experiments three

and four, “Titration of NaOH” and “Standardization of NaOH with KHP” had implied the

practice of titrations to find the molarities of our NaOH solution and HCl. Experiment 5,

“Determination of Equivalent Weight”, also used titrations to determine the equivalent weight of

the unknown acid. Following the titration experiments was the computer search of the compound

in which we collected data from previous experiments and find possible acids of our unknown

acid and potential pKas as well. The final experiment was the determination of the pKa of the
unknown organic acid, which used titrations to determine the final characteristics of the

unknown acid and also determine the identity of the unknown organic acid.

Introduction

Experiment 1: Recrystallization Of An Unknown Solid

The purpose of this experiment is to purify an unknown solid through the process of

dissolving the unknown solid, filtrating the remaining impurities of the solid, and lastly

recrystallizing the unknown solid. To first purify the sample of the unknown acid, we dissolve it

into a solution of both water and ethanol. Once the acid has been completely dissolved, the

process of gravity and vacuum filtration is set up to fully separate the larger impurities that

remained, and allow the filtration system to remove all unnecessary liquids so it can be dry.

Once, the filtration process is finally complete, the remains should be placed in a secured place

for additional drying before it is finally weighed and used for calculating the percent yield of the

recrystallization.

Before any type of solid can be truly identified, the solid must be purified and set free of

unnecessary impurities that can negatively impact the calculations of the recrystallization

process. However, the recrystallization process is most commonly used to help determine the

characteristics of the solid and what further experiments can be conducted which will provide

accurate results.

Experiment 2: Solubility And Melting Point Determination of the Unknown Organic Acid

The purpose of this experiment is to understand the concept of how to get the melting

point of a solid through the use of the melting point apparatus. The melting point apparatus helps

us determine the specific melting point of the unknown organic acid. To determine the melting
point of the unknown acid one must use capillary tubes to put both the unknown acid as well as

the given standard acid compound into the apparatus. Additionally, the melting point ranges are

recorded from the initial temperature at which they begin to melt, to when the solid is fully

dissolved. Furthermore, one will be determining the melting point of the given standard

compound which is used to determine how similar the melting point is compared to the unknown

acid.

The determination of the melting point and solubility are crucial aspects of trying to

identify of the unknown organic acid. The melting point is the range in which the temperature of

the solid changes states to liquid matter and is dependent on how pure a compound is. When

calculating the melting point it should always be recorded as a specific range between two

temperatures. (add something in between) the narrower the range is, the purer the solid is. Once

melting point ranges are recorded, one must determine the solubility of the acid. The solubility of

an acid is significant because it is used to find a satisfying solvent in which the acid can be easily

dissolved into a clear form. The solvent will most likely be determined with 3 options: 25%

ethanol, 50% ethanol, or 75% ethanol.

Experiment 3: Preparation and Standardization of NaOH

The purpose of the preparation for NaOH(Sodium Hydroxide) is to produce a solution

that contains a specific concentration of NaOH to be titrated over other solutions. The solution is

prepared by figuring out the amount of NaOH necessary in grams for both volume and

concentration requirements. Once the solution is prepared, it is ready for standardization and

becomes titrated against the KHP(Potassium Hydrogen Phthalate) and calculations should be

recorded to determine an accurate standard of the NaOH in the solution.

 Throughout the process of the preparation for NaOH, it is very critical that no other

solutions come in contact with the final solution. Moreover, the NaOH solution which is

prepared is also composed of other components such as water. If excess water is present in the

NaOH, it can lead to further inaccurate data for other experiments which will mislead to another

acid that is incorrect.

Experiment 4: Determination of HCl Molarity

The purpose of this experiment is to determine the molarity of the HCl acid and to

understand the characteristics of the unknown acid as well. To determine the molarity of the acid

HCl, a titration is necessary against the NaOH solution. In an Erlenmeyer flask, the solution of

HCl and DI(Distilled) water is added together while NaOH is placed on a buret for the titration

process. Additionally, a drop of phenolphthalein indicator should be present in the flask as well.

Begin the titration process until a bright pink color is achieved meaning the equivalence point is

reached. Conduct the titration process three more times and after determine the molarity of the

HCl and the amount of NaOH added.

Throughout the process of the HCl titration, the acid-base titrations are conducted to

determine the specific concentration of an acid or base reaction. The base of the NaOH solution

is dropped in increments and is slowly added to the acid(HCl) until a solution is neutral. The

equivalence point determines the point when the acid and base are formally neutralized and

displays the amount of solution that would be needed to “be equal”.

Experiment 5: Determination of Equivalent Weight of The Unknown Organic Acid

 The equivalent weight is the specific weight of an acid converted in grams that has one

mole of acidic hydrogens and has a molecular weight equal to the acid divided by the number of

acidic hydrogens per mole of the acid. Through the process of titration, the solutions are paired

against one another in order to determine the value of the equivalent weight. The equivalence

weight begins when acquiring the specific mass of the unknown acid and fully dissolving it

within the solvent for titration. The solution is titrated against the prepared NaOH and should be

recorded for further calculations to determine the equivalent weight. Additionally, at the

equivalence point, the solution will become a faint pink and the titration is set to have reached

the endpoint.

Experiment 6: Computer Search of the Unkown Organic Acid

To understand the identity of the unknown organic acid, we have conducted multiple

experiments which have helped us provide further characteristics of the unknown acid for

accurate results. Moreover, we will be using the organic acid search engine provided by the

Georgia State University Chemistry department. All of the information which is needed to

successfully determine the unknown organic acid which was found from the prior experiments in

this lab. In the computer search, the values of the melting point and equivalent point are entered

into the search process. Once all values are entered, the search engine will give a list of the acids

that could possibly correlate to the unknown acid.

Experiment 7: Determination of pKa of The Unknown Organic Acid

 As we have found the components of the melting point and equivalent weight of the

unknown acid, we must determine the final value of the unknown acid through the pKa

experiment. The pKa experiment is a unique method to help indicate the strength of an acid.

Furthermore, this experiment is composed of the titration which will be used for determining the

acidity through a pH meter and creating a titration curve which provides a visual aspect of how

the pH of the acid was titrated. The equivalence point in an aqueous titration is the volume of the

titrant which is equal to the number of milliequvalents of the unknown acid that would be

titrated.

In a titration of weak acids with strong bases, the two points will never be the same.

When in process of titration, a weak acid against a strong base will be very difficult to

“neutralize” due to their points not being the same. When titrating, a neutral pH may not be

titrated to the stablized form because of the remaining acids which can lead to errors when

illustrating the curve. Therefore, the titration must be well oriented and should be consistent with

no issues. It is significant that all data is recorded and is fit best on the unknown organic acid.

Experimental

Experiment 1: Recrystallization of An Unknown Solid

To begin this laboratory experiment, weigh approximately 2.0g of an unknown acid and

transfer it into a 125mL Erlenmeyer flask. Alongside, Pour 20mL of DI(Distilled water) and treat

the solution in a hot bath on a hot plate inside a 400mL beaker with 50mL of water inside. Place

a stir bar inside the Erlenmeyer flask to help dissolve the solution more efficiently as well. While
the solution is being stirred, add approximately 1mL of ethanol using a pipette every 2 minutes

until the acid is completely dissolved and only insoluble particles remain in the flask. To receive

all remaining crystals of the solution, use the short stem funnel and place a piece of fluted filter

paper and place it over the 125mL Erlenmeyer flask. Next, pour the solution through the filter

paper, making sure it remains hot so crystals do not form inside the funnel. Once all the solution

has been poured through the filter, prepare to set up the vacuum filtration system.

For vacuum filtration, start by connecting the suction filter flask sidearm to the vacuum

port through the tube. Attach a Buchner funnel to the top with the adapter to fully seal the funnel.

Once filtration is set, apply another filter paper into the funnel and wet it with 1mL of ethanol

solvent and pour the crystal solution onto the filter paper. Once all solution is poured onto the

paper, wash with 5mL of cold DI water, then allow the air to be pulled through the crystals

through the vacuum filtration system until all dripping stops. Remove the top of the funnel with

remaining impurities and cover over so no impurities come out. Store impurities in a drawer for

one week. Calculate the specific percentage of ethanol that was used to recrystallize the

unknown compound with the equation given. After impurities are fully dried in one week, use

the one-place balance and record the weight of the crystal and calculate the percentage yield of

crystallization.

Calculations:

Figure 1:
Results: In conclusion, I was successfully able to recrystallize my solid and was able to remove

all impurities that remained in the solid. My percent ethanol was 20% and had approximately

1.2g of the unknown solid. After one week of drying the recrystallization, I calculated the

percentage yield of my recrystallization which was 55%.

Experiment 2: Solubility And Melting Point Determination of the Unknown Organic Acid

To begin this experiment, we must determine the melting point beginning with inserting a

2-3 mm layer of the unknown acid into the capillary tube and sliding it into the melting point

apparatus. Once the capillary tube is inserted, turn the apparatus on and set it to plateau mode up

to 260 degrees Celcius. Once the plateau is ready, press the start button to begin the heating

process. When acid is starting to melt, it is considered the initial temperature until fully melted.

After determining the melting point of the unknown acid, turn the apparatus machine off to cool

down and begin conducting the given standard compound that should have a similar melting

point range to the unknown acid. First, fill one capillary tube with the unknown acid and another

tube with the standard compound chosen and slide the tubes into the melting point apparatus. To

determine the plateau of the apparatus, set the plateau 10-15 degrees lower than the original
melting point recorded before. Once the plateau has been reached, press start to begin the heating

process for both tubes and observe very carefully. Record both melting point ranges and press

stop when finished heating.

To determine the satisfied solvent of the acid, weigh approximately 0.1g of the unknown

acid and add it into a test tube with 2mL of DI(Distilled) water. The solution could be 100%

distilled water if it can be dissolved at room temperature. The test tube should be placed in a hot

bath for approximately 5 minutes and once cooled off it should be remained dissolved. However,

if crystals begin to appear after removing them from the hot bath, repeat the same steps as

previously mentioned and use 25% ethanol with DI(Distilled) water mixture. If crystals appear

again, use a higher percentage of ethanol using 50% or 75%, for accurate results.

Calculations:

Results: The acid did not dissolve in the 100% DI or the 25% concentration of ethanol. When

placed in the 100% DI water no reaction occurred and the acid remained solid even after heating.

For the 25% ethanol concentration some of the acid dissolved after being heated but

recrystallized after cooling. The 50% ethanol concentration was used and the acid fully dissolved
within the solution. In conclusion of this experiment it is determined that the percentage of

ethanol needed to dissolve the acid is 50%.

Experiment 3: Preparation and Standardization of NaOH

To begin this experiment, We must collect the mass of NaOH needed from an 800mL

solution with a molar concentration of 0.1M and determined it through the molecular equation of

M=Mol/Liter. A total mass of 3.2 g is collected and should fully be dissolved in 800mL of

DI(Distilled) water. Thereafter, weigh 0.3367g of KHP and add to a 125mL Erlenmeyer flask

with approximately 15-20mL of distilled water as well. To fully dissolve the KHP, place the

solution in a hot bath to help completely dissolve the solution. Once fully dissolved, apply 1 drop

of phenolphthalein indicator to the flask with KHP to indicate the equivalence point being met

and proceed with the titration process. The titration process was conducted with NaOH until the

equivalence point was met. The volume of the base solution is required to neutralize the acid and

further record the data. Repeat the same procedure two more times and reset the NaOH back to

the top of the buret with the KHP weight being close to the original weight as well.

Calculations:

Table 1:
Trials Initial Final Volume of NaOH
Volume(KHP/DI) Volume(KHP/DI) added

1 0.00mL 16.2mL 20mL

2 0.00mL 17.5mL 20mL

3 0.00mL 17.6mL 20mL

 Figure 1:

Results:

Figure 2: Final calculations and average value of NaOH

Experiment 4: Determination of HCl Molarity

This laboratory experiment consisted of the beginning preparation of the sample of the

NaOH solution. While using the one-place analytical balance, weigh approximately 3.2 grams of

NaOH for it to be dissolved in 800mL of prepared DI water. Once mixed together, the solution

should be stored in a large capped bottle and placed in a respective area that is safe from other

solutions and labeled appropriately.

Prior to the titration process, a buret is required and should be cleaned beforehand before

any further solutions are poured into. Pour approximately 100mL of NaOH into the buret and

should be filled up to 0.00mL marker with excess air bubbles removed as well. The initial
volume should be recorded to two decimal places. Next, Pour 20.00mL of HCl and transfer it

into a 125-150mL Erlenmeyer flask with 2-3 drops of Phenolphthalein indicator added to the

HCl. Once properly mixtured, titrate the NaOH carefully into the HCl until a light pink is

present. Once the solution is light pink, the volume of NaOH remaining is marked as the final

volume. Repeat the following steps two more times for three total trials. Finally, calculate the

ratio of the volume of NaOH to the volume of the HCl and calculate the percent average

deviation which should be within the margin of 0.5%.

Calculations: Table 1:

Trials Initial Final Volume of HCl added

Volume(KHP/DI) Volume(KHP/DI)

1 0.00mL 20.6mL 10mL

2 0.00mL 19.5mL 10mL

3 0.00mL 20.5mL 10mL

Experiment 5: Determination of Equivalent Weight of The Unknown Organic Acid

 To begin this experiment, use the 4-place analytical balance scale and weigh 0.3g-.05g of

the unknown acid and dissolve in a 250mL Erlenmeyer flask with approximately 40mL of the

solvent determined in the solubility experiment. In Addition, use a hot bath to help dissolve the

acid and ensure that it is placed aside to cool at room temperature once finally dissolved. Once

dissolved, add one drop of phenolphthalein indicator and fill the buret up to 0.00mL with the

NaOH solution. Begin the titration process with the acid and record the initial volume and slowly

release the NaOH until a bright pink color is present. Repeat the experiment two more times and

record all data. Make sure all data is accurately recorded from the experiment which will be used

to calculate the equivalent weight.

Calculations:

Figure 1:

Results:

Figure 2:(Corrected)
Experiment 6: Computer Search of the Unkown Organic Acid

To decide the potential specification of the unknown acid through the computer database,

begin by locating the Georgia State University department of chemistry webpage. On the

webpage, click on the students tab which is located in the top right corner of the page, which will

provide you with a drop-down window. Locate the tab resources on the drop-down window and

access the link saying, “CHEM1211 resources.” Under the “CHEM1211 resources”, locate and

click on the link which says, “CHEM1211 organic acid search engine” which will direct you to

the scientific database. Thereafter, one can input the parameters of the melting point and

equivalent weight data. Once all information is imputed, press the search button to proceed to

receive your unknown organic acid. Lastly, record all data of the computer search and input it

into the laboratory notebook.

Calculations: No calculations were needed for this experiment.

Results:
Figure 1: Table of computer search results

Experiment 7: Determination of pKa of The Unknown Organic Acid

To begin this experiment, one must make a decision based on the specific percentage of

ethanol needed to dissolve the unknown organic acid. Refer to figure 1 to make a determination

of which choice is best suitable for the unknown organic acid. Next, use the analytical balance

and weigh approximately 2mMol multiplied by the average of the equivalent weight for the

unknown acid. Once the acid has been weighed, place acid in a 250mL beaker for choices A &

B, or for choices C & D use a 600mL beaker. For this experiment, choice B was chosen and

.3240g of the acid was placed into a 250 mL beaker with a stir bar. Allow the acid to be fully

dissolved before proceeding further in the experiment. A separate pH meter is arranged and must

be calibrated before use. The pH meter provides an accurate value of pH and replaces the

phenolphthalein indicator from previous experiments. Once the pH meter is calibrated, place the

pH electrode into the beaker and ensure that the electrode does not hit anything around. Record

the initial pH reading and begin the titration process and record the pH after every increment of
NaOH. Add the NaOH solution in separate increments of 1.00mL to 2.00mL and added measure

the pH every time. As the NaOH solution is added, the pH will slowly rise and when reached to

at least 5.00mL, go by half increments. As the titration continues, there will be a big jump in pH

value which is indicating that you have reached the equivalence point. As you reach the

equivalence point, The endpoint will be close after the big jump, indicating that the pH has

reached close to the value around 11-12pH, then conclude the trial. Repeat this experiment two

more times using Choice B and the respective amount of ethanol/water ratio that is necessary.

After completing all three trials, proceed to calculations and titration curve.

Figure 1: Table of determination of ethanol-water ratio

Figure 2: Titration Curve trial 1

Figure 3:Titration Curve trial 2

Figure 4:Titration Curve trial 3

 Discussion & Conclusion

Throughout the entire lab project, there have been various experiments conducted to test

and collect key data to help successfully determine my unknown organic acid. Each lab

experiment had provided the skills and knowledge of understanding the concepts of determining

the identity of the unknown organic acid. Even the procedures that didn’t provide explicit values

related to the acid gave insight into the process normally required when determining an organic

acid. Upon further research and reviewing the computer search of the unknown acid, I have

determined at my organic acid sample is Naphthalenecarboxylic acid, C10H7COOH. This is

determined firstly by calculating the melting point of my acid and from my experimental data,

my melting point was close to 166 °C with a deviation of ±7°C which similarly agrees to the

name acid’s 1643-164 melting point range. Furthermore, the equivalent weight of the unknown

acid was about 172g/eq with a deviation of ±10g/eq and the named acid had fairly corresponded

in the deviation of the original equivalent weight of 162 g/eq. The final characteristic tested

which helped conclude my choice was the pKa value. During the pKa titration process, the pKa

value tested by me was around 4.48, and the closest pKa value matching this was

Naphthalenecarboxylic acid at 4.3. Overall this labatory experiment was very successful and the

unknown organic acid was properly found through rigorous experiments and extensive

calculations.