Identification of an Unknown Organic Compound

Unknown #731 is 3-Hydroxybenzoic Acid

Monday, July 16th, 2012

Fatima Casden TA: Alvin Gatimu Lab section 10

AbstractProcedureProcedures for Titrations can be found in the Chemistry 221 Lab Manual (Winter 2011), by Margaret D. Haak (Pages 57-63). Titrations are performed to obtain a titration curve so the molar mass of the compound can be determined. Between 0.3 and 0.4 grams of the unknown are dissolved in 30mL of deionized water. Since the material was a solid, the melting point is determined by using a Stuart Melting Point Apparatus. An infrared spectrum and an elemental analysis is obtain through the lab. DataThe melting point of the unknown is experimentally observed three times. Melting Point of Unknown #731

Trial

Start of Melting C Completely Melted C 1 200 205 2 202 208 3 202 210 Average 201 207

To determine the molar mass, four titrations using the Vernier drop-counter system are performed. In each trial, the mass of the unknown, the amount of NaOH

used, the volume of NaOH at the half-equivalence point, and the volume of NaOH at the equivalence point are recorded. Unknown #731 Titrations
Titration Mass (g) Half-equivalence Point (mL) Equivalence Point (mL) 1 0.3757 11.57 23.19 2 0.3622 9.07 18.18 3 0.3416 9.39 18.79 4 0.3658 15.12 30.2

The Infrared spectrum and Elemental analysis are included at the end of the report. The Titration curves, with graphs of both the first derivative and the second derivative, are also included, and are labeled as acid-Base Titration 1, 2, 3, and 4. After comparisons of Infrared Spectrums, melting points, and elemental analysis, others that have 3-Hydroxybenzoic acid as an unknown include Peyton Hummel and Jeff Popowhich. CalculationsTo calculate the molar mass using the titration curves, the number of moles of NaOH is found by multiplying the molarity of NaOH by the amount of NaOH used to reach the first equivalence point.

The number of moles of NaOH is then related to the number of moles of the unknown compound. Since there is no equation reference, the volume at the first

equivalence point, found on the titration curve, is used since it represents a 1:1 molar ratio between the acid and base.

Now that the moles of the unknown are known, the mass of the unknown used in the titration is divided by the number of moles of the unknown.

The pKa value of the unknown is determined using the volume of NaOH and that corresponding pH value at the half-equivalence point. According to the HendersonHasselbalch equation, at the half-equivalence point the pH value is equal to the pKa value when the concentration of the acid and base exist in equal amounts.

The peak in the first derivative graph indicates the volume of NaOH at which the half-equivalence point takes place. That volume is then used to determine what the pH of the solution is during the half-equivalence point. This number is the resulting pKa

value. To find the Ka value, the negative log of the pKa is rearranged to solve for the Ka value.

Titration Results
Titration Molar mass (g/mol) pKa 1 166.68 2 204.97 3 187.04 4 124.6 Average 170.8225 Ka 4.01 9.77x10-5 4.06 8.71x10-5 3.91 1.23x10-4 3.91 1.23x10-4 3.97 1.077x10-4

The empirical formula is determined by using the percent composition from the elemental analysis. For each element, that percentage is used to find the molar amount that is present within the compound. To do that, the percentage is converted to a mass and the mass is divided by the molar mass of that element. Then all three numbers are divided by the smallest molar amount. From there, each element will be multiplied by a factor that will make each value a whole number or close to a whole number. The

resulting number for each element represents the subsctipts that belong to each element. For example, assuming there are 100 g of the compound:

Error AnalysisWhile observing the melting point, results varied due to different amounts of unknown being observed. Each trial contained a different amount being observed. This would cause a difference in range and assumed melting point. Considering the sample is very small, the actual start of the melting process may remain unseen to the human eye, thus skewing results. The actual melting point of 3-Hydroxybenzoic acid ranges from between 200 about three degrees. The titrations are inconsistent and offer unreliable sources for identifying the unknown compound. The titrations, offer an average molar mass that is inaccurate by over 30g/mol. This may be due to different temperatures in solutions during titrating, for heat was necessary to dissolve the solid in water. The experimental results and the actual results differ by

ConclusionReferences-

Acid-Base Titration 1-

Acid-Base Titration 1
14 12 10 pH 8 6 4 2 0 0 10 20 30 40 50 60 Volume of NaOH (mL) pH

First derivative 1
3 2.5 2 pH 1.5 1 0.5 0 -0.5 0 10 20 30 40 50 60 Volume of NaOH (mL) First derivative

Acid-Base Titration 2

Acid-Base Titration 2
14 12 10 pH 8 6 4 2 0 0 10 20 30 40 50 Volume in NaOH (mL) pH

First derivative 2
4.5 4 3.5 3 2.5 2 1.5 1 0.5 0 -0.5 0 -1

pH

First derivative

10

20

30

40

50

Volume in NaOH (mL)

Acid-Base Titration 3

Acid-Base Titration 3
14 12 10 pH 8 6 4 2 0 0 10 20 30 40 50 60 Volume in NaOH (mL) pH

First derivative 3
2.5 2 1.5 pH 1 0.5 0 -0.5 -1 0 10 20 30 40 50 60 First derivative

Volume of NaOH (mL)

Acid-Base Titration 4

Akcid-Base Titration 4
12 10 8 pH 6 4 2 0 0 10 20 30 40 50 60 70 Volume of NaOH (mL) pH

First derivative 4
2 1.5 1 First derivative 0.5 0 0 -0.5 10 20 30 40 50 60