Determination of Kc for an Esterification Reaction

The experiment is based on the following chemical equilibrium: CHCOOH + CHOH CHCOOCH + H0 Data collection and processing:

Table 1 mass, volume and uncertainties of reactants: Type of measurements Volume (0.1ml) Mass (0.01g) HCl(aq) HO CHCOOCH Mixture #1 5.0 3.76 Mixture #2 4.0 3.11 Mixture #3 3.0 2.55 Mixture #4 2.0 2.31 Uncertainties

5.0 4.81

0 0

0.1ml+0ml+0.1ml=0.2ml %uncertainty = 100 = 2% 0.01g+0g+0.01g = 0.02g %uncertainty = 100 0.23% 0.1ml+0ml+0.1ml=0.2ml %uncertainty = 100 = 3% 100 0.35% 0.01g+0.01g+0.01g = 0.03g %uncertainty = 0.1ml+0ml+0.1ml=0.2ml %uncertainty = 100 = 3% 100 0.32% 0.01g+0.01g+0.01g = 0.03g %uncertainty = 0.1ml+0ml+0.1ml=0.2ml %uncertainty = 100 = 3% 100 0.31% 0.01g+0.01g+0.01g = 0.03g %uncertainty =

Volume (0.1ml) Mass (0.01g)

5.0 4.79

1.0 0.64

Volume (0.1ml) Mass (0.01g)

5.0 4.75

2.0 1.95

Volume (0.1ml) Mass (0.01g)

5.0 4.78

3.0 2.62

Table 2 volume of NaOH (1M) needed for titration of the mixtures and HCl (3M) solutions: HCl + CHCOOH + NaOH Mixture #1 #2 #3 #4 HCl solution #1 HCl solution #2 NaCl + CHCOONa + HO Volume of NaOH (0.05ml) 8.5 7.6 8.3 7.5 7.5 7.3 % uncertainty 100 0.59% 100 0.66% 100 0.60% 100 0.67% 100 0.67% 100 0.68%

Table 3 moles of NaOH needed for titration: n = volume x concentration of NaOH Mixture #1 #2 #3 #4 HCl solution #1 HCl solution #2 Calculation 0.0085 x 1.00 0.0076 x 1.00 0.0083x 1.00 0.0075x 1.00 0.0075 x 1.00 0.0073 x 1.00 n (mol) 0.0085 0.0076 0.0083 0.0075 0.0075 0.0073

Average number of moles of HCl solution = (0.0075+0.0073)/2 = 0.0074 mol Table 4 moles of ethanoic acid and ethanol n(CHCOOH) = n(CHOH)= n(NaOH) n(HCl) Mixture #1 #2 #3 #4 Calculation 0.0085 0.0074 0.0076 0.0074 0.0083 0.0074 0.0075 0.0074 n(CHCOOH) and n(CHOH)(mol) 0.0011 0.0002 0.0009 0.0001

Table 5 Moles of the reactants: n (moles) of CHCOOCH = mass/Mr(CHCOOCH) Mr (CHCOOCH) = 4ArC + 8ArH + 2ArO = (12.01 x 4) + (1.01 x 8) + (16.00 x 2) = 88.12 n (moles) of (HO) = total mass of water/Mr(HO) Mr(HO) = 2ArH +ArO = (1.01 x 2) + 16.00 = 18.02 Total mass of water = mass of water in HCl(aq)+ mass of water = (mass of HCl(aq) mass of HCl) + mass of water Mass of HCl = moles x Mr Mr (HCl) = ArH + ArCl = 1.01 + 35.45 = 36.46 Type of measurements Volume (0.1ml) n (mol) 5.0 0.0074 HCl HO Mixture #1 0 [4.81 (0.0074 x 36,46)]/18.020.2520 Mixture #2 1.0 [4.79 (0.0074 x 36,46) + 0.64]/18.020.2864 Mixture #3 2.0 [4.75 (0.0074 x 36,46) + 1.95]/18.020.3568 Mixture #4 3.0 [4.78 (0.0074 x 36,46) + 2.62]/18.020.3957 CHCOOCH 5.0 3.76/88.120.0426

Volume (0.1ml) n (mol)

5.0 0.0074

4.0 3.11/88.120.0353

Volume (0.1ml) n (mol)

5.0 0.0074

3.0 2.55/88.120.0289

Volume (0.1ml) n (mol)

5.0 0.0074

2.0 2.31/88.120.0262

Table 6 equilibrium calculations based on the equation CHCOOCH + H0 CHCOOH + CHOH: n (mol) of Initial At equilibrium Initial At equilibrium Initial At equilibrium Initial At equilibrium CHCOOCH 0.0426 -0.0011 0.0415 0.0353 -0.0002 0.0351 0.0289 -0.0009 0.0280 0.0262 -0.0001 0.0261 H 0 Mixture #1 0.2520 -0.0011 0.2509 Mixture #2 0.2864 -0.0002 0.2862 Mixture #3 0.3568 -0.0009 0.3559 Mixture #4 0.3957 -0.0001 0.3956 CHCOOH 0 +0.0011 0.0011 0 +0.0002 0.0002 0 +0.0009 0.0009 0 +0.0001 0.0001 CHOH 0 +0.0011 0.0011 0 +0.0002 0.0002 0 +0.0009 0.0009 0 +0.0001 0.0001

Table 7 calculations of equilibrium constants (Kc): Based on the formula for aA + bB cC + dD and the formula of concentration (moles/volume): [C] eqm[D] eqm a b [A] eqm[B] eqm
c d

[CH COOH [C H OH [CH COOC H [H O Calculation Kc -4 1.16 x 10 3.98 x 10 8.13 x 10

-6

Mixture #1 #2 #3 #4

[ [ [ [ [ [ [ [

[ [ [ [ [ [ [ [

-5

9.65 x 10

-7

Table 8 total percentage errors: Total percentage error = sum of percentage errors of: Mass of reactants Mixture #1 0.23% 2.82% Mixture #2 0.35% 4.01% Mixture #3 0.32% 3.92% Mixture #4 0.31% 3.98%

Volume of reactants 2%

Volume of NaOH 0.59%

3%

0.66%

3%

0.60%

3%

0.67%

Table 9 Kc with percentage error values: Kc with percentage error values no percentage error Mixture #1 2.82% -4 1.16 x 10 Mixture #2 4.01% -6 3.98 x 10 Mixture #3 3.92% -5 8.13 x 10 Mixture #4 3.98% -7 9.65 x 10
-7

- percentage error

+ percentage error

1.13 x 10

-4

1.19 x 10

-4

3.82 x 10

-6

4.14 x 10

-6

7.81 x 10

-5

8.45 x 10

-5

9.27 x 10

-7

10.03 x 10

-7

Table 10 Kc with percentage error values (x 10 ) Kc with percentage error values no percentage error Mixture #1 2.82% -7 1160 x 10 Mixture #2 4.01% -7 39.8 x 10 Mixture #3 3.92% -7 813 x 10 Mixture #4 3.98% -7 9.65 x 10

- percentage error

+ percentage error

1130 x 10

-7

1190 x 10

-7

38.2 x 10

-7

41.4 x 10

-7

781 x 10

-7

845 x 10

-7

9.27 x 10

-7

10.03 x 10

-7

Diagram 1 range of Kc of mixtures (drawn not to scale)

Mixture #4
9.27 x 10-7 10.03 x 10-7

Mixture #2
38.2 x 10-7 41.4 x 10-7

Mixture #3
781 x 10-7 845 x 10-7 1130 x 10-7

Mixture #1
1190 x 10-7

Conclusion: As we know, when equilibrium constant is less than 1 the reactants dominate the products. In the case of my experiment on the esterification reaction, the equilibrium constants of four different mixtures are all very small, which means the reactants strongly dominated the products. Therefore I came to the conclusion that none of my mixtures have achieved equilibrium. However, we can see relatively large differences between the equilibrium -7 -7 constant values of the four mixtures: Kc of mixture #1 (1160 x 10 2.82%) and #3 (813 x 10 3.92%) are -7 -7 significantly larger than those of mixture #2 (39.8 x 10 4.01%) and #4 (9.65 x 10 3.98%), and there was no common shared range of errors equilibrium constant. I think this phenomenon can be explained by the size of the -7 equilibrium constant values. Because these values were very small units (all x 10 in the final table) so although the experiment was carried out under same condition, even the slightest random errors can cause enormous effects on reaction and change the equilibrium constant values.

Evaluation: Although I have tried my best to keep the experiment to carry out accurately by providing similar conditions for four different mixtures to react, however the final outcomes did not satisfy me very much. During this experiment, none of the mixtures was able to reach equilibrium and I noticed some places that can be improved next time if I will do a similar experiment: 1. Systematic errors as we can see from my results, the percentage errors are quite high (about 3 to 4% on average). This means I couldnt receive very precise data for me to analyze. This problem can be reduced if I will use the more precise measuring tools next time. Random errors random error is another important source of errors that might have affected my results, and I think it did affect them quite much. Even with quite large percentage error ranges of the results I couldnt find a shared equilibrium constant value between any of the four mixtures. As I have already -7 stated in the conclusion, because the equilibrium constant values were very small (all x 10 in the final table) even if the random error wasnt so big it will still affect the results significantly. The primary problem was that I was not able to repeat the reaction of any of the mixtures, so next time I need to repeat the reactions at least three times to get average results that will reduce the effects of random errors. Titration I had used the titration method during the experiment to find out the moles of the reactants and products after reaction was taken place for a week. However, this method is highly unreliable as I needed to use my eyes to observe the color change and it was hard to tell when I should stop titrating at what degree of pink color. This source of error can be reduced next time if I will be able to use another way to measure the color change such as the light intensity machine if possible, which will be a lot more accurate than using human eyes.

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