Frist year

Chemistry Laboratory Report

Ndando Sume Metuge Alex Bur Bill Henderson

10/5/2011

OBJECT

This experiment has two purposes which includes the following

Making aspirin by an acid catalyzed reaction between salicylic acid and acetic anhydride. Determining the percentage yield of aspirin from the reaction.

THEORY C7H6O3 + C4H6O3 -------------- C9H8O4 +CH3COOH

Table.1 Compounds Salicylic acid

The Physical Properties of Salicylic acid, Acetic Anhydride and Acetylsalicylic Acid Phase at room temp White to off white crystalline powder Colorless liquid with pungent smell Odorless, colorless or white crystalline powder Melting point 159 degrees high -73 degrees Low melting point 136 degree Fairly high Density Boiling point 4.8 Higher boiling point than water 139.6 degrees Fairly high boiling pint 1.39 140 degrees Decomposes near melting point

Acetic anhydride

3.5

Acetylsalicylic acid

From the understanding of stoichiometry we can thus say one mole of salicylic acid reacts with one mole of acetic anhydride to from one mole acetylsalicylic acid. Resulting to form a 1:1:1 ratio. We then calculate the percentage yield by dividing the actual yield of ASA by the theoretical yield of ASA then multiply by a hundred. Table.2 illustrates this more. A condensation reaction is a chemical reaction in which two molecules or moieties (functional group) combine to form one single molecule, together with the loss of a small molecule.]When this small molecule is water, it is known as a dehydration reaction; other possible small molecules lost are hydrogen chloride, methanol, or acetic acid. The word "condensation" suggests a process in which two or more things are brought "together" (Latin "con") to form

something "dense", like in condensation from gaseous to liquid state of matter; this does not imply, however, that condensation reaction products have greater density than reactants. Hydrolysis is a chemical process in which a molecule of a target substance is split into two parts by the addition of molecules of water which is also split before or during splitting of the target substance molecule. One fragment of the target molecule (or parent molecule) gains a hydrogen ion (H+) from the split water molecule. The other portion of the target molecule collects the hydroxyl group (OH) of the split water molecule. a by-product is a secondary product derived from a manufacturing process, chemical reaction, and is not the primary or service being produced. A by-product can be useful and marketable or it can be considered product waste. In chemistry, recrystallization is a procedure for purifying compounds the most typical situation is that a desired "compound A" is contaminated by a small amount of "impurity B". There are various methods of purification that may be attempted, which includes recrystallization. There are also different recrystallization techniques that can be used. Yield also referred to as chemical yield and reaction yield, is the amount of product obtained in chemical reaction. The absolute yield can be given as the weight in grams or in moles (molar yield). The fractional yield, relative yield, or percentage yield, which serves to measure the effectiveness of a synthetic procedure, is calculated by dividing the amount of the obtained product by the theoretical yield (the unit of measure for both must be the same):

Based on your balanced equation, we can easily calculate theoretical yield. There is a one to one mole ration between salicylic acid and acetic anhydride, which makes things easier. Basically, you need to determine the limiting reactant which is that reactant which runs out first. Since it is a 1:1 ratio thus the number moles of salicylic acid equals the number of moles of aspirin that is (for every 1 mole of acetic anhydride that you use up produces one mole of aspirin)cause the mole ratio is 1:1, in this case the limiting reagent is the one with the least number of moles (acetic anhydride) Theoretical yield of aspirin is gotten by dividing the number of moles by the relative atomic mass of aspirin. Also you can get the actual yield by simply measuring the amount of aspirin you produced grams. Finally calculate the percentage yield of aspirin by dividing the actual yield of aspirin by the theoretical yield multiplied by a hundred.

Considering the fact that acetic anhydride is the limiting reactant the following might cause the percentage to be low or high.
HIGH

An increase in the amount of reactants(limiting reactant) might cause percentage yield to increase since more of the reactants will be available to form products If all of the mixture completely dissolved to form a solution, then more of the compounds are thus reacting to form products. Resulting to an increase in the percentage yield. The absence of any contaminants will also increase the percentage yield since no side reactions occur

LOW A decrease in the quantity of reactants particularly the limiting reactants causes the percentage yield to drop due to less reactants are available to form products. If the salicylic acid and the acid anhydride dont react completely (dissolve) then less aspirin will be formed thus reducing the percentage yield. Also the presence of any contaminants can also decrease the yield due the possibility of side reaction interfering with the initial reaction.

This because acetic acid is formed as a by-product from this reaction thus when acetylsalicylic acid reacts with moisture in air it breaks down releasing acetic acid. This process is continues thus releasing the characteristic odor of acetic acid. When aspirin becomes old, it gradually reacts with the moisture present in the air. The resultant chemical process is aspirin, which is nothing but a byproduct of acetic acid. Incidentally, vinegar too has acetic acid as its most important component. Aspirin tablets that have high concentrations of acetic acid undergo a reverse reaction when exposed to wet surrounding or kept past their expiration date. Salicylic acid and acetic acid are released due to the breaking down of ASA. The splitting up process is continuous, producing a smell identifiable with vinegar.

CALCULATIONS: Moles of SA = Mass/Molar mass = 2.98(g )/ 138.12(g/mol) = 0.0216 mol

Moles of ASA = 0.0216 (mol of ASA)* 1mol (ASA) / 1 mol (SA) = 0.0216 moles of ASA

Theoritical yield of ASA (g) = 0.0216 mol * 180.157 g/mol = 3.8913g Mass = moles * molar mass

The actual yield is got by simply measuring the mass of aspirin produced which was 0.01g

Percentage error = (theoretical yield - actual yield / theoretical)

* 100

= (3.89g 0.01g / 3.89) * 100 = 99.74%

Table.2

Experimental Observations for Percentage Yield SA + AA ------ASA

Molar mass Mass SA used (g) 3g to nearest 0.01g Moles Theoretical yield of ASA Actual ASA Yield(g) Actual ASA yield(g)/ x 100

138.12g/mol 2.98g 0.0216mol / / /

/ / / / /

/ 180.157g/mol / 0.0216mol 3.89g 0.01g 0.25%

Theoretical ASA yield(g) (%)

CONCLUSION :

To conclude, the percentage yield was measured to 0.25% while the percentage error was found to be 99.74%. These show that there was low yield of aspirin due to either of the reasons discussed in the theory of this report. Furthermore, the percentage error gives more proof as to the low yield of aspirin. Showing why the percentage yield of aspirin is low due to a relatively high degree of errors in the production process of aspirin.