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Aspirin can be produced by reacting salicylic acid with ethanoic anhydride - AQA - A-Level Chemistry - Question 4 - 2020 - Paper 2

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Aspirin can be produced by reacting salicylic acid with ethanoic anhydride. An incomplete method to determine the yield of aspirin is shown. 1. Add about 8 g of sal... show full transcript

Worked Solution & Example Answer:Aspirin can be produced by reacting salicylic acid with ethanoic anhydride - AQA - A-Level Chemistry - Question 4 - 2020 - Paper 2

Step 1

Describe the instruction that is missing from step 4 of the method. Justify why this step is necessary.

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Answer

Instruction: Reweigh the empty boat.

Justification: This step is necessary to calculate the exact mass of salicylic acid added to the reaction mixture, allowing accurate yield calculations.

Step 2

Suggest a suitable piece of apparatus to measure out the ethanoic anhydride in step 5.

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A 50 cm³ measuring cylinder should be used, as it allows for accurate volume measurement (between 10 to 100 cm³).

Step 3

Identify a hazard of using concentrated phosphoric acid in step 6.

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Concentrated phosphoric acid is corrosive and can cause skin burns or permanent eye damage.

Step 4

Complete the equation for the reaction of salicylic acid with ethanoic anhydride to produce aspirin.

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Answer

Salicylic acid + Ethanoic anhydride → Aspirin + Acetic acid

Step 5

6.01 g sample of salicylic acid (M_r = 138.0) is reacted with 10.5 cm³ of ethanoic anhydride (M_r = 102.0). In the reaction the yield of aspirin is 84.1%. Show by calculation which reagent is in excess. Calculate the mass, in g, of aspirin (M_r = 180.0) produced.

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Answer

  1. Moles of salicylic acid = ( \frac{6.01 \text{ g}}{138.0 \text{ g/mol}} = 0.04355 \text{ mol} )
  2. Volume of ethanoic anhydride = 10.5 cm³ = 0.0105 L. Density = 1.08 g/cm³.

Mass of ethanoic anhydride = 10.5 cm³ × 1.08 g/cm³ = 11.34 g.

  1. Moles of ethanoic anhydride = ( \frac{11.34 \text{ g}}{102.0 \text{ g/mol}} = 0.1118 \text{ mol} )

  2. The reaction is a 1:1 ratio, salicylic acid is the limiting reagent since 0.04355 mol < 0.1118 mol.

  3. Moles of aspirin formed = 0.04355 mol (from salicylic acid).

  4. Mass of aspirin produced = 0.04355 mol × 180.0 g/mol = 7.836 g.

  5. For the yield, Actual yield = Theoretical yield × percent yield = 7.836 g × 0.841 = 6.60 g.

Reagent in excess: Ethanoic anhydride. Mass of aspirin: 6.60 g.

Step 6

Suggest two ways in which the melting point of the crude aspirin collected in step 9 would differ from the melting point of pure aspirin.

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Answer

Difference 1: The melting point of crude aspirin would be lower than that of pure aspirin due to impurities present in the crude sample.

Difference 2: The melting point range of crude aspirin would be broader, reflecting the presence of various impurities compared to the sharp melting point of pure aspirin.

Step 7

Describe two important precautions when heating the mixture of ethanol and crude aspirin.

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Precaution 1: Use a water bath instead of direct heat to avoid overheating and potential decomposition of the aspirin.

Precaution 2: Do not place the mixture on a flame; ensure the heating is gentle to prevent the risk of ignition.

Step 8

Explain the purpose of adding a small amount of cold ethanol.

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The cold ethanol is added to reduce the temperature of the solution, which helps in the crystallization process of aspirin, allowing for purer product formation.

Step 9

Describe one difference in appearance you would expect to see between these two solid samples.

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Answer

The crude aspirin would typically appear as larger, irregular crystals and may be off-white in color, while the purified aspirin would have smaller, clear, and needle-like crystals.

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