Aspirin synthesis: salicylic acid + acetic anhydride --> acetylsalicylic acid (a

Question

Aspirin synthesis: salicylic acid + acetic anhydride --> acetylsalicylic acid (aspirin) + acetic acid

Given:

Mass of salicylic acid used for reaction: 2.0 g

Volume of acetic anhydride used for reaction: 4.0 mL

Experimental yield of aspirin = 1.210 g

Theoretical yield of aspirin: 2.613 g

1) What is the mass loss (g) of aspirin due to residual solubility, after using two 10 mL volumes of ice water (20.0 mL total) to wash the aspirin product (crystals)? The solubility of aspirin in water is 0.25 g per 100 mL at room temperature.

2) What is the new experimental yield, corrected for solubility? (g)

3) What is the percent yield?

Explanation / Answer

1) the mass loss of aspirin = 0.25 g x 20.0mL )/ 100.0mL

= 0.05 g

2) the new experimental yield = 1.210 g - 0.05 g

= 1.160g

3) % yield = experimental yield / theoretical yield ) x 100

= (1.16 / 2.613 ) x 100

= 44.39%

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