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Date November 2016 Marks available 2 Reference code 16N.3.sl.TZ0.18
Level SL Paper 3 Time zone TZ0
Command term Determine Question number 18 Adapted from N/A

Question

The mild analgesic aspirin can be prepared in the laboratory from salicylic acid.

(CH3CO)2O + HOC6H4COOH → CH3CO2C6H4COOH + CH3COOH

Salicylic acid            Aspirin       

 

After the reaction is complete, the product is isolated, recrystallized, tested for purity and the experimental yield is measured. A student’s results in a single trial are as follows.

Literature melting point data: aspirin = 138–140 °C

Determine the percentage experimental yield of the product after recrystallization. The molar masses are as follows: M(salicylic acid) = 138.13 g mol−1, M(aspirin) = 180.17 g mol−1. (You do not need to process the uncertainties in the calculation.)

[2]
a.

Suggest why isolation of the crude product involved the addition of ice-cold water.

[1]
b.

Justify the conclusion that recrystallization increased the purity of the product, by reference to two differences between the melting point data of the crude and recrystallized products.

[2]
c.

State why aspirin is described as a mild analgesic with reference to its site of action.

[1]
d.

Markscheme

ALTERNATIVE 1:
«theoretical yield = \(\frac{{1.552\,{\text{g}}}}{{138.13\,{\text{g}}\,{\text{mo}}{{\text{l}}^{ - 1}}}}\) × 180.17 g mol−1 =» 2.024 «g»

«experimental yield = \(\frac{{1.124{\rm{g}}}}{{2.024{\rm{g}}}}\) × 100 =» 55.53 «%»

ALTERNATIVE 2:
«\(\frac{{1.552\,{\text{g}}}}{{138.13\,{\text{g}}\,{\text{mo}}{{\text{l}}^{ - 1}}}}\)»= 0.01124 «mol salicylic acid/aspirin theoretical» AND

«\(\frac{{1.124\,{\text{g}}}}{{180.17\,{\text{g}}\,{\text{mo}}{{\text{l}}^{ - 1}}}}\)»= 0.006239 «mol aspirin experimental»

«experimental yield = \(\frac{{0.006239{\rm{mol}}}}{{0.01124{\rm{mol}}}}\) x 100 =» 55.51 «%»

Accept answers in the range 55.4 % to 55.7 %.
Award [2] for correct final answer.

a.

low temperature gives greater difference between solubility of aspirin and impurities
OR
«product» crystallizes out from cold solution/«ice-cold water/lower temperature» speeds up crystallization process
OR
aspirin/product has low solubility «in water» at low temperatures

b.
[N/A]
c.

intercepts pain stimulus at source/acts at site of pain
OR
interferes with production of pain sensitizing substances/prostaglandins «at site of pain»

d.

Examiners report

[N/A]
a.
[N/A]
b.

recrystallized melting point is higher
OR
recrystallized melting point is closer to pure substance/literature value

smaller range of values

c.
[N/A]
d.

Syllabus sections

Core » Topic 1: Stoichiometric relationships » 1.3 Reacting masses and volumes
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