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Date May 2017 Marks available 1 Reference code 17M.3.sl.TZ2.15
Level SL Paper 3 Time zone TZ2
Command term Compare Question number 15 Adapted from N/A

Question

Aspirin is one of the most widely used drugs in the world.

Aspirin was synthesized from 2.65 g of salicylic acid (2-hydroxybenzoic acid) (Mr = 138.13) and 2.51 g of ethanoic anhydride (Mr = 102.10).

Calculate the amounts, in mol, of each reactant.

[1]
a.i.

Calculate, in g, the theoretical yield of aspirin.

[1]
a.ii.

State two techniques which could be used to confirm the identity of aspirin.

[2]
a.iii.

State how aspirin can be converted to water-soluble aspirin.

[1]
b.i.

Compare, giving a reason, the bioavailability of soluble aspirin with aspirin.

[1]
b.ii.

Markscheme

n(salicylic acid) = « 2.65  g 138.13  g mo l 1 » 0.0192 «mol»

AND

n(ethanoic anhydride) = « 2.51  g 102.10  g mo l 1 » 0.0246 «mol»

[1 mark]

a.i.

«mass = 0.0192 mol x 180.17 g mol–1 =» 3.46 «g»

 

Award ECF mark only if limiting reagent determined in (i) has been used.

[1 mark]

a.ii.

Any two of:

melting point

mass spectrometry/MS

high-performance liquid chromatography/HPLC

NMR/nuclear magnetic resonance

X-ray crystallography

elemental analysis «for elemental percent composition»

 

Accept “spectroscopy” instead of “spectrometry” where mentioned but not “spectrum”.

Accept “infra-red spectroscopy/IR” OR “ultraviolet «-visible» spectroscopy/UV/UV-Vis”.

Do not accept “gas chromatography/GC”.

Accept “thin-layer chromatography/TLC” as an alternative to “HPLC”.

[2 marks]

a.iii.

react with NaOH

 

Accept “NaHCO3” or “Na2CO3” instead of “NaOH”.

Accept chemical equation OR name for reagent used.

[1 mark]

b.i.

«marginally» higher AND increase rate of dispersion
OR
«marginally» higher AND increase absorption in mouth/stomach «mucosa»
OR
«approximately the» same AND ionic salt reacts with HCl/acid in stomach to produce aspirin again

 

Do not accept “«marginally» higher AND greater solubility in blood”.

[1 mark]

b.ii.

Examiners report

[N/A]
a.i.
[N/A]
a.ii.
[N/A]
a.iii.
[N/A]
b.i.
[N/A]
b.ii.

Syllabus sections

Options » D: Medicinal chemistry » D.1 Pharmaceutical products and drug action
Options » D: Medicinal chemistry
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