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Date November 2011 Marks available 1 Reference code 11N.3.hl.TZ0.D5
Level HL Paper 3 Time zone TZ0
Command term State Question number D5 Adapted from N/A

Question

Some drugs can be converted into ionic salts in order to increase their solubility in water.

State the equation for the formation of the ionic salt of aspirin, CH3COO(C6H4)COOH.

[1]
a.i.

Chiral auxiliaries are used in drug design. Describe how a chiral auxiliary works.

[2]
b.

Markscheme

CH3COO(C6H4)COOH+NaOHCH3COO(C6H4)COONa+H2O;

Accept Na2CO3 or NaHCO3.

Accept ions for strong base and salt or net ionic equation.

a.i.

chiral auxiliaries are enantiomers/optically active;

auxiliary creates stereochemical condition necessary to follow a certain pathway / is used to manufacture one enantiomer (so avoids need to separate a racemic mixture);

attaches/connects itself to non-chiral molecule / makes it optically active;

only desired/one enantiomer/molecule formed (and chiral auxiliary removed);

b.

Examiners report

The equations for the formation of the ionic salt of aspirin and the ionic salt of fluoxetine were poorly done with H2O, NaCl, HCl and Na used in the first case instead of NaOH and H2O and NaOH used in the second case instead of HCl.

a.i.

Description of how a chiral auxiliary works was not well understood and chiral axillaries function in synthesis was also sometimes confused.

b.

Syllabus sections

Options » D: Medicinal chemistry » D.2 Aspirin and penicillin
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