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Date November 2018 Marks available 2 Reference code 18N.3.hl.TZ0.21
Level HL Paper 3 Time zone TZ0
Command term Explain Question number 21 Adapted from N/A

Question

Taxol is a chiral cancer drug which is synthesized using a chiral auxiliary.

The diagram shows part of a Taxol molecule in skeletal form.

Draw a circle around each chiral carbon.

[1]
a.

Outline how chiral auxiliaries are used to synthesize the desired enantiomer.

[2]
b.

Explain the process of solvent extraction by which Taxol is isolated.

[2]
c.

Markscheme

 

Do not penalize any other notation (eg *) used for a circle.

a.

chiral auxiliary creates stereochemical condition necessary to follow a certain pathway

OR

stereochemical induction

OR

existing chiral centre affects configuration of new chiral centres ✔

 

chiral molecule/auxiliary/optically active species is used/added/connected to the starting molecule «to force reaction to follow a certain path»

OR

«after new chiral centre created» chiral auxiliary removed «to obtain desired product» ✔

b.

Any two of:

immiscible solvents ✔

partitioning of Taxol between the two solvents

Taxol more soluble in one solvent ✔

extraction carried out multiple times «to improve extraction» ✔

shaking/stirring the mixture ✔

separating the two layers ✔

evaporation of the solvent from the final solution «to obtain pure Taxol» ✔

c.

Examiners report

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

Syllabus sections

Options » D: Medicinal chemistry » D.7 Taxol—a chiral auxiliary case study (HL only)
Options » D: Medicinal chemistry » D.9 Drug detection and analysis (HL only)
Options » D: Medicinal chemistry
Options

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