| Date | November 2019 | Marks available | 1 | Reference code | 19N.3.hl.TZ0.26 |
| Level | HL | Paper | 3 | Time zone | TZ0 |
| Command term | Describe | Question number | 26 | Adapted from | N/A |
Question
Taxol is an anticancer drug.
State the feature of Taxol that is a major challenge in its synthesis. Use section 37 of the data booklet.
Describe how the challenge in (a) was resolved by pharmaceutical companies.
Markscheme
numerous stereoisomers/chiral carbons/chiral centres/stereocentres/optical isomers ✔
NOTE: Accept exact number of chiral carbons ie 11, but do not accept just “chiral”.
chiral auxiliaries/molecule binds to reactant blocking one reaction site «by steric hindrance»
OR
asymmetric synthesis / enantioselective catalysis «producing a specific enantiomer»
OR
biosynthesis / genetically modified bacteria/microorganisms ✔
NOTE: Accept “use of a chiral auxiliary leading to «the synthesis of» the desired enantiomer”.
Examiners report
Syllabus sections
- 16N.3.hl.TZ0.26c: Omeprazole exists as a racemic mixture whereas esomeprazole is a single enantiomer. Outline...
- 18N.3.hl.TZ0.21c: Explain the process of solvent extraction by which Taxol is isolated.
- 18N.3.hl.TZ0.21b: Outline how chiral auxiliaries are used to synthesize the desired enantiomer.
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17M.3.hl.TZ1.28b:
A mixture of enantiomers shows optical rotation.
Suggest a conclusion you can draw from this data.
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19M.3.hl.TZ1.25a:
Identify the chiral carbon atom using an asterisk, *.
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17N.3.hl.TZ0.23b:
Explain the role of the chiral auxiliary in the synthesis of Taxol.
- 19N.3.hl.TZ0.26a: State the feature of Taxol that is a major challenge in its synthesis. Use section 37 of the...
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19M.3.hl.TZ1.25b:
Enantiomers can be identified using a polarimeter. Outline how this instrument differentiates the enantiomers.
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18N.3.hl.TZ0.21a:
The diagram shows part of a Taxol molecule in skeletal form.
Draw a circle around each chiral carbon.
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18M.3.hl.TZ1.16e:
Many drugs are chiral. Explain how a polarimeter can be used to determine the relative proportion of two enantiomers.
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19M.3.hl.TZ2.25b:
Outline the operation of a polarimeter used to distinguish between enantiomers.
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18M.3.hl.TZ2.25:
Taxol was originally obtained from the bark of the Pacific yew tree.
Outline how Green Chemistry has improved the process of obtaining Taxol.
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17M.3.hl.TZ2.25:
Taxol is produced using a chiral auxiliary. Describe how the chiral auxiliary functions to produce the desired product.
- 20N.3.hl.TZ0.19d: Circle two chiral carbons in the section of the Taxol structure below.
