Organic Chemistry: Chirality (Edexcel International A Level Chemistry)

Exam Questions

11 mark

Menthol has a number of medicinal uses. It can be extracted from the peppermint plant.
The structure of menthol is

q8

How many chiral centres are there in one molecule of menthol?

  • 1

  • 2

  • 3

  • 4

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21 mark

Citronellol is found in rose and geranium oils.

q10-paper-4-oct-2021-edexcel-ial-chemistry

The type(s) of stereoisomerism shown by citronellol is

  • optical and geometric isomerism

  • optical isomerism only

  • geometric isomerism only

  • neither optical nor geometric isomerism

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31 mark

How many optical isomers does this molecule have?

q13-paper-4-2021-june-edexcel-ial-chemistry

  • 2

  • 3

  • 6

  • 8

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11 mark

Which of these reactions does not result in the formation of a racemic mixture?

  •  but-2-ene with HCl

  • but-1-ene with HCl

  • propanal with HCN

  • propanone with HCN

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21 mark

When a single enantiomer of 2-iodobutane reacts with sodium hydroxide, the product is a mixture of enantiomers. This is because

  • the reaction is a nucleophilic substitution

  • the reaction proceeds via a negatively charged transition state

  • the reaction proceeds via a carbocation intermediate

  • the reaction rate depends on the concentration of 2-iodobutane

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31 mark

A sample of a bromoalkane, RBr, containing a single optical isomer reacts with hydroxide ions in an SN1 mechanism.

RBr + OH rightwards arrow ROH + Br

The alcohol formed is a racemic mixture.

From this information, it can be deduced that RBr is most likely to be

  • primary only

  • secondary only

  • tertiary only

  • primary, secondary or tertiary

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41 mark

Which of these structures is not identical to the others?

q14-paper-4-2021-june-edexcel-ial-chemistry

  • Structure A

  • Structure B

  • Structure C

  • Structure D

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