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Carbonyls, Carboxylic Acids and Derivatives

Hazards of KCN and Formation of Enantiomers

  • 3 things to know
  • Papers 2 and 3

Overview

The hazards of using KCN, and why attack on a planar carbonyl gives a racemic mixture.

What you need to know

Answer each one before you reveal it.

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Key term

What is the main hazard associated with using KCN in organic reactions?

Key term

When an aldehyde reacts with KCN followed by dilute acid, what type of product mixture is formed?

Key term

When an unsymmetrical ketone reacts with KCN followed by dilute acid, what type of product mixture is formed?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    What is the main hazard associated with using KCN in organic reactions?

    Model answer

    KCN is highly toxic.

  2. 2

    When an aldehyde reacts with KCN followed by dilute acid, what type of product mixture is formed?

    Model answer

    A mixture of enantiomers (a racemic mixture).

  3. 3

    When an unsymmetrical ketone reacts with KCN followed by dilute acid, what type of product mixture is formed?

    Model answer

    A mixture of enantiomers (a racemic mixture).

  4. 4

    Why does the reaction of an aldehyde with KCN followed by dilute acid produce a mixture of enantiomers?

    Model answer

    The planar carbonyl group can be attacked equally from either side by the cyanide nucleophile, producing both enantiomers in equal amounts.

  5. 5

    What structural feature is created in the hydroxynitrile product that leads to enantiomer formation?

    Model answer

    A chiral centre (asymmetric carbon atom) is created at the former carbonyl carbon.

  6. 6

    Why is the carbonyl carbon in an aldehyde attacked equally from both sides by the cyanide nucleophile?

    Model answer

    The carbonyl group is planar, so there is no steric or electronic preference for attack from one side over the other.

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