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Carbonyls, Carboxylic Acids and Derivatives

Nucleophilic Addition with KCN and Hydroxynitrile Formation

  • 3 things to know
  • Papers 2 and 3

Overview

The mechanism with the cyanide ion, and why it extends the carbon chain.

What you need to know

Answer each one before you reveal it.

Your recallNot started
Process

How does an aldehyde form a hydroxynitrile when it reacts with KCN followed by dilute acid?

Key term

What reagent is used in the nucleophilic addition reaction with carbonyl compounds to produce hydroxynitriles?

Key term

After reacting a carbonyl compound with KCN, what additional step is required to form the hydroxynitrile product?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    What reagent is used in the nucleophilic addition reaction with carbonyl compounds to produce hydroxynitriles?

    Model answer

    KCN (potassium cyanide)

  2. 2

    After reacting a carbonyl compound with KCN, what additional step is required to form the hydroxynitrile product?

    Model answer

    Treatment with dilute acid

  3. 3

    What is the overall equation for the formation of a hydroxynitrile from an aldehyde using HCN?

    Model answer

    RCHO + HCN → RCH(OH)CN

  4. 4

    What is the overall equation for the formation of a hydroxynitrile from a ketone using HCN?

    Model answer

    RCOR' + HCN → RC(OH)(CN)R'

  5. 5

    What type of mechanism occurs when KCN reacts with a carbonyl compound?

    Model answer

    Nucleophilic addition

  6. 6

    In the nucleophilic addition mechanism with KCN, what acts as the nucleophile?

    Model answer

    The cyanide ion (CN⁻)

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