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Amines

Reaction with ethanoyl chloride and identifying amines

  • 3 things to know
  • Unit A2 2

Overview

Formed when a primary amine reacts with ethanoyl chloride, mechanism by which an amine reacts with ethanoyl chloride and observed when ethanoyl chloride is added to a primary amine.

What you need to know

Answer each one before you reveal it.

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Process

Describe, in words, the mechanism by which ethylamine reacts with ethanoyl chloride.

Key term

What is formed when a primary amine reacts with ethanoyl chloride?

Key term

Write the equation for the reaction of ethylamine with ethanoyl chloride

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    What is formed when a primary amine reacts with ethanoyl chloride?

    Model answer

    An N-substituted amide, together with hydrogen chloride.

  2. 2

    Write the reaction of ethylamine with ethanoyl chloride.

    Model answer

    CH₃COCl + 2CH₃CH₂NH₂ → CH₃CONHCH₂CH₃ + CH₃CH₂NH₃⁺Cl⁻.

  3. 3

    Name the mechanism by which an amine reacts with ethanoyl chloride.

    Model answer

    Nucleophilic addition–elimination.

  4. 4

    Describe, in words, the mechanism by which ethylamine reacts with ethanoyl chloride.

    Model answer

    The lone pair on the amine nitrogen attacks the carbonyl carbon, the carbon to oxygen double bond opens onto the oxygen, that pair then reforms the double bond and expels the chloride ion, and a second amine molecule removes a proton from the nitrogen.

  5. 5

    What is observed when ethanoyl chloride is added to a primary amine?

    Model answer

    A vigorous reaction with steamy fumes of hydrogen chloride and the formation of a solid product.

  6. 6

    How is the melting temperature used to identify the amine?

    Model answer

    The purified solid's melting temperature is measured and compared with tabulated values for the derivatives of known amines.

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