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Organic Chemistry I

Nucleophilic substitution of halogenoalkanes

  • 3 things to know
  • Papers 2 and 3

Overview

Nucleophiles, halogenoalkanes substituted by aqueous potassium hydroxide, by water from silver nitrate in ethanol, by cyanide ions to lengthen the chain and by excess ammonia to give a primary amine, and hydroxide acting as a base with ethanolic potassium hydroxide.

What you need to know

Answer each one before you reveal it.

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Key term

What is a nucleophile?

Key term

Why is the reaction of a halogenoalkane with potassium cyanide synthetically useful?

Key term

In a primary halogenoalkane, how many other carbon atoms are attached to the carbon bearing the halogen?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    In a primary halogenoalkane, how many other carbon atoms are attached to the carbon bearing the halogen?

    Model answer

    One other carbon atom.

  2. 2

    What is a nucleophile?

    Model answer

    An electron-pair donor that attacks an electron-deficient carbon atom.

  3. 3

    What product is formed when a halogenoalkane reacts with aqueous potassium hydroxide?

    Model answer

    An alcohol.

  4. 4

    In the reaction of a halogenoalkane with aqueous KOH, what species acts as the nucleophile?

    Model answer

    The hydroxide ion (OH⁻).

  5. 5

    What type of reaction is favoured when a halogenoalkane reacts with aqueous potassium hydroxide?

    Model answer

    Nucleophilic substitution, producing an alcohol.

  6. 6

    Halogenoalkanes are hydrolysed with silver nitrate solution in ethanol — which species is the nucleophile?

    Model answer

    Water.

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