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Halogenoalkanes

Nucleophilic substitution of primary halogenoalkanes

  • 3 things to know
  • Components 1 and 2

Overview

Mechanism by which hydroxide ions react with a primary halogenoalkane and leaving group.

What you need to know

Answer each one before you reveal it.

Your recallNot started
Key term

Explain why the carbon atom bonded to the halogen in a halogenoalkane carries a partial positive charge.

Process

Name the mechanism by which hydroxide ions react with a primary halogenoalkane.

Key term

Describe the second curly arrow in the reaction of hydroxide ions with bromoethane.

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    Explain why the carbon atom bonded to the halogen in a halogenoalkane carries a partial positive charge.

    Model answer

    The halogen is more electronegative than carbon, so it draws the bonding pair towards itself and leaves the carbon atom electron deficient.

  2. 2

    Name the mechanism by which hydroxide ions react with a primary halogenoalkane.

    Model answer

    The mechanism is nucleophilic substitution.

  3. 3

    Why is the hydroxide ion described as a nucleophile?

    Model answer

    It carries lone pairs of electrons on the oxygen atom and a negative charge, so it donates a pair to an electron-deficient carbon.

  4. 4

    Describe the first curly arrow in the reaction of hydroxide ions with bromoethane.

    Model answer

    An arrow runs from a lone pair on the oxygen of the hydroxide ion to the δ+ carbon atom, showing the new carbon-oxygen bond being formed.

  5. 5

    Describe the second curly arrow in the reaction of hydroxide ions with bromoethane.

    Model answer

    An arrow runs from the middle of the C—Br bond to the bromine atom, showing heterolytic fission that releases a bromide ion.

  6. 6

    From which direction does the nucleophile approach the carbon atom in this reaction, and why?

    Model answer

    It approaches from the side opposite the halogen, because that keeps it as far as possible from the electron-rich leaving group.

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