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Core Organic Chemistry

Nucleophilic substitution and carbon-halogen bond strength

  • 2 things to know
  • Components 02 and 03

Overview

Recall questions on the mechanism step by step, and on why the C-F bond is hardest and the C-I bond easiest to break.

What you need to know

Answer each one before you reveal it.

Your recallNot started
Process

What does the second curly arrow show in nucleophilic substitution of a haloalkane, what becomes of the halogen, and why is the C–F bond hardest to break?

Process

Why does the C-I bond break most readily, and how does bond strength relate to the rate of hydrolysis?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    In the nucleophilic substitution mechanism of a primary haloalkane with aqueous alkali, what does the hydroxide ion donate to the carbon atom?

    Model answer

    The hydroxide ion donates an electron pair (lone pair) to the carbon atom.

  2. 2

    What new bond forms during the nucleophilic substitution of a primary haloalkane with hydroxide ions?

    Model answer

    A new carbon-oxygen bond forms.

  3. 3

    How does the carbon-halogen bond break during nucleophilic substitution of a primary haloalkane?

    Model answer

    The carbon-halogen bond breaks heterolytically.

  4. 4

    What is the fate of the halogen after the carbon-halogen bond breaks in nucleophilic substitution?

    Model answer

    The halide ion leaves as the leaving group.

  5. 5

    In the mechanism for nucleophilic substitution of a primary haloalkane, where does the first curly arrow originate and where does it point?

    Model answer

    The first curly arrow originates from the lone pair on the hydroxide ion and points to the carbon atom.

  6. 6

    In the mechanism for nucleophilic substitution of a primary haloalkane, what does the second curly arrow represent?

    Model answer

    The second curly arrow shows the movement of the electron pair from the carbon-halogen bond to the halogen atom.

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Foundations in Chemistry
Bonding and Structure
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AThe first step is Cl• + O₃ → ClO• + O₂.
BThe second step is ClO• + O → Cl• + O₂.
CThe overall equation is O₃ + O → 2O₂.

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In ClO⁻, chlorine has oxidation number +1.
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