R3.3.1/R3.4.3 Heterolytic/homolytic bond fission

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Homolytic bond fission

Covalent bond breaks evenly

Each atom takes one electron.

Forms free radicals with unpaired electrons.

Represented with a dot (•).

<p>Covalent bond breaks evenly</p><p>Each atom takes one electron.</p><p>Forms free radicals with unpaired electrons.</p><p>Represented with a dot (•).</p>
2
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Heterolytic bond fission

Covalent bond breaks unevenly

One atom takes both electrons.

Forms positive and negative ions.

More electronegative atom gets both electrons.

<p>Covalent bond breaks unevenly</p><p>One atom takes both electrons.</p><p>Forms positive and negative ions.</p><p>More electronegative atom gets both electrons.</p>
3
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Homolytic fission example

Cl–Cl bond breaks under UV light

Each Cl takes one electron.

Produces two Cl• radicals.

Seen in free radical substitution.

<p>Cl–Cl bond breaks under UV light</p><p>Each Cl takes one electron. </p><p>Produces two Cl• radicals. </p><p>Seen in free radical substitution.</p>
4
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Heterolytic fission example

C–Cl bond in haloalkane breaks unevenly.

Cl gets both electrons forming Cl⁻.

Seen in nucleophilic substitution.

<p>C–Cl bond in haloalkane breaks unevenly. </p><p>Cl gets both electrons forming Cl⁻. </p><p>Seen in nucleophilic substitution.</p>