Hydrolysis of haloalkanes by nucleophilic substituion

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Last updated 3:18 PM on 6/27/26
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Explain the bonding in haloalkanes.

The covalent bond between carbon atom and halogen atom is a polar bond.

This polarity is due to the fact that the halogen atom is more electronegative than the carbon atom. because of this greater electronegativity , the electron pair in the covalent bond is closer to the halogen atom than the carbon atom.

Halogen has partial negative charge, carbon has partial pos charge.

<p>The covalent bond between carbon atom and halogen atom is a polar bond.</p><p>This polarity is due to the fact that the halogen atom is more electronegative than the carbon atom. because of this greater electronegativity , the electron pair in the covalent bond is closer to the halogen atom than the carbon atom.</p><p>Halogen has partial negative charge, carbon has partial pos charge.</p>
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Whats a nucleophile

All nucleophiles have a lone pair of electrons. This lone pair of electrons is attracted to an electron deficient carbon atom.

Electron deficient carbon atoms have a pos charge, either a full pos charge or partial pos charge

The nucleophile donates the lone pair of electrons to form a covalent bond between nucleophile and carbon atom

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How does nucleophilic addition work with haloalkane chloromethane.

Chloromethane has an electron deficient carbon atom with partial pos charge, hydroxide ion also shown.

In hydroxide ion, the oxygen atom has a lone pair of electrons and negative charge, its an example of nucleophile

Lone pair of electrons on hydroxide ion are attracted to electron deficient carbon atom in chloromethane

Nucleophile donates lone pair of electrons to form covalent bond to electron deficientcarbon atom

<p>Chloromethane has an electron deficient carbon atom with partial pos charge, hydroxide ion also shown.</p><p>In hydroxide ion, the oxygen atom has a lone pair of electrons and negative charge, its an example of nucleophile</p><p>Lone pair of electrons on hydroxide ion are attracted to electron deficient carbon atom in chloromethane</p><p>Nucleophile donates lone pair of electrons to form covalent bond to electron deficientcarbon atom</p>
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What happens as the nucleophile donates lone pair of electrons

Since carbon can only form 4 covalent bonds, the covalent bond between carbon and halogen atom breaks, with pair of electrons moving onto halogen atom


<p>Since carbon can only form 4 covalent bonds, the covalent bond between carbon and halogen atom breaks, with pair of electrons moving onto halogen atom</p><p></p>
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What happens at end of nucleophilic substitution

We produce alcohol molecule (in this case methanol)

We also release halide ion, in this case the chloride ion. As this has left haloalkane ,halide ion is called leaving group

<p>We produce alcohol molecule (in this case methanol)</p><p>We also release halide ion, in this case the chloride ion. As this has left haloalkane ,halide ion is called leaving group</p>
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What are conditions for hydrolysis of haloalkane.

We use aqueous solution of hydroxide ions.

e.g sodium hydroxide or potassium hydroxide dissolved in water

Haloalkanes insoluble in water so ethanol must be added to reaction (ethanol solubilises the haloalkane so it can react with aqeuous hydroxide ions)

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