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Account for the fact that halogen in chlorobenzene is less weve than in methyl chloride,

Question

Account for the fact that halogen in chlorobenzene is less weve than in methyl chloride,

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Solution

The difference in reactivity between chlorobenzene and methyl chloride can be attributed to two main factors: the type of hybridization and the resonance effect.

  1. Type of Hybridization: In chlorobenzene, the carbon atom to which the chlorine atom is attached is sp2 hybridized, while in methyl chloride, the carbon atom is sp3 hybridized. sp2 hybridized carbons are more electronegative than sp3 hybridized carbons, which means they can hold onto the electrons more tightly. This makes it harder for the chlorine atom in chlorobenzene to leave as a chloride ion, making chlorobenzene less reactive than methyl chloride.

  2. Resonance Effect: In chlorobenzene, the chlorine atom is part of the aromatic ring and can participate in resonance, which helps to delocalize the negative charge that would build up if the chlorine were to leave as a chloride ion. This delocalization of charge stabilizes the molecule, making it less likely for the chlorine to leave and thus making chlorobenzene less reactive than methyl chloride.

In conclusion, the decreased reactivity of chlorobenzene compared to methyl chloride can be attributed to the increased electronegativity of the sp2 hybridized carbon and the stabilizing effect of resonance in the aromatic ring.

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