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प्रश्न
Chlorobenzene is extremely less reactive towards a nucleophilic substitution reaction. Give two reasons for the same.
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उत्तर
Chlorobenzene is extremely less reactive towards a nucleophilic substitution reaction because of the following reasons:
(1) Resonance effect: The electron pair on chlorine atom is in conjugation with the π - electrons of the benzene ring which results in the following resonance structures:
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This results in delocalization of the electrons of C − Cl bond and a partial double bond character develops in the bond, which makes it difficult for the nucleophile to cleave the C − Cl bond.
(2) The nucleophile suffers repulsion from the increased electron density on the benzene ring as a result the nucleophile is unable to make a close approach for the attack on the molecule.
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संबंधित प्रश्न
Write the final product(s) in each of the following reactions:
The presence of nitro group (−NO2) at o/p positions increases the reactivity of haloarenes towards nucleophilic substitution reactions.
Give reasons:
The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
Write the product formed on reaction of D-glucose with Br2 water.
What is Grignard reagent?
Assertion: Presence of a nitro group at ortho or para position increases the reactivity of haloarenes towards nucleophilic substitution.
Reason: Nitro group, being an electron-withdrawing group decreases the electron density over the benzene ring.
Arrange the following compounds in increasing order of rate of reaction towards nucleophilic substitution.
| (a) |  |
| (b) |  |
| (c) |  |
Arrange the following compounds in increasing order of rate of reaction towards nucleophilic substitution.
| (a) |  |
| (b) |  |
| (c) |  |
Allyl chloride is hydrolysed more readily than n-propyl chloride. Why?
Assertion: Chlorobenzene is resistant to nucleophilic substitution reaction at room temperature.
Reason (R): C–Cl bond gets weaker due, to resonance.
