Home
Class 12
CHEMISTRY
Why alkenes are more reactive than alkan...

Why alkenes are more reactive than alkanes?

Text Solution

Verified by Experts

Haloarenes or aryl halide are less reactive than alkyl halide. The low reactivity in comparison to alkyl halide is due to the following reactions :
(i) Resonance effect : In aryl halide the electron pairs .Brtilie halogen atom are in conjugation with n-electrons of the ring and the follo~ing resonating structures are possible:

As a results resonance there is delocalisation of electron on C - Cl bond which acquires a partial double bond character. This is also evident from the contribution. of structure III, IV and V. As a result the bond cleavage in aryl halide is less. reactive towards nucleophilic substitution reaction.
(iz) Hybridisation : In haloalkane the carbon atom of the C - X bond is `sp^3` hybidisation while in haloarene, the carbon atom attached to the halogen `sp^2` hybridisation. The hybridised carbon atom with a greater s-character is more electronegatitive. It can hold the electron pair of the bond more tightly that the `sp^3` hybridised carbon atom in alkyl halide with less s-character. Therefore C - X bond of aryl halide is shorter than alkyl halide.

(iii) Polarity of carbon-halogen bond : The `sp^2` hybridised carbon atom involve in C - X bond in haloarenes molecules is more electronegative than the `sp^3` hybrid carbon atom in alkyl halide. Therefore this `sp^2` hybridised carbon has less tendency to release electron to the Cl-atom and the C-Cl bond in aryl halide is less polar than in alkyl halide. This is supported by the fact that the dipole moment of chlorobenzene is 1. 73 D while the dipole moment of chloro ethene is 2.05 D. Thus lesser the polarity of C - Cl bond, lesser is the reactivity.
Doubtnut Promotions Banner Mobile Dark
|

Topper's Solved these Questions

  • HALOALKANES AND HALOARENES

    ACCURATE PUBLICATION|Exercise TRUE AND FALSE (1 MARK)|10 Videos
  • HALOALKANES AND HALOARENES

    ACCURATE PUBLICATION|Exercise 2 OR 5 MARKS QUESTIONS|23 Videos
  • ELECTRO CHEMISTRY

    ACCURATE PUBLICATION|Exercise Numbericals Practice|44 Videos
  • IMPORTANT NAMING REACTION

    ACCURATE PUBLICATION|Exercise DISTINGUISH TEST|5 Videos

Similar Questions

Explore conceptually related problems

Why aldehydes are more reactive than ketone?

Why haloalkanes are more reactive than haloarenes towards nuclophilic subsition reaction ?

Why alkynes are more acidic than alkenes and alkanes ?

Explain why aldehydes are more reactive than ketones towards nucleophilic addition reactions ?

What are the interhalogen compounds ? Why are these more reactive than halogens ?

Why Haloarenes are less reactive than haloalkanes. Explain with resonance and hybridisation.

Why Haloarenes are less reactive than haloalkanes. Explain with reasonance and hybridisation.

In general, alkyl halides are more reactive than aryl halides.

Aldehydes are more reactive than ketones. Justify.

Account for the following: Interhalogens are more reactive than pure halogens.