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With the help of polarity of the carbon halogen bond show that aryl halides are less reactive than alkyl halides.

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Hydrolysis of alkyl or aryl halides is a nucleophilic substitution reaction. The lesser reactivity of haloarenes (say chlorobenzene) than haloalkanes (say chloromethane) in nucleophilic substitution reactions can be explained as follows: (i) Resonance effect: Haloarenes are resonance stabilised, For example, chlorobenzene is a resonance. hybrid of various contributing structures (I) to (V) as shown below:

As a result of resonance, in structure (IT) to (IV), C-Cl bond acquires some double bond character. On the other hand, no such resonance occurs in alkyl halides. Therefore, C-Cl bond in aryi halides is stronger than carbon-halogen bond in haloalkanes and hence can not be easily broken, so chlorobenzene is less reactive. (ii) Hybridisation of carbon bearing the halogen atom. In haloalkanes, the carbon atom attached to the halogen atom (C--X). is `sp^3` -hybridised whereas in haloarenes, the carbon atom attached to the halogen atom is `sp^2`-hybridised. Now `sp^2`-hybrid orbital of carbon is slightly smaller in size than the `sp^3`-hybrid orbital. Therefore, the nalogen bond in haloarenes is shorter and stronger than the carbon-halogen bond in haloalkanes. This also justify the low reactivity of haloarenes as compared to haloalkanes
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BETTER CHOICE PUBLICATION-HALOALKANES AND HALOARENES-QUESTIONS
  1. What are ambident uncleophiles ? Explain with an example.

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  2. Alkyl Chloride is more reactive than chlorobenzene towards nucleophili...

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  3. With the help of polarity of the carbon halogen bond show that aryl ha...

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  4. Why are haloarenes more stable than haloalkanes ?

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  5. Why do alkyi haldies undergo hydrolysis more readily than aryl halides...

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  6. With the help of resonance show that aryl halides are lesser reactive ...

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  7. With the help of hybridisation show that aryl halides are lesser react...

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  8. With the help of polarity of the carbon halogen bond show that aryl ha...

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  9. Why does electrophilic substitution take place at ortho and para posit...

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  10. Why does electrophilic substitution take place at ortho and para posit...

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  11. Haloarene is ortho and para directing Explain.

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  12. Write short notes on : Wurtz reaction

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  13. Write Fittig reaction.

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  14. Write short notes on : Friedel Craft's reaction

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  15. Write Fittig reaction.

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  16. Write Ullmann reaction.

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  17. Write the following reactions : Friedel Craft alkylation.

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  18. Name the reagent used to convert 1-chloroproane to 1- nitropropane.

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  19. Name the reagent used to convert bromoethane to ether.

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  20. Write a chemical reaction to illustrate Saytzeff's rule.

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