Home
Class 12
CHEMISTRY
Aryl halides are less reactive towards n...

Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halides due to

A

formation of a less stable carbonium ion in aryl halides

B

resonance stabilisation in ary halides

C

presence of double bonds in alkyl halides

D

inductive effect in aryl halides.

Text Solution

AI Generated Solution

The correct Answer is:
To understand why aryl halides are less reactive towards nucleophilic substitution reactions compared to alkyl halides, we can analyze the factors involved in these reactions step by step. ### Step-by-Step Solution: 1. **Understanding Nucleophilic Substitution**: - In nucleophilic substitution reactions, a nucleophile attacks the carbon atom bonded to the leaving group (halogen) and replaces it. The stability of the intermediate formed during this process is crucial for the reaction to proceed. 2. **Structure of Alkyl Halides**: - Alkyl halides have a carbon atom bonded to a halogen (like Cl, Br, or I). When a nucleophile approaches, it can easily attack the carbon atom because there is no significant resonance stabilization of the carbon-halogen bond. This allows the bond to break and the nucleophile to substitute the halogen. 3. **Structure of Aryl Halides**: - Aryl halides, on the other hand, have a halogen atom bonded to a carbon atom that is part of an aromatic ring (like benzene). The halogen atom has lone pairs of electrons that can participate in resonance with the aromatic system. 4. **Resonance Stabilization**: - In aryl halides, the lone pair of electrons on the halogen can delocalize into the aromatic ring, creating resonance structures. This delocalization gives the carbon-halogen bond a partial double bond character, making it stronger and less reactive. The resonance structures stabilize the aryl halide and hinder the nucleophile's ability to attack. 5. **Comparison of Stability**: - The resonance in aryl halides leads to a situation where the carbon-halogen bond is more stable due to the partial double bond character. In contrast, alkyl halides do not have this resonance stabilization, making their carbon-halogen bonds more susceptible to nucleophilic attack. 6. **Conclusion**: - Therefore, the correct reason why aryl halides are less reactive towards nucleophilic substitution compared to alkyl halides is due to the resonance stabilization in aryl halides, which makes the carbon-halogen bond stronger and less likely to break. ### Final Answer: Aryl halides are less reactive towards nucleophilic substitution reactions compared to alkyl halides due to **resonance stabilization in the aryl halides**.
Doubtnut Promotions Banner Mobile Dark
|

Topper's Solved these Questions

  • HALOALKANES AND HALOARENES

    NCERT FINGERTIPS ENGLISH|Exercise Higher order thinking skills|8 Videos
  • HALOALKANES AND HALOARENES

    NCERT FINGERTIPS ENGLISH|Exercise Exemplar problems|24 Videos
  • HALOALKANES AND HALOARENES

    NCERT FINGERTIPS ENGLISH|Exercise Physical properties|7 Videos
  • GENERAL PRINCIPLES AND PROCESSES OF ISOLATION OF ELEMENTS

    NCERT FINGERTIPS ENGLISH|Exercise Assertion And Reason|15 Videos
  • POLYMERS

    NCERT FINGERTIPS ENGLISH|Exercise NCERT Exemplar|9 Videos

Similar Questions

Explore conceptually related problems

Statement-I: Vinylic halides are reactive towards nucleophilic substitution reaction. Because Statement-II: Reactivity is due to the polarity of carbon-halogen bond.

STATEMENT : Aryl halides are more reactive than alkyl towards nucleophilic substitution reaction STATEMENT : 2 Aryl halides have stronger C-X bond asa compared to alkyl halides

Knowledge Check

  • Assertion: Aryl halides are highly reactive towards nucleophilic substitution reactions. Reason: In case of halorenes, halogen atom is attached to sp hybridised carbon atom.

    A
    If both assertion and reason are true and reason Is the correct explanation of assertion.
    B
    If both assertion and reason are true but reason is not the correct explanation of assertion.
    C
    If assetion is true but reason is false.
    D
    If both assertion and reason are false.
  • Which ofthe following is most reactive towards nucleophilic substitution reaction ?

    A
    `CH_2=CH-Cl`
    B
    `C_6H_5Cl`
    C
    `CH_3CH=CHCl`
    D
    `ClCH_2-CH=CH_2`
  • Vinylic halides are unreactive towards nucleophilic substitution because of the following except :

    A
    C-halogen bond is strong
    B
    The halogen is bonded to `sp^(2)` carbon
    C
    A double bond character is developed in the carbon-halogen bond by reasonance
    D
    Halide ions are not good leaving groups
  • Similar Questions

    Explore conceptually related problems

    Which is least reactive towards nucleophilic substitution (S_(N^(2)))

    Which is least reactive towards nucleophilic substitution (S_(N^(2)))

    Anyl halides are practically inert toward nucleophilic substitution reactions . The reasons for this fact are

    Chlorobenzene is extremely less reactive towards nucleophilic substitution reaction. Give two reasons for the same.

    Which one of the following is most reactive towards nucleophilic substitution reaction ?