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Aryl halides are practically inert t...

Aryl halides are practically inert toward nucleophilic substitution reactions . The reasons for this fact are
(a) Because C -X bond has partial double bond character due to conjugation bewteen lone pair of X and π electrons of aromatic ring .
(b) No S N 1 reaction beacuase aryl carbocations are unstable
(c) No S N 2 reaction because aromatic π electron cloud do not allow backside attack of N u −
(d) Product obtained through nucleophilic substitution reactions are non aromatic

A

Because C -X bond has partial double bond character due to conjugation bewteen lone pair of X and `pi` electrons of aromatic ring .

B

No `S_(N)1` reaction beacuase aryl carbocations are unstable

C

No`S_(N)2` reaction because aromatic `pi` electron cloud do not allow backside attack of `Nu^(-)`

D

Product obtained through nucleophilic substitution reactions are non aromatic

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question regarding why aryl halides are practically inert toward nucleophilic substitution reactions, we will analyze each of the provided statements step by step. ### Step 1: Understand Aryl Halides and Nucleophilic Substitution Aryl halides are compounds where a halogen atom (X) is bonded to an aromatic ring. Nucleophilic substitution reactions involve a nucleophile (Nu-) attacking a positively charged carbon atom, leading to the substitution of the halogen atom. **Hint:** Aryl halides are distinct from alkyl halides due to the presence of the aromatic ring. ### Step 2: Analyze Statement (a) **Statement (a):** Because C-X bond has partial double bond character due to conjugation between lone pair of X and π electrons of aromatic ring. - The C-X bond in aryl halides exhibits partial double bond character due to resonance. The lone pair of electrons on the halogen can participate in resonance with the π electrons of the aromatic ring, making the bond stronger and less reactive. **Conclusion:** This statement is **true**. **Hint:** Look for resonance structures to understand the stability of the C-X bond. ### Step 3: Analyze Statement (b) **Statement (b):** No SN1 reaction because aryl carbocations are unstable. - Aryl carbocations are indeed unstable due to the inability to stabilize the positive charge effectively on the aromatic ring. This instability prevents the formation of the carbocation necessary for an SN1 reaction. **Conclusion:** This statement is **true**. **Hint:** Consider the stability of carbocations in different environments. ### Step 4: Analyze Statement (c) **Statement (c):** No SN2 reaction because aromatic π electron cloud does not allow backside attack of Nu-. - In an SN2 reaction, the nucleophile must attack from the opposite side of the leaving group. However, the π electron cloud of the aromatic ring creates steric hindrance and electronic repulsion, preventing effective backside attack. **Conclusion:** This statement is **true**. **Hint:** Visualize the spatial arrangement of the aromatic ring and the nucleophile's approach. ### Step 5: Analyze Statement (d) **Statement (d):** Products obtained through nucleophilic substitution reactions are non-aromatic. - This statement is misleading. While some products may be non-aromatic, it is not universally true. The aromaticity of the product depends on the specific reaction and the structure of the substituents. **Conclusion:** This statement is **false**. **Hint:** Consider how substituents affect the aromaticity of the resulting compound. ### Final Answer The correct statements regarding why aryl halides are practically inert toward nucleophilic substitution reactions are: - (a) True - (b) True - (c) True - (d) False Thus, the correct options are (a), (b), and (c).
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Knowledge Check

  • 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.
  • Which pairs are not required for a nucleophilic aromatic substitution reaction ?

    A
    An `-NO_(2)` substituent and a strong electrophile.
    B
    A ring bearing a strong activating group and a strong acid.
    C
    An aryl halide with an `-NO_(2)` and a strong nucleophile.
    D
    Anunsubstituted benzene ring and a strong electrophile.
  • 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
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