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In the electrophilic substitution of ben...

In the electrophilic substitution of benzene, to restore aromatic character sigma complex releases proton from 

A

`sp^3` hybridised carbon

B

`sp^2` hybridised carbon

C

`sp` hybridised carbon

D

Any one of the carbons

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The correct Answer is:
A
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Electrophilic substitution on mono substituted benzene is determined by electronic effects +1, -M groups are ortho, para directors, where as -1,-M groups are meta directions. When there is a competition between inductive and mesomeric effects, the latter wins over. Electrophilic substitution on disubstituted benzene is determined by the combined effect of both groups. Usually activating group wins over deactivating group. When one of the groups has a lone pair of electrons, that will determine the product formation. Usually a third group will not enter the position in between the two existing groups due to steric reasons.

The typical reaction of benzene and other aromatic compounds is electrophilic substitution. Presence of electron donating group activates the ring towards electrophilic substitution, while presence of electron withdrawing group deactivates the ring towards electrophilic substitution but at the same time activates the ring towards nucleophilic substitution. Some groups are predominantly meta directing and all of these are deactivating. Except halogen, most of the o- and p- directing groups are activating groups. (E.A.S = Electrophilic aromatic substation) Presence of nitro group in benzene ring:

Knowledge Check

  • In the electrophilic substitution of benzene, to restore aromatic character sigma comlex releases proton from

    A
    `sp^(3)`- hybridised carbon
    B
    `sp^(2)`- hybridised carbon
    C
    sp - hybridised carbon
    D
    Any one of the carbons

  • The electrophilic aromatic substitution proceeds through a

    A
    Free radical
    B
    Sigma complex
    C
    Benzyne
    D
    Carbene

  • Correct statement about the electrophilic substitution in benzene ring is

    A
    Halogens are benzene ring deactivating groups due to resonance.
    B
    Halogens are ortho and para directing groups due to their - I effect.
    C
    Halogens are ortho and para directing and benzene ring activating groups.
    D
    Halogens are benzene ring deactivating groups due to their – I effect.
    • AAKASH SERIES-AROMATIC HYDROCARBONS-OBJECTIVE EXERCIES - 2 (BENZENE)
    1. In the electrophilic substitution of benzene, to restore aromatic char...

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    2. According to Huckel's rule to explain aromaticity the compound has to ...

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    3. During ozonolysis of Imole of benzene, number of moles of ozone consum...

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    4. Compounds A and B respectively are

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    5. C2H4Br2 overset(alc KOH)(rarr) A underset("Metal tube")overset("Red ho...

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    6. Which of the following is not aromatic ?

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    7. Benzene does not undergo addition reaction easily because

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    8. The reagent used for converting benzene to ethyl benzene is

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    9. Benzene on treating with a mixture of conc. HNO3 and H2SO4 at 100^@C g...

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    10. The correct relation among the following is

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    11. Arrange the following compounds in the descending order of their react...

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    12. Match the following {:("List - I ","List - II"),("1)" O^(-) ", "p -"...

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    13. The ratio of the number of hybrid and pure orbitals in C6H6 used for b...

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    14. Number of sigma sp^2 - sp^2 bonds present in a molecule of X in the pr...

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    15. In which of the following reactions, aromatic character is retained ?

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    16. The correct arrangement for decreasing order of electrophilic subsitut...

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    17. Which one of the following is benzene ring deactivating group towards ...

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    18. When acetylene is passed through red hot iron tube, compound X is form...

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    19. Identify the reagents A and B used in the following reactions

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    20. Choose the correct reagents used in the conversion,  CH2 = CH2 overs...

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