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Q.

What is the correct order of reactivity towards sulphonation or iodination?

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a

C6H6=C6D6>C6T6

b

C6H6=C6D6=C6T6

c

C6H6>C6D6>C6T6

d

C6H6>C6D6=C6T6

answer is B.

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Detailed Solution

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  • The correct order of the rate of reaction of C6​H6​, C6​D6​ and C6​T6​ towards sulphonation is C6​H6​>C6​D6​>C6​T6​. 
  • As the hydrogen atom of benzene is successively substituted with deuterium and tritium, the rate of the electrophilic aromatic substitution decreases. 
  • Concentrated sulphuric acid releases a molecule of SO3​. 
  • The electrophile attacks the benzene ring to form a sigma complex. 
  • The abstraction of H+ is the rate determining step. 
  • The bond strength increases in the order C−H < C−D < C−T. 
  • Hence, the rate of the reaction decreases in the order C6​H6​>C6​D6​>C6​T6​.
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