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Question: Answered & Verified by Expert

Arrange the following structure according to their increasing order of acidic behaviour in  polar solvent:

ChemistryHydrocarbonsNEET
Options:
  • A i > ii < iii
  • B i < iii < ii
  • C i < ii < iii
  • D ii < iii < i
Solution:
1687 Upvotes Verified Answer
The correct answer is: i < ii < iii

This is because of the negative charge delocalizing on the vacant d-orbitals of chlorine atom present in the para position and this is not possible with fluorine atom. Thus, the conjugate base of p-chloro phenol is more stable and hence a weak base. So, p-chloro phenol is more acidic than p-fluoro phenol.
 

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