Join the Most Relevant JEE Main 2025 Test Series & get 99+ percentile! Join Now
Search any question & find its solution
Question: Answered & Verified by Expert
The most likely protonation site in the following molecule is
ChemistryGeneral Organic ChemistryWBJEEWBJEE 2014
Options:
  • A $\mathrm{C}-1$
  • B $\mathrm{C}-2$
  • C $\mathrm{C}-3$
  • D $C-6$
Solution:
1282 Upvotes Verified Answer
The correct answer is: $\mathrm{C}-1$
Addition of a proton at $\mathrm{C}^{-1}$ results in the formation of tropylium carbocation (an aromatic species with more stability due to delocalisation of $\pi$ electrons). thus, it is the most reactive site towards protonation. Addition of proton at any other carbon atom interupt in the delocalisation of it electrons by disturbing planarity of molecules and herce makes it less stable. Thus, these all are lest reactive towards protonation.

Looking for more such questions to practice?

Download the MARKS App - The ultimate prep app for IIT JEE & NEET with chapter-wise PYQs, revision notes, formula sheets, custom tests & much more.