Quantrex Quantrex AcademyJEE · NEET · NDA PYQs with solutions Open app
Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Which of the indicated carbon atoms is the least likely site of protonation in the conjugated alkene shown below?

Options

  1. ASite d
  2. BSite b
  3. CSite c
  4. DSite a

Correct answer

D. Site a

Step-by-step solution

The given molecule is a substituted fulvene, which contains a cyclopentadiene ring with an exocyclic double bond. To find the least likely site of protonation, we must evaluate the stability of the carbocation formed after a proton ( H^+ ) is added to each indicated site. The least likely site will form the most unstable carbocation. If protonation occurs at site 'a' (the exocyclic CH₂ carbon), the electrons from the exocyclic double bond are used to form a bond with the proton. This leaves a positive charge on the

Practice General Organic Chemistry on Quantrex Academy →

More from General Organic Chemistry

All General Organic Chemistry questions Full General Organic Chemistry list All Fundamentals of Organic Chemistry PYQs