JEE MainChemistryAlcohols Phenols and Ethers
When 1-(1-phenylcyclobutyl)ethan-1-ol is heated with concentrated H ₂ SO ₄ , the major organic product formed is:
Options
- A1-ethenyl-1-phenylcyclobutane
- B5-methyl-1-phenylcyclopent-1-ene
- C1-(1-phenylethyl)cyclobut-1-ene
- D1-methyl-2-phenylcyclopent-1-ene
Correct answer
D. 1-methyl-2-phenylcyclopent-1-ene
Step-by-step solution
Step 1: Protonation of the hydroxyl group of 1-(1-phenylcyclobutyl)ethan-1-ol followed by the loss of a water molecule generates a secondary carbocation at the side chain. Step 2: The highly strained four-membered cyclobutane ring undergoes expansion to relieve ring strain. A C-C bond migrates to the secondary carbocation, expanding the ring to a five-membered cyclopentane ring. This shifts the positive charge to the carbon bearing the phenyl group, forming a highly stable tertiary benzylic carbocation (1-phenyl-2-