When 1-(1-methylcyclopentyl)ethan-1-ol is heated with concentrated H ₂ SO ₄ , the major organic product formed is:

Step-by-step solution

Protonation of the hydroxyl group followed by the loss of a water molecule generates a secondary carbocation adjacent to the five-membered ring: a 1-(1-methylcyclopentyl)ethyl cation. The secondary carbocation is adjacent to a quaternary carbon. To increase stability and relieve the ring strain of the five-membered ring, a ring expansion occurs. One of the ring C-C bonds migrates to the carbocationic center. This alkyl shift expands the ring to a more stable six-membered cyclohexane ring, resulting in a tertiary ca