Question:
The total number of alkene products possible from the dehydrobromination of 3-bromo-3-cyclopentylhexane using alcohol KOH is :
This question was asked here before but I am getting more products than those mentioned there
Dehydrobromination of 3-bromo-3-cyclopentylhexane and number of possible alkene products
My doubt is, why doesn't Hydride shift and ring expansion take place here? I would expect the Elimination reaction to be E1 as Br is a good leaving group and it is 3° halide. So there should be a carbocation intermediate on C3.
There is an alpha hydrogen in the cyclopentyl ring wrt this carbocation. Why won't hydride shift or ring expansion into cyclohexane (more stable ring) take place here?