# The problem

Source : MS Couhan (problems in organic chemistry . Chapter: Alcohols , phenols and ethers).

# My Thoughts

If I proceed along $$\ce{path 1}$$ , $$\ce1a$$ is formed . It is unstable due to inductive withdrawing effect of $$\ce{C=O}$$ neighboring to it. Eventually $$\ce2$$ is obtained.

However, along $$\ce{path 2}$$ relatively more stable $$\ce{3a}$$ (compared to $$\ce{1a}$$) is formed. $$\ce3a$$ on ring expansion gives $$\ce{3b}$$ , leading to $$\ce{4}$$ ($$\ce{3b}$$ is relatively unstable compared to $$\ce{1b}$$).

# My question

Which of the two paths should I choose that would lead to a major product ?