Chemistry Stack Exchange is a question and answer site for scientists, academics, teachers, and students in the field of chemistry. It only takes a minute to sign up.
Sign up to join this community
I think the ethereal oxygen in THFA gets protonated. Due to greater +I effect, the electron density on it is higher, hence it is more likely to behave as a Lewis base. Consequently, the product formed is pent-2-en-1,5-diol:
Apparently, this is wrong. What exactly happens here and why my answer is wrong?
The alcohol group of your educt (tetrahydrofurfuryl alcohol) is protonated, and after subsequent loss of water, the resulting primary carbocation can rearrange to a more stable 6-membered ring cation, which is stabilized by resonance. Initial protonation at the ether oxygen is therefore disfavored, as it will not result in the formation of a similarly stable carbocation (with positive charge adjacent to oxygen). After final deprotonation, 2,3-dihydropyran is obtained.
