# Reaction of cyclohexane-1,2,4-triol with acetone Tags: organic-chemistry, carbonyl-compounds, ethers - Score: 8 - Views: 3990 - Answers: 1 - Answered: yes - Asked by: Aditya Dev (7922 rep) - Asked: 2015-12-20 - Edited: 2020-06-11 - Site: chemistry ## Question What is the product formed when cyclohexane-1,2,4-triol reacts with 1 equivalent of acetone in an acidic medium? There are 3 possible hemiacetal products. The major one is formed via nucleophilic attack by a less hindered hydroxyl group: There is one possible cyclic acetal formed by the two adjacent $\ce{- OH}$ groups: But which of the two products will be formed in a larger quantity? I have heard that cyclic acetals are more stable than acyclic ones but don't know the reason (because of entropy change or something?). ## Answers ### Answer by Jan (score: 11 [ACCEPTED]) As long as you have a proton source in your solution (hint: all the time) these acetals will equilibrate back and forth until they find the thermodynamic hole. So you will never observe a hemiketal like the one you drew; rather, it will always move forward with the elimination of water (there is only little water around if acetone is the solvent, so