Ester reaction with sulfuric acid

lat3ralus65

OK, so I just got out of an organic chemistry exam. I feel pretty good about every question except one which I did not know - please help me put my mind at ease!

What is the major product of the reaction of this molecule:



with the following steps:

1.) 1% aq H2SO4, boil
2.) isolate product
3.) PCC/dichloromethane

I had no idea how the reaction occurred. I guessed that the final product was an aldehyde (methanal?) because I know PCC reacts with alcohols to form aldehydes/ketones (and that's all I knew).

What is it?

Kushal

the H2SO4 + boil will hydrolyse the ester into ethanoic acid and the alcohol 3 hydroxy cyclo octene.

i just corrected this post. i made a mistake, the alcohol is secondary

chemisttree

What happens to a cis olefin upon treatment with hot, dilute acid? The alcohol(s) are secondary.