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Homework Help: Ester reaction with sulfuric acid

  1. Mar 28, 2008 #1
    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?
  2. jcsd
  3. Mar 28, 2008 #2
    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
    Last edited: Mar 29, 2008
  4. Mar 29, 2008 #3


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