What is the Major Product of This Ester Reaction with Sulfuric Acid?

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SUMMARY

The major product of the reaction involving the specified molecule with 1% aqueous sulfuric acid (H2SO4) followed by PCC and dichloromethane is a secondary alcohol, specifically 3-hydroxycyclooctene. The initial step hydrolyzes the ester into ethanoic acid and the secondary alcohol. The use of PCC subsequently oxidizes the secondary alcohol to form a ketone, confirming the transformation of the alcohol into a more oxidized product.

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lat3ralus65
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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:

http://img216.imageshack.us/my.php?image=stupidthingdw3.jpg

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

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