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Ester reaction with sulfuric acid

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?
 

Answers and Replies

437
1
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:
chemisttree
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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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