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How does a hydronium ion react with a lactone?
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Topic: How does a hydronium ion react with a lactone? (Read 3211 times)
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Mobiu5
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How does a hydronium ion react with a lactone?
«
on:
March 11, 2013, 11:03:43 PM »
From what I understand, an ester will form but I'm confused how the hydronium ion will begin to break apart the lactone. Will it attack the carbonyl group first or use the second oxygen to begin the reaction?
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camptzak
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Re: How does a hydronium ion react with a lactone?
«
Reply #1 on:
March 12, 2013, 01:06:18 AM »
http://www.chemtube3d.com/model/nucleophilic_substitution/acid-cat_ester_hydrol/mechanism.png
here is an ester hydrolysis mechanism, it works in the same fashion. The carboxylic acid and and the alcohol are in equilibrium with the ester and H
2
O.
I am pretty sure that only unstable lactones like butyrolactone are susceptible to acid hydrolysis. I think most of the other ones will not react with H
3
O
+
.
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How does a hydronium ion react with a lactone?