April 17, 2021, 10:45:01 PM
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Topic: Mechanism for lactone formation from 3-noneoic acid.  (Read 168 times)

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Offline JoeyBob

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Mechanism for lactone formation from 3-noneoic acid.
« on: April 03, 2021, 03:18:40 AM »
Im trying to figure out the mechanism for the above and am quite confused. I can find a lot of literature involving lactone formation when a reaction occurs between an alcohol and carboxylic acid group, but have not found anything for a reaction between an alkene and a carboxylic acid group.

I have a mechanism shown here that would give the right product after reacting with a base, but I really doubt that such a reaction would occur, since 2 cations are formed. Intuitively the C=O part of the compound also feels like a better electrophile than the OH, but if this reaction occurred no ester is formed.

The catalysis is amberlyst-15, an acid, but I dont really see how protonation here leads to a lactone. I could see this causing water to leave the compound, but that would give the wrong product.

Offline chenbeier

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Re: Mechanism for lactone formation from 3-noneoic acid.
« Reply #1 on: April 03, 2021, 05:31:21 AM »
You have to much positive charges. In my opinion the H+ from the carboxyl group attack the double bond and on the second carbon there will a positive charge.  This charge react with negativ charge on  COO- to build the Lacton.

Offline Orcio_Dojek

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Re: Mechanism for lactone formation from 3-noneoic acid.
« Reply #2 on: April 03, 2021, 08:08:55 AM »
@chenbeier True, but after addition of H+ positive charge will located on the first, rather than second carbon atom.
« Last Edit: April 03, 2021, 09:22:01 AM by Orcio_Dojek »

Offline chenbeier

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Re: Mechanism for lactone formation from 3-noneoic acid.
« Reply #3 on: April 03, 2021, 10:07:15 AM »
Yes it is the first one (Markovnikov), otherwise the product can not be formed.

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