Organic chemistry : cyclic alkane from esters

AI Thread Summary
The discussion centers on the formation of cyclic alkanes from esters, with a focus on the proposed mechanism involving hydrolysis under acidic conditions. The initial suggestion involves converting the ester to a carboxylic acid, followed by a hydroxide attack on the carbonyl to form a ring structure, potentially resulting in an epoxide. However, participants note that hydroxide may not persist in acidic environments, questioning the viability of this approach. The importance of providing a specific example for clarity is emphasized, along with the consideration of decarboxylation as a relevant factor in the reaction process.
ephemeral1
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Hi, I am trying to understanding how esters can form a cyclic alkane. Could someone explain the mechanism for this? I would guess that we'd have to hydrolyze the ester in acidic condition to carboxylic acid. The hydroxide then can attack the carbonyl to form a ring, but that would give us an epoxide. Don't know if I am correct or what to do next. Please help. Studying for final. Thank you.
 
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Do you have a specific example in mind? Hydroxide probably won't exist that long in the presence of acid, in my opinion
 
sjb is right, specific example would be useful.
plus, I would think about decarboxylation.
 

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