Organic chemistry : cyclic alkane from esters

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SUMMARY

The discussion centers on the mechanism of forming cyclic alkanes from esters in organic chemistry. Participants suggest that hydrolyzing the ester under acidic conditions to produce a carboxylic acid is a necessary first step. The subsequent attack of hydroxide on the carbonyl is debated, with concerns raised about the stability of hydroxide in acidic environments. Additionally, the concept of decarboxylation is introduced as a potential factor in the reaction process.

PREREQUISITES
  • Understanding of ester hydrolysis mechanisms
  • Knowledge of acidic conditions in organic reactions
  • Familiarity with carbonyl chemistry
  • Basic principles of decarboxylation
NEXT STEPS
  • Study the mechanism of ester hydrolysis under acidic conditions
  • Research the formation of cyclic compounds from carbonyls
  • Learn about the role of hydroxide in acidic environments
  • Investigate decarboxylation reactions and their applications
USEFUL FOR

Students and educators in organic chemistry, particularly those focusing on reaction mechanisms involving esters and cyclic compounds.

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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