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Understanding Triglycerols and Hydrolysis
Aug 14, 2024
Lecture Notes: Triglycerols and Ester Hydrolysis
Introduction to Triglycerols
Triglycerols are hydrolyzable lipids.
Can be broken down into smaller pieces via hydrolysis reactions.
Specifically, they undergo ester hydrolysis, breaking down the ester bonds.
Ester Hydrolysis
Ester: Carbon double-bonded to an oxygen and bonded to an OR group.
Ester hydrolysis involves breaking these ester bonds.
Can occur with either an acid or a base.
Base-Promoted Ester Hydrolysis
Focus is on base-promoted hydrolysis due to its implications for triglycerols.
Reaction Mechanism
Nucleophilic Addition
OH group (base) attacks the carbon.
Results in a carbanion tetrahedral intermediate.
Formation of Carboxylic Acid
OR group leaves as a strong base.
Formation of a carboxylic acid.
Acid-Base Proton Transfer
OR group picks up the proton.
Results in a carboxylate anion and an alcohol.
Results and Significance
This is the mechanism to start fat metabolism.
Enzymes called lipases facilitate this reaction in the body.
Reaction is crucial for energy metabolism from fat.
Saponification: An Application of Base-Promoted Ester Hydrolysis
Saponification: The process of making soap from triglycerols.
Use of a strong base like sodium hydroxide (NaOH).
Formation of anionic salt (soap) from carboxylate anion and sodium cation.
Properties of Soap
Long non-polar tail with a polar head (ionic bond).
Non-polar tail dissolves grease and oil.
Polar head dissolves in water, allowing soap to wash away dirt.
Conclusion
Base-promoted ester hydrolysis is important for metabolism and soap production.
Saponification refers specifically to this hydrolysis reaction in soap making.
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