Can Oxygen Labeling Prove the Esterification Reaction Mechanism in P&D Lab?

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In summary, Student A believes that the -OH group from the ethanoic acid combines with the H from the ethanol to form an ester. To test this hypothesis, they suggest using O-18 labeled water in the esterification reaction and analyzing the resulting ester with a mass spectrometer. However, concerns about separating the ester from water arise, and it is suggested to use a GC-MS or diluting in solvent and drying with Na2SO4 before analysis.
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rock.freak667
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Homework Statement


Some students had a disagreement about the esterification reaction between ethanol and ethanoic acid. Student A feels that the -OH group from the acid combines with the H from the alcohol functional group.
Suggest a hypothesis for his feeling and design a lab to test the hypothesis.

Homework Equations



[tex]C_2H_5OH + CH_3COOH \rightarrow CH_3COOC_2H_5 + H_2O[/tex]

The Attempt at a Solution



Ok, well my idea would be to somehow label the oxygen on either the acid or the alcohol. I chose O-18. But I am not sure what steps are taken to actually label the oxygen like that.
Then react the two, extract the ester formed, and run it through a mass spectrometer. But when the ester is formed, it is formed in a layer with water,how do I separate the two? (Simple pipette and extract until it looks like all has been pipetted?)
 
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  • #2
rock.freak667 said:

Homework Statement


Some students had a disagreement about the esterification reaction between ethanol and ethanoic acid. Student A feels that the -OH group from the acid combines with the H from the alcohol functional group.
Suggest a hypothesis for his feeling and design a lab to test the hypothesis.

Homework Equations



[tex]C_2H_5OH + CH_3COOH \rightarrow CH_3COOC_2H_5 + H_2O[/tex]

The Attempt at a Solution



Ok, well my idea would be to somehow label the oxygen on either the acid or the alcohol. I chose O-18. But I am not sure what steps are taken to actually label the oxygen like that.

You can buy O-18 labelled water. Any help?

Then react the two, extract the ester formed, and run it through a mass spectrometer. But when the ester is formed, it is formed in a layer with water,how do I separate the two? (Simple pipette and extract until it looks like all has been pipetted?)
If you injected it into a GC-MS you wouldn't have to separate anything...
 
  • #3
Ah well all I need to say is that I labelled the oxygen. So no need to elaborate on it.
But apparently I must use the normal mass spec. I know so I would need to extract it somehow. I'm thinking steam distillation.
 
  • #4
rock.freak667 said:
I'm thinking steam distillation.
Not a good idea in the presence of either an acid or base. Maybe diluting in solvent and drying with Na2SO4 after washing with bicarb.
 

What is esterification?

Esterification is a chemical reaction in which an alcohol and an acid react to form an ester and water. This reaction is commonly used in organic synthesis and in the production of fragrances, flavors, and various other chemicals.

What is the purpose of a P&D lab esterification?

The purpose of a P&D (process and development) lab esterification is to optimize and develop a synthetic process for producing a specific ester compound. This involves testing different reaction conditions, catalysts, and purification methods to determine the most efficient and effective way to produce the desired ester.

What are some common challenges in P&D lab esterification?

Some common challenges in P&D lab esterification include low yields, difficulty in separating the ester from the reaction mixture, and the formation of unwanted side products. These challenges can be addressed by carefully optimizing reaction conditions and purification methods.

What techniques are commonly used in P&D lab esterification?

Common techniques used in P&D lab esterification include reflux, distillation, chromatography, and spectroscopy. Reflux is used to heat the reaction mixture and drive the reaction forward, while distillation is used to separate the ester from the reaction mixture. Chromatography and spectroscopy are used for purification and analysis of the resulting ester product.

Why is P&D lab esterification important in the field of chemistry?

P&D lab esterification is important in the field of chemistry because it allows for the development and optimization of new synthetic processes for producing esters. These compounds have a wide range of applications in various industries, making them valuable products for commercial use. Additionally, the techniques and skills learned in P&D lab esterification can be applied to other areas of chemical research and production.

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