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Topic: What is the product of the reaction.  (Read 648 times)

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Offline sharbeldam

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What is the product of the reaction.
« on: January 20, 2021, 11:25:53 AM »
Ofcourse not an exam , Im not a student. please tell me if my way of thinking is correct.

they want me to find the main product of this reaction after a long time has passes, so basically I think in this question they wanted us to figure which is the best leaving group/strongest base, my question is this, if the R group connected to the -OCO larger, does that mean that the base is strongest since the R group is more donating because it's larger? or does the size not matter at all? if it doesn't matter i have no way of knowing which will be the best nucleophile and stay for the longest time.

My answer would be B
« Last Edit: January 20, 2021, 02:07:39 PM by sharbeldam »
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Offline rolnor

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Re: What is the product of the reaction.
« Reply #1 on: January 20, 2021, 03:00:44 PM »
If you consider this being a equlibrium, what would then happen with this large excess reagent in the end? Electronic effects are minor I would say.

Offline sharbeldam

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Re: What is the product of the reaction.
« Reply #2 on: January 20, 2021, 03:22:14 PM »
can you be more clear? what happens with the reagent?

 does it react again with the product that i drew? there are so many possibilities :/
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Online Babcock_Hall

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Re: What is the product of the reaction.
« Reply #3 on: January 20, 2021, 04:41:37 PM »
If you consider this being a equlibrium, what would then happen with this large excess reagent in the end? Electronic effects are minor I would say.
Indeed, mass action might have the last word.

Offline sharbeldam

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Re: What is the product of the reaction.
« Reply #4 on: January 20, 2021, 04:45:52 PM »
if i understand the chemists language correctly, should D be the answer?
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Offline sharbeldam

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Re: What is the product of the reaction.
« Reply #5 on: January 21, 2021, 05:01:51 PM »
someone?
tell me if this is right? the fourth compound should be the answer yes?
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Offline AWK

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Re: What is the product of the reaction.
« Reply #6 on: January 21, 2021, 05:26:42 PM »
There is no clear answer to your question.
The reaction will undoubtedly be equilibrium and fairly slow. With a large excess of the propionate soluble salt, preferentially mixed anhydrides will be formed initially. The anhydrides will be formed later. I believe that after equilibrium is achieved, symmetrical propionic anhydride will be in advantage.
But the reaction can be carried out under different conditions of pressure, temperature with different salts of propionic acid, e.g. using trimethylammonium propionate and heating to about 100 ° C under a pressure of about 0.2-0.3 Atm, I would expect that acetic anhydride and trimethylammonium acetate would be removed from the system by slow distillation and the reaction will end there.
This reaction is extremely badly designed. There is no good method to analyze it and there is no good method to quantify it well.
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