How Many Molecules Are Needed for the Grignard Reaction with a Carbonate?

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SUMMARY

The discussion centers on determining the number of molecules required for the Grignard reaction with a carbonate. Participants suggest that 3 molecules are needed for complete reduction of the carbonate, while others propose that 5 molecules may be necessary when considering the involvement of anhydrides and alcohols. The conversation highlights the confusion between carbonates and anhydrides, emphasizing that carbonates should be treated similarly to esters in these reactions. Ultimately, the consensus leans towards 3 molecules for the carbonate reaction.

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  • Understanding of Grignard reagents and their reactivity
  • Knowledge of carbonate and anhydride chemistry
  • Familiarity with organic reaction mechanisms
  • Basic principles of acid-base chemistry, particularly regarding terminal alkynes
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Homework Statement
Ho wmany molecules of grignard reagent are consumed by 1 molecule of following compound-:
The complete question is in attempt at a solution.
Relevant Equations
Grignard reagent
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According to me the answer should be 5.I don't have the answer.I thought that 2 molecules will be used in anhydride,1 molecule in alcohol,2 molecule in cyclic ether.Can somebody tell the answer.
 
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Terminal alkynes are acidic and can react with Grignard reagents as well.
 
Ygggdrasil said:
Terminal alkynes are acidic and can react with Grignard reagents as well.
thanks for the information.Is my rest of the things correct.If it is,I would give my answer as 6.Please tell if I am wrong.
 
Why ether cleavage?
 
I’ll also point out that a hydroxyl and a nitro group on the same carbon would disproportionate to HONO and a ketone. So the compound in question wouldn’t even exist in the first place.
 
TeethWhitener said:
Why ether cleavage?
Sorry,I forgot that grignard reagent does not react with ether.I have another doubt now.For anhydride we will take 3 or 2 molecules,because anhydride consumes 3 grignard reagent to reduce completely and 2 to reduce partially.I think we should report it as 3.
 
TeethWhitener said:
I’ll also point out that a hydroxyl and a nitro group on the same carbon would disproportionate to HONO and a ketone. So the compound in question wouldn’t even exist in the first place.
ok it may happens but here i just have to tell the no. of molecules.
 
Physics lover said:
ok it may happens but here i just have to tell the no. of molecules.
My point is that it appears impossible to answer the question as written because the molecule can’t exist. It’s like asking what would happen if you had an aqueous solution with a pH of 20. That isn’t how pH works. Or in your case, that isn’t how molecules work.
 
Also, you don’t have an anhydride; you have a carbonate. Treat it the same way you would treat an ester, and then repeat the process.
 
  • #10
TeethWhitener said:
Also, you don’t have an anhydride; you have a carbonate. Treat it the same way you would treat an ester, and then repeat the process.
Sorry that was a typo.The carbonate would need 3 molecules.
So the answer should be 5.Is it correct?
 

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