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Application of Grignard reagent

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.

Homework Equations:

Grignard reagent
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According to me the answer should be 5.I dont 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.
 

Answers and Replies

Ygggdrasil
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Terminal alkynes are acidic and can react with Grignard reagents as well.
 
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.
 
TeethWhitener
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Why ether cleavage?
 
TeethWhitener
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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.
 
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.
 
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.
 
TeethWhitener
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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.
 
TeethWhitener
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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.
 
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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