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Sourav posted an Question

September 13, 2020 • 17:08 pm

30 points

IIT JAM
Chemistry (CY)

Plz solve this.

2 Answer(s)

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S
Suman Kumar

Hope you find this helpful 😊🙏
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Ashutosh singh

A option is correct.
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After benzilic rearrangement, do nucleophilic substitution on Benzyl chloride, Sourav.
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i m not able to do that from 2nd step.
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from which oxygen should i act base and act phch2cl
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Have a look, Sourav! 😊 Tell me Kahan pe doubt h!
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i was asking why base didn't attack carboxylate ion and then carboxylate ion attack phch2cl2
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Dear Sourav, even if takes H from carboxylate, it is not strong enough nucleophile to attack benzyl chloride.
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it will remain in the form of O-Na+
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EtO- will abstract both H, but the nucleophile associated with carboxylate is less nucleophilic than second one.
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Hope you're getting what am trying to convey here, buddy.
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S
Suman Kumar Best Answer

option A is correct
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yes how
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Benzilic acid rearrangement you can do na
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yes.. plz explain from 2nd step.. i formed up to benzilic.
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Here EtO- is given in excess so both proton will be removed
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yes.. after that im having trouble
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But benzyl chloride is taken 1 equivalent so it attack oxide anion
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As carboxylate anion is more stable
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Sourav are you there
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sir there should be sodium carboxylate na?
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carboxylate anion will not attack
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yes Sourav
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im talking abt this.
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yes Sourav you are right
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only in one option there is both na and phch2cl used.. so i was having doubt.
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it's okay.
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understanding is more important
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Boddu rama krishna

c
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no answer is A
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T