Simun Mishra posted an Question
July 26, 2020 โ€ข 14:18 pm 30 points
  • IIT JAM
  • Chemistry (CY)

In this reaction how can isocynide form ...?it is primary amine na the product of the reaction?

2 Answer(s) Answer Now
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    Dinesh khalmaniya 1 Best Answer

    yes, addition of H2O on isocyanate gives amine

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    just like it

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    here Azide ion is nucleophile and attack on carbony carbon. now wolff rearrangement takes place and isocyanate is formed

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    got it??

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    wolff rearrangment ?

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    yes, like this..

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    yes sir but here how migratory aptitude works

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    which group migrate first decided by migratory aptitude

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    you have to remember migratory aptitude order.

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    sir here NH why not attached to the C having 3 Hydrogen

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    because migratory aptitude of benzene ring is more than CH3

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    ohhh I got it sir

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    sir in which case the migratory aptitude is applied

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    wait..

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    ok sir

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    it will work in asymmetric ketone. if both the groups are different then check the migratory aptitude. NH adds on those groups side of C=O which have more migratory aptitude

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    got it??

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    check this example

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    now got it??๐Ÿ˜Š

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    yes sir I m asking that like in Baeyer villiger oxidation and this schmidt rearrangment ...like that in which cases it use

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    only for ketone or any other compounds

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    only in asymmetric ketone

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    ether ...ester ....and in alkene ..?is it works or not

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    no, simun apply it only on ketone

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    no sir I m not asking about this reaction I m generally asking migratory aptitude rule works on which which compounds

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    all the rearrangement have different migratory aptitude. so accordingly we will apply according to that rearrangement

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    ohhh so migratory aptitude is diff for diff reaction ?

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    yes yes๐Ÿ˜Š๐Ÿ˜Š

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    ohhh...finally my confusion is clear ...tq sir ..๐Ÿ™๐Ÿ™

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    you welcome ๐Ÿ˜Š

  • Suman Kumar best-answer

    Yes Simun after H2O attack final product will be amine

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    Isocyanate is formed as an intermediate

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    yes sir

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    here migratory aptitude how can work

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    Migratory aptitude is experimentally determined. With little change in the subtrate they see the product formed and accordingly they have given the order of migratory aptitude

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    Have you studied migratory aptitude in Bayer villiger oxidation

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    See the marked step. There is migration of R.

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    yes

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    Migration step is called Wolff rearrangement Simun

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    ok sir

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