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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: tautomerism ; THE ONE WITH HIGHER ENOLIC CONTENT
Forum Index -> Organic Chemistry like the article? email it to a friend.  
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x4 (300)

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hey guys just help me out with this




 


O        O


  \\      //


  C---C


  /       \


 C      C


   \     /


     C


 


 


      O           O


       ||            ||


C---C---C---C---C


               |


             CN


WHICH ONE WILL GIVE U A HIGHER ENOL CONTENT GIVE REASONS


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x4 (300)

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THE FIRST COMPOUND IS

CYCLOPENTAN 1,2 DIONE

COMPOUND TWO IS

PENTAN 3 NITRILE 2,4 DIONE .

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ashish_banga (927)

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SECOND ONE - AS IT FORMS A SIX MEMBERED RING BY CHELATION WHICH IS MORE STABLE







THE FIRST COMPOUND SHOWS LESS TAUTOMERISM

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x4 (300)

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CN group has tremendous -i effect decreasing electron cloud around carbonyl group thus increasing acidity of alpha hydrogen so iti is expected to be giving higher enol content .



ANSWER IS THE FIRST ONE




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tarinbansal (3304)

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Yes, the answer shud be first one.


Luk at the figure. After tautomerisation of the first compounds, u have-


1-H-Bonding


2-Hyperconjugation(of double bonds with circled Carbon)


 


Whereas in compound 2, after tautomerisation, u hav ONLY H-bonding.


 


And H-bonding+Hyperconjugation > Only H-bonding.


 


Hope U get it.



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anandghegde (1697)

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 hey there X4


u ask the question and u urself answer it?:huh:huh:huh:huh


"I a universe of atoms.......an atom in the universe"
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