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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: tautomerism
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manja (0)

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give me the tautomer of geraniol


 


    
x4 (302)

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ya manja look in this qn. the compound exhibits hyperconjugation effect so tautomerism is possible and by shifting the double bonds due to this hyperconjugation effect u can create a number of different tautomers it is not just one keto tautomer that u can create cozu have two double bonds so for each applying hyperconjugation u can have a number of structures .




 


the most stable one however shud be -




 


 

SEE THIS IS THE MOST STABLE FORM OF GERAGINOL  B COZ U SEE ITS A CONJUGATED SYSTEM SO THERE IS +M EFFECT HENCE THE H ATTACHED TO O IS MOST ACIDIC IN THIS CASE SO THIS FORM IS MOST STABLE ENOL FORM DRAW THE KETO FORM OF THIS  


 


            C                        CH3


             ||                          |                   ..


H3C---C---C==C---C==C---C==C---O-H                    MOST STABLE ENOL FORM



 



            C                         CH3


             ||                           |                   


H3C---C---C==C---C==C---C---C==O                          KETO FORM .


                                                 |


                                                H      


 



 


 PLEASE CORRECT ME IF I HAVE MADE ANY MISTAKE


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x4 (302)

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please see if u can migrate the h to many more positions wherever u see the double bond now some champions must tell me where to migrate h so please check 4 thecorrect ness of the final answr.

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angel.angelina (24)

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X4  YOU HAVE DONE A CORRECT JOB . BUT YOU ARE ASKING THAT YOU CAN TRANSFER  H  TO ANY OTHER DOUBLE BOND  .  HERE IN TAUTOMERISM ONLY H ATTACHED TO A FUNCTIONAL  GROUP CONTRIBUTES  WHICH WE CALL alpha H .  CHO GROUP IS ATTACHED TO A DOBLE BONDED C HAVING 1 alpha H  .HENCE WE WILL CONCENTRATE ON IT ONLY.


 

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