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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: ACIDITY 2
Forum Index -> Organic Chemistry like the article? email it to a friend.  
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x4 (300)

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NOW WHICH ONE OF THESE IS MORE ACIDIC ?


 


 


         CF3


           |


CF3 – C -- OH


           |


         CF3


 


 


 


         CF3


           |


   H – C -- OH


           |


         CF3


 


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donnowatnametochoose (34)

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Is it the first? since the ion will be stabilized by the inductive effect of the three CF3


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x4 (300)

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NOOOOOOPPPPPP ITS THE SECOND .



SEE I ALLWAYS GIVE U A 50 % PROBABILITY OF GETTING IT RIGHT .


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ashgirl (1429)

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steric hinderance??


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arpan1 (665)

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its the same reason i mentioned in ur nudge book x4


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cutepooja (441)

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see fluorine is electron withdrawing in nature(due to e vity)
so there are 3 fluorine per carbon indirectly attached to
C---OH so cause this bond more polar furthur causin
O~H bond more polar
in first case 9 f
in second 6
so addn effect of 3 f
so 1st one more acidic

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x4 (300)

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@ ASHGIRL

I GUESS STERIC HINDRANCE IS HIGHER IN THE FIRST CASE THAN 2ND CASE SO BY THAT 1ST ONE IS MORE ACIDIC .

@ARPAN

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arpan1 (665)

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thanks for the comments


 


in case u need  more detailed ans , nudge me


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x4 (300)

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TAKE INTO CONSIDERATION THE 3D PICTURE DONT U SEE EXTENSIVE HYDROGEN BONDING IN TWO ?

SEE THE F-F ATOM REPULSION IS HIGHER IN TWO FORCING THE CF3 TO GO MORE TOWARDS THE OH GREOUP INCREASING THE SYTRENGTH OF HYDROGEN BOND

BUT IN ONE THE CF3 ARE FEE TO ORIENT SUCH THAT H BONDING IS NOT POSSIBLE .

F-F REPULSION IS MORE THAN F-O REPULSION COZ F IS MORE E.N THAN O

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arpan1 (665)

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what makes u think f-f repulsion is greater in 2


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x4 (300)

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SEE IF U HAVE







THEN F-F REPULSION IS WAY BEYOND F-O REPULSION







 


      F


       |


F—C—OH     


       |


      F


          


            F


           /                                    IT WILL ORIENT LIKE  THIS


F—C—OH


        \


          F


 




 






 


         APPLY SIMILAR THING HERE


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arpan1 (665)

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what i am asking is that why do u think f-f repulsion is gr8er in second than in first


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x4 (300)

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IN FIRST ONE THIS IS WHAT HAPPENS


      F


       |


H—C—OH                                                              HERE THST ADDITIONAL F IS NOT THWERE TO OPPOSE IT


       |


      F


          


        F   


          \


H—C—OH


       /


     F


IT ORIENTS LIKE THIS


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