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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: out of p-nitrophenol and 3,5-dinitrophenol which one is more acidic????
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ajain6691 (9)

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out of p-nitrophenol and 3,5-dinitrophenol which one is more acidic????


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paddy.dude (1154)

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the ans should be para nitro phenol coz .........there are 2 nitro groups in the second one but still due to the symmetry of para nitro phenol it will be more acidic
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cutepooja (441)

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no its 35 dinitro paddy dude u have applied the concept used for isomeric class they r non isomers where u just compare inductive effect and 35 has more -i

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cutepooja (441)

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correct me if i am wrong

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EXPECT MORE FROM URSELF THAN FRM OTHERS AS EXPECTATION FRM OTHERS HURTS U WHILE FROM UR SELF INSPIRES U A lot
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paddy.dude (1154)

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ya ur rght but para has more symmetry that 3,5
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smarsh (263)

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@pooja .....please tell




is the inductive effect of two no2 gps is greater than resonance as well as inductive effect of one no2 grp.......?


i think no.....so my ans will be:


paranitrophenol

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pujasinghtwinkle (120)

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i will agree wid 


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vnkt.swaroop (353)

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it is p-nitro phenol because in 3,5dinitrophenol both are electron withdrawing groups whic are present at m-positions.So it is stabilized.but in p-nitro phenol nitro withdraws the electron density over hydroxy group.so the answer is p-nitro phenol is more acidic than 3,5dinitro phenol.If i am wrong correct me and if i am correct please vote me.

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cutepooja (441)

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i dun know wether i am correct but from some valuable sourcesi have gathered info !
http://www.kayelaby.npl.co.uk/chemistry/3_9/3_9_7.html
see here it is given
for 3,5 dinitro phenol pka1 is 6.69
and p nitro phenol is 7.15 i jst appled the concepts i have studied and frm the help of some frnds i have gained that
higher the pka lesser is the acidic strength now tell me puja singhtwinkle and smarsh where am i makin flaw

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vnkt.swaroop (353)

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in p-nitro phenol the delocalization of electrons takes place which is not possible in 3,5dinitro phenol.Also due to the removal of electron charge over -OH a partial double bond forms between O&C.Hence it is easier to remove H in case of p-nitro phenol.

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smarsh (263)

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i think , there might be ortho effect taking place in 3,5 compound...........and we all know that ortho effect increases acidity



hp this is right and correct me if vice versa.




 


 

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sahilmadaan12 (810)

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see it is very tough to say by theortical concepts which is more acidic....bcoz we cant say will 2 strong inductive can overcome the 1 mesomeric effect or not......

but as said by pooja for 3,5 dinitro phenol pka1 is 6.69

and p nitro phenol is 7.15

so 3,5 dintrophenol is more acidic......

remember first practicals are done and then theories are given


SAHIL MADAAN
MECHANICAL ENGINEERING (B.Tech. 4 Yr)
IIT PATNA
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vnkt.swaroop (353)

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but the resonance and hybridization were not perfectly observed by any one.So how can you say that all theories are based on practicals.

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arg121 (34)

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ppl i waana no that does stability of the compound has to do any thin with the acidic nature of tho compounds bcuz p-nitro phenol is both resonance stabilised and it also has alt. double and single bond...or is it the stability of the radical formed which matters..


plz tell me..and correct if wrong...

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arg121 (34)

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