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Organic Chemistry

arushi  jain's Avatar
Cool goIITian

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27 Jun 2008 13:11:30 IST
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out of p-nitrophenol and 3,5-dinitrophenol which one is more acidic????
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out of p-nitrophenol and 3,5-dinitrophenol which one is more acidic????


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Halo's Avatar

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27 Jun 2008 13:45:51 IST
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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

Blazing goIITian

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27 Jun 2008 14:01:58 IST
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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

Blazing goIITian

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27 Jun 2008 14:02:28 IST
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correct me if i am wrong
Halo's Avatar

Blazing goIITian

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27 Jun 2008 14:04:40 IST
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ya ur rght but para has more symmetry that 3,5

Blazing goIITian

Joined: 16 Jun 2008
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27 Jun 2008 14:06:36 IST
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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

puja singh's Avatar

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27 Jun 2008 14:38:13 IST
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i will agree wid 


vnkt.swaroop..........
vnkt.  swaroop's Avatar

Blazing goIITian

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27 Jun 2008 15:28:44 IST
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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.


Blazing goIITian

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27 Jun 2008 15:39:11 IST
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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
vnkt.  swaroop's Avatar

Blazing goIITian

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27 Jun 2008 15:47:27 IST
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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.


Blazing goIITian

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27 Jun 2008 15:47:43 IST
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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.




 


 

sahil madaan's Avatar

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27 Jun 2008 16:22:36 IST
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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

vnkt.  swaroop's Avatar

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27 Jun 2008 21:30:43 IST
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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.

gaurang's Avatar

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27 Jun 2008 23:36:28 IST
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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...

gaurang's Avatar

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28 Jun 2008 00:09:25 IST
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hey ppl plz tel me whether im wrong or right...plz


Blazing goIITian

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28 Jun 2008 00:16:33 IST
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acidic nature has nothing to do with the stability of the compound..


the stability of a compound is determined by various factors and acidity is none of the factors


 

gaurang's Avatar

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28 Jun 2008 00:25:48 IST
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but afet a proton is removed , if the radical is stable then the com pound would be highly acidic then why doesnt the stability matter...


plz reply


Blazing goIITian

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28 Jun 2008 00:42:35 IST
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acidic nature of generally O-H COMPOUNDS IS SEEN BY THE EASE WITH WHICH THE RUPTURE OF O-H BOND TAKES PLACE.......THIS CAN BE SEEN BY THE ELECTRON DISPLACEMENT EFFECTS AND THE OTHER WAY TO C WHTHER THE COMPOUND IS ACIDIC OR NOT IS TO REMOVE A PROTON AND CHECK FOR STABILITY OF COMPOUND SO FORMED.............................THIS IS THE WAY OF DETERMINING ACIDIC NATURE..........................................................................................................COMES TO THE STABILITY OF THE COMPOUND ................STABILITY OF A COMPOUND IS DETERMINED BY ITS REACTIONS.......................///.REACTIVE.....-UNSTABLE AND VICE VERSA......


 


 


""ACIDIC NATURE CAN BE SEEN BY STABILITY OF COMPOUND SO FORMED BUT STABILITY OF THE COMPOUND CANNNOT BE PREDICTED FULLY BY ITS ACIDIC OR BASIC NATURE"

gaurang's Avatar

Cool goIITian

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28 Jun 2008 00:50:18 IST
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thanks...


 


can u ans another ques which i have asked reguarding nucleophile




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