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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: organic chemistry
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Tanya_verma (5)

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The correct increasing acid strengths is
 
1. X>Z>Y
 
2.Z<X>Y
 
3.X>Y>Z
 
4 . Z>X>Y
    
dev_22oct (1326)

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ans is a
 
becoz -COOH is acidic group it has to be fst then Z which is close to acidic part then y
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tarinbansal (2432)

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Sir, R U sure about the answer?
I think the answer should be 4.

Although COOH is a strong acidic group, but +ve on N is quite unstable and it wud lose an H+ more easily and willingly than COOH.
So, Z shud be more acidic than COOH. And least acidic shud be Y becoz of high +I effect.
So the answer shud be Z>X>Y.

Am I wrong???

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ramkumar_november (1249)

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yes tha answer is 1..... i am sure....

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tarinbansal (2432)

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U maybe sure, but why am I wrong.

Charged species are always less stable than uncharged ones. So in any case, Z will try to lost a H+ faster and more willingly than X.

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It is during our darkest moments that we must focus to see the light.

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sandeepramesh (1090)

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no that isnt the case, mostly the COOH is way acidic than the NH3+.
this may be bcos the system is in eqbm (?)
 
but thats a sure fact
 
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varshavallig (793)

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yup its a) for sure
COOH is more acidic than N+.
Z is very close to an e- withdrawing group so e- density on Z's N+ is lesser than the other N+.
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iberis22 (547)

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COOH will be more acidic than protonated amine because the species that'll be formed after loss of proton will be resonance stabilized in case of acid.

Happines is like a butterfly;
the more you chase it,
the more it will elude you,
but if you turn you attention to other things,
it will come and sit softly on your shoulders...
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tarinbansal (2432)

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OK,
If U think that COOH is more acidic that NH3+, then tell me this-

Br-Ph-NH3+
Br-Ph-COOH
(both the groups are para to each other in both compounds)

Which is more acidic of both?

The quality of a person's life is in direct proportion to their commitment to excellence, regardless of their chosen field of endeavor.

It is during our darkest moments that we must focus to see the light.

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dev_22oct (1326)

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yes i m very much sure.
 
Ka for NH3+ is 10-10 whereas for -COOH its 10-3
 
NH3+CHRCOOH------>NH3+CHRCOO-  +  H+
 
 
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tarinbansal (2432)

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But sir Ka for -

Br-Ph-NH3+ = 3.9

Br-Ph-COOH =4.0

So, how to explain this????????

The quality of a person's life is in direct proportion to their commitment to excellence, regardless of their chosen field of endeavor.

It is during our darkest moments that we must focus to see the light.

''Darr sabko lagta hai, Gala sabka sookhta hai
Par, darr ke aage hi jeet hai''
To mountain dew piyo and IIT mai jaao. :P

For those giving JEE in 2008-

http://www.goiit.com/posts/list/about-iits-how-many-of-u-are-giving-hav-given-jee-08-52658.htm
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dev_22oct (1326)

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kb for aromatic amine is less (10-10) than that of  -COO- (10-9) thats y -COO- can be easily protonated then aromatic -NH2 ...or u can say that  -COO- is stronger base than aromatic -NH2.
 
so if its difficult to protonate AROMATIC -NH2 toh NH3+ fatak se dissociate ho jayega..ye aliphatic ka ikdam ulta hai...
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dev_22oct (1326)

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n if its not clear then refer aminoacid chemistry frm ne book!!!
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