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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 (1355)

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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 (3306)

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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 (1266)

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

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tarinbansal (3306)

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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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sandeepramesh (1245)

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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 (798)

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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 (575)

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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.

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tarinbansal (3306)

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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?

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dev_22oct (1355)

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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 (3306)

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But sir Ka for -

Br-Ph-NH3+ = 3.9

Br-Ph-COOH =4.0

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

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dev_22oct (1355)

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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 (1355)

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