acid

BITSAT 2015 Guidance › Organic Chemistry questions › acid

H₃N⁺ (2)
N⁺H_3. (3)
COOH
(1)

WRITE ORDER OF ACIDITY FOR 1,2&3

a) 3>1>2 b) 1>2>3
c) 1>3>2 d) 2>1>3

#Chemistry #Organic Chemistry

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6 Answers

39

Pritish Chakraborty ·2010-09-21 08:26:16

I'm not being able to explain this on basis of conjugate bases...so I'll just be direct.
The -I effect of -COOH increases the acidity of -NH₃⁺ and the same for -NH₃⁺ on -COOH.
Now the inductive effect of (1) on (2) is stronger than that of (2) on (1). Hence (2) is more acidic than (1). (3) is obviously the weakest acid.
So the acidity order is 2 > 1 > 3.

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23

qwerty ·2010-09-22 03:01:53

i go with 1 > 2 > 3

carboxylic acids are more acidic than -NH₃+ ( as R-NH₂ are more basic than RCOO-)

so 1 will be most acidic

now due to -I of COOH grp , 2 is more acidic than 3

so 1 > 2 > 3

wats the ans given ?

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39

Pritish Chakraborty ·2010-09-22 06:33:00

Possibly so...even I'm a bit confused about this one.

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23

qwerty ·2010-09-22 22:43:33

i think 1> 2> 3 hi hona chahiye, harry ans to batade

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nihal raj ·2010-09-22 23:04:14

i will go with 1>2>3 becoz obviously due to -i effect 2>3 but -i effect is a weak effect and so much change in acidity of cooH should not take place.

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harrys ·2010-09-22 23:39:20

ans is 1>2>3

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