Place the following in the correct order of acidic nature CH - C - COOH- CH2 - CH - COOH - CH3 CH2COOH I II III

Higher the stability of the conjugate base (carboxylate ion) more the acidic strength. (I) HC ≡sp↑C COO^ (II) CH_2 = sp^2↑CH COO^ (III) CH_3 sp^3↑C ...

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Standard XII

Chemistry

Organic Compounds

Place the fol...

Question

Place the following in the correct order of acidic nature $C H \equiv C - C O O H; C H_{2} = C H - C O O H; C H_{3} C H_{2} C O O H$
(I) (II) (III)

I > II > III

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III > II > I

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II > I > III

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I > III > II

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Solution

The correct option is A I > II > III
As more stable is conjugate base (carboxylate ion) more is acidic strength.
$(I) H C \equiv C ↑ s p - C O O^{-} (I I) C H_{2} = C H ↑ s p^{2} - C O O^{-} (I I I) C H_{3} - C H_{2} ↑ s p^{3} - C O O^{-}$
% s-character $\propto$ Electronegativity of carbon $\propto$ stability of anion.
$Thus Stability of conjugate base is I I I < I I < I$
$and hence, correct order of acidity is I I I < I I < I$

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Similar questions

Q. Place the following in the correct order of acidic nature

C H \equiv C - C O O H; C H_{2} = C H - C O O H; C H_{3} C H_{2} C O O H

(I) (II) (III)

Q. Arrange the acids

C H_{3} C H_{2} C O O H

(I)

C H_{2} = C H - C O O H

(II) and

H C \equiv C - C O O H

(III) in order of decrease in acidity :

Q. Which is the stronger acid in each of the following pairs?
(i)

C H_{3} - C O O H

and

C H_{2} = C H - C O O H

(ii)

C_{6} H_{5} - C O O H

and

C_{6} H_{5} - C H_{2} - C O O H

(iii)

C H_{3} - C H_{2} - C O O H

and

C H_{3} - C H | O H - C O O H

Q. Decreasing order of acidic nature of following is:

(i) H C O O H (i i) P h - C O O H (i i i) P h - O H

(i v) C H_{3} C O O H

Q. Which of the following is the correct order of acidity of a carboxylic acid?

(i)

{C l}_{3} C C O O H > {C l}_{2} C H C O O H > C l {C H}_{2} C O O H

(ii)

{C H}_{3} C H_{2} C O O H > {(C H}_{3})_{2} C H C O O H > {(C H}_{3})_{3} C C O O H

(iii)

F_{2} C H_{2} C O O H > F C H_{2} C O O H > C l {C H}_{2} C O O H

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Organic Compounds

Standard XII Chemistry

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Place the following in the correct order of acidic nature CH≡C−COOH;CH2=CH−COOH;CH3CH2COOH (I) (II) (III)

Place the following in the correct order of acidic nature $C H \equiv C - C O O H; C H_{2} = C H - C O O H; C H_{3} C H_{2} C O O H$
(I) (II) (III)