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Question

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


(i) Cl3CCOOH>Cl2CHCOOH>ClCH2COOH

(ii) CH3CH2COOH>(CH3)2CHCOOH>(CH3)3CCOOH

(iii) F2CH2COOH>FCH2COOH>ClCH2COOH

A
(i) and (ii)
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B
(ii) and (iii)
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C
(i) and (iii)
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D
(i), (ii) and (iii)
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Solution

The correct option is D (i), (ii) and (iii)
The strength of the acid increases with the negative inductive effect of the electronegative group attached to it ( -I effect) and decreases with the presence of the positive inductive effect of electrons releasing group ( +I effect).
(i) More the number of electronegative atoms attached, more the acidic character of that acid.
Thus (i) is correct.
(ii) More the number of electron releasing group, less the acidic character of acid.
Thus, (ii) is correct.
(iii) Since F is more electronegative than Cl, thus (iii) is also correct.
Hence, All orders of acidity of carboxylic acid are correct.

Hence, the correct option is D

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