Consider the acidity of the carboxylic acids:

(i) PhCOOH

(ii) o-NO_2C_6H_4COOH

(iii) p-NO_2C_6H_4COOH

(iv) m-NO_2C_6H_4COOH

Which of the following order is correct?

  • Option 1)

    i > ii > iii > iv

  • Option 2)

    ii > iv > iii > i

  • Option 3)

    ii > iv > i > iii

  • Option 4)

    ii > iii > iv > i.

 

Answers (1)

As we learnt in 

Effects of substituents on acidity of phenols -

1.  Electron withdrawing group like   -NO_{2},-CN,-X,-CHO

2.  Electron donating group like    -R,-OR,-NH_{2}

- wherein

1.  Increase the acidic strength of phenol.

2.  Decrease the acidic strength of phenol.

 

 -NO_{2} group increases the acid strength by showing electron withdrawing effects. O-nitro benzoate ion is stablilised by intramolecular H-bonding

Hence, ii>iii>iv>i


Option 1)

i > ii > iii > iv

This option is incorrect

Option 2)

ii > iv > iii > i

This option is incorrect

Option 3)

ii > iv > i > iii

This option is incorrect

Option 4)

ii > iii > iv > i.

This option is correct

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