Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Aldehydes, Ketones and Carboxylic Acids

Question:

The acid strength of saturated aliphatic carboxylic acids depends mainly upon the inductive effect of the substituent and its position w.r.t. the -COOH group. Where as electron donating substituents tend to increase the acid strength. The acidic strength of aromatic carboxylic acids, on the other hand, depends upon both the inductive and the resonance effect of the substituents.

Which is the strongest acid among the following? 

Options:

CH3COOH

C6H5COOH

m-CH3OC6H4COOH

p-CH3OC6H4COOH

Correct Answer:

m-CH3OC6H4COOH

Explanation:

Since in C6H5COOH, the -COOH group is attached to more electronegative sp2 carbon of the C6H5 ring while in CH3COOH, it is attached to less electronegative  sp3 carbon of CH3 group, therefore, benzoic acid is stronger acid than acetic acid. Since methoxy group acts as an electron withdrawing group at meta position but electron donating group at para position, therefore, m-methoxy benzoic acid is even more acidic than benzoic acid.