First slide

Organic reagents and intermediates

Question

What is the correct increasing order of extent of deprotonation of the following acids in its aqueous solution?
(I) (CH₃)₂CHCOOH (II) CH₃CH₂COOH (III) Cl₂CHCH₂COOH (IV) CH₃CCl₂COOH

Moderate

A

I<II<III<IV
B

IV<III<I<II
C

I<IV<III<II
D

I<II<IV<III

Solution

Electron withdrawing group (Cl) increases acidic strength while electron donating group (CH₃) decreases acidic strength.
Also magnitude of inductive effect decreases drastically on increasing distance, IV is stronger acid than III.
Two methyl groups (in I) gives greater +I effect than one methyl group (in II), hence I is a weaker acid than II
Two -Cl from closer position in IV exert greater -I effect than the same from larger distance in III, hence IV is stronger acid than III.

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