CBSE Class 12 · 2008 · Delhi · Aldehydes Ketones and Carboxylic AcidsVery Short Answer

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Arrange the following compounds in increasing order of their acid strengths:
(CH₃)₂CHCOOH, CH₃CH₂CH(Br)COOH, CH₃CH(Br)CH₂COOH.

Answer: (CH₃)₂CHCOOH < CH₃CH(Br)CH₂COOH < CH₃CH₂CH(Br)COOH.

Solution

Electron-withdrawing Br strengthens the acid, and more so the closer it sits to –COOH (−I falls off with distance); the alkyl +I of the first weakens it:

(C H_{3})_{2} CHCOOH < C H_{3} CH (Br) C H_{2} COOH < C H_{3} C H_{2} CH (Br) COOH

CBSE Class 12 Board · 2008 · Delhi · Subjective

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