Question
Download Solution PDFThe correct order of decreasing acidity of the following aliphatic acids is:
Answer (Detailed Solution Below)
Detailed Solution
Download Solution PDFCONCEPT:
Acidity of Aliphatic Carboxylic Acids
- The acidity of carboxylic acids is influenced by the nature of the substituents attached to the carbon chain.
- Electron-withdrawing groups increase acidity by stabilizing the conjugate base (carboxylate ion), while electron-donating groups decrease acidity by destabilizing the conjugate base.
- Formic acid (HCOOH) is the most acidic among simple aliphatic carboxylic acids because it has no alkyl groups, which are electron-donating by nature.
- As the size of the alkyl group increases, the electron-donating inductive effect (-I effect) becomes stronger, making the acid weaker.
EXPLANATION:
- HCOOH (formic acid): No alkyl group, highest acidity.
- CH₃COOH (acetic acid): One methyl group (-CH₃), moderately acidic. (+I)
- (CH₃)₂CHCOOH (isobutyric acid): Two methyl groups attached to the same carbon, further decreases acidity. ( two +I)
- (CH₃)₃CCOOH (pivalic acid): Three methyl groups attached to the same carbon, lowest acidity due to strong electron-donating effect. (three +I)
- The correct order of decreasing acidity is:
HCOOH > CH₃COOH > (CH₃)₂CHCOOH > (CH₃)₃CCOOH
Therefore, the correct answer is Option 3: HCOOH > CH₃COOH > (CH₃)₂CHCOOH > (CH₃)₃CCOOH.
Last updated on Jun 16, 2025
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