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CS-991 · Module O-XII4
Carboxylic Acids
Class XII · Organic Chemistry
🎥 Video lesson coming soon
⚖️ Acidity of Carboxylic Acids (-COOH)
Carboxylic acids are acidic because the carboxylate ion formed after losing H⁺ is resonance-stabilized, with the negative charge shared equally across both oxygen atoms.
Acidity is further affected by substituents on the carbon chain: electron-withdrawing groups (like -Cl, -NO₂) increase acidity by further stabilizing the negative charge, while electron-donating groups (like alkyl groups) decrease acidity.
🔧 Preparation
- Oxidation of primary alcohols or aldehydes
- Hydrolysis of nitriles (R-CN + H₂O → R-COOH)
- Hydrolysis of esters
- Grignard reagent + CO₂, followed by acidification
📊 Carboxylic Acid Derivatives & Reactivity
Carboxylic acids form several important derivatives, all sharing the acyl group. Their reactivity towards nucleophilic acyl substitution follows this order:
| Derivative | Relative Reactivity |
|---|---|
| Acid Chloride (R-COCl) | Most reactive |
| Anhydride (R-CO-O-CO-R) | High |
| Ester (R-COOR') | Moderate |
| Amide (R-CONH₂) | Least reactive |
📝 Practice MCQs
Q1: Carboxylic acids are acidic mainly because:
a) They contain oxygen b) The carboxylate ion is resonance-stabilized c) They are organic compounds d) They contain hydrogen
Show Answer
✅ b) The carboxylate ion is resonance-stabilized
Q2: Electron-withdrawing groups on a carboxylic acid:
a) Decrease acidity b) Increase acidity c) Have no effect d) Remove the -COOH group
Show Answer
✅ b) Increase acidity
Q3: Hydrolysis of a nitrile (R-CN) produces:
a) An alcohol b) A carboxylic acid c) An amine d) An ether
Show Answer
✅ b) A carboxylic acid
Q4: Which carboxylic acid derivative is the MOST reactive towards nucleophilic acyl substitution?
a) Amide b) Ester c) Acid chloride d) Anhydride
Show Answer
✅ c) Acid chloride
Q5: Which carboxylic acid derivative is the LEAST reactive?
a) Acid chloride b) Anhydride c) Ester d) Amide
Show Answer
✅ d) Amide
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