Official JEE Chemistry Revision Material: JEE Chemistry Aldehydes Ketones and Carboxylic Acids Notes Set 03
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Reactivity of Carboxylic Acid Derivatives
Nucleophilic acyl substitution reactivity: acid chloride > anhydride > ester > amide. A better leaving group and less resonance donation to the carbonyl make the derivative more reactive. Boiling points rise in the opposite way as hydrogen bonding grows: amide has the highest.
| Reaction | Result |
|---|---|
| Rosenmund reduction | Acid chloride with \(\ce{H2}\), \(\ce{Pd/BaSO4}\) gives an aldehyde |
| Ester with excess Grignard | Tertiary alcohol, two identical groups from the Grignard reagent |
| Ester with hydroxylamine | Hydroxamic acid, \(\ce{RCONHOH}\) |
| Esterification | Acyl-oxygen fission: acid loses OH, alcohol loses H |
| Hofmann bromamide | Amide with \(\ce{NaOBr}\) gives amine with one carbon less |
| Hell-Volhard-Zelinsky | \(\ce{P/Cl2}\) gives alpha-chloro acid, which is a stronger acid |
| Ketonic decarboxylation | Acid heated over \(\ce{MnO}\) gives ketone, loses \(\ce{CO2}\) and \(\ce{H2O}\) |
| Grignard plus \(\ce{CO2}\) | Carboxylic acid |
| Red P and HI | Reduces \(\ce{-COOH}\) to \(\ce{-CH3}\) |
1. Claisen condensation needs an ester with alpha hydrogen, so ethyl benzoate does not undergo it.
2. Schotten-Baumann reaction is benzoylation of phenols and alcohols with benzoyl chloride and alkali.
3. Sodium borohydride reduces ketones and aldehydes but not esters.
4. Formic acid is the only carboxylic acid that reduces Tollens' reagent.
5. Pyridinium chlorochromate stops oxidation of a primary alcohol at the aldehyde.
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