Revision Notes for JEE Chemistry: Aldehydes Ketones And Carboxylic Acids
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Carboxylic Acids: Preparation
| Method | Reaction |
|---|---|
| Oxidation of primary alcohols or aldehydes | strong oxidants such as \( \ce{KMnO4} \) |
| Oxidation of alkylbenzenes | side chain to -COOH with \( \ce{KMnO4} \) |
| Hydrolysis of nitriles, amides, esters, acid chlorides | gives RCOOH |
| Grignard reagent + \( \ce{CO2} \) | then \( \ce{H3O+} \) gives acid with one more carbon |
| Hydrolysis of 1,1,1-trihaloalkanes | RCX3 gives RCOOH |
| Haloform reaction | methyl ketone with \( \ce{NaOX} \) gives RCOO- with one less carbon |
Properties and Acidity of Carboxylic Acids
Carboxylic acids form hydrogen-bonded dimers and so have higher boiling points than alcohols, aldehydes, ketones and esters of comparable mass. The lower acids are water soluble. They are acidic because the carboxylate ion is stabilised by resonance, with the charge shared equally by the two oxygens.
Electron-withdrawing groups near the -COOH group (halogens, \( \ce{NO2} \)) increase the acidity, and the effect grows as the group gets closer or more numerous: \( \ce{CCl3COOH} \) is much stronger than \( \ce{CH3COOH} \). Alkyl groups decrease acidity. Formic acid is stronger than acetic acid, and benzoic acid is stronger than acetic acid.
Carboxylic acids dissolve in \( \ce{NaHCO3} \) with brisk evolution of \( \ce{CO2} \); phenols do not.
Reactions of Carboxylic Acids
| Reaction | Product |
|---|---|
| Salt formation with metals, bases, carbonates | carboxylate salts |
| Esterification with alcohol and \( \ce{H+} \) (Fischer) | ester + water (reversible) |
| \( \ce{SOCl2} \), \( \ce{PCl5} \), \( \ce{PCl3} \) | acid chloride |
| \( \ce{P2O5} \) or heat | anhydride |
| \( \ce{NH3} \), then heat | amide |
| \( \ce{LiAlH4} \) or \( \ce{B2H6} \) | primary alcohol |
| Hell-Volhard-Zelinsky (\( \ce{X2} \)/red P) | 2-halo acid |
| Decarboxylation (soda lime) | alkane with one carbon less; beta-keto acids lose \( \ce{CO2} \) very easily |
| Kolbe electrolysis | alkane from two radicals |
Acid Derivatives and Their Reactivity
Acid chlorides, anhydrides, esters and amides all react by nucleophilic acyl substitution, in which the nucleophile adds to the carbonyl carbon and then the leaving group leaves. The reactivity order is acid chloride, then anhydride, then ester, then amide, decreasing with poorer leaving group and greater donation by the heteroatom.
| Derivative | Important reactions |
|---|---|
| Acid chloride | hydrolysis to acid; alcohol gives ester; ammonia gives amide; Rosenmund reduction to aldehyde; benzene/\( \ce{AlCl3} \) gives ketone |
| Anhydride | acylating agent (e.g. acetylation of salicylic acid to aspirin) |
| Ester | acid hydrolysis (reversible), alkaline hydrolysis (saponification); ammonolysis; \( \ce{LiAlH4} \) gives two alcohols; Claisen condensation gives beta-keto ester |
| Amide | hydrolysis; dehydration with \( \ce{P2O5} \) gives nitrile; \( \ce{LiAlH4} \) gives amine; Hofmann bromamide reaction (\( \ce{Br2/NaOH} \)) gives amine with one carbon less |
The Hofmann reaction passes through the N-bromoamide and an isocyanate; the carbonyl carbon is lost as carbonate. Amides are the least basic and the least reactive of the four derivatives, and they show N-H hydrogen bonding.
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