Carboxylic Acid: Reactions

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Last updated 3:06 PM on 4/22/26
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9 Terms

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Acid-metal reaction (redox)

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Acid-alkali reaction (redox)

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Acid-carbonate reaction (redox)

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Why can carboxylic acids undergo nucleophilic substitution while aldehydes and ketones cannot?

  • C=O bond is polar as O is more electronegative

  • C=O(carboxylate) carbon carries the partial positive charge and susceptible to nucleophlic attack

  • the leaving group -OH- is a relatively stable species

For ketones and aldehydes:

  • H- and R-(alkyl grp) are unstable species and may not be eliminated easily

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Condensation reaction with alcohol

RnCs: few drops of concentrated H2SO4, heat

Note: reaction is slow and reversible

<p>RnCs: few drops of concentrated H<sub>2</sub>SO<sub>4</sub>, heat</p><p>Note: reaction is slow and reversible</p>
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Formation of acyl chlorides

RnCs: PCl5

Observations: Dense white fumes of HCl

Note:

  • good distinguishing test for alcohols

  • reaction has same products as the one with alcohol except the acyl chloride

<p>RnCs: PCl<sub>5</sub></p><p>Observations: Dense white fumes of HCl</p><p>Note: </p><ul><li><p>good distinguishing test for alcohols </p></li><li><p>reaction has same products as the one with alcohol except the acyl chloride</p></li></ul><p></p>
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Reduction to primary alcohols

RnCs: LiAlH4 (Lithium aluminium hydride)

Note:

  • cannot reduce carboxylic acids to aldehydes

  • weaker reducing agents such as NaBH4 or H2 with catalyst cannot reduce (FYI: lithium is more electronegative than boron, more negative charge is borne by H atom, making LiAlH4 a stronger RA)

<p>RnCs: LiAlH<sub>4</sub> (Lithium aluminium hydride)</p><p>Note:</p><ul><li><p>cannot reduce carboxylic acids to aldehydes</p></li><li><p>weaker reducing agents such as NaBH<sub>4</sub> or H<sub>2</sub> with catalyst cannot reduce (FYI: lithium is more electronegative than boron, more negative charge is borne by H atom, making LiAlH<sub>4</sub> a stronger RA)</p></li></ul><p></p>
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Oxidation of methanoic acid and ethanedioic acid

RnCs: KMnO4, diilute H2SO4, heat (under reflux)

Observation: Purple(MnO4- ) solution declourises(Mn2+)

Note:

  • other carboxylic acids have no easily oxidisable groups (it is alr very difficult to raise oxidation state +3 of C in -COOH to +4 in CO2)

  • methanoic acid has a C-H bond that can be oxidised

  • ethanedioic acid has an unusually weak C-C bond due to electron-wtihdrawing O atoms

<p>RnCs: KMnO<sub>4</sub>, diilute H<sub>2</sub>SO<sub>4</sub>, heat (under reflux)</p><p>Observation: Purple(MnO<sub>4</sub><sup>-</sup> ) solution declourises(Mn<sup>2+</sup>)</p><p>Note: </p><ul><li><p>other carboxylic acids have no easily oxidisable groups (it is alr very difficult to raise oxidation state +3 of C in -COOH to +4 in CO<sub>2</sub>)</p></li><li><p>methanoic acid has a C-H bond that can be oxidised</p></li><li><p>ethanedioic acid has an unusually weak C-C bond due to electron-wtihdrawing O atoms </p></li></ul><p></p>
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