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Question 48

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Consider the above reaction sequence and identify the major product $$P$$.

Solution

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  • Step (i) & (ii): Oxidation
    • Reactant: Ethanol ($$\text{CH}_3\text{CH}_2-\text{OH}$$)
    • Reagents: Jones' Reagent followed by $$\text{KMnO}_4$$ (Strong oxidizing agents)
    • Transformation: Primary alcohols are oxidized completely past the aldehyde stage into carboxylic acids with the same number of carbons.
    • Intermediate: Ethanoic acid ($$\text{CH}_3\text{COOH}$$)
  • Step (iii): Decarboxylation
    • Reactant: Ethanoic acid ($$\text{CH}_3\text{COOH}$$)
    • Reagents: $$\text{NaOH, CaO, }\Delta$$ (Soda lime)
    • Transformation: This combination undergoes a soda-lime decarboxylation reaction. It removes the entire $$-\text{COOH}$$ group as carbon dioxide ($$\text{CO}_2$$, which leaves as $$\text{Na}_2\text{CO}_3$$), shortening the carbon chain by one carbon atom.
    • Formula: $$\text{CH}_3\text{COOH} \xrightarrow{\text{NaOH, CaO, }\Delta} \text{CH}_4 + \text{Na}_2\text{CO}_3$$

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