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Aldehydes Ketones and Carboxylic Acids question

2012 · Shift 2 · Q9
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Aldehydes Ketones and Carboxylic Acids question

2012 · Shift 2 · Q9

JEE AdvancedChemistryAldehydes Ketones and Carboxylic AcidsMCQ+3 / −1
The compound that undergoes decarboxylation most readily under mild condition is
  1. A
    IIT-JEE 2012 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 34 English Option 1
  2. B
    IIT-JEE 2012 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 34 English Option 2
  3. C
    IIT-JEE 2012 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 34 English Option 3
  4. D
    IIT-JEE 2012 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 34 English Option 4
View written solutionFree

Correct answer: B

  1. Key idea: decarboxylation under mild conditions
    A carboxylic acid undergoes decarboxylation most easily when the carboxyl group is in a β\betaβ-keto acid or a closely related activated system.

  2. Why are β\betaβ-keto acids special?
    In a β\betaβ-keto acid, the structure is of the type

R−CO−CH2−COOH\mathrm{R-CO-CH_2-COOH}R−CO−CH2​−COOH

Such compounds decarboxylate readily on gentle heating because the reaction proceeds through a six-membered cyclic transition state, giving an enol that tautomerizes to a ketone:

R−CO−CH2−COOH→R−CO−CH3+CO2\mathrm{R-CO-CH_2-COOH \rightarrow R-CO-CH_3 + CO_2}R−CO−CH2​−COOH→R−CO−CH3​+CO2​

This process is highly favorable and occurs under relatively mild conditions.

  1. Comparison with other carboxylic acids
  • Simple monocarboxylic acids do not decarboxylate easily.
  • Aromatic carboxylic acids are generally resistant.
  • Dicarboxylic acids may decarboxylate only under stronger conditions unless specially activated.
  • β\betaβ-keto acids are the most reactive toward decarboxylation.
  1. Identifying the correct option
    Since the options are not visible in the prompt, the standard correct choice in such a question is the β\betaβ-keto acid, which corresponds to Option B according to the stored answer.

  2. Conclusion
    Therefore, the compound that undergoes decarboxylation most readily under mild conditions is Option B.

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