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Alcohols Phenols and Ethers question

2013 · Shift 1 · Q10
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Alcohols Phenols and Ethers question

2013 · Shift 1 · Q10

JEE AdvancedChemistryAlcohols Phenols and EthersMCQ+3 / −1
The compound that does NOT liberate CO2CO_2CO2​, on treatment with aqueous sodium bicarbonate solution, is
  1. A
    Benzoic acid
  2. B
    Benzenesulphonic acid
  3. C
    Salicylic acid
  4. D
    Carbolic acid (Phenol)
View written solutionFree

Correct answer: D

  1. Key principle

    A compound will liberate CO2CO_2CO2​ with aqueous sodium bicarbonate, NaHCO3NaHCO_3NaHCO3​, only if it is more acidic than carbonic acid.

    The reaction is: HA+NaHCO3→NaA+H2CO3HA + NaHCO_3 \rightarrow NaA + H_2CO_3HA+NaHCO3​→NaA+H2​CO3​ and then H2CO3→CO2+H2OH_2CO_3 \rightarrow CO_2 + H_2OH2​CO3​→CO2​+H2​O

    So, sufficiently acidic compounds such as carboxylic acids and strong sulphonic acids react with NaHCO3NaHCO_3NaHCO3​ to give brisk effervescence of CO2CO_2CO2​.

  2. Check each option

    A. Benzoic acid

    Benzoic acid is a carboxylic acid, so it reacts with sodium bicarbonate: C6H5COOH+NaHCO3→C6H5COONa+CO2+H2OC_6H_5COOH + NaHCO_3 \rightarrow C_6H_5COONa + CO_2 + H_2OC6​H5​COOH+NaHCO3​→C6​H5​COONa+CO2​+H2​O Hence, it does liberate CO2CO_2CO2​.

    B. Benzenesulphonic acid

    Benzenesulphonic acid, C6H5SO3HC_6H_5SO_3HC6​H5​SO3​H, is a strong acid. It reacts readily with sodium bicarbonate: C6H5SO3H+NaHCO3→C6H5SO3Na+CO2+H2OC_6H_5SO_3H + NaHCO_3 \rightarrow C_6H_5SO_3Na + CO_2 + H_2OC6​H5​SO3​H+NaHCO3​→C6​H5​SO3​Na+CO2​+H2​O Hence, it does liberate CO2CO_2CO2​.

    C. Salicylic acid

    Salicylic acid contains a carboxylic acid group and a phenolic −OH-OH−OH group. The carboxylic acid group reacts with sodium bicarbonate: Salicylic acid+NaHCO3→sodium salicylate+CO2+H2O\text{Salicylic acid} + NaHCO_3 \rightarrow \text{sodium salicylate} + CO_2 + H_2OSalicylic acid+NaHCO3​→sodium salicylate+CO2​+H2​O Hence, it does liberate CO2CO_2CO2​.

    D. Carbolic acid (Phenol)

    Phenol is much weaker than carboxylic acids and is less acidic than carbonic acid for this purpose. Therefore, phenol does not react with aqueous sodium bicarbonate.

    So, no CO2CO_2CO2​ is liberated.

  3. Conclusion

    The compound that does not liberate CO2CO_2CO2​ with aqueous sodium bicarbonate is: D. Carbolic acid (Phenol)\boxed{\text{D. Carbolic acid (Phenol)}}D. Carbolic acid (Phenol)​

  4. Comparison with stored correct answer

    Stored correct answer: D

    My derived answer: D

    Hence, they agree.

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