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Basics of Organic Chemistry question

2022 · 25 Jun · Shift 1 · Q7
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Basics of Organic Chemistry question

2022 · 25 Jun · Shift 1 · Q7

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Phenol on reaction with dilute nitric acid, gives two products. Which method will be most efficient for large scale separation?
  1. A
    Chromatographic separation
  2. B
    Fractional Crystallisation
  3. C
    Steam distillation
  4. D
    Sublimation
View written solutionFree

Correct answer: C

  1. Identify the reaction products

Phenol reacts with dilute nitric acid to give a mixture of:

  • o-nitrophenol (2-nitrophenol)
  • p-nitrophenol (4-nitrophenol)

So we need a method to separate these two isomers efficiently on a large scale.

  1. Compare properties of the two products

The key difference is due to hydrogen bonding:

  • o-Nitrophenol shows intramolecular hydrogen bonding.

    • Because of this, its molecules are less associated with each other.
    • Hence it is more volatile.

  • p-Nitrophenol shows intermolecular hydrogen bonding.

    • This causes stronger association between molecules.
    • Hence it is less volatile.
  1. Choose the best separation method

Since o-nitrophenol is steam volatile while p-nitrophenol is not, the mixture can be separated efficiently by steam distillation:

  • o-nitrophenol distils over with steam.
  • p-nitrophenol remains behind.

This is the standard industrial/laboratory method for separating these two isomers.

  1. Check other options

  • A: Chromatographic separation

    • Useful analytically, but not most efficient for large scale separation.

  • B: Fractional crystallisation

    • Possible in some cases, but not the most efficient here compared with steam distillation.

  • D: Sublimation

    • Not the standard or efficient method for separating this pair.
  1. Final answer

Therefore, the most efficient method for large scale separation is:

C: Steam distillation\boxed{\text{C: Steam distillation}}C: Steam distillation​

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