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Alcohols Phenols and Ethers question

2008 · Shift 0 · Q16
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Alcohols Phenols and Ethers question

2008 · Shift 0 · Q16

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
Phenol, when it first reacts with concentrated sulphuric acid and then with concentrated nitric acid, gives
  1. A
    2,4,6-trinitrobenzene
  2. B
    o-nitrophenol
  3. C
    p-nitrophenol
  4. D
    nitrobenzene
View written solutionFree

Correct answer: B

  1. First reaction: phenol with concentrated sulphuric acid

Phenol undergoes sulphonation with concentrated sulphuric acid. The −OH-OH−OH group is ortho/para directing, so phenol forms mainly:

o-hydroxybenzenesulphonic acidandp-hydroxybenzenesulphonic acido\text{-hydroxybenzenesulphonic acid} \quad \text{and} \quad p\text{-hydroxybenzenesulphonic acid}o-hydroxybenzenesulphonic acidandp-hydroxybenzenesulphonic acid

  1. Second reaction: treatment with concentrated nitric acid

Now nitration occurs. In this process, the sulphonic acid group (−SO3H)(-SO_3H)(−SO3​H) is a meta-directing group, while −OH-OH−OH is ortho/para directing.

A well-known result is that sulphonation followed by nitration of phenol is used to control substitution and gives mainly ortho-nitrophenol after replacement/removal of the sulphonic acid group.

Thus, the product asked in standard JEE chemistry is:

o-nitrophenolo\text{-nitrophenol}o-nitrophenol

  1. Checking the options
  • A: 2,4,62,4,62,4,6-trinitrobenzene — incorrect; this is not formed here.
  • B: ooo-nitrophenol — correct.
  • C: ppp-nitrophenol — not the expected product in this sequence.
  • D: nitrobenzene — incorrect; phenol does not lose its −OH-OH−OH group.
  1. Final answer

The correct option is:

B: o-nitrophenol\boxed{\text{B: } o\text{-nitrophenol}}B: o-nitrophenol​

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