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Alcohols Phenols and Ethers question

2022 · 26 Jun · Shift 1 · Q19
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Alcohols Phenols and Ethers question

2022 · 26 Jun · Shift 1 · Q19

JEE MainChemistryAlcohols Phenols and EthersNumerical+4 / −1
Compound 'P' on nitration with dil. HNO3HNO_3HNO3​ yields two isomers (A) and (B). These isomers can be separated by steam distillation. Isomers (A) and (B) show the intramolecular and intermolecular hydrogen bonding respectively. Compound (P) on reaction with conc. HNO3HNO_3HNO3​ yields a yellow compound 'C', a strong acid. The number of oxygen atoms is present in compound 'C' ‾\underline{\hspace{2cm}}​.
Numerical answer
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Correct answer: 7

  1. Identify compound PPP from the nitration behavior

A compound which on nitration with dilute HNO3HNO_3HNO3​ gives two isomers that can be separated by steam distillation, where one shows intramolecular hydrogen bonding and the other intermolecular hydrogen bonding, is phenol.

On mononitration of phenol, we get:

  • ooo-nitrophenol: shows intramolecular H-bonding
  • ppp-nitrophenol: shows intermolecular H-bonding

These can be separated by steam distillation because ooo-nitrophenol is steam volatile.

So, P=phenolP = \text{phenol}P=phenol

  1. Reaction of phenol with concentrated HNO3HNO_3HNO3​

Phenol with concentrated nitric acid gives 2,4,6-trinitrophenol, commonly called picric acid.

The reaction is: Phenol→conc.HNO32,4,6-trinitrophenol\text{Phenol} \xrightarrow[\text{conc.}]{HNO_3} \text{2,4,6-trinitrophenol}PhenolHNO3​conc.​2,4,6-trinitrophenol

This is a yellow compound and a strong acid, matching the description of compound CCC.

  1. Count oxygen atoms in compound CCC

Picric acid = 2,4,6-trinitrophenol

Its structure contains:

  • one phenolic −OH-OH−OH group ⇒1\Rightarrow 1⇒1 oxygen
  • three nitro groups (−NO2)(-NO_2)(−NO2​), each containing 222 oxygen atoms

So total oxygen atoms: 1+3×2=71 + 3 \times 2 = 71+3×2=7

  1. Final answer

The number of oxygen atoms in compound CCC is: 7\boxed{7}7​

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