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Percentage Increase of Oxygen in Nitration Product of Phenol

One mole of phenol is treated with dilute HNO3\text{HNO}_3 at 298 K298\text{ K} to give a mixture of products. The mixture is separated by steam distillation. The steam volatile compound (X) is separated. The increase in percentage of oxygen in (X) with respect to phenol is __________ ×101%\times 10^{-1}\% (Given molar mass in g mol1\text{g mol}^{-1} H:1,C:12,N:14,O:16\text{H}: 1, \text{C}: 12, \text{N}: 14, \text{O}: 16)

Official Numerical Answer175

Topics & Concepts

Step-by-Step Solution

To find the increase in the percentage of oxygen in compound (X)(\text{X}) with respect to phenol, we follow these steps:

Step 1: Identify the Steam Volatile Compound (X)

When phenol is treated with dilute HNO3\text{HNO}_3 at 298 K298\text{ K}, it undergoes mononitration to yield a mixture of oo-nitrophenol and pp-nitrophenol:

Phenol (C6H5OH)dil. HNO3, 298 Ko-nitrophenol+p-nitrophenol\text{Phenol } (\text{C}_6\text{H}_5\text{OH}) \xrightarrow{\text{dil. }\text{HNO}_3,\ 298\text{ K}} \text{o-nitrophenol} + \text{p-nitrophenol}

  • oo-Nitrophenol possesses intramolecular hydrogen bonding, which makes it steam volatile.
  • pp-Nitrophenol possesses intermolecular hydrogen bonding, making it non-volatile in steam.

Thus, the steam volatile compound (X)(\text{X}) is oo-nitrophenol (C6H5NO3\text{C}_6\text{H}_5\text{NO}_3).


Step 2: Calculate the Percentage of Oxygen in Phenol

  • Molecular Formula of Phenol: C6H6O\text{C}_6\text{H}_6\text{O}
  • Molar Mass of Phenol: Molar Mass=(6×12)+(6×1)+(1×16)=72+6+16=94 g mol1\text{Molar Mass} = (6 \times 12) + (6 \times 1) + (1 \times 16) = 72 + 6 + 16 = 94\text{ g mol}^{-1}
  • Percentage of Oxygen in Phenol: %Ophenol=1×1694×100=160094%17.0213%\% \text{O}_{\text{phenol}} = \frac{1 \times 16}{94} \times 100 = \frac{1600}{94}\% \approx 17.0213\%

Step 3: Calculate the Percentage of Oxygen in Compound (X)

  • Molecular Formula of oo-Nitrophenol: C6H5NO3\text{C}_6\text{H}_5\text{NO}_3
  • Molar Mass of oo-Nitrophenol: Molar Mass=(6×12)+(5×1)+(1×14)+(3×16)=72+5+14+48=139 g mol1\text{Molar Mass} = (6 \times 12) + (5 \times 1) + (1 \times 14) + (3 \times 16) = 72 + 5 + 14 + 48 = 139\text{ g mol}^{-1}
  • Percentage of Oxygen in oo-Nitrophenol: %O(X)=3×16139×100=4800139%34.5324%\% \text{O}_{(\text{X})} = \frac{3 \times 16}{139} \times 100 = \frac{4800}{139}\% \approx 34.5324\%

Step 4: Determine the Increase in Percentage of Oxygen

Increase in % O=%O(X)%Ophenol\text{Increase in } \% \text{ O} = \% \text{O}_{(\text{X})} - \% \text{O}_{\text{phenol}}

Increase in % O=34.5324%17.0213%=17.5111%\text{Increase in } \% \text{ O} = 34.5324\% - 17.0213\% = 17.5111\%

Expressing this in the form Value×101%\text{Value} \times 10^{-1}\%: 17.5111%=175.111×101%175×101%17.5111\% = 175.111 \times 10^{-1}\% \approx 175 \times 10^{-1}\%

Thus, the required value is 175.

Percentage Increase of Oxygen in Nitration Product of Phenol | Chemistry PYQ Solution - JEE Challenger