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Chapter 3: Problem 27

Which of the following statement(s) regarding ortho and para nitrophenol is/are correct? (a) o-Nitrophenol is less soluble in water than p-nitrophenol. (b) o-Nitrophenol is more acidic than p-nitrophenol. (c) o-Nitrophenol is steam volatile while p-nitrophenol is not. (d) o-Nitrophenol has higher melting point than p-nitrophenol.

Short Answer

Expert verified
a) Ortho-nitrophenol has lower solubility than para-nitrophenol in water. b) Ortho-nitrophenol is more acidic than para-nitrophenol. c) Ortho-nitrophenol has higher steam volatility compared to para-nitrophenol. d) Ortho-nitrophenol has a higher melting point compared to para-nitrophenol. Answer: a, b, c.

Step by step solution

01

Statement (a) Evaluation

To verify the solubility of o-nitrophenol and p-nitrophenol in water, we need to consider their molecular structures and the presence of any intermolecular hydrogen bonding. o-Nitrophenol has an intramolecular hydrogen bond between the hydroxyl (-OH) group and the nitro (-NO2) group. This intramolecular hydrogen bonding makes it less likely for o-nitrophenol to form hydrogen bonds with water molecules. In contrast, p-nitrophenol has intermolecular hydrogen bonds which can form easily with water molecules, making it more soluble. Therefore, statement (a) is correct.
02

Statement (b) Evaluation

To compare the acidity of o-nitrophenol and p-nitrophenol, we can examine their ability to lose a proton (H+) from the hydroxyl group. The presence of intramolecular hydrogen bonding in o-nitrophenol would make it easier to lose a proton compared to p-nitrophenol, and hence be more acidic. Therefore, statement (b) is also correct.
03

Statement (c) Evaluation

To evaluate the steam volatility of o-nitrophenol and p-nitrophenol, we can consider their molecular weights and hydrogen bonding capabilities. o-Nitrophenol has a lower molecular weight and weaker intermolecular hydrogen bonding compared to p-nitrophenol, which allows it to be more easily vaporized with steam. In contrast, p-nitrophenol would be more likely to form larger aggregates due to stronger intermolecular hydrogen bonding, making it less steam volatile. Therefore, statement (c) is correct.
04

Statement (d) Evaluation

The melting point of a compound is affected by its intermolecular interactions. Since o-nitrophenol has weaker intermolecular hydrogen bonding compared to p-nitrophenol, it would be expected to have a lower melting point rather than a higher one as stated in the question. Thus, statement (d) is incorrect. In conclusion, statements (a), (b), and (c) are correct, while statement (d) is incorrect.

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