MCQEasyJEE 2025Nomenclature (IUPAC & Common)

JEE Chemistry 2025 Question with Solution

What is the correct IUPAC name of

Benzene ring with carboxylic acid at one position, hydroxy at adjacent lower right, bromo at bottom, and nitro at upper left substituent.
  • A

    33-Bromo-22-hydroxy-55-nitrobenzoic acid

  • B

    33-Bromo-44-hydroxy-11-nitrobenzoic acid

  • C

    22-Hydroxy-33-bromo-55-nitrobenzoic acid

  • D

    55-Nitro-33-bromo-22-hydroxybenzoic acid

Answer

Correct answer:A

Step-by-step solution

Standard Method

Given: The compound shown is a substituted benzoic acid.

Find: The correct IUPAC name.

The main functional group is carboxylic acid, so the parent compound is benzoic acid. The carbon attached to CO2H\text{CO}_2\text{H} is assigned position 11.

From the structure, the substituents are:

  • OH\text{OH} at position 22
  • Br\text{Br} at position 33
  • NO2\text{NO}_2 at position 55

In IUPAC nomenclature, the substituent prefixes are written in alphabetical order: bromo, hydroxy, nitro.

Therefore, the correct IUPAC name is 33-Bromo-22-hydroxy-55-nitrobenzoic acid. Hence, the correct option is A.

Detailed Numbering Logic

Given: A benzene ring bearing CO2H\text{CO}_2\text{H}, OH\text{OH}, Br\text{Br} and NO2\text{NO}_2 substituents.

Find: The correct IUPAC name after proper numbering and ordering.

The parent is benzoic acid because the ring contains a carboxylic acid group. Thus, CO2H\text{CO}_2\text{H} must be at position 11.

Now choose the direction of numbering that gives the lowest locants to the remaining substituents. Clockwise numbering gives:

  • OH\text{OH} at 22
  • Br\text{Br} at 33
  • NO2\text{NO}_2 at 55

The opposite direction would place OH\text{OH} at 66, which is not preferred.

After numbering, list substituents alphabetically by name, not by position. So the order is bromo, hydroxy, nitro.

Hence the name is 33-bromo-22-hydroxy-55-nitrobenzoic acid. This matches option A.

Common mistakes

  • Placing the CO2H\text{CO}_2\text{H} group at any position other than 11 is incorrect because carboxylic acid is the principal functional group in benzoic acid derivatives. Always start numbering from the ring carbon attached to CO2H\text{CO}_2\text{H}.

  • Choosing the wrong direction of numbering leads to higher locants such as hydroxy at 44 or 66. Use the numbering direction that gives the lowest possible set of locants to substituents.

  • Writing substituents in positional order instead of alphabetical order gives an incorrect IUPAC name. After assigning positions, list prefixes alphabetically as bromo, hydroxy, nitro.

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