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MCQEasyJEE 2025Nomenclature (IUPAC & Common)

JEE Chemistry 2025 Question with Solution

The IUPAC name of the following compound is:

Structural formula showing CH3-CH-CH2-CH2-CH-CH3 with a COOH group attached to the second carbon and a COOCH3 group attached to the fifth carbon.
  • A

    2-Carboxy-5-methoxycarbonylhexane

  • B

    Methyl-6-carboxy-2,5-dimethylhexanoate

  • C

    Methyl-5-carboxy-2-methylhexanoate

  • D

    6-Methoxycarbonyl-2,5-dimethylhexanoic acid

Answer

Correct answer:D

Step-by-step solution

Standard Method

Given: A compound structure is shown.

Find: The correct IUPAC name of the compound.

  1. Identify the longest carbon chain: The parent chain contains 66 carbon atoms, so the parent hydrocarbon is hexane.

  2. Identify the principal functional group: The structure contains a carboxylic acid group and a methoxycarbonyl group. The carboxylic acid group has higher priority, so the parent name must end with hexanoic acid.

  3. Number the chain: Numbering starts from the end nearest the carboxylic acid group, so that group is at carbon 11.

  4. Locate substituents: The methoxycarbonyl group is at carbon 66, and the methyl groups are at carbons 22 and 55.

  5. Construct the name: Combining the substituents with the parent name gives 6-Methoxycarbonyl-2,5-dimethylhexanoic acid.

Therefore, the correct option is D.

Common mistakes

  • Choosing the ester part as the principal functional group is incorrect because carboxylic acid has higher IUPAC priority. Always assign the suffix to the highest priority functional group first.

  • Numbering the chain from the wrong end gives incorrect locants for the substituents. Start numbering from the end nearest the −COOH-COOH group.

  • Treating methoxycarbonyl as part of the main chain is incorrect here. It must be named as a substituent because the parent chain is based on the carboxylic acid-containing chain.

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