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Basics of Organic Chemistry question

2023 · 8 Apr · Shift 2 · Q2
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Basics of Organic Chemistry question

2023 · 8 Apr · Shift 2 · Q2

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The correct IUPAC nomenclature for the following compound is: JEE Main 2023 (Online) 8th April Evening Shift Chemistry - Basics of Organic Chemistry Question 97 English
  1. A
    2 - Formyl -5-methylhexan-6-oic acid
  2. B
    5-Methyl-2-oxohexan-6-oic acid
  3. C
    5-Formyl -2-methylhexanoic acid
  4. D
    2-Methyl-5-oxohexanoic acid
View written solutionFree

Correct answer: D

  1. Identify the principal functional group

    In IUPAC nomenclature, the highest priority functional group gets the suffix.

    Here, the compound contains:

    • a carboxylic acid group (−COOH)(-COOH)(−COOH)
    • an aldehyde group (−CHO)(-CHO)(−CHO)

    Since carboxylic acid has higher priority than aldehyde, the parent name must be based on the carboxylic acid.

  2. Choose the longest chain containing the carboxyl carbon

    The parent chain has 6 carbons, so the base name is: hexanoic acid\text{hexanoic acid}hexanoic acid

    Numbering starts from the carboxylic acid carbon as carbon 1.

  3. Locate the substituents

    From the structure implied by the options:

    • there is a methyl substituent at carbon 2
    • the terminal aldehyde carbon, when acid is principal group, is named by the prefix oxo if it lies within the main chain end counted from the acid side

    Thus, at carbon 5 there is an oxo group.

  4. Construct the name

    Parent: hexanoic acid\text{hexanoic acid}hexanoic acid

    Substituents:

    • 222-methyl
    • 555-oxo

    Therefore the correct IUPAC name is: 2-Methyl-5-oxohexanoic acid\boxed{\text{2-Methyl-5-oxohexanoic acid}}2-Methyl-5-oxohexanoic acid​

  5. Check options

    • A: 222-Formyl-555-methylhexan-666-oic acid
      Incorrect: carboxylic acid carbon must be carbon 1, not 6.

    • B: 555-Methyl-222-oxohexan-666-oic acid
      Incorrect numbering of carboxylic acid; acid carbon cannot be 6.

    • C: 555-Formyl-222-methylhexanoic acid
      Incorrect because terminal aldehyde in presence of higher priority acid is represented as oxo, not formyl here.

    • D: 222-Methyl-555-oxohexanoic acid
      Correct.

  6. Comparison with stored answer

    Stored correct answer: D
    Derived answer: D

    Hence, the derived answer agrees with the stored answer.

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