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Basics of Organic Chemistry question

2020 · 2 Sep · Shift 1 · Q9
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Basics of Organic Chemistry question

2020 · 2 Sep · Shift 1 · Q9

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The IUPAC name for the following compound is JEE Main 2020 (Online) 2nd September Morning Slot Chemistry - Basics of Organic Chemistry Question 186 English
  1. A
    2, 5-dimethyl-6-carboxy-hex-3-enal
  2. B
    6-formyl-2-methyl-hex-3-enoic acid
  3. C
    2, 5-dimethyl-5-carboxy-hex-3-enal
  4. D
    2, 5-dimethyl-6-oxo-hex-3-enoic acid
View written solutionFree

Correct answer: D

  1. Identify the principal functional group

    The options show that the compound contains both:

    • an aldehyde group (−CHO)(-CHO)(−CHO) or equivalently an oxo at terminal position,
    • a carboxylic acid group (−COOH)(-COOH)(−COOH).

    By IUPAC priority, carboxylic acid has higher priority than aldehyde.

    Therefore, the parent name must be based on an alkenoic acid, and any aldehyde carbon not included as the principal suffix is written as oxo (if part of the chain) or formyl (if attached as a substituent).

  2. Choose the parent chain

    Since the carboxylic acid is the highest priority group, numbering starts from the carboxyl carbon as carbon 1.

    The longest chain including the acid carbon has 6 carbons, so the parent is hex-...-oic acid.

  3. Locate the double bond

    From the options, the double bond is between carbons 3 and 4, so the parent is: hex-3-enoic acid\text{hex-3-enoic acid}hex-3-enoic acid

  4. Locate the aldehyde carbon in the acid-based nomenclature

    If the aldehyde carbon lies at the terminal carbon of the main chain opposite the acid end, then under acid nomenclature it is represented as an oxo group at carbon 6.

    Hence this gives: 6-oxo-hex-3-enoic acid\text{6-oxo-hex-3-enoic acid}6-oxo-hex-3-enoic acid

  5. Locate the methyl substituents

    The structure has methyl groups at carbons 2 and 5.

    Therefore the full name becomes: 2,5-dimethyl-6-oxo-hex-3-enoic acid\text{2,5-dimethyl-6-oxo-hex-3-enoic acid}2,5-dimethyl-6-oxo-hex-3-enoic acid

  6. Check the options

    • A: Uses enal as suffix, but acid should have higher priority than aldehyde. Incorrect.
    • B: Has only one methyl and uses formyl instead of incorporating the terminal carbon in chain. Incorrect.
    • C: Uses enal as suffix and carboxy as substituent; wrong priority choice. Incorrect.
    • D: 2,5-dimethyl-6-oxo-hex-3-enoic acid. Correct.

Therefore, the correct IUPAC name is: 2,5-dimethyl-6-oxo-hex-3-enoic acid\boxed{\text{2,5-dimethyl-6-oxo-hex-3-enoic acid}}2,5-dimethyl-6-oxo-hex-3-enoic acid​

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