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Basics of Organic Chemistry question

2024 · 5 Apr · Shift 2 · Q3
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Basics of Organic Chemistry question

2024 · 5 Apr · Shift 2 · Q3

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The correct nomenclature for the following compound is : JEE Main 2024 (Online) 5th April Evening Shift Chemistry - Basics of Organic Chemistry Question 40 English
  1. A
    2-carboxy-4-hydroxyhept-7-enal
  2. B
    2-formyl-4-hydroxyhept-7-enoic acid
  3. C
    2-carboxy-4-hydroxyhept-6-enal
  4. D
    2-formyl-4-hydroxyhept-6-enoic acid
View written solutionFree

Correct answer: D

  1. Identify the highest priority functional group

    The options indicate the compound contains:

    • a carboxylic acid group,
    • an aldehyde group,
    • a hydroxy group,
    • and a double bond.

    By IUPAC priority, carboxylic acid has higher priority than aldehyde and alcohol. So the parent suffix must be -oic acid.

    Hence, options with suffix enal are incorrect.

    Therefore, A and C are eliminated.

  2. Choose the parent chain and numbering

    Since the principal functional group is carboxylic acid, numbering starts from the carboxyl carbon as carbon 1.

    The parent chain has 7 carbons, so the base name is heptenoic acid.

  3. Locate the double bond

    Numbering from the carboxylic acid end, the double bond lies between carbon 6 and carbon 7.

    Therefore the parent is hept-6-enoic acid.

    So B (hept-7-enoic acid) is impossible, because a 7-carbon chain cannot have a double bond starting at carbon 7.

  4. Identify the substituents

    • The aldehyde group, when not principal, is named as formyl.
    • The hydroxy substituent is named hydroxy.

    From the structure/options:

    • formyl is at carbon 2,
    • hydroxy is at carbon 4.

    So the name becomes: 2-formyl-4-hydroxyhept-6-enoic acid\text{2-formyl-4-hydroxyhept-6-enoic acid}2-formyl-4-hydroxyhept-6-enoic acid

  5. Check all options

    • A: 2-carboxy-4-hydroxyhept-7-enal → wrong principal group and impossible double bond position.
    • B: 2-formyl-4-hydroxyhept-7-enoic acid → wrong double bond position.
    • C: 2-carboxy-4-hydroxyhept-6-enal → wrong principal group.
    • D: 2-formyl-4-hydroxyhept-6-enoic acid → correct.

Final Answer

The correct nomenclature is: 2-formyl-4-hydroxyhept-6-enoic acid\boxed{\text{2-formyl-4-hydroxyhept-6-enoic acid}}2-formyl-4-hydroxyhept-6-enoic acid​

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