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Basics of Organic Chemistry question

2025 · 4 Apr · Shift 2 · Q8
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Basics of Organic Chemistry question

2025 · 4 Apr · Shift 2 · Q8

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The IUPAC name of the following compound is: JEE Main 2025 (Online) 4th April Evening Shift Chemistry - Basics of Organic Chemistry Question 6 English
  1. A
    4-Hydroxyhept-6-en-1-yne
  2. B
    Hept-1-en-6-yn-4-ol
  3. C
    Hept-6-en-1-yn-4-ol
  4. D
    4-Hydroxyhept-1-en-6-yne
View written solutionFree

Correct answer: B

  1. Identify the parent carbon chain

    The compound has a longest chain of 7 carbons, so the parent name begins with hept-.

  2. Identify the functional groups and multiple bonds

    From the structure/options, the molecule contains:

    • one alcohol group: −OH-OH−OH
    • one double bond: C=CC=CC=C
    • one triple bond: C≡CC\equiv CC≡C

    Hence the suffix must include ol, en, and yn.

  3. Choose the principal functional group

    The alcohol group has highest priority among these, so numbering must give the lowest possible locant to −OH-OH−OH.

    In all options, the hydroxyl group is at carbon 444, so this condition is satisfied either way.

  4. Resolve numbering using multiple bonds

    Since the hydroxyl locant is tied, we next minimize the locants of the multiple bonds.

    Compare the two possible numberings:

    • One direction gives:

      • double bond at 111
      • triple bond at 666
      • alcohol at 444

      So locants: (1,6,4)(1,6,4)(1,6,4)

    • Opposite direction gives:

      • double bond at 666
      • triple bond at 111
      • alcohol at 444

      So locants: (6,1,4)(6,1,4)(6,1,4)

    For enyne systems, when there is a choice, the set with the lowest locant at the first point of difference is preferred. Thus (1,6,4)(1,6,4)(1,6,4) is preferred over (6,1,4)(6,1,4)(6,1,4).

    Therefore numbering should be:

    • alkene at 111
    • alkyne at 666
    • alcohol at 444
  5. Write the IUPAC name

    The correct format is: Hept-1-en-6-yn-4-ol\text{Hept-1-en-6-yn-4-ol}Hept-1-en-6-yn-4-ol

  6. Check the options

    • A: 4-Hydroxyhept-6-en-1-yne ❌ Older-style naming; also not preferred because alcohol should be suffix, not prefix.
    • B: Hept-1-en-6-yn-4-ol ✅
    • C: Hept-6-en-1-yn-4-ol ❌
    • D: 4-Hydroxyhept-1-en-6-yne ❌
  7. Comparison with stored correct answer

    My derived answer is B, which matches the stored correct answer.

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