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Basics of Organic Chemistry question

2018 · 15 Apr · Shift 1 · Q11
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Basics of Organic Chemistry question

2018 · 15 Apr · Shift 1 · Q11

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The IUPAC name of the following compound is : JEE Main 2018 (Online) 15th April Morning Slot Chemistry - Basics of Organic Chemistry Question 224 English
  1. A
    4-methyl-3-ethylhex-4-ene
  2. B
    3-ethyl-4-methylhex-4-ene
  3. C
    4-ethyl-3-methylhex-2-ene
  4. D
    4, 4- diethyl-3-methylbut-2-ene
View written solutionFree

Correct answer: C

  1. Identify the longest chain containing the double bond

    We must choose the parent chain such that:

    • it contains the double bond,
    • it is the longest possible chain.

    From the given structure, the correct parent chain has 6 carbon atoms and includes the double bond.

    Therefore, the parent hydrocarbon is hexene.

  2. Number the chain to give the double bond the lowest locant

    In IUPAC nomenclature, the double bond gets priority in numbering.

    Numbering from the end nearer the double bond gives: hex-2-ene\text{hex-2-ene}hex-2-ene and not hex-4-ene, because: 2<42 < 42<4

  3. Locate the substituents

    After numbering the main chain as hex-2-ene, the substituents are:

    • one ethyl group at carbon 4,
    • one methyl group at carbon 3.

    So the substituent positions are:

    • 444-ethyl
    • 333-methyl
  4. Arrange substituents alphabetically

    In IUPAC naming, substituents are written in alphabetical order:

    • ethyl
    • methyl

    Hence the name becomes: 4-ethyl-3-methylhex-2-ene4\text{-ethyl-}3\text{-methylhex-2-ene}4-ethyl-3-methylhex-2-ene

  5. Check options

    • A: 4-methyl-3-ethylhex-4-ene
      Incorrect: double bond locant is not lowest.

    • B: 3-ethyl-4-methylhex-4-ene
      Incorrect: double bond locant is not lowest.

    • C: 4-ethyl-3-methylhex-2-ene
      Correct.

    • D: 4,4-diethyl-3-methylbut-2-ene
      Incorrect: does not use the longest valid parent chain.

  6. Final answer

    The correct IUPAC name is: 4-ethyl-3-methylhex-2-ene\boxed{4\text{-ethyl-}3\text{-methylhex-2-ene}}4-ethyl-3-methylhex-2-ene​

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