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Basics of Organic Chemistry question

2019 · 10 Jan · Shift 2 · Q7
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Basics of Organic Chemistry question

2019 · 10 Jan · Shift 2 · Q7

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
What is the IUPAC name of the following compound ? JEE Main 2019 (Online) 10th January Evening Slot Chemistry - Basics of Organic Chemistry Question 208 English
  1. A
    4–Bromo-3-methylpent-2-ene
  2. B
    3–Bromo 1, 2-dimethylbut-1-ene
  3. C
    3–Bromo-3-methyl-1, 2-dimethylprop-1-ene
  4. D
    2-Bromo-3-methylpent-3-ene
View written solutionFree

Correct answer: A

  1. Interpret the structure

    The compound corresponds to the carbon skeleton:

    CH3−CH=C(CH3)−CH(Br)−CH3\mathrm{CH_3-CH=C(CH_3)-CH(Br)-CH_3}CH3​−CH=C(CH3​)−CH(Br)−CH3​

    We now assign the correct IUPAC name.

  2. Choose the longest chain containing the double bond

    The longest continuous chain containing the double bond has 5 carbons.

    So the parent hydrocarbon is pentene.

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

    Numbering from the left:

    CH3−CH=C(CH3)−CH(Br)−CH3\mathrm{CH_3-CH=C(CH_3)-CH(Br)-CH_3}CH3​−CH=C(CH3​)−CH(Br)−CH3​

    gives:

    • double bond between C-2 and C-3
    • methyl substituent at C-3
    • bromo substituent at C-4

    Hence the parent is:

    pent-2-ene\mathrm{pent\text{-}2\text{-}ene}pent-2-ene

    If we number from the right, the double bond would get locant 3, which is not preferred.

  4. Identify substituents

    • Bromo at C-4
    • Methyl at C-3
  5. Write the name in alphabetical order of substituents

    Alphabetically, bromo comes before methyl.

    Therefore the IUPAC name is:

    4-Bromo-3-methylpent-2-ene\boxed{\text{4-Bromo-3-methylpent-2-ene}}4-Bromo-3-methylpent-2-ene​

  6. Check options

    • A: 4–Bromo-3-methylpent-2-ene ✅ Correct
    • B: Incorrect parent chain / numbering
    • C: Incorrect naming; not based on the longest proper parent chain
    • D: Gives double bond locant 3 instead of 2, so incorrect
  7. Comparison with stored correct answer

    Stored correct answer: A

    Derived answer: A

    They match.

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