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Basics of Organic Chemistry question

2006 · Shift 0 · Q20
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Basics of Organic Chemistry question

2006 · Shift 0 · Q20

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The IUPACIUPACIUPAC name of the compound shown below is : AIEEE 2006 Chemistry - Basics of Organic Chemistry Question 231 English
  1. A
    333-bromo - 111-chlorocyclohexene
  2. B
    111-bromo - 333-chlorocyclohexene
  3. C
    222-bromo - 666-chlorocyclohex - 111 -ene
  4. D
    666-bromo - 222 - chlorocyclohexene
View written solutionFree

Correct answer: A

  1. Parent ring identification

    The structure is a substituted cyclohexene ring, so the parent hydrocarbon is cyclohexene.

  2. Rule for numbering in cycloalkenes

    In a cycloalkene, the double bond must get locants 1 and 2.

    So we begin numbering from one carbon of the double bond and proceed through the ring in the direction that gives the substituents the lowest set of locants.

  3. Assign substituent positions

    From the given structure, the substituents are:

    • one chloro group on a double-bond carbon,
    • one bromo group elsewhere on the ring.

    Numbering the double bond as 1,21,21,2 and choosing the correct direction gives:

    • chloro at C-1
    • bromo at C-3

    Hence the locants are 1-chloro and 3-bromo.

  4. Write substituents in alphabetical order

    In IUPAC naming, substituents are written alphabetically:

    • bromo before chloro

    Therefore the name becomes: 3-bromo−1-chlorocyclohexene3\text{-bromo}-1\text{-chlorocyclohexene}3-bromo−1-chlorocyclohexene

  5. Check options

    • A: 333-bromo-111-chlorocyclohexene ✅
    • B: 111-bromo-333-chlorocyclohexene ❌ substituent positions interchanged
    • C: 222-bromo-666-chlorocyclohex-111-ene ❌ numbering does not give lowest locants correctly
    • D: 666-bromo-222-chlorocyclohexene ❌ incorrect numbering
  6. Derived answer

    The correct IUPAC name is: 3-bromo−1-chlorocyclohexene\boxed{3\text{-bromo}-1\text{-chlorocyclohexene}}3-bromo−1-chlorocyclohexene​

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