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Basics of Organic Chemistry question

2019 · 9 Apr · Shift 1 · Q8
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Basics of Organic Chemistry question

2019 · 9 Apr · Shift 1 · Q8

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The correct IUPAC name of the following compound is : JEE Main 2019 (Online) 9th April Morning Slot Chemistry - Basics of Organic Chemistry Question 201 English
  1. A
    2-methyl-5-nitro-1-chlorobenzene
  2. B
    2-chloro-1-methyl-4-nitrobenzene
  3. C
    3-chloro-4-methyl-1-nitrobenzene
  4. D
    5-chloro-4-methyl-1-nitrobenzene
View written solutionFree

Correct answer: B

  1. Interpret the substituted benzene ring

    The compound has three substituents on benzene:

    • one methyl group,
    • one chloro group,
    • one nitro group.
  2. Apply IUPAC numbering rule

    For a trisubstituted benzene, we must number the ring so that the substituents get the lowest set of locants.

    From the given arrangement, if we assign:

    • methyl as position 1,
    • chloro as position 2,
    • nitro as position 4,

    then the locant set is: 1,2,41,2,41,2,4

    This is lower than alternatives such as: 1,3,4, 1,4,5, 1,2,51,3,4,\, 1,4,5,\, 1,2,51,3,4,1,4,5,1,2,5

    Hence the correct numbering is:

    • 1-methyl
    • 2-chloro
    • 4-nitro
  3. Write substituents in alphabetical order

    Prefixes are written alphabetically:

    • chloro
    • methyl
    • nitro

    Therefore the name becomes: 2-chloro-1-methyl-4-nitrobenzene\boxed{2\text{-chloro-}1\text{-methyl-}4\text{-nitrobenzene}}2-chloro-1-methyl-4-nitrobenzene​

  4. Check options

    • A: 2-methyl-5-nitro-1-chlorobenzene → numbering not lowest.
    • B: 2-chloro-1-methyl-4-nitrobenzene → correct.
    • C: 3-chloro-4-methyl-1-nitrobenzene → locants not lowest.
    • D: 5-chloro-4-methyl-1-nitrobenzene → locants not lowest.

So, the correct option is B.

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