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Basics of Organic Chemistry question

2017 · Shift 1 · Q13
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Basics of Organic Chemistry question

2017 · Shift 1 · Q13

JEE AdvancedChemistryBasics of Organic ChemistryMultiple correct+4 / −1
The IUPAC name(s) of the following compound is (are) JEE Advanced 2017 Paper 1 Offline Chemistry - Basics of Organic Chemistry Question 39 English
  1. A
    111-chloro-444-methylbenzene
  2. B
    444-chlorotoluene
  3. C
    444-methylchlorobenzene
  4. D
    111-methyl-444-chlorobenzene
View written solutionFree

Correct answer: A, B

  1. Identify the structure

    The compound is a benzene ring having two substituents:

    • one chloro group, −Cl-Cl−Cl
    • one methyl group, −CH3-CH_3−CH3​

    These are placed at the para positions relative to each other, i.e. positions 111 and 444.

  2. Apply IUPAC naming rules

    For a disubstituted benzene:

    • Number the ring to give the lowest set of locants.
    • If there is a tie, assign locant 111 to the substituent that comes first in alphabetical order.

    Here, the substituents are:

    • chloro
    • methyl

    Alphabetically, chloro comes before methyl. So the correct IUPAC name is: 1-chloro-4-methylbenzene1\text{-chloro-}4\text{-methylbenzene}1-chloro-4-methylbenzene

    Hence, Option A is correct.

  3. Check retained/common IUPAC name

    The compound can also be named as a derivative of toluene:

    • toluene = methylbenzene
    • chloro group is at the para position

    So the name is: 4-chlorotoluene4\text{-chlorotoluene}4-chlorotoluene

    Hence, Option B is also correct.

  4. Examine Option C: 444-methylchlorobenzene

    This is not the proper IUPAC form. In benzene derivatives with two substituents, both substituents should be cited separately with benzene as parent, giving: 1-chloro-4-methylbenzene1\text{-chloro-}4\text{-methylbenzene}1-chloro-4-methylbenzene not "444-methylchlorobenzene".

    So Option C is incorrect.

  5. Examine Option D: 111-methyl-444-chlorobenzene

    Though the locants are 1,41,41,4, in a tie the substituent cited first alphabetically should get locant 111. Since chloro comes before methyl, the correct numbering must be: 1-chloro-4-methylbenzene1\text{-chloro-}4\text{-methylbenzene}1-chloro-4-methylbenzene not 1-methyl-4-chlorobenzene1\text{-methyl-}4\text{-chlorobenzene}1-methyl-4-chlorobenzene

    So Option D is incorrect.

  6. Final answer

    The correct IUPAC/accepted names are:

    • A. 111-chloro-444-methylbenzene
    • B. 444-chlorotoluene
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