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Basics of Organic Chemistry question

2020 · 4 Sep · Shift 1 · Q20
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Basics of Organic Chemistry question

2020 · 4 Sep · Shift 1 · Q20

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The IUPAC name of the following compound is : JEE Main 2020 (Online) 4th September Morning Slot Chemistry - Basics of Organic Chemistry Question 182 English
  1. A
    3-Bromo-5-methylcyclopentane carboxylic acid
  2. B
    3-Bromo-5-methylcyclopentanoic acid
  3. C
    4-Bromo-2-methylcyclopentane carboxylic acid
  4. D
    5-Bromo-3-methylcyclopentanoic acid
View written solutionFree

Correct answer: C

  1. Identify the principal functional group

    The compound contains a carboxylic acid group, −COOH-COOH−COOH.

    When a −COOH-COOH−COOH group is attached to a ring and the carbon of the carboxyl group is not part of the ring, the correct IUPAC form is: cycloalkane carboxylic acid\text{cycloalkane carboxylic acid}cycloalkane carboxylic acid So the parent name must be of the form: cyclopentane carboxylic acid\text{cyclopentane carboxylic acid}cyclopentane carboxylic acid

    Hence, options with cyclopentanoic acid are incorrect.

    Therefore, B and D are eliminated.

  2. Fix the numbering of the ring

    In cycloalkane carboxylic acids, the ring carbon attached to the −COOH-COOH−COOH group is numbered as C-1.

    Now number the ring in the direction that gives the substituents the lowest set of locants.

  3. Locate the substituents

    From the given structure, the substituents on the cyclopentane ring are:

    • one methyl group
    • one bromo group

    Taking the carbon attached to −COOH-COOH−COOH as C-1, numbering in the correct direction gives:

    • methyl at C-2
    • bromo at C-4

    So the name becomes: 4-Bromo-2-methylcyclopentane carboxylic acid\boxed{4\text{-Bromo-}2\text{-methylcyclopentane carboxylic acid}}4-Bromo-2-methylcyclopentane carboxylic acid​

  4. Check with options

    • A: 333-Bromo-555-methylcyclopentane carboxylic acid →\rightarrow→ incorrect locants
    • B: 333-Bromo-555-methylcyclopentanoic acid →\rightarrow→ wrong parent suffix
    • C: 444-Bromo-222-methylcyclopentane carboxylic acid →\rightarrow→ correct
    • D: 555-Bromo-333-methylcyclopentanoic acid →\rightarrow→ wrong parent suffix
  5. Final answer

    C: 4-Bromo-2-methylcyclopentane carboxylic acid\boxed{\text{C: 4-Bromo-2-methylcyclopentane carboxylic acid}}C: 4-Bromo-2-methylcyclopentane carboxylic acid​

  6. Comparison with stored correct answer

    Stored correct answer: C

    My derived answer: C

    Hence, they agree.

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