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Basics of Organic Chemistry question

2019 · 8 Apr · Shift 1 · Q7
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Basics of Organic Chemistry question

2019 · 8 Apr · Shift 1 · Q7

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The IUPAC name of the following compound is : JEE Main 2019 (Online) 8th April Morning Slot Chemistry - Basics of Organic Chemistry Question 204 English
  1. A
    3-Hydroxy-4-methylpentanoic acid
  2. B
    4,4-Dimethyl-3-hydroxybutanoic acid
  3. C
    2-Methyl-3-hydroxypentan-5-oic acid
  4. D
    4-Methyl-3-hydroxypentanoic acid
View written solutionFree

Correct answer: A

  1. Identify the principal functional group

    The compound contains a carboxylic acid group, so the parent name must end with -oic acid.

  2. Choose the longest chain containing the carboxyl carbon

    The longest carbon chain including the −COOH-COOH−COOH carbon has 5 carbons.

    Therefore, the parent hydrocarbon is: pentanoic acid\text{pentanoic acid}pentanoic acid

  3. Number the chain

    In carboxylic acids, numbering starts from the carboxyl carbon as carbon 111.

    So the chain is numbered as: C1−C2−C3−C4−C5C_1- C_2- C_3- C_4- C_5C1​−C2​−C3​−C4​−C5​

  4. Locate substituents

    From the given structure:

    • There is a hydroxy group on carbon 333
    • There is a methyl group on carbon 444
  5. Write the name in proper IUPAC format

    Substituents are written alphabetically:

    • hydroxy
    • methyl

    Hence the name is: 3-Hydroxy-4-methylpentanoic acid\boxed{\text{3-Hydroxy-4-methylpentanoic acid}}3-Hydroxy-4-methylpentanoic acid​

  6. Check options

    • A: 3-Hydroxy-4-methylpentanoic acid ✅ Correct
    • B: 4,4-Dimethyl-3-hydroxybutanoic acid ❌ Wrong parent chain
    • C: 2-Methyl-3-hydroxypentan-5-oic acid ❌ Incorrect numbering/suffix usage
    • D: 4-Methyl-3-hydroxypentanoic acid ❌ Same locants, but substituents should be listed alphabetically, so hydroxy should come before methyl

Therefore, the correct answer is Option A.

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