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NCERT Exemplar · Q2

Q.The IUPAC name for CH3—C(=O)—CH2—CH2—C(=O)—OH is ______.

(i) 1-hydroxypentane-1,4-dione
(ii) 1,4-dioxopentanol
(iii) 1-carboxybutan-3-one
(iv) 4-oxopentanoic acid
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The compound contains both a carboxylic acid and a ketone group. The carboxylic acid is the principal functional group, making the compound a pentanoic acid with an "oxo" substituent at position 4. The correct IUPAC name is 4-oxopentanoic acid.

When naming organic compounds using IUPAC nomenclature, the fundamental principle is to identify the most important functional group, determine the longest continuous carbon chain that includes it, and then number the chain to give the principal functional group the lowest possible number. Substituents are then named and placed in alphabetical order with their corresponding numbers.

Here's how we apply this to CH₃—C(=O)—CH₂—CH₂—C(=O)—OH:

  1. Identify all functional groups:

    The given compound is CH₃—C(=O)—CH₂—CH₂—C(=O)—OH.

    We can identify two functional groups:

    • A carboxylic acid group (—COOH) at one end.
    • A ketone group (—C(=O)—) within the carbon chain.
  2. Determine the principal functional group (PFG):

    IUPAC rules establish a hierarchy of functional groups. Carboxylic acids have higher priority than ketones.

    Important

    The priority order for common functional groups (highest to lowest) is: Carboxylic acid > Sulfonic acid > Ester > Acyl halide > Amide > Nitrile > Aldehyde > Ketone > Alcohol > Amine > Alkene > Alkyne > Alkane.

    Since the carboxylic acid group has higher priority, it will be the principal functional group, and the compound will be named as a carboxylic acid. The suffix for a carboxylic acid is "-oic acid". The ketone group will be treated as a substituent.

  3. Select the parent carbon chain:

    The parent chain must be the longest continuous carbon chain that includes the carbon atom of the principal functional group (the carboxylic acid).

    Let's write out the structure and count the carbons:

    O

    ||

    CH₃ — C — CH₂ — CH₂ — C — OH

    ||

    O

    The carbon of the carboxylic acid group is always designated as C1 when it is the principal functional group.

    • C1: Carbon of the —COOH group.
    • C2: —CH₂—
    • C3: —CH₂—
    • C4: Carbon of the —C(=O)— (ketone) group.
    • C5: —CH₃

    The longest continuous chain containing the carboxylic acid group has 5 carbon atoms. Therefore, the parent alkane is pentane, and the parent carboxylic acid is pentanoic acid.

  4. Number the carbon chain:

    As established, the carbon of the carboxylic acid group is C1. Numbering proceeds from C1 towards the other end of the chain.

    CH₃ — C(=O) — CH₂ — CH₂ — C(=O) — OH

    5 4 3 2 1

  5. Identify and name substituents:

    The ketone group (—C(=O)—) is located at position C4. When a ketone group is not the principal functional group, it is named using the prefix "oxo-".

  6. Assemble the full IUPAC name:

    Combine the substituent name and its position with the parent chain name and the principal functional group suffix.

    • Substituent: 4-oxo
    • Parent chain: pentanoic acid The full IUPAC name is 4-oxopentanoic acid.
    Watch out

    A common mistake is to incorrectly identify the principal functional group or to number the chain from the wrong end. Always prioritize the functional groups and ensure the PFG carbon gets the lowest possible number (C1 for carboxylic acids).

Comparing this with the given options:

  1. 1-hydroxypentane-1,4-dione: Incorrect. "Hydroxy" is for -OH (alcohol), not -COOH. "Dione" implies two ketone groups.
  2. 1,4-dioxopentanol: Incorrect. "Dioxo" implies two ketone groups. "Pentanol" implies an alcohol.
  3. 1-carboxybutan-3-one: Incorrect. "Carboxy" is a prefix for -COOH when it's a substituent, but here it's the PFG. "Butanone" implies a 4-carbon chain with a ketone as PFG.
  4. 4-oxopentanoic acid: This matches our derived name.
    ✓Final answer

    The IUPAC name for CH₃—C(=O)—CH₂—CH₂—C(=O)—OH is 4-oxopentanoic acid.

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