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Number and name the above ☝️ compound

Chemistry

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Answer

3-bromo-5-fluoro-5-hydroxy-3,6-dimethylheptanoic acid\text{3-bromo-5-fluoro-5-hydroxy-3,6-dimethylheptanoic acid}

Step-by-step solution

3 steps
  1. Identify the parent chain.

    The compound contains a carboxylic acid (-COOH\text{-COOH}) group, which is the highest priority functional group. We identify the longest continuous carbon chain that includes this group.
    Starting from the carbon of the -COOH\text{-COOH} group (C1):
    C1: -COOH\text{C1: -COOH}
    C2: -CH2-\text{C2: -CH}_2\text{-}
    C3: -CH-\text{C3: -CH-} (attached to Br\text{Br} and CH3\text{CH}_3)
    C4: -CH2-\text{C4: -CH}_2\text{-}
    C5: -C-\text{C5: -C-} (attached to F\text{F} and OH\text{OH})
    C6: -CH-\text{C6: -CH-} (attached to CH3\text{CH}_3)
    C7: -CH3\text{C7: -CH}_3
    The longest chain containing the carboxylic acid group has 7 carbons. Therefore, the parent name is heptanoic acid.

  2. Number the carbon chain and identify substituents.

    The carbon of the -COOH\text{-COOH} group is always designated as C1.

    • At C3: Bromine (Br\text{Br}) and a Methyl (CH3\text{CH}_3) group.
    • At C5: Fluorine (F\text{F}) and a Hydroxyl (OH\text{OH}) group.
    • At C6: A Methyl (CH3\text{CH}_3) group.
  3. Assemble the name.

    List the substituents in alphabetical order. Prefixes like "di-" are ignored for alphabetical ordering.
    The substituents are:

    • Bromo (at C3)
    • Fluoro (at C5)
    • Hydroxy (at C5)
    • Methyl (at C3 and C6, so 3,6-dimethyl)

    Arranging them alphabetically: Bromo, Fluoro, Hydroxy, Dimethyl.

    The full IUPAC name is:

    3-bromo-5-fluoro-5-hydroxy-3,6-dimethylheptanoic acid\text{3-bromo-5-fluoro-5-hydroxy-3,6-dimethylheptanoic acid}
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