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Home/Practice questions/Chemistry
ChemistryOrganic: Haloalkanes and Haloarenes

The correct IUPAC name of the compound (CH3)2CHCH(Br)CH2CH2Cl, is

The correct IUPAC name of the compound (CH3)2CHCH(Br)CH2CH2Cl, is

Answer & explanation+

Correct answer: option 3

The correct answer is Option (3) → 3-bromo-1-chloro-4-methylpentane

To name a haloalkane by the IUPAC system:

  • Choose the longest carbon chain; groups not in it are substituents.

  • Number the chain so that the substituents together get the lowest set of locants (compare at the first point of difference). Halogens and alkyl groups are treated alike here.

  • Write the prefixes in alphabetical order: bromo, chloro, methyl.

The compound written out is:

    \( \displaystyle \ce{CH3-CH(CH3)-CH(Br)-CH2-CH2-Cl} \)

The longest chain has five carbons (pentane); one \( \ce{CH3} \) of the isopropyl end is a methyl branch.

  • Numbering from the Cl end: Cl on C-1, Br on C-3, \( \ce{CH3} \) on C-4, locants {1, 3, 4}.

  • Numbering from the other end: \( \ce{CH3} \) on C-2, Br on C-3, Cl on C-5, locants {2, 3, 5}.

At the first point of difference 1 is lower than 2, so the chain is numbered from the Cl end. The name is 3-bromo-1-chloro-4-methylpentane.

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