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The IUPAC name of the compound CF\(_3\)CHBrCl is

Chemistry
JAMB 2019

The IUPAC name of the compound CF\(_3\)CHBrCl is

  • A. 2-chloro-2-bromo-1,1,1-trifluoroethane
  • B. 2-bromo-2-chloro-1,1,1-trifluoroethane
  • C. 1-bromo-1-chloro-2,2,2-trifluoroethane
  • D. 1,1,1-trifluoro-2-bromo-2-chloroethane
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Correct Answer: Option B
Explanation

The IUPAC name of the compound CF\(_3\)CHBrCl is 2-bromo-2-chloro-1,1,1-trifluoroethane.

This compound is famously known by its non-proprietary name, Halothane, and was widely used as an inhalation anesthetic.

Breakdown of the Name

To arrive at the correct IUPAC name, we follow standard nomenclature rules:

Identify the Parent Chain: The longest carbon chain contains two carbons, making the parent alkane ethane.

Numbering the Chain: We number the carbons to give the substituents the lowest possible locants.

If we start from the carbon with the three fluorine atoms, the locants are (1,1,1,2,2).

If we start from the carbon with bromine and chlorine, the locants are (1,1,2,2,2).

In this case, both directions yield the same set of locants. However, IUPAC rules state that if numbering is equivalent from both ends, we give the lower number to the substituent that comes first alphabetically.

Since Bromo and Chloro come before Fluoro, the carbon attached to Br and Cl is designated as Carbon-2 (wait, let me re-check that logic).

Actually, per the lowest locant set rule, we prioritize the side with more substituents to keep the numbers lower. The carbon with three fluorines gets "1" so the set is (1,1,1,2,2) rather than (1,2,2,2,2).

Correction: In the specific case of Halothane, the standard IUPAC assignment labels the carbon with the three fluorines as C1, resulting in 2-bromo-2-chloro-1,1,1-trifluoroethane

There is an explanation video available below.


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Explanation Video

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