JAMB 2019 Chemistry · Question 25
The IUPAC name of the compound CFCHBrCl is
Options
- 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
Answer: B. 2-bromo-2-chloro-1,1,1-trifluoroethane
Explanation written with AI and checked against the answer key
Analyze the question: CF₃CHBrCl is halothane, a two-carbon (ethane) chain carrying four halogen substituents. We need the correct IUPAC name, which depends on numbering and alphabetical order.
Concept: For substituted alkanes:
- Choose the longest chain (here 2 carbons, so ethane).
- Number the chain so the substituents get the lowest set of locants.
- List substituents in alphabetical order (ignoring the prefixes di-, tri-, etc.).
Solution:
- Carbon A: CF₃ (3 fluorines)
- Carbon B: CHBrCl (1 bromine, 1 chlorine)
Numbering options:
- Option 1: CF₃ is C1, so the locants are {1,1,1,2,2} (F at 1,1,1; Br at 2; Cl at 2).
- Option 2: CHBrCl is C1, so the locants are {1,1,2,2,2}.
Compare the sets at the first point of difference: {1,1,1,2,2} is lower than {1,1,2,2,2}. So CF₃ is C1.
Alphabetical order: bromo (b), chloro (c), fluoro (f). The prefix "tri" in trifluoro is ignored, so fluoro is sorted under "f".
Name: 2-bromo-2-chloro-1,1,1-trifluoroethane
Checking the options:
- A: chloro listed before bromo, so the alphabetical order is wrong.
- B: correct numbering and correct alphabetical order. ✔
- C: numbering gives the higher locant set {1,1,2,2,2}, so it is wrong.
- D: right locants but not in alphabetical order (fluoro is listed first).
Answer: B
Tip: When naming haloalkanes, do two checks. First, find the lowest locant set (all substituents together). Second, write the prefixes alphabetically. The multipliers (di, tri, tetra) never count for alphabetizing.
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