
- A4-Bromo-3-cyanophenol
- B2-Bromo-5-hydroxybenzonitrile
- C2-Cyano-4-hydroxybromobenzene
- D6-Bromo-3-hydroxybenzonitrile
View written solutionFree
Correct answer: B
Step-by-Step Solution:
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Identify the Functional Groups: The given compound is a substituted benzene ring. The substituents are:
-CN(cyano group)-OH(hydroxyl group)-Br(bromo group)
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Determine the Principal Functional Group: According to the IUPAC rules for nomenclature of polyfunctional compounds, we must determine the principal functional group based on the priority order. The priority order for the relevant groups is: Nitrile (
-CN) > Alcohol/Phenol (-OH) > Halo (-Br) Therefore, the cyano group (-CN) is the principal functional group. This means the parent name of the compound will be derived from the nitrile. -
Identify the Parent Compound: Since the principal functional group
-CNis attached to a benzene ring, the parent compound is benzonitrile. -
Number the Carbon Atoms of the Benzene Ring: The carbon atom of the benzene ring attached to the principal functional group (
-CN) is assigned the number 1. We then number the ring to give the lowest possible locants to the other substituents (-Brand-OH). There are two possible numbering schemes:- Path A (Clockwise): The
-Brgroup is at position 2, and the-OHgroup is at position 5. The locant set is (1, 2, 5). - Path B (Counter-clockwise): The
-OHgroup is at position 3, and the-Brgroup is at position 6. The locant set is (1, 3, 6).
- Path A (Clockwise): The
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Apply the Lowest Locant Rule: We compare the two locant sets (1, 2, 5) and (1, 3, 6). At the first point of difference, 2 is lower than 3. Therefore, the correct numbering scheme is Path A, which gives the locant set (1, 2, 5).
C1: attached to-CNC2: attached to-Br(Bromo)C5: attached to-OH(Hydroxy)
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Assemble the IUPAC Name: The substituents are listed in alphabetical order before the parent name. The substituents are Bromo and Hydroxy.
- Alphabetical order: Bromo comes before Hydroxy.
- The name is constructed as: [locant for bromo]-[Bromo]-[locant for hydroxy]-[hydroxy][parent name]
- Substituting the values:
2-Bromo-5-hydroxybenzonitrile.
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Evaluate the Given Options:
- A: 4-Bromo-3-cyanophenol: Incorrect. This name treats
-OHas the principal functional group, which has lower priority than-CN. - B: 2-Bromo-5-hydroxybenzonitrile: Correct. This matches our derived IUPAC name.
- C: 2-Cyano-4-hydroxybromobenzene: Incorrect. This treats
-Bras the basis for the parent name, which has the lowest priority of the three functional groups. - D: 6-Bromo-3-hydroxybenzonitrile: Incorrect. This uses the wrong numbering scheme (counter-clockwise), which does not follow the lowest locant rule.
- A: 4-Bromo-3-cyanophenol: Incorrect. This name treats
Therefore, the correct IUPAC name for the given compound is 2-Bromo-5-hydroxybenzonitrile.
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