JEE Challenger
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IUPAC Name of Substituted Benzonitrile Derivative

The IUPAC name of the following compound is

Diagram 0

Options

A

4-Bromo-3-cyanophenol

B

2-Bromo-5-hydroxybenzonitrile

Correct
C

2-Cyano-4-hydroxybromobenzene

D

6-Bromo-3-hydroxybenzonitrile

Step-by-Step Solution

To determine the IUPAC name of the given compound, we follow the standard IUPAC nomenclature rules:

  1. Identification of the Principal Functional Group:
    The compound contains three functional groups:

    • Nitrile (−CN-\text{CN})
    • Alcohol (−OH-\text{OH})
    • Halogen (−Br-\text{Br})

    According to the IUPAC priority order of functional groups:
    Nitrile (−CN)>Alcohol (−OH)>Halogen (−Br)\text{Nitrile } (-\text{CN}) > \text{Alcohol } (-\text{OH}) > \text{Halogen } (-\text{Br})
    Therefore, the principal functional group is the nitrile group (−CN-\text{CN}), and the parent compound is benzonitrile.

  2. Numbering the Ring:

    • The ring carbon attached to the principal functional group (−CN-\text{CN}) is assigned position 11.
    • The ring substituents are a bromo group (−Br-\text{Br}) adjacent to the nitrile carbon, and a hydroxy group (−OH-\text{OH}) located para to the bromo group.
    • We number the ring to give the lowest locant set at the first point of difference:
      • Numbering clockwise (towards the −Br-\text{Br} substituent):
        C-1: −CN,C-2: −Br,C-5: −OH  ⟹  Locant set: (2,5)\text{C-1: } -\text{CN}, \quad \text{C-2: } -\text{Br}, \quad \text{C-5: } -\text{OH} \implies \text{Locant set: } (2, 5)
      • Numbering counter-clockwise:
        C-1: −CN,C-3: −OH,C-6: −Br  ⟹  Locant set: (3,6)\text{C-1: } -\text{CN}, \quad \text{C-3: } -\text{OH}, \quad \text{C-6: } -\text{Br} \implies \text{Locant set: } (3, 6)
    • Comparing the sets at the first point of difference, 2<32 < 3, so the correct numbering assigns locant 22 to bromine and locant 55 to the hydroxy group.
  3. Alphabetical Ordering of Substituents:

    • The substituents as prefixes are "bromo" and "hydroxy".
    • Alphabetically, "bromo" precedes "hydroxy".

Combining the prefixes with the parent name gives:
2-Bromo-5-hydroxybenzonitrile\text{2-Bromo-5-hydroxybenzonitrile}

Therefore, the correct option is B.