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Identification Condition of Beta Naphthol Using Dye Test

To identify β\beta-naphthol through the dye test, it is essential to utilize

Options

A

a dichloromethane solution of β\beta-naphthol.

B

an acidic solution of β\beta-naphthol.

C

a neutral solution of β\beta-naphthol.

D

an alkaline solution of β\beta-naphthol.

Correct

Step-by-Step Solution

To identify β\beta-naphthol using the azo dye test, it is essential to prepare an alkaline solution of β\beta-naphthol.

Detailed Chemical Explanation:

  1. Role of Alkaline Medium:

    • Phenols, such as β\beta-naphthol (C10H7OH\text{C}_{10}\text{H}_7\text{OH}), are weakly acidic and dissolve in basic solutions (such as dilute NaOH\text{NaOH}) to form the naphthoxide ion (C10H7O−\text{C}_{10}\text{H}_7\text{O}^-): C10H7OH+OH−⇌C10H7O−+H2O\text{C}_{10}\text{H}_7\text{OH} + \text{OH}^- \rightleftharpoons \text{C}_{10}\text{H}_7\text{O}^- + \text{H}_2\text{O}
    • The phenoxide/naphthoxide anion (−O−-\text{O}^-) is a significantly stronger electron-donating group than the neutral hydroxyl group (−OH-\text{OH}). This increases the electron density of the aromatic naphthalene ring through resonance, making it sufficiently reactive toward weak electrophiles like the diazonium cation (Ar-N2+\text{Ar-N}_2^+).
  2. Coupling Reaction:

    • When an alkaline solution of β\beta-naphthol is mixed with freshly prepared benzene diazonium chloride (C6H5N2+Cl−\text{C}_6\text{H}_5\text{N}_2^+\text{Cl}^-) at 0−5∘C0-5^\circ\text{C}, an electrophilic aromatic substitution reaction occurs at position 11 (α\alpha-position) of β\beta-naphthol: C6H5N2+Cl−+C10H7O−→Alkaline MediumC6H5−N=N−C10H6OH+Cl−\text{C}_6\text{H}_5\text{N}_2^+\text{Cl}^- + \text{C}_{10}\text{H}_7\text{O}^- \xrightarrow{\text{Alkaline Medium}} \text{C}_6\text{H}_5-\text{N}=\text{N}-\text{C}_{10}\text{H}_6\text{OH} + \text{Cl}^-
    • This forms 1-(phenylazo)-2-naphthol, an intense orange-red precipitate/dye, confirming the presence of β\beta-naphthol.

Thus, an alkaline solution of β\beta-naphthol is required for the azo dye test.

Correct Option: D