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Color of Compound X in Phenolphthalein Synthesis Reaction Scheme

Identify the colour of compound 'X' in the sequence of the reaction.

Question Diagram 1

Options

A

Violet

B

Green

C

Red

D

Colourless

Correct

Step-by-Step Solution

The detailed step-by-step reaction mechanism and reasoning are as follows:

  1. Synthesis of Phenolphthalein:
    Two moles of phenol condense with one mole of phthalic anhydride in the presence of concentrated sulfuric acid (H2SO4\text{H}_2\text{SO}_4), acting as a dehydrating agent, to produce phenolphthalein (lactoid form, which is colourless in neutral and acidic media).

  2. Formation of the Pink Dianion:
    When dilute sodium hydroxide (NaOH\text{NaOH}) is added (pH8.310\text{pH} \approx 8.3 - 10), phenolphthalein undergoes ring opening of the lactone ring along with deprotonation of phenolic groups to form a dianion. This species contains a conjugated quinoid ring system (chromophore) that absorbs green light and imparts a characteristic pink (or magenta) color to the solution.

  3. Effect of Excess NaOH\text{NaOH} (Formation of Compound 'X'):
    In a strongly basic medium (pH>10\text{pH} > 10) created by adding excess NaOH\text{NaOH}, a hydroxide ion (OH\text{OH}^-) acts as a nucleophile and attacks the electron-deficient central sp2sp^2-hybridized carbon atom.
    Dianion (Pink)+OHExcess NaOHCompound ’X’ (Trianion carbinol derivative)\text{Dianion (Pink)} + \text{OH}^- \xrightarrow{\text{Excess NaOH}} \text{Compound 'X' (Trianion carbinol derivative)}

  4. Change in Hybridization and Color Disappearance:

  • The nucleophilic addition of OH\text{OH}^- changes the hybridization of the central carbon atom from sp2sp^2 to sp3sp^3.
  • This change interrupts and breaks the extended π\pi-electron conjugation existing between the aromatic rings and the quinoid system.
  • Due to the destruction of the chromophore, Compound 'X' loses its ability to absorb light in the visible spectrum and becomes completely colourless.

Thus, the colour of compound 'X' is Colourless.

Correct Option: D

Color of Compound X in Phenolphthalein Synthesis Reaction Scheme | Chemistry PYQ Solution - JEE Challenger