Question
Identify the colour of compound 'X' in the sequence of the reaction.
Identify the colour of compound 'X' in the sequence of the reaction.
D. Colourless
The given reaction sequence represents the synthesis and acid-base behaviour of phenolphthalein. When phenol reacts with phthalic anhydride in the presence of concentrated H_2SO_4, phenolphthalein is formed. In acidic or neutral medium, phenolphthalein exists in a lactone form which is colourless. Upon addition of a moderate amount of alkali (NaOH), the lactone ring opens and a proton is removed, forming a dianion with an extended conjugated quinonoid structure. This extended conjugation is responsible for the characteristic pink colour of phenolphthalein in basic medium. When excess NaOH is added (strongly alkaline medium), a hydroxide ion attacks the central sp^2 hybridized carbon atom of the quinonoid structure. This converts the central carbon to an sp^3 hybridized state, forming a carbinol structure (compound X). Because the central carbon is now sp^3 hybridized, the extended conjugation is broken. As a result, the compound loses its colour and becomes colourless. Therefore, compound X is colourless. Answer: Colourless
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