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Question 58

The major product of the following reaction is:

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  1. Step 1: Acid-Catalyzed Hydrolysis (Cleavage)

    Treating the substrate with dilute $$\text{HCl}$$ and heat ($$\Delta$$) selectively hydrolyzes both the methoxy ether ($$-\text{OCH}_3$$) and the ester group ($$-\text{O--C}(=\text{O})\text{CH}_3$$). This unmasks two phenolic hydroxyl groups ($$-\text{OH}$$) on the aromatic ring, yielding a catechol-like intermediate with a net total of two reactive phenolic hydroxyl groups.


  2. Step 2: Condensation Polymerization

    The resulting dihydroxy aromatic intermediate reacts with oxalic acid ($$(\text{COOH})_2$$), which acts as a dicarboxylic acid monomer. A step-growth condensation polymerization takes place, eliminating water ($$\text{H}_2\text{O}$$) molecules to form alternating ester linkages (a polyester backbone).


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