Sigma Percentile
JEE Main 2019
LEVELJEE Advanced

Animated Solution for Chemistry - Organic Chemistry: The major product of the following reaction is [2019, 10 Jan Shift-II]

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Visualized Solution

Analyzing the Reactant

  • The reactant is -methoxyphenol, which has an ether group () and a phenolic hydroxyl group ().

Reaction with Dilute HCl

  • The first step involves heating with dilute .
  • Ether cleavage occurs in acidic medium, converting the group to an group.

Polymerisation with Oxalic Acid

  • The intermediate formed is hydroquinone (benzene-1,4-diol).
  • It reacts with oxalic acid () to undergo a condensation polymerisation reaction.

Formation of the Polymer

  • The groups of hydroquinone react with the groups of oxalic acid, eliminating water molecules to form ester linkages.
  • This results in the formation of a linear polymer.

The Sigma Insight: Alcohols, Phenols, Ethers

Solution Diagram

Analyzing the Setup We are given a reactant, -methoxyphenol, which contains both an ether group () and a phenolic hydroxyl group ()

The reaction proceeds in two steps: first with dilute and heat, and then with oxalic acid () under polymerisation conditions.

Step 1

Ether Cleavage When -methoxyphenol is heated with dilute , the ether linkage undergoes cleavage. The acidic medium protonates the ether oxygen, making it a good leaving group. Water then attacks the methyl group, resulting in the formation of hydroquinone (benzene-1,4-diol) and methanol. The phenolic group remains unaffected under these conditions.

Step 2

Condensation Polymerisation The intermediate, hydroquinone, is a diol. It reacts with oxalic acid, which is a dicarboxylic acid. This is a classic condensation polymerisation reaction where the groups of the diol react with the groups of the dicarboxylic acid, eliminating water molecules to form ester linkages. The resulting polymer is a linear polyester with alternating hydroquinone and oxalate units.

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