Organic Chemistry Carboxylic Acids and Derivatives: Nucleophilic Acyl Substitution Reactions

Carbonyl Polymers like Polyesters

Topic overview

Start with the big picture

In step-growth condensation polymerization, reactive groups on bifunctional monomers form covalent links while releasing small molecules such as water or HCl. Polyesters contain ester linkages and can be made from a diol paired with a dicarboxylic acid or diacyl chloride; PET, made from ethylene glycol and terephthalic acid, is a key example used in fibers and bottles. Ester linkages lack the strong hydrogen-bond donors found in polyamides, contributing to differences in polarity, melting behavior, and hydrolytic stability. The lesson also introduces transesterification catalysts and ring-opening routes to biodegradable polyesters such as PLA and PCL. High chain length depends on suitable monomer ratios and purity, limiting moisture and removing by-products.

Learning objectives

What you'll learn

  • Explain how nucleophilic acyl substitution links monomers during step-growth polymerization.
  • Identify the monomer pair and ester linkage used to form PET.
  • Compare polyester and polyamide properties using their linkage and hydrogen-bonding differences.
  • Describe how catalysts, moisture, and by-product removal affect polyester synthesis.
  • Recognize ring-opening polymerization as a route to biodegradable aliphatic polyesters.
Ready for the complete lesson?

Continue your study

Work through the complete notes and reinforce the topic with the study tools available in the full lesson.

PharmaProLearn

Excel Beyond Limits