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Organic Mechanisms: Nucleophilic Substitution, Elimination and Electrophilic Addition · Semester 2

Amino Acids: Zwitterions, Isoelectric Point and Peptide Bond Formation

Students will be introduced to amino acids as building blocks of proteins and understand the basic concept of protein formation and function.

Key Questions

  1. Explain the formation of a zwitterion from an amino acid and calculate the isoelectric point from pKa data for the α-amino and α-carboxyl groups, predicting the net charge at physiological pH.
  2. Construct the mechanism for peptide bond formation via nucleophilic acyl substitution and explain why the peptide bond exhibits partial double-bond character, relating this to restricted rotation and secondary structure consequences.
  3. Analyse how the R-group polarity and charge state of amino acids at a given pH determines their separation by gel electrophoresis and ion-exchange chromatography.

MOE Syllabus Outcomes

MOE: Biomolecules (Proteins) - MSMOE: Amino Acids (Basic) - MS
Level: JC 2
Subject: Chemistry
Unit: Organic Mechanisms: Nucleophilic Substitution, Elimination and Electrophilic Addition
Period: Semester 2

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