In this post, we will discuss and show the mechanisms of some important reactions of lactones and lactams, such as their preparation, acid- and base-catalyzed hydrolysis, and reduction by LiAlH4. We will also go over the Grignard reaction of lactones.
A quick reminder that lactones are cyclic esters formed when a molecule contains both an alcohol and a carboxylic acid (or carboxyl derivative) that react intramolecularly to create a ring. They commonly appear in natural products and can vary in ring size, with γ- and δ-lactones being especially common.
Lactams are cyclic amides formed when an amino group within the same molecule reacts with a carboxylic acid or its derivative to form a ring.
They are key structural motifs in many biologically active compounds, including β-lactam antibiotics like penicillin and cephalosporins. See the last row of this list of important nitrogen-containing compounds with biological and medical significance:
1) Formation of Lactones from Hydroxy Carboxylic Acids
This content is for registered users only.
By joining Chemistry Steps, you will gain instant access to the answers and solutions for all the Practice Problems, including over 40 hours of problem-solving videos, Multiple-Choice Quizzes, Puzzles, Reaction Maps, and the powerful set of Organic Chemistry 1 and 2 Summary Study Guides.
