What is the Difference Between Epoxidation and Oxidation

The key difference between epoxidation and oxidation is that epoxidation refers to the conversion of a double-bonded carbon group into an epoxide group, whereas oxidation refers to the combination of oxygen with a substance.

Epoxidation and oxidation are common terms in organic synthesis reactions. Epoxidation can be described as a special form of oxidation that specifically gives a cyclic oxide compound/ epoxide compound.

CONTENTS

1. Overview and Key Difference
2. What is Epoxidation
3. What is Oxidation
4. Similarities – Epoxidation and Oxidation
5. Epoxidation vs Oxidation in Tabular Form
6. Summary – Epoxidation vs Oxidation 

What is Epoxidation?

Epoxidation is the chemical process that can convert a C-C chemical bond into an epoxide bond. An epoxide is a cyclic ether having both carbon atoms of a double bond bound to the same oxygen atom. These compounds are also called oxiranes.

We can create an epoxide through the reaction between peracids and the double-bonded carbon atoms. In peracids, there is an oxygen-oxygen bond that is not only weak but also a polarized bond. Therefore, the acyloxy group in this compound has a negative charge, and the hydroxyl group has a positive charge. However, a dipolar intermediate is unlikely to form, so scientists believe that this reaction occurs in a single step through a transition that incorporates all the chemical bonding and bond-breaking events at the same time.

What is Oxidation?

Oxidation is the process of increasing the oxidation number of chemical species. However, there are three distinct definitions for this term; the addition of oxygen, removal of hydrogen, or loss of electrons means oxidation. But all these definitions have exceptions on different occasions. Thus, we use the above definition as a general definition for all occasions.

Oxidation is a type of redox reaction. A redox reaction essentially has two parallel reactions: oxidation reactions and reduction reactions. These reactions always involve the electron transfer between two chemical species. Moreover, the chemical species that undergoes oxidation will always release electrons, while the chemical species which undergoes reduction will always obtain those electrons. Therefore, releasing electrons makes more protons that have no electrons to neutralize their charge. Thus, the electron removal will increase the oxidation number of the chemical species.

What are the Similarities Between Epoxidation and Oxidation?

1. Epoxidation and oxidation are types of oxidation reactions that involve the addition of oxygen atoms to organic compounds.
2. Both reactions are important in organic synthesis reactions.
3. These reactions give types of oxide compounds as the end product.

What is the Difference Between Epoxidation and Oxidation?

Epoxidation and oxidation are common terms in organic synthesis reactions. The key difference between epoxidation and oxidation is that epoxidation refers to the conversion of a double-bonded carbon group into an epoxide group, whereas oxidation refers to the combination of oxygen with a substance. Therefore, the epoxidation reaction gives an epoxide as the end product of the reaction, which is a cyclic group involving an oxygen atom and two carbon atoms. On the other hand, oxidation gives an oxide compound as the end product, which has a carbon to oxygen bond that is non-cyclic.

The following infographic presents the difference between epoxidation and oxidation in tabular form.

Summary – Epoxidation vs Oxidation

Epoxidation and oxidation are common terms in organic synthesis reactions. The key difference between epoxidation and oxidation is that epoxidation refers to the conversion of a double-bonded carbon group into an epoxide group, whereas oxidation refers to the combination of oxygen with a substance.

Reference:

1. “Epoxidation.” Chemistry LibreTexts, Libretexts, 13 Sept. 2020.

Image Courtesy:

1. “Epoxide generic” By Tomas Kindahl – Own work (Public Domain) via Commons Wikimedia
2. “Redox example” By Cmglee – Own work (CC BY-SA 4.0) via Commons Wikimedia