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Difference Between Exocyclic and Endocyclic Double Bond

August 18, 2020 Posted by Madhu

The key difference between exocyclic and endocyclic double bond is that one carbon atom of the exocyclic double bond is in the ring structure and the other carbon atom is located outside the ring structure whereas two carbon atoms of the endocyclic double bond are in the ring structure.

Exocyclic and endocyclic double bonds are parts of chemical compounds which are cyclic or ring structures. These two double bonds differ from each other according to the location of the two carbon atoms that are involved in the formation of the double bond.

CONTENTS

1. Overview and Key Difference
2. What is an Exocyclic Double Bond 
3. What is an Endocyclic Double Bond 
4. Side by Side Comparison – Exocyclic vs Endocyclic Double Bond in Tabular Form
5. Summary

What is an Exocyclic Double Bond?

Exocyclic double bonds are covalent chemical bonds which contain two carbon atoms bonded to each other via a sigma bond and a pi bond. This type of double bonds has one of the two carbon atoms in the ring structure. We can observe exocyclic double bonds only in unsaturated organic compounds (unsaturated compounds are chemical compounds having either double bonds or triple bonds). Specifically, these covalent bonds can be observed in alkenes.

Difference Between Exocyclic and Endocyclic Double Bond

Figure 01: Chemical Structure of Methylenecyclohexane

The name exocyclic refers to the presence of the double bond external to the cyclic structure. But this double bond is still connected to the cyclic structure via one of the two double-bonded carbon atoms. It is very important to recognize exocyclic double bonds form endocyclic double bonds when naming a chemical compound using the IUPAC nomenclature method. An example of a chemical compound containing an exocyclic double bond is methylcyclohexane.

What is an Endocyclic Double Bond?

Endocyclic double bonds are covalent chemical bonds that contain two carbon atoms bonded to each other via a sigma bond and a pi bond (the composition of a double bond). These covalent chemical bonds have both carbon atoms of the double bond in the ring structure. In other words, both carbon atoms of the endocyclic double bond are members of the cyclic structure.

Key Difference - Exocyclic vs Endocyclic Double Bond

Figure 02: Chemical Structure of Cyclopentene

An example of a chemical compound containing an endocyclic double bond is cyclopentene. Cyclopentene contains an endocyclic double bond since both double-bonded carbon atoms are members of the cyclic structure. It is very important to recognize exocyclic double bonds form endocyclic double bonds when naming a chemical compound using the IUPAC nomenclature method.

What is the Difference Between Exocyclic and Endocyclic Double Bond?

Exocyclic and endocyclic double bond are parts of cyclic structures which differ from each other according to the location of the double bond. The key difference between exocyclic and endocyclic double bond is that one carbon atom of the exocyclic double bond is in the ring structure and the other carbon atom is located outside the ring structure whereas two carbon atoms of the endocyclic double bond are in the ring structure.

Below infographic summarizes the differences between exocyclic and endocyclic double bond in tabular form.

Difference Between Exocyclic and Endocyclic Double Bond in Tabular Form

Summary – Exocyclic vs Endocyclic Double Bond

Exocyclic and endocyclic double bond are parts of cyclic structures which differ from each other according to the location of the double bond. The key difference between exocyclic and endocyclic double bond is that one carbon atom of the exocyclic double bond is in the ring structure while the other carbon atom is located outside the ring structure whereas two carbon atoms of the endocyclic double bond are in the ring structure.

Reference:

1. “3.6: Alkenes.” Chemistry LibreTexts, Libretexts, 11 Aug. 2020, Available here.

Image Courtesy:

1. “Methylenecyclohexane” By Edgar181 – Own work (Public Domain) via Commons Wikimedia
2. “Cyclopentene-2D-skeletal” Von Benjah-bmm27 – Eigenes Werk (Gemeinfrei) via Commons Wikimedia

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Difference Between Homocyclic and Heterocyclic CompoundsDifference Between Homocyclic and Heterocyclic Compounds Difference Between Wittig and Wittig Horner ReactionDifference Between Wittig and Wittig Horner Reaction Difference Between Classical and Nonclassical CarbocationDifference Between Classical and Nonclassical Carbocation Difference Between Pyridine and PyrimidineDifference Between Pyridine and Pyrimidine Difference Between Solvolysis and AminolysisDifference Between Solvolysis and Aminolysis

Filed Under: Organic Chemistry

About the Author: Madhu

Madhu is a graduate in Biological Sciences with BSc (Honours) Degree and currently persuing a Masters Degree in Industrial and Environmental Chemistry. With a mind rooted firmly to basic principals of chemistry and passion for ever evolving field of industrial chemistry, she is keenly interested to be a true companion for those who seek knowledge in the subject of chemistry.

Comments

  1. Muhammad Owais says

    January 19, 2022 at 4:15 pm

    Respected madam i have learned many things from these topics. I want to learn more and more. I need your contact if possible. I am M. Phil scholar and doing government job.
    Thanks

    Reply

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