H

Heterolytic Cleavage

A-B → A⁺ + B⁻ (ionic cleavage)
Quick Reference
Formula / NotationA-B → A⁺ + B⁻ (ionic cleavage)
Also Known AsHeterolysis, ionic cleavage, polar bond dissociation

What is Heterolytic Cleavage?

The breaking of a covalent bond in which both electrons go to one atom, producing a cation and an anion (or a carbocation and a carbanion in organic chemistry). This type of bond breaking is common in polar reactions like SN1, SN2, E1, and E2 mechanisms.

Formula & Notation

A-B → A⁺ + B⁻ (ionic cleavage)

Other Names / Synonyms: Heterolysis, ionic cleavage, polar bond dissociation

Properties & Characteristics

Heterolytic cleavage is the breaking of a covalent bond in which both electrons of the bond go to one atom or fragment, producing an ion pair (a cation and an anion). The more electronegative atom retains both electrons (becomes the anion). Example: H-Cl → H⁺ + Cl⁻. Heterolytic cleavage generates charged species: carbocations, carbanions, or simple ions. It is characteristic of ionic and polar mechanisms (SN1, SN2, E1, E2, electrophilic addition).

Uses & Applications

Heterolytic cleavage mechanisms underpin all polar organic reactions: nucleophilic substitutions, eliminations, electrophilic additions, and acid-base reactions. Predicting which bond undergoes heterolytic cleavage based on polarity and leaving group ability is central to mechanistic organic chemistry.

Safety Information

Reactions proceeding by heterolytic mechanisms often involve highly reactive cationic or anionic intermediates that can react with biological molecules. Strong acid catalysts and reactive leaving groups used in industrial heterolytic reactions require appropriate PPE and waste management.

Always consult the SDS/MSDS before handling any chemical. This information is for educational purposes only.

Key Facts

Term Heterolytic Cleavage
Formula A-B → A⁺ + B⁻ (ionic cleavage)
Synonyms Heterolysis, ionic cleavage, polar bond dissociation

Frequently Asked Questions

The breaking of a covalent bond in which both electrons go to one atom, producing a cation and an anion (or a carbocation and a carbanion in organic chemistry). This type of bond breaking is common in polar reactions like SN1, SN2, E1, and E2 mechanisms.

More "H" Terms

View all "H" terms →
A B C D E F G H I J K L M N O P Q R S T U V W X Y Z