What is the Difference Between Electrophilic and Nucleophilic Substitution?
🆚 Go to Comparative Table 🆚The main difference between electrophilic and nucleophilic substitution lies in the reactants involved and the nature of the substitution reaction. Here are the key differences:
- Electrophilic Substitution:
- Involves the substitution of a hydrogen atom in an aromatic ring by an electrophile, which is a species that accepts electrons.
- The electrophile attacks the aromatic ring, forming a carbocation intermediate.
- This type of substitution reaction typically results in the retention of the absolute configuration.
- Nucleophilic Substitution:
- Involves the substitution of a leaving group in an aromatic ring by a nucleophile, which is a species that donates electrons.
- The nucleophile attacks the aromatic ring, displacing the leaving group.
- There are two types of nucleophilic substitution reactions: ${{S}{N}}^{1}$ and ${{S}{N}}^{2}$, which take place in one and two steps, respectively. The ${{S}_{N}}^{2}$ reaction follows the inversion of configuration.
In summary, electrophilic substitution involves the replacement of a hydrogen atom by an electrophile, while nucleophilic substitution involves the replacement of a leaving group by a nucleophile. The reactants, mechanism, and configuration changes differ between the two types of substitution reactions.
Comparative Table: Electrophilic vs Nucleophilic Substitution
Here is a table comparing the differences between electrophilic and nucleophilic substitution:
Feature | Electrophilic Substitution | Nucleophilic Substitution |
---|---|---|
Definition | Electrophilic substitution is a reaction where an electrophile (a positively charged or partially positive species) attacks a molecule, forming a new covalent bond. | Nucleophilic substitution is a reaction where a nucleophile (a molecule rich in electrons) attacks a molecule, forming a new covalent bond. |
Reactants | Electrophiles are reactants that accept a pair of electrons to form a new covalent bond. | Nucleophiles are reactants that donate a pair of electrons to form a new covalent bond. |
Charge | Electrophiles are typically positively charged or partially positive species. | Nucleophiles are typically negatively charged or neutral species. |
Bond Formation | Electrophiles make bonds using the electron pairs of nucleophiles. | Nucleophiles make bonds using their own electron pairs. |
Examples | 1. Addition of water to a carbonyl group, specifically the aldehyde. | Addition of hydroxide ion to a carbonyl group. |
Stereochemistry | Electrophilic substitution proceeds with retention of absolute configuration. | Nucleophilic substitution proceeds with inversion of configuration. |
In summary, electrophilic substitution occurs when an electrophile (a positively charged or partially positive species) attacks a molecule, while nucleophilic substitution occurs when a nucleophile (a molecule rich in electrons) attacks a molecule. Electrophilesaccept electron pairs, while nucleophiles donate electron pairs. These differences in reactivity and stereochemistry can be useful in understanding and predicting the outcomes of various reactions in organic and inorganic chemistry.
- Nucleophilic vs Electrophilic Addition
- Free Radical Substitution vs Nucleophilic Substitution
- Nucleophile vs Electrophile
- Nucleophilicity vs Basicity
- Synthesis Reaction vs Substitution Reaction
- Base vs Nucleophile
- Elimination vs Substitution Reaction
- Electrocyclic vs Cycloaddition Reaction
- Addition vs Substitution Reaction
- Free Radical Substitution vs Free Radical Addition
- Electropositive vs Electronegative
- Electropositive vs Electronegative Radicals
- Functional Group vs Substituent
- Photocatalysis vs Electrocatalysis
- Chemoselectivity vs Regioselectivity
- Alternate vs Substitute
- Oxidative Addition vs Reductive Elimination
- Electronegativity vs Polarity
- Monosubstituted vs Disubstituted Alkene