What is the Difference Between Free Radical Substitution and Nucleophilic Substitution?
🆚 Go to Comparative Table 🆚The key difference between free radical substitution and nucleophilic substitution lies in the nature of the reactants involved in each type of reaction. Here are the main differences:
- Free Radical Substitution: In this type of reaction, a free radical is involved. Free radicals are highly reactive atoms or molecules with an unpaired electron, making them very reactive. Free radical substitution reactions often involve the breakdown of a carbon-hydrogen bond in alkanes, followed by the formation of a new bond between carbon and another atom or molecule.
- Nucleophilic Substitution: In nucleophilic substitution reactions, a nucleophile is involved. Nucleophiles are electron-rich chemical components that tend to replace another atom or molecule in a compound. Nucleophilic substitution reactions typically involve the displacement of a leaving group (C-LG) by a nucleophile (C-Nu), forming a new bond between carbon and the nucleophile.
In summary, free radical substitution reactions involve highly reactive free radicals, while nucleophilic substitution reactions involve electron-rich nucleophiles. The nature of the reactants and the mechanisms of these reactions are distinct, leading to different outcomes and applications in organic chemistry.
Comparative Table: Free Radical Substitution vs Nucleophilic Substitution
Here is a table comparing free radical substitution and nucleophilic substitution:
| Feature | Free Radical Substitution | Nucleophilic Substitution |
|---|---|---|
| Definition | A type of organic synthetic chemical reaction where one atom in a molecule is replaced by another atom. | A type of chemical reaction where an electron-rich chemical component tends to replace a weakly bound leaving group. |
| Reactive Species | Free radicals, which are atoms or molecules with unpaired electrons. | Nucleophiles, which are electron-rich chemical species. |
| Bond-Forming Mechanism | Hemolytic fission, where chemical bonds split evenly, and each atom gets one of the two bonding electrons. | Concerted bond-making and bond-breaking, where the incoming nucleophile attacks the electrophilic carbon from the side. |
| Intermediates | Carbocations or other reactive intermediates form in some cases. | No intermediates formed; the reaction is concerted. |
| Solvent Effects | Polar protic solvents (H2O, ROH, etc.) favor SN1 reactions. | Polar aprotic solvents (acetone, DMSO, DMF, etc.) favor SN2 reactions. |
In summary, free radical substitution reactions involve the breakdown of a carbon-hydrogen bond in alkanes, followed by the formation of a new bond in alkyl groups such as methyl and ethyl. On the other hand, nucleophilic substitution reactions involve nucleophiles, which are electron-rich chemical components, replacing a weakly bound leaving group.
- Electrophilic vs Nucleophilic Substitution
- Free Radical Substitution vs Free Radical Addition
- Nucleophilic vs Electrophilic Addition
- Synthesis Reaction vs Substitution Reaction
- Nucleophilicity vs Basicity
- Nucleophile vs Electrophile
- Free Radical vs Ionic Polymerization
- Elimination vs Substitution Reaction
- Free Radical vs Ion
- Addition vs Substitution Reaction
- Acidic Radical vs Basic Radical
- Base vs Nucleophile
- Functional Group vs Substituent
- Free Radicals vs Reactive Oxygen Species
- Electropositive vs Electronegative Radicals
- Oxidative Addition vs Reductive Elimination
- Mutation Rate vs Substitution Rate
- Base Excision Repair vs Nucleotide Excision Repair
- Substitution Insertion vs Deletion Mutations