4: Aliphatic Nucleophilic Substitution
- Page ID
- 189859
- 4.2: Mechanism of Aliphatic Nucleophilic Substitution
- Aliphatic nucleophilic substitution clearly involves the donation of a lone pair from the nucleophile to the tetrahedral, electrophilic carbon bonded to a halogen. We might expect this carbon to be electrophilic because of the halogen attached to it. For that reason, it attracts to nucleophile. However, the mechanism of the reaction might happen in a couple of different ways.
- 4.5: Regiochemistry
- Regiochemistry is the term for where changes take place in a reaction. It can be another indication of how the reaction occurred.
- 4.11: Addition to Strained Rings - Epoxides
- Sometimes oxygen doesn't need much help to become a leaving group. Epoxides, or oxiranes, are three-membered ring ethers. They are good electrophiles, and a C-O bond breaks easily when a nucleophile donates electrons to the carbon.
- 4.12: Elimination
- Sometimes, elimination reactions occur instead of aliphatic nucleophilic substitutions. In an elimination reaction, instead of connecting to the electrophilic carbon, the nucleophile takes a proton from the next carbon away from it. The halide or other leaving group is still displaced. A double bond forms between the two carbons.