Electrophilic addition and regiochemistry
In carbocation-mediated addition of HX to an alkene, protonation creates an intermediate that a nucleophile subsequently captures.
Key knowledge
In carbocation-mediated addition of HX to an alkene, protonation creates an intermediate that a nucleophile subsequently captures. Regiochemical preference often reflects formation of the better stabilized carbocation; rearrangement can change connectivity. Radical or concerted additions follow different mechanistic rules.
Conditions and scope
- Markovnikov trends refer to the stated electrophilic pathway, not every alkene addition.
- Resonance, substituents and reaction conditions can change preference; degree of alkyl substitution alone is insufficient.
Sources · 1
References
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Evidence and review
Inspected carbocation-based Markovnikov interpretation and bounded it to the stated mechanism.
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Entry details
Permanent link to this entry ↗- Record identity
- uni-chem-electrophilic-alkene-addition
- Revision
- core.1
- Structured reference record
- University core expansion