MLchartDataset catalogue

Hofmann rule

Term · Chemistry · MLC-T-CHM-005331

A regioselectivity rule in elimination reactions, particularly for the Hofmann elimination of quaternary ammonium salts, which states that the major product is the least substituted alkene. This outcome is favored when the leaving group is bulky or when the reaction proceeds via an E2 mechanism with a bulky base. It contrasts with Saytzeff's rule, which favors the more substituted alkene.

Table 1. Record
IdentifierMLC-T-CHM-005331
FieldChemistry
SubjectOrganic and Biomolecular Chemistry
ReferencesPAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1121 (https://doi.org/10.1351/pac199466051077)
See alsoSaytzeff rule; Alkenes; Alkyl groups; Decomposition; Elimination
Record as JSON
{
  "id": "MLC-T-CHM-005331",
  "term": "Hofmann rule",
  "field": "Chemistry",
  "definition": "A regioselectivity rule in elimination reactions, particularly for the Hofmann elimination of quaternary ammonium salts, which states that the major product is the least substituted alkene. This outcome is favored when the leaving group is bulky or when the reaction proceeds via an E2 mechanism with a bulky base. It contrasts with Saytzeff's rule, which favors the more substituted alkene.",
  "subject": "Organic and Biomolecular Chemistry",
  "see_also": [
    "Saytzeff rule",
    "alkenes",
    "alkyl groups",
    "decomposition",
    "elimination"
  ],
  "references": [
    "PAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1121 (https://doi.org/10.1351/pac199466051077)"
  ],
  "url": "https://mlchart.com/terminology/chemistry/hofmann-rule/"
}

Record 5,648 of 13,676 in Chemistry terminology (MLC-0109). Request the full dataset.