Methyl group
alkyl group derived from methane
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula CH3 (whereas normal methane has the formula CH4). In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bonded to the rest of the molecule by a single covalent bond (−CH3), it can be found on its own in any of three forms: methanide anion (CH−3), methylium cation (CH+3) or methyl radical (CH•3). The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.
Methyl cation, anion, and radical
Methyl cation
The methylium cation (CH+3) exists in the gas phase, but is otherwise not encountered. Some compounds are considered to be sources of the CH+3 cation, and this simplification is used pervasively in organic chemistry. For example, protonation of methanol gives an electrophilic methylating reagent that reacts by the SN2 pathway:
CH3OH + H+ → [CH3OH2]+
Similarly, methyl iodide and methyl triflate are viewed as the equivalent of the methyl cation because they readily undergo SN2 reactions by weak nucleophiles.
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This entry incorporates text from “Methyl group” on English Wikipedia. Contributors are listed in the page history. Text is available under the Creative Commons Attribution-ShareAlike 4.0 License. Selected authority identifiers and statements are retrieved from Wikidata under CC0; their references and qualifiers remain part of the verification path.