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Tertiary carbon radicals have three σ C-H bonds that donate, secondary radicals only two, and primary radicals only one. Therefore, tertiary radicals are the most stable and primary radicals the least stable. The relative stabilities of tertiary, secondary, primary and methyl radicals can be explained by hyperconjugation
Tertiary is a term used in organic chemistry to classify various types of compounds (e. g. alcohols, alkyl halides, amines) or reactive intermediates (e. g. alkyl radicals, carbocations). Red highlighted central atoms in various groups of chemical compounds.
The experimental relative chlorination rates at primary, secondary, and tertiary positions match the corresponding radical species' stability: tertiary (5) > secondary (3.8) > primary (1). Thus any single chlorination step slightly favors substitution at the carbon already most substituted.
Compounds bearing carbon–hydrogen bonds react with radicals in the order primary < secondary < tertiary < benzyl < allyl reflecting the order in C–H bond dissociation energy [4] Many stabilizing effects can be explained as resonance effects, an effect specific to radicals is the captodative effect.
The ammonium radical intramolecularly abstracts a sterically favored hydrogen atom to afford an alkyl radical which, in a chain reaction, abstracts chlorine from another N-chloroammonium ion to form an alkyl chloride and a new ammonium radical. The alkyl chloride later cyclizes during the basic work-up to the cyclic tertiary amine.
Free radicals are formed upon splitting the carbon-carbon bond. Free radicals are extremely reactive and short-lived. When a free radical in a polymer chain undergoes a beta scission, the free radical breaks two carbons away from the charged carbon producing an olefin (ethylene) and a primary free radical, which has two fewer carbon atoms.
Free alkyls occur as neutral radicals, as anions, or as cations. The cations are called carbocations. The anions are called carbanions. The neutral alkyl free radicals have no special name. Such species are usually encountered only as transient intermediates. However, persistent alkyl radicals with half-lives "from seconds to years" have been ...
Alkyl radicals are often considered as a series, a progression sequenced by the number of carbon atoms involved. In that progression, Butyl (containing 4 carbon atoms) is the fourth, and the last with preferred IUPAC name derived from its history. The word "butyl" is derived from butyric acid, a four-carbon carboxylic acid found in rancid ...