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News About Butyl

20-September-2008 09:55:59 - Butyl In organic chemistry, butyl is a four-carbon alkyl substituent with chemical formula -C4H9 . It is derived from either of the two isomers of the alkane called butane. Each of the two isomers of butane give rise to two isomers of the butyl substituent. Thus, n-butane can connect at either the terminal or an internal carbon atoms, giving rise to n-butyl and sec-butyl substituents. n-Butyl group: CH3-CH2-CH2-CH2- fully systematic name: butyl sec-Butyl group: CH3-CH2-CHCH3- fully systematic name: 1-methylpropyl The second, branched isomer of butane, isobutane can also connect either terminal methyl or internal carbon atoms, giving rise to isobutyl and tertiary butyl substituents, respectively. Isobutyl group: CH32CH-CH2- fully systematic name: 2-methylpropyl tert-Butyl group: CH33C- fully systematic name: 1,1-dimethylethyl Contents 1 Nomenclature 2 Some examples 3 Etymology 4 Tert-butyl effect 5 See also 6 References Nomenclature According to IUPAC nomenclature, isobutyl, sec-butyl, and tert-butyl are all retained trivial names. skeletal formula common name IUPAC name systematic name alternate notation n-butyl butyl butyl butan-1-yl isobutyl isobutyl 2-methylpropyl 2-methylpropan-1-yl sec-butyl sec-butyl 1-methylpropyl butan-2-yl tert-butyl tert-butyl 1,1-dimethylethyl 2-methylpropan-2-yl Butyl is the largest substituent for which trivial names are commonly used for all isomers. The prefixes iso, sec and tert refer to the number of carbons connected to the primary carbon also known as RI R prime, the carbon that is connected to R. Iso means one, sec- means two and tert- means three. Some examples The following are the four isomers of butyl acetate: butyl acetate isobutyl acetate sec-butyl acetate tert-butyl acetate n-butyl acetate isobutyl acetate sec-butyl acetate tert-butyl acetate Etymology As the number of carbons in an alkyl chain increases, butyl is the last to be named historically instead of through Greek numbers. The name is derived from butyric acid, a four carbon carboxylic acid found in rancid butter. The name of butyric acid, in turn, comes from Latin butyrum, butter. Tert-butyl effect The tert-butyl substituent is very bulky and used in chemistry for kinetic stabilisation together with other bulky groups such as the related trimethylsilyl group. The effect that the t-butyl group exerts on the progress of a chemical reaction is called the tert-butyl effect. This effect is illustrated in the Diels-Alder reaction below where the tert-butyl substituent causes a reaction rate acceleration by a factor of 240 compared to hydrogen as the substituent.1 Tert-butyl effect See also Methyl Ethyl Propyl Pentyl / amyl References ^ Factors affecting ease of ring formation. The effect of anchoring substitution on the rate of an intramolecular diels-alder reaction with furan-diene Serge Cauwberghs and Pierre J. De Clercq B. Tinant and J. P. Declercq Tetrahedron Letters Volume 29, Issue 20 , 1988, Pages 2493-2496 doi:10.1016/S0040-40390087916-2 Retrieved from http://en..org/wiki/Butyl Categories: Functional groups Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Polski РуÑ?Ñ?кий Svenska This page was last modified on 25 June 2008, at 07:39

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