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. Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting of primarily carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... An alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... In chemistry, radicals (often referred to as free radicals) are atomic or molecular species with unpaired electrons on an otherwise open shell configuration. ... This article or section does not cite any references or sources. ... Chemical structure of methane, the simplest alkane Alkanes are chemical compounds that consist only of the elements carbon (C) and hydrogen (H) (i. ... Butane, also called n-butane, is the unbranched alkane with four carbon atoms, CH3CH2CH2CH3. ...

Isomers

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. In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of chemical bonds between atoms, but in which the atoms are arranged differently (analogous to a chemical anagram). ... In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of bonds between atoms, but in which the atoms are arranged differently. ...

• n-butyl group; CH₃CH₂CH₂CH₂–, (fully systematic name "butyl")
• sec-butyl group; CH₃CH₂(CH₃)CH–, (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 (Common Name) or 2-Methylpropyl (IUPAC) is a substituent group with the formula C4H9. ...

• isobutyl group; (CH₃)₂CHCH₂–, (fully systematic name "2-methylpropyl")
• tert-butyl group; (CH₃)₃C–, (fully systematic name "1,1-dimethylethyl")

Nomenclature

According to IUPAC nomenclature, "isobutyl", "sec-butyl", and "tert-butyl" are all retained trivial names. IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...

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. A skeletal formula is a three-dimensional model of the molecule that demonstrates the molecular shape, including bond angles. ... In science, a common name is any name by which a species or other concept is known that is not the official scientific name. ... There are millions of possible objects that can be described in science, too many to create common names for every one. ... Image File history File links Size of this preview: 800 × 221 pixelsFull resolution (1100 × 304 pixel, file size: 9 KB, MIME type: image/png) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links Size of this preview: 800 × 468 pixelsFull resolution (1100 × 643 pixel, file size: 12 KB, MIME type: image/png) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links Size of this preview: 800 × 521 pixelsFull resolution (1100 × 716 pixel, file size: 12 KB, MIME type: image/png) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links Size of this preview: 645 × 600 pixelsFull resolution (914 × 850 pixel, file size: 6 KB, MIME type: image/png) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ...

Some examples

The following are the four isomers of "butyl acetate":

Image File history File links Butyl_acetate. ... Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... The chemical compound n-butyl acetate, also known as 1-butyl ethanoate, is commonly used as a solvent in the production of lacquers and other products. ... Flash point 18 °C R/S statement R: S: , , , RTECS number  ? Supplementary data page Structure and properties n, εr, etc. ... Flash point R/S statement , , , S: - RTECS number AF7400000 Supplementary data page Structure and properties n, εr, etc. ... The chemical compound t-butyl acetate, also known as tert-butyl acetate, is commonly used as a solvent in the production of lacquers and other products. ...

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". Butyric acid, (from Greek βουτυρος = butter) IUPAC name n-Butanoic acid, or normal butyric acid, is a carboxylic acid with structural formula CH3CH2CH2-COOH. It is notably found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... “Spoilage” redirects here. ... Butter is commonly sold in sticks (pictured) or blocks, and frequently served with the use of a butter knife. ... Latin is an ancient Indo-European language originally spoken in Latium, the region immediately surrounding Rome. ...

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. In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. ... Thermodynamic reaction control or kinetic reaction control in a chemical reaction can decide the composition in a reaction product when competing reactions lead to different products under different reaction conditions. ... Chemical structure of Tetramethylsilane Chemical structure of a Trimethylsilyl group The name Tetramethylsilane stands for a chemical compound whose molecular structure is essentially like a silane (SiH4) molecule with four methyl groups substituted for the four hydrogen atoms in it. ...

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] The Diels-Alder reaction The Diels-Alder reaction is an organic chemical reaction (specifically, a cycloaddition) between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. ... Iron rusting - a chemical reaction with a slow reaction rate. ...

Image File history File links Size of this preview: 800 × 272 pixelsFull resolution (869 × 296 pixel, file size: 7 KB, MIME type: image/png) Tert butyl effect I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms of the...

See also

• methyl
• ethyl
• propyl
• pentyl / amyl

In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Ethyl is a two-carbon substituent in organic chemistry. ... In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula -C3H7. ... In organic chemistry, pentyl is a five-carbon alkyl substituent with chemical formula -C5H11. ... Amyl is a linguistic root word derived from the Latin amylum, from Greek αμυλον, meaning starch. ...

References