In organic chemistry, butyl is a four-carbon alkyl substituent with chemical formula -C4H9 . Organic chemistry is a discipline within Chemistry which involves the scientific study of the structure properties composition reactions, and preparation Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 An alkyl is a Univalent radical consisting of Carbon and Hydrogen atoms arranged in a chain In Chemistry, radicals (often referred to as free radicals) are atoms molecules or ions with Unpaired electrons on an otherwise Open shell A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes It is derived from either of the two isomers of the alkane called butane. Alkanes, also known as Paraffins 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
Each of the two isomers of butane give rise to two isomers of the butyl substituent. This article is about the chemical concept For "isomerism" of atomic nuclei see Nuclear isomer. This article is about the chemical concept For "isomerism" of atomic nuclei see Nuclear isomer. 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–CH(CH3)– (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. In Organic chemistry, butyl is a four- Carbon Alkyl substituent with Chemical formula -C4H9.
- Isobutyl group: (CH3)2CH–CH2– (fully systematic name: 2-methylpropyl)
- tert-Butyl group: (CH3)3C– (fully systematic name: 1,1-dimethylethyl)
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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 |
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n-butyl | butyl | butyl | butan-1-yl |
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isobutyl | isobutyl | 2-methylpropyl | 2-methylpropan-1-yl |
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sec-butyl | sec-butyl | 1-methylpropyl | butan-2-yl |
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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 skeletal formula of an Organic compound is a shorthand representation of its molecular structure. For Wikipedia aspects see WikipediaNaming conventions (common names, WikipediaNaming conventions, and WikipediaStyle manual. There are millions of possible objects that can be described in science too many to create Common names for every one
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). A carbon-carbon bond is a Covalent bond between two Carbon Atoms. Iso means one, sec- means two and tert- means three.
Some examples
The following are the four isomers of "butyl acetate":
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Etymology
As the number of carbons in an alkyl chain increases, butyl is the last to be named historically instead of through Greek numbers. n -Butyl acetate, also known as butyl ethanoate, is an Organic compound commonly used as a Solvent in the production of Lacquers The Chemical compound isobutyl acetate, with systematic name 2-methylpropyl ethanoate, is a common solvent sec -Butyl acetate, or s -butyl acetate is a Solvent commonly used in the production of Lacquers and other products tert -Butyl acetate, or t -butyl acetate is a colourless flammable liquid with a camphor- or blueberry-like smell Greek (el ελληνική γλώσσα or simply el ελληνικά — "Hellenic" is an Indo-European language, spoken today by 15-22 million people mainly The name is derived from butyric acid, a four carbon carboxylic acid found in rancid butter. Butyric acid (from Greek βούτυρος = butter) also known under the systematic name butanoic acid, is a Carboxylic acid with the structural Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H Decomposition (or spoilage) refers to the break down of tissue of a formerly living Organism into simpler forms of matter Butter is a Dairy product made by churning fresh or fermented Cream or Milk. The name of butyric acid, in turn, comes from Latin butyrum, "butter". Latin ( lingua Latīna, laˈtiːna is an Italic language, historically spoken in Latium and Ancient 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. 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 For tetramethylsilane which also abbreviated as TMS see Tetramethylsilane. 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. The Diels-Alder reaction is an Organic chemical reaction (specifically a Cycloaddition) between a conjugated Diene and a substituted Alkene, The reaction rate or rate of reaction for a Reactant or product in a particular reaction is intuitively defined as how fast a reaction takes [1]
See also
References
- ^ Factors affecting ease of ring formation. In Chemistry, a methyl group is a Hydrophobic Alkyl Functional group named after Methane (4 In Organic chemistry, propyl is a three- Carbon Alkyl substituent with Chemical formula - C 3 H 7 In Organic chemistry, pentyl is a five- Carbon Alkyl substituent with Chemical formula -C5H11. The word or root amyl has two meanings in Organic chemistry and Biochemistry. 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/S0040-4039(00)87916-2
Dictionary
butyl
-noun
- (organic chemistry) Either of four isomeric univalent hydrocarbon radicals, C4H9, formally derived from butane by the loss of a proton.
- A synthetic rubber made by the polymerization of isobutylene.
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