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Butyl

 

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Butyl



 
 
In organic chemistry
Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
, butyl is a four-carbon
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
 alkyl
Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
 substituent
Radical (chemistry)

In chemistry, radicals are atoms, molecules or ions with unpaired electrons on an otherwise open shell configuration. These unpaired electrons are usually highly chemical reaction, so radicals are likely to take part in chemical reactions....
 with chemical formula
Chemical formula

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 in chemical reactions....
 -C4H9 . It is derived from either of the two isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
s of the alkane
Alkane

Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
 called butane
Butane

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. Thus, n-butane can connect at either the terminal or an internal carbon atoms, giving rise to "n-butyl" and "sec-butyl" substituents.



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.



Nomenclature
According to IUPAC nomenclature
IUPAC nomenclature

IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry ....
, "isobutyl", "sec-butyl", and "tert-butyl" are all retained trivial names.



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).






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Encyclopedia


In organic chemistry
Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
, butyl is a four-carbon
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
 alkyl
Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
 substituent
Radical (chemistry)

In chemistry, radicals are atoms, molecules or ions with unpaired electrons on an otherwise open shell configuration. These unpaired electrons are usually highly chemical reaction, so radicals are likely to take part in chemical reactions....
 with chemical formula
Chemical formula

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 in chemical reactions....
 -C4H9 . It is derived from either of the two isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
s of the alkane
Alkane

Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
 called butane
Butane

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. 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.

  • Isobutyl group: (CH3)2CH–CH2– (fully systematic name: 2-methylpropyl)
  • tert-Butyl group: (CH3)3C– (fully systematic name: 1,1-dimethylethyl)


Nomenclature


According to IUPAC nomenclature
IUPAC nomenclature

IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry ....
, "isobutyl", "
sec-butyl", and "tert-butyl" are all retained trivial names.

skeletal formula
Skeletal formula

The skeletal formula of an organic compound is a shorthand representation of its molecular geometry. Skeletal formulae are ubiquitous in organic chemistry because they show complicated structures clearly and they are quick and simple to draw....
common name
Common name

A common name is a name in general use within a community . A common name is not necessarily a commonly used name.Many of the conventions and traditions described in this article are based on the English language, and thus may not apply to common names in other languages....
IUPAC namesystematic name
Systematic name

There are millions of possible objects that can be described in science, too many to create common names for every one. As a response, a number of systems of systematic names have been created....
alternate notation
n-butylbutylbutylbutan-1-yl
isobutylisobutyl2-methylpropyl2-methylpropan-1-yl
sec-butylsec-butyl1-methylpropylbutan-2-yl
tert-butyltert-butyl1,1-dimethylethyl2-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
S Butyl Acetate
T Butyl Acetate
n-butyl acetate
Butyl acetate

n-Butyl acetate, also known as butyl ethanoate, is an organic compound commonly used as a solvent in the production of lacquers and other products....
isobutyl acetate
Isobutyl acetate

The chemical compound isobutyl acetate, with systematic name 2-methylpropyl ethanoate, is a common solvent. It is produced from the esterification of isobutanol with acetic acid....
sec-butyl acetate
Sec-Butyl acetate

sec-Butyl acetate, or s-butyl acetate, is a solvent commonly used as a solvent in lacquers and enamels, where it is used in the production of acyclic poluymers, vinvyl resins and nitrocellulose ....
tert-butyl acetate
Tert-Butyl acetate

tert-Butyl acetate, or t-butyl acetate is a colourless flammable liquid with a camphor- or blueberry-like smell. It is used as a solvent in the production of lacquers, enamels, inks, adhesives, thinners and industrial cleaners....


Etymology

As the number of carbons in an alkyl chain increases, butyl is the last to be named historically instead of through Greek
Greek language

Greek is an Indo-European languages native to the southern Balkan peninsula, the language of the Greek people. It forms an independent branch within Indo-European....
 numbers. The name is derived from butyric acid
Butyric acid

Butyric acid , also known under the systematic name butanoic acid, is a carboxylic acid with the structural formula carbonhydrogen3CH2CH2-carboxyl group....
, a four carbon carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
 found in rancid
Decomposition

Decomposition refers to the process by which tissues of dead organisms break down into simpler forms of matter. Such a breakdown of dead organisms is essential for new growth and development of living organisms because it recycles the finite chemical constituents and frees up the limited physical space in the biome....
 butter
Butter

Butter is a dairy product made by churning fresh or fermentation cream or milk. It is generally used as a spread and a condiment, as well as in cooking applications such as baking, sauce making, and frying....
. The name of butyric acid, in turn, comes from Latin
Latin

Latin is an Italic language, historically spoken in Latium and Ancient Rome. Through the Military history of the Roman Empire, Latin spread throughout the Mediterranean and a large part of Europe....
 
butyrum, "butter".

Tert-butyl effect

The tert-butyl substituent
Substituent

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. The suffix -yl is used when naming organic compounds that contain a substituent....
 is very bulky and used in chemistry for kinetic stabilisation together with other bulky groups such as the related trimethylsilyl
Trimethylsilyl

A trimethylsilyl group is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom [−Si3], which is in turn bonded to the rest of a molecule....
 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
Diels-Alder reaction

The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
 below where the tert-butyl substituent causes a reaction rate
Reaction rate

The reaction rate or rate of reaction for a reactant or product in a particular chemical reaction is intuitively defined as how fast a reaction takes place....
 acceleration by a factor of 240 compared to hydrogen as the substituent.

See also


  • Methyl
  • Ethyl
    Ethyl group

    In chemistry, an ethyl group is an alkyl functional group derived from ethane . It has the chemical formula -Carbon2Hydrogen5 and is very often abbreviated -Et....
  • Propyl
    Propyl

    In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula -Carbon3Hydrogen7. It is the substituent form of the alkane propane....
  • Pentyl
    Pentyl

    In organic chemistry, pentyl is a five-carbon alkyl radical with chemical formula -C5H11. It is the substituent form of the alkane pentane....
     / amyl
    Amyl

    The word or root amyl has two meanings, in organic chemistry and biochemistry....