Tetramethylbutane

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Tetramethylbutane
Tetramethylbutane skeletal.png
Tetramethylbutane 3D 1.png
Names
Preferred IUPAC name
2,2,3,3-Tetramethylbutane [1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.961 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-855-6
PubChem CID
UNII
UN number 1325
  • InChI=1S/C8H18/c1-7(2,3)8(4,5)6/h1-6H3 Yes check.svgY
    Key: OMMLUKLXGSRPHK-UHFFFAOYSA-N Yes check.svgY
  • CC(C)(C)C(C)(C)C
Properties
C8H18
Molar mass 114.232 g·mol−1
AppearanceWhite, opaque, waxy crystals
Odor Odorless
Melting point 98 to 104 °C; 208 to 219 °F; 371 to 377 K
Boiling point 106.0 to 107.0 °C; 222.7 to 224.5 °F; 379.1 to 380.1 K
2.9 nmol Pa−1 kg−1
Thermochemistry
232.2 J K−1 mol−1 (at 2.8 °C)
Std molar
entropy
(S298)
273.76 J K−1 mol−1
−270.3 – −267.9 kJ mol−1
−5.4526 – −5.4504 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H228, H304, H315, H336, H410
P210, P240, P241, P261, P264, P271, P273, P280, P301+P310, P302+P352, P304+P340, P312, P321, P331, P332+P313, P362, P370+P378, P391, P403+P233, P405, P501
Flash point 4 °C (39 °F; 277 K)
Explosive limits 1–?%
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetramethylbutane, sometimes called hexamethylethane, is a hydrocarbon with formula C8H18 or (H3C-)3C-C(-CH3)3. It is the most heavily branched and most compact of the many octane isomers, the only one with a butane (C4) backbone. Because of its highly symmetrical structure, it has a very high melting point and a short liquid range; in fact, it is the smallest saturated acyclic hydrocarbon that appears as a solid at a room temperature of 25 °C. (Among cyclic hydrocarbons, cubane, C8H8 is even smaller and is also solid at room temperature.) It is also the most stable C8H18 isomer, with a heat of formation 4.18 kcal/mol (17.5 kJ/mol) lower than that of n-octane, a fact that has been attributed to stabilizing dispersive interactions (electron correlation) between the methyl groups (protobranching). [2]

The compound can be obtained by reaction of Grignard reagent tert-Butylmagnesium bromide with ethyl bromide, or of ethylmagnesium bromide with tert-butyl bromide in the presence of manganese(II) ions. [3] This transformation is believed to go through the dimerization of two tert-butyl radicals, which are generated by decomposition of the organomanganese compounds generated in situ.

The full IUPAC name of the compound is 2,2,3,3-tetramethylbutane, but the numbers are superfluous in this case because there is no other possible arrangement of "tetramethylbutane".

Related Research Articles

<span class="mw-page-title-main">Alkene</span> Hydrocarbon compound containing one or more C=C bonds

In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins.

<span class="mw-page-title-main">Heptane</span> Chemical compound

Heptane or n-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 point is 100% iso-octane). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and isooctane which is expressed as the percentage of isooctane in heptane and is listed on pumps for gasoline (petrol) dispensed globally.

<span class="mw-page-title-main">Organolithium reagent</span> Chemical compounds containing C–Li bonds

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers. They have also been applied in asymmetric synthesis in the pharmaceutical industry. Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C−Li bond is highly ionic. Owing to the polar nature of the C−Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes pyrophoric.

In organic chemistry, an aryl halide is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. The haloarene are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

<i>n</i>-Butyllithium Chemical compound

n-Butyllithium C4H9Li (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry.

<span class="mw-page-title-main">1-Bromobutane</span> Chemical compound

1-Bromobutane is the organobromine compound with the formula CH3(CH2)3Br. It is a colorless liquid, although impure samples appear yellowish. It is insoluble in water, but soluble in organic solvents. It is primarily used as a source of the butyl group in organic synthesis. It is one of several isomers of butyl bromide.

<span class="mw-page-title-main">Grignard reagent</span> Organometallic compounds used in organic synthesis

A Grignard reagent or Grignard compound is a chemical compound with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.

<span class="mw-page-title-main">Methyllithium</span> Chemical compound

Methyllithium is the simplest organolithium reagent with the empirical formula CH3Li. This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used in solution with an ether as the solvent, is a reagent in organic synthesis as well as organometallic chemistry. Operations involving methyllithium require anhydrous conditions, because the compound is highly reactive toward water. Oxygen and carbon dioxide are also incompatible with MeLi. Methyllithium is usually not prepared, but purchased as a solution in various ethers.

<span class="mw-page-title-main">Organocopper chemistry</span> Compound with carbon to copper bonds

Organocopper chemistry is the study of the physical properties, reactions, and synthesis of organocopper compounds, which are organometallic compounds containing a carbon to copper chemical bond. They are reagents in organic chemistry.

Pivalic acid, also known as neovaleric acid, is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. A common abbreviation for the pivalyl or pivaloyl group (t-BuC(O)) is Piv and for pivalic acid (t-BuC(O)OH) is PivOH. It is an isomer of valeric acid, the other two isomers of it are 2-Methylbutanoic acid and 3-Methylbutanoic acid.

Morris Selig Kharasch was a pioneering organic chemist best known for his work with free radical additions and polymerizations. He defined the peroxide effect, explaining how an anti-Markovnikov orientation could be achieved via free radical addition. Kharasch was born in the Russian Empire in 1895 and immigrated to the United States at the age of 13. In 1919, he completed his Ph.D. in chemistry at the University of Chicago and spent most of his professional career there.

The Kulinkovich reaction describes the organic synthesis of cyclopropanols via reaction of esters with dialkyldialkoxytitanium reagents, generated in situ from Grignard reagents bearing hydrogen in beta-position and titanium(IV) alkoxides such as titanium isopropoxide. This reaction was first reported by Oleg Kulinkovich and coworkers in 1989.

<span class="mw-page-title-main">Group 2 organometallic chemistry</span>

Group 2 organometallic chemistry refers to the chemistry of compounds containing carbon bonded to any group 2 element. By far the most common group 2 organometallic compounds are the magnesium-containing Grignard reagents which are widely used in organic chemistry. Other organmetallic group 2 compounds are rare and are typically limited to academic interests.

<span class="mw-page-title-main">2-Chlorobutane</span> Chemical compound

2-Chlorobutane is a compound with formula C4H9Cl. It is also called sec-butyl chloride. It is a colorless, volatile liquid at room temperature that is not miscible in water.

Ether cleavage refers to chemical substitution reactions that lead to the cleavage of ethers. Due to the high chemical stability of ethers, the cleavage of the C-O bond is uncommon in the absence of specialized reagents or under extreme conditions.

<span class="mw-page-title-main">2,2-Dimethylpentane</span> Chemical compound

2,2-Dimethylpentane is one of the isomers of heptane. It is also called neoheptane as it contains the (CH3)3C grouping. It has the most extreme properties of the isomers.

<i>tert</i>-Butyl peroxybenzoate Chemical compound

tert-Butyl peroxybenzoate (TBPB) an organic compound with the formula C6H5CO2CMe3 (Me = CH3). It is the most widely produced perester. It is often used as a radical initiator in polymerization reactions, such as the production of LDPE from ethylene, and for crosslinking, such as for unsaturated polyester resins.

<span class="mw-page-title-main">Vinyllithium</span> Chemical compound

Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagent in synthesis of organic compounds, especially for vinylations.

References

  1. "Hexamethylethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Information. Retrieved 11 March 2012.
  2. Joyce, Justin P.; Shores, Matthew P.; Rappè, Anthony K. (2020-07-29). "Protobranching as repulsion-induced attraction: a prototype for geminal stabilization". Physical Chemistry Chemical Physics. 22 (29): 16998–17006. doi:10.1039/D0CP02193H. ISSN   1463-9084.
  3. M. S. KHARASCH; J. W. HANCOCK; W. NUDENBERG; P. O. TAWNEY (1956). "Factors Influencing the Course and Mechanism of Grignard Reactions. XXII. The Reaction of Grignard Reagents with Alkyl Halides and Ketones in the Presence of Manganous Salts". Journal of Organic Chemistry. 21 (3): 322–327. doi:10.1021/jo01109a016.