Undecane

Last updated
Undecane
Undecane-2D-Skeletal.svg
UndecaneFull.png
Undecane 3D ball.png
Names
Preferred IUPAC name
Undecane [1]
Identifiers
3D model (JSmol)
1697099
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.013.001 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 214-300-6
MeSH undecane
PubChem CID
RTECS number
  • YQ1525000
UNII
UN number 2330
  • InChI=1S/C11H24/c1-3-5-7-9-11-10-8-6-4-2/h3-11H2,1-2H3 Yes check.svgY
    Key: RSJKGSCJYJTIGS-UHFFFAOYSA-N Yes check.svgY
  • CCCCCCCCCCC
Properties
C11H24
Molar mass 156.313 g·mol−1
AppearanceColorless liquid
Odor Gasoline-like to Odorless
Density 740 g/L
Melting point −26 °C (−15 °F; 247 K)
Boiling point 196 °C (385 °F; 469 K)
log P 6.312
Vapor pressure 55 Pa (at 25 °C) [2]
5.4 nmol Pa−1 kg−1
-131.84·10−6 cm3/mol
1.417
Thermochemistry
345.05 J K−1 mol−1
Std molar
entropy
(S298)
458.15 J K−1 mol−1
−329.8–−324.6 kJ mol−1
−7.4339–−7.4287 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-silhouette.svg
Danger
H304, H315, H319, H331, H335
P261, P301+P310, P305+P351+P338, P311, P331
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point 60.0 °C (140.0 °F; 333.1 K)
240 °C (464 °F; 513 K)
Lethal dose or concentration (LD, LC):
> 2000 mg/kg (rat, oral)
> 5000 mg/kg (rat, dermal)
> 20 mg/L (rat, 8 hours)
Safety data sheet (SDS) Fisher Scientific
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Undecane (also known as hendecane) is a liquid alkane hydrocarbon with the chemical formula CH3(CH2)9CH3. It is used as a mild sex attractant for various types of moths and cockroaches, and an alert signal for a variety of ants. [3] It has 159 isomers. [4]

Contents

Undecane may also be used as an internal standard in gas chromatography when working with other hydrocarbons. Since the boiling point of undecane (196 °C) is well known, it may be used as a comparison for retention times in a gas chromatograph for molecules whose structure has been freshly elucidated. For example, if one is working with a 50 m crosslinked methyl silicone capillary column with an oven temperature increasing slowly, beginning around 60 °C, an 11-carbon molecule like undecane may be used as an internal standard to be compared with the retention times of other 10-, 11-, or 12- carbon molecules, depending on their structures.

See also

Related Research Articles

<span class="mw-page-title-main">Alkane</span> Type of saturated hydrocarbon compound

In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.

<span class="mw-page-title-main">Aliphatic compound</span> Hydrocarbon compounds without aromatic rings

In organic chemistry, hydrocarbons are divided into two classes: aromatic compounds and aliphatic compounds. Aliphatic compounds can be saturated like hexane, or unsaturated, like hexene and hexyne. Open-chain compounds, whether straight or branched, and which contain no rings of any type, are always aliphatic. Cyclic compounds can be aliphatic if they are not aromatic.

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

In organic chemistry, an alkene, or olefin, 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">Alkyne</span> Hydrocarbon compound containing one or more C≡C bonds

In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula CnH2n−2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.

<span class="mw-page-title-main">Functional group</span> Group of atoms giving a molecule characteristic properties

In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis.

<span class="mw-page-title-main">Hydrocarbon</span> Organic compound consisting entirely of hydrogen and carbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic; their odor is usually faint, and may be similar to that of gasoline or lighter fluid. They occur in a diverse range of molecular structures and phases: they can be gases, liquids, low melting solids or polymers.

<span class="mw-page-title-main">Cycloalkane</span> Saturated alicyclic hydrocarbon

In organic chemistry, the cycloalkanes are the monocyclic saturated hydrocarbons. In other words, a cycloalkane consists only of hydrogen and carbon atoms arranged in a structure containing a single ring, and all of the carbon-carbon bonds are single. The larger cycloalkanes, with more than 20 carbon atoms are typically called cycloparaffins. All cycloalkanes are isomers of alkenes.

Decane is an alkane hydrocarbon with the chemical formula C10H22. Although 75 structural isomers are possible for decane, the term usually refers to the normal-decane ("n-decane"), with the formula CH3(CH2)8CH3. All isomers, however, exhibit similar properties and little attention is paid to the composition. These isomers are flammable liquids. Decane is present in small quantities (less than 1%) in gasoline (petrol) and kerosene. Like other alkanes, it is a nonpolar solvent, and does not dissolve in water, and is readily combustible. Although it is a component of fuels, it is of little importance as a chemical feedstock, unlike a handful of other alkanes.

<span class="mw-page-title-main">RP-1</span> Highly refined form of kerosene used as rocket fuel

RP-1 (alternatively, Rocket Propellant-1 or Refined Petroleum-1) is a highly refined form of kerosene outwardly similar to jet fuel, used as rocket fuel. RP-1 provides a lower specific impulse than liquid hydrogen (H2), but is cheaper, is stable at room temperature, and presents a lower explosion hazard. RP-1 is far denser than H2, giving it a higher energy density (though its specific energy is lower). RP-1 also has a fraction of the toxicity and carcinogenic hazards of hydrazine, another room-temperature liquid fuel.

In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the Nomenclature of Organic Chemistry. Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There is also an IUPAC nomenclature of inorganic chemistry.

<span class="mw-page-title-main">Pentane</span> Alkane with 5 carbon atoms

Pentane is an organic compound with the formula C5H12—that is, an alkane with five carbon atoms. The term may refer to any of three structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, pentane means exclusively the n-pentane isomer, in which case pentanes refers to a mixture of them; the other two are called isopentane (methylbutane) and neopentane (dimethylpropane). Cyclopentane is not an isomer of pentane because it has only 10 hydrogen atoms where pentane has 12.

In organic chemistry, a cycloalkene or cycloolefin is a type of alkene hydrocarbon which contains a closed ring of carbon atoms and either one or more double bonds, but has no aromatic character. Some cycloalkenes, such as cyclobutene and cyclopentene, can be used as monomers to produce polymer chains. Due to geometrical considerations, smaller cycloalkenes are almost always the cis isomers, and the term cis tends to be omitted from the names. Cycloalkenes require considerable p-orbital overlap in the form of a bridge between the carbon-carbon double bond; however, this is not feasible in smaller molecules due to the increase of strain that could break the molecule apart. In greater carbon number cycloalkenes, the addition of CH2 substituents decreases strain. trans-Cycloalkenes with 7 or fewer carbons in the ring will not occur under normal conditions because of the large amount of ring strain needed. In larger rings, cistrans isomerism of the double bond may occur. This stability pattern forms part of the origin of Bredt's rule, the observation that alkenes do not form at the bridgehead of many types of bridged ring systems because the alkene would necessarily be trans in one of the rings.

Butene, also known as butylene, is an alkene with the formula C4H8. The word butene may refer to any of the individual compounds. They are colourless gases that are present in crude oil as a minor constituent in quantities that are too small for viable extraction. Butene is therefore obtained by catalytic cracking of long-chain hydrocarbons left during refining of crude oil. Cracking produces a mixture of products, and the butene is extracted from this by fractional distillation.

<span class="mw-page-title-main">Eclipsed conformation</span> Molecular form in which substituents on two adjacent atoms are closest together

In chemistry an eclipsed conformation is a conformation in which two substituents X and Y on adjacent atoms A, B are in closest proximity, implying that the torsion angle X–A–B–Y is 0°. Such a conformation can exist in any open chain, single chemical bond connecting two sp3-hybridised atoms, and it is normally a conformational energy maximum. This maximum is often explained by steric hindrance, but its origins sometimes actually lie in hyperconjugation.

In organic chemistry, a rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. Often a substituent moves from one atom to another atom in the same molecule, hence these reactions are usually intramolecular. In the example below, the substituent R moves from carbon atom 1 to carbon atom 2:

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

Neopentane, also called 2,2-dimethylpropane, is a double-branched-chain alkane with five carbon atoms. Neopentane is a flammable gas at room temperature and pressure which can condense into a highly volatile liquid on a cold day, in an ice bath, or when compressed to a higher pressure.

<span class="mw-page-title-main">Spiro compound</span> Organic molecule with two or more rings sharing a common atom

In organic chemistry, spiro compounds are compounds that have at least two molecular rings with only one common atom. The simplest spiro compounds are bicyclic, or have a bicyclic portion as part of the larger ring system, in either case with the two rings connected through the defining single common atom. The one common atom connecting the participating rings distinguishes spiro compounds from other bicyclics: from isolated ring compounds like biphenyl that have no connecting atoms, from fused ring compounds like decalin having two rings linked by two adjacent atoms, and from bridged ring compounds like norbornane with two rings linked by two non-adjacent atoms.

<span class="mw-page-title-main">Isomer</span> Chemical compounds with the same molecular formula but different atomic arrangements

In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Diamond and graphite are a familiar example; they are isomers of carbon. Isomerism refers to the existence or possibility of isomers.

Group 14 hydrides are chemical compounds composed of hydrogen atoms and group 14 atoms.

<span class="mw-page-title-main">2,3-Dimethylpentane</span> Chemical compound

2,3-Dimethylpentane is an organic compound of carbon and hydrogen with formula C
7
H
16
, more precisely CH
3
CH(CH
3
)
CH(CH
3
)
CH
2
CH
3
: a molecule of pentane with methyl groups –CH
3
replacing hydrogen atoms on carbon atoms 2 and 3. It is an alkane, a fully saturated hydrocarbon; specifically, one of the isomers of heptane.

References

  1. "undecane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 5 January 2012.
  2. Yaws, Carl L. (1999). Chemical Properties Handbook. New York: McGraw-Hill. pp. 159–179. ISBN   0-07-073401-1.
  3. Hölldobler B, Wilson EO (1990). The Ants. Harvard University Press. p. 287. ISBN   0-674-04075-9.
  4. Stoermer, Martin (2023). "Undecane Isomers". Figshare. doi:10.6084/M9.FIGSHARE.24309724.