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Ketone
In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group−C(=O)− (a carbon-oxygen double bond C=O). A ketone derived from an alkane is an alkanone. The simplest ketone is acetone (where R and R' are methyl), with the formula (CH3)2CO. Many ketones are of great importance in biology and industry.
SubstituentIn organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. The suffix -yl is used when naming organic compounds that contain a single bond replacing one hydrogen; -ylidene and -ylidyne are used with double bonds and triple bonds, respectively.
AcetoneNames IUPAC nameAcetonePreferred IUPAC namePropan-2-oneSystematic IUPAC namePropan-2-oneOther names Acetonum (Latin pronunciation:)Dimethyl ketoneDimethyl carbonylKetone propaneβ-KetopropanePropanonePyroacetic spirit (archaic)Spirit of Saturn (archaic)Identifiers CAS Number67-64-13D model (JSmol)Interactive imageAbbreviations Me2CO Beilstein Reference635680 ChEBICHEBI:15347ChEMBLChEMBL14253ChemSpider175ECHA InfoCard100.000.602EC Number200-662-2Gmelin Reference1466 KEGGD02311MeSHAcetonePubChemCID180RTECS numberAL3150000UNII1364PS73AFUN number1090 CompTox Dashboard(EPA)DTXSID8021482InChIInChI=1S/C3H6O/c1-3(2)4/h1-2H3Key: CSCPPACGZOOCGX-UHFFFAOYSA-NInChI=1/C3H6O/c1-3(2)4/h1-2H3Key: CSCPPACGZOOCGX-UHFFFAOYAFSMILESCC(=O)CProperties Chemical formulaC3H6OMolar mass58.080 g·mol Appearance Colourless liquid OdorPungent, fruity, dry Density0.7845 g/cm (25 °C) Melting point−94.9 °C (−138.8 °F; 178.2 K) Boiling point56.08 °C (132.94 °F; 329.23 K) Critical point (T, P) 508 K (235 °C), 48 bar Solubility in waterMiscible SolubilityMiscible in benzene, diethyl ether, methanol, chloroform, ethanollog P−0.24 Vapor pressure9.39kPa (0 °C)30.6kPa (25 °C)374kPa (100 °C)2.8MPa (200 °C)Acidity (pKa) 19.16 (H2O)26.5 (DMSO)Magnetic susceptibility (χ)−33.8·10 cm/mol Thermal conductivity0.161W/(m·K) (25 °C) Refractive index (nD)1.3588 (20 °C) Viscosity0.4013 mPa·s (0 °C)0.3311mPa·s at 20 °C0.306mPa·s (25 °C)0.2562mPa·s at 50 °C Structure Coordination geometryTrigonal planar at C2 Molecular shapeDihedral at C2 Dipole moment2.88 D Thermochemistry Heat capacity(C)126.3J/(mol·K) (liquid)75J/(mol·K) (gas)96J/(mol·K) (solid) Std molarentropy(S298)199.8J/(mol·K) (liquid)295.35J/(mol·K) (gas) Std enthalpy offormation(ΔfH298)−248.4kJ/mol (liquid)−218.5 kJ/mol (gas) Std enthalpy ofcombustion(ΔcH298)−1.79MJ/mol Enthalpy of fusion(ΔfHfus)+5.7kJ/mol Enthalpy of vaporization(ΔfHvap)+30.3kJ/mol Hazards Occupational safety and health (OHS/OSH): Main hazardsHighly flammable GHS labelling: PictogramsSignal wordDangerHazard statementsH225, H302, H319, H336, H373Precautionary statementsP210, P235, P260, P305+P351+P338NFPA 704 (fire diamond) 130Flash point−20 °C (−4 °F; 253 K) Autoignitiontemperature465 °C (869 °F; 738 K) Explosive limits2.5–12.8% Threshold limit value (TLV)250 ppm (STEL), 500 ppm (C) Lethal dose or concentration (LD, LC): LD50 (median dose)5800mg/kg (rat, oral)3000mg/kg (mouse, oral)5340mg/kg (rabbit, oral)LC50 (median concentration)20,702ppm (rat, 8 h) LCLo (lowest published)45,455ppm (mouse, 1 h) NIOSH (US health exposure limits): PEL (Permissible)1000ppm (2400mg/m) REL (Recommended)TWA 250ppm (590mg/m) IDLH (Immediate danger)2500ppm Related compounds Related compoundsButanoneIsopropyl alcoholFormaldehydeUreaCarbonic acidSupplementary data page Acetone (data page)Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Yverify ( ?)
AlkaneType of saturated hydrocarbon compoundChemical structure of methane, the simplest alkaneIn organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclicsaturatedhydrocarbon. 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.
Carbonyl groupIn organic chemistry, a carbonyl group is a functional group with the formula C=O, composed of a carbonatomdouble-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such as aldehydes, ketones and carboxylic acid), as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound.
SteroidPolycyclic organic compound having sterane as a core structureStructure of 24-ethyl-lanostane, a prototypical steroid with 32 carbon atoms. Its core ring system (ABCD), composed of 17 carbon atoms, is shown with IUPAC-approved ring lettering and atom numbering.A steroid is an organic compound with four fused rings (designated A, B, C, and D) arranged in a specific molecular configuration.
Organic compoundOrganic compounds are a subclass of chemical compounds of carbon. Little consensus exists among chemists on the exact definition of organic compound; the only universally accepted definition is the quasi-tautological "organic compounds are the subject matter of organic chemistry". Generally, any large chemical compound containing a carbon–hydrogen or carbon–carbon bond is accepted as an organic compound.
Organic chemistryOrganic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials (i.e. matter in its various forms that contain carbonatoms). It involves studying the structure of organic material to determine the structural formula, analyzing physical and chemical properties, and evaluating chemical reactivity to understand the behavior of organic compounds.
CarbonChemical element with atomic number 6 (C)–↑C↓Siboron ← carbon → nitrogen
Methyl groupIn organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula CH3 (whereas normal methane has the formula CH4). In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules.
SugarSweet-tasting, water-soluble carbohydratesSugars (clockwise from top-left): white refined, unrefined, brown, unprocessed cane sugar Sugar is a class of sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose and galactose.
KetoseIn organic chemistry, a ketose is a monosaccharide containing one ketone (>C=O) group per molecule. The simplest ketose is dihydroxyacetone ((CH2OH)2C=O), which has only three carbon atoms. It is the only ketose with no optical activity. All monosaccharide ketoses are reducing sugars, because they can tautomerize into aldoses via an enediol intermediate, and the resulting aldehyde group can be oxidised, for example in the Tollens' test or Benedict's test.
Double bondIn chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist between two different elements: for example, in a carbonyl group between a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds (N=N), imines (C=N), and sulfoxides (S=O).
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