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Ketone

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	Topics Ketone Topic Home A ketone (pronounced as key tone) is either the functional groupFunctional group In organic chemistry functional groups are specific groups of atoms within molecules, that are responsible for the characte... characterized by a carbonylCarbonyl In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O... group (O=C) linked to two other carbonCarbon Overview Carbon is a chemical element in the periodic table that has the symbol C and atomic number 6.... atoms or a chemical compoundChemical compound A chemical compound is a chemical substance consisting of two or more different chemically bonded chemical elements, with a ... that contains a carbonyl group. A ketone can be generally represented by the chemical formulaChemical formula A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compoun... : R₁(CCarbon Carbon is a chemical element in the periodic table that has the symbol C and atomic number 6.... OOxygen Oxygen is a chemical element with the chemical symbol O and atomic number 8.... )R₂. A carbonyl carbon bonded to two carbon atoms distinguishes ketones from carboxylic acidCarboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula --OH, usua... s, aldehydeAldehyde An aldehyde is an organic compound containing... s, esterEster Overview In chemistry, esters are organic compounds in which an organic group replaces a hydrogen atom in an oxygen acid.... s, amideAmide n chemistry, an *amide* is one of two kinds of compounds: ... s, and other oxygenOxygen Oxygen is a chemical element with the chemical symbol O and atomic number 8.... -containing compounds. The double-bond of the carbonyl group distinguishes ketones from alcoholAlcohol In chemistry, an alcohol is any organic compound in which a hydroxyl group is bound to a carbon atom of an alkyl or substit... s and etherEther Ether is the general name for a class of chemical compounds which contain an ether group an oxygen atom connected to two a... s. The simplest ketone is acetoneAcetone In chemistry, acetone is the simplest representative of the ketones.... (systematically named propan-2-one). The carbon atom adjacent to a carbonyl group is called the a-carbon. Hydrogens attached to this carbon are called a-hydrogens. In the presence of an acid catalyst the ketone is subjected to so-called keto-enol tautomerismKeto-enol tautomerism Summary In organic chemistry, keto-enol tautomerism refers to a chemical equilibrium between a ketone or aldehyde 1 and an eno... . The reaction with a strong baseFacts About Strong base A strong base is a basic chemical compound that is able to deprotonate very weak acids in an acid-base reaction.... gives the corresponding enolate. A diketoneDiketone A diketone is a molecule containing two carbonyl groups.... is a compound containing two ketone groups. Nomenclature In general, ketones are named using IUPAC nomenclatureIUPAC nomenclature IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general.... by changing the suffix -e of the parent alkaneAlkane An alkane is an acyclic saturated hydrocarbon.... to -one. For common ketones, some traditional names such as acetoneAcetone In chemistry, acetone is the simplest representative of the ketones.... and benzophenoneBenzophenone Summary Benzophenone is the organic compound with the formula2CO, generally abbreviated Ph2CO.... predominate, and these are considered retained IUPAC names , although some introductory chemistry texts use names such as propanone. Oxo is the formal IUPAC nomenclature for a ketone functional groupFunctional group Overview In organic chemistry functional groups are specific groups of atoms within molecules, that are responsible for the characte... . However, other prefixes are also used by various books and journals. For some common chemicals (mainly in biochemistry), keto or oxo is the term used to describe the ketone (also known as alkanone) functional groupFunctional group In organic chemistry functional groups are specific groups of atoms within molecules, that are responsible for the characte... . Oxo also refers to a single oxygen atom coordinated to a transition metal (a metal oxo). Physical properties A carbonyl group is polar. This makes ketones polar compounds. The carbonyl groups interact with water by hydrogen bondHydrogen bond In chemistry, a hydrogen bond is a type of attractive intermolecular force that exists between two partial electric charges ... ing, and ketones are soluble in water. It is a hydrogen-bond acceptor, but not a hydrogen-bond donor, and cannot hydrogen-bond to itself. This makes ketones more volatile than alcoholAlcohol In chemistry, an alcohol is any organic compound in which a hydroxyl group is bound to a carbon atom of an alkyl or substit... s and carboxylic acidCarboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula --OH, usua... s of similar molecular weight. Acidity The a-hydrogen of a ketone is far more acidic than the hydrogen of a regular alkane (pKa ˜ 50). This is due to resonance stabilization of the enolate ion that is formed through dissociation. The relative acidity of the a-hydrogen is important in the enolization reactions of ketones and other carbonyl compounds. Spectroscopic properties SpectroscopySpectroscopy Spectroscopy is the study of matter by investigating light, sound, or particles that is emitted, absorbed or scattered by th... is an important means for identifying ketones. Ketones and aldehydes will display a significant peak in infrared spectroscopyInfrared spectroscopy Infrared spectroscopy is the subset of spectroscopy that deals with the Infrared part of the electromagnetic spectrum.... , at around 1700 cm^-1Wavenumber Wavenumber in most physical sciences is a wave property inversely related to wavelength, having units of inverse length.... (slightly higher or lower, depending on the chemical environment) Synthesis Several methods exist for the preparation of ketones in the laboratory: Ketones can be created by oxidation of secondary alcoholAlcohol In chemistry, an alcohol is any organic compound in which a hydroxyl group is bound to a carbon atom of an alkyl or substit... s. The process requires a strong oxidizing agent such as potassium permanganatePotassium permanganate Overview Potassium permanganate is the chemical compound KMnO4.... , potassium dichromatePotassium dichromate Potassium dichromate, K2Cr2O7 is used in oxidation reactions.... or other agents containing Cr(VI)Chromium Chromium is a chemical element in the periodic table that has the symbol Cr and atomic number 24. ... . The alcohol is oxidized by heating under refluxReflux Reflux is a technique used in chemistry to apply energy to reactions over an extended period of time.... in acidified solution. For example propan-2-ol is oxidised to acetoneAcetone In chemistry, acetone is the simplest representative of the ketones.... : H₃C-CH(OH)-CH₃ ? H₃C-CO-CH₃ Two atoms of hydrogen are removed, leaving a single oxygen atom double-bonded to a carbon atom. Ketones are also prepared by Gem halide hydrolysis. Alkynes can be turned into enolEnol Enol is an alkene with hydroxyl group on one of the carbon atoms of the double bond.... s through a hydration reactionHydration reaction In organic chemistry, a hydration reaction is a chemical reaction in which a hydroxyl group and a hydrogen cation are added... in the presence of an acid and HgSO₄ Mercury(II) sulfate Mercury sulfate, commonly called mercuric sulfate is the chemical compound HgSO4.... , and subsequent enol-keto tautomerization gives a ketone. This always produces a ketone, even with a terminal alkyne, and Sia2BH is needed to get an aldehyde from an alkyne Aromatic ketones can be prepared in the Friedel-Crafts reactionFriedel-Crafts reaction The Friedel-Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877.... , the related Houben-Hoesch reaction and the Fries rearrangementFries rearrangement The Fries rearrangement is a rearrangement reaction of a phenyl ester to a hydroxy aryl ketone by catalysis of lewis acids ... . In the Kornblum–DeLaMare rearrangementKornblum–DeLaMare rearrangement The Kornblum?DeLaMare rearrangement is a rearrangement reaction in organic chemistry in which a primary or secondary organic... ketones are prepared from peroxides and base In the Ruzicka cyclization, cyclic ketones are prepared from dicarboxylic acids. In the Nef reactionNef reaction The Nef reaction is an organic reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane to a... , ketones form by hydrolysis of salts of secondary nitro compounds In the Fukuyama couplingFukuyama coupling The Fukuyama coupling is a coupling reaction taking place between a thioester and an organozinc halide in the presence of a ... , ketones form from a thioester and a organozinc compound Ketones are also prepeared by the reaction of acid chloride with organocadmium compoundOrganocadmium compound An organocadmium compound is a organometallic compound containing a carbon to cadmium chemical bond.... s or organocopper compoundFacts About Organocopper compound Organocopper compounds in organometallic chemistry contain carbon to copper chemical bonds.... s. Reactions Ketones engage in many organic reactionOrganic reaction Organic reactions are chemical reactions involving organic compounds.... s: Nucleophilic additionNucleophilic addition In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a pi bond is rem... . The reaction of a ketone with a nucleophileNucleophile In chemistry, a nucleophile is a reagent that forms a chemical bond to its reaction partner by donating both bonding elect... gives a tetrahedral carbonyl addition compoundTetrahedral carbonyl addition compound A tetrahedral carbonyl addition compound is an organic compound formed by nucleophilic addition to a carbonyl compound such ... . the reaction with the anion of a terminal alkyneAlkyne Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms.... gives a hydroxyalkyne the reaction with ammoniaAmmonia Ammonia is a compound of nitrogen and hydrogen with the formula NH3.... or a primary amine gives an imineImine An imine is a functional group or chemical compound containing a carbon-nitrogen double bond.... + water the reaction with secondary amine gives an enamineEnamine An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by lo... + water the reaction with a Grignard reagent gives a magnesium alkoxide and after aqueous workup a tertiary alcohol the reaction with an organolithium reagentOrganolithium reagent An organolithium reagent is an organometallic compound with a direct bond between a carbon and a lithium atom.... also gives a tertiary alcohol the reaction with an alcoholAlcohol Summary In chemistry, an alcohol is any organic compound in which a hydroxyl group is bound to a carbon atom of an alkyl or substit... , an acidFacts About Acid An acid is traditionally considered any chemical compound that when dissolved in water, gives a solution with a pH of less ... or baseBase (chemistry) DefinitionA base is a substance which has a free pair of electrons to bind a proton .... gives a hemiketal + water and further reaction with an alcohol gives the ketalKetal A ketal is a functional group or molecule containing the functional group of a carbon bonded to two -OAlkyl groups.... + water. This is a carbonylCarbonyl In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O... -protecting reaction. reaction of RCOR' with sodium amideSodium amide Sodium amide, also called sodamide, is NaNH2.... results in cleavage with formation of the amide RCONH2 and the alkane R'H, a reaction called the Haller-Bauer reaction (1909) Electrophilic additionElectrophilic addition Summary In Organic chemistry, an Electrophilic addition reaction is an addition reaction where, in a chemical compound, a pi bond is... , reaction with an electrophileElectrophile In chemistry, an electrophile is a reagent attracted to electrons that participates in a chemical reaction by accepting an e... gives a resonance stabilized cation. the reaction with phosphonium ylides in the Wittig reactionWittig reaction The Wittig reaction is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide to give an alkene and... gives alkeneAlkene In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one ... s reaction with water gives geminalGeminal In chemistry, the term geminal refers to the relationship between two functional groups that are attached to the same atom.... diolDiol Summary A diol is a chemical compound containing two hydroxyl groups.... s reaction with thiolThiol In organic chemistry, a thiol is a compound that contains the functional group composed of a sulfur atom and a hydrogen atom... s gives a thioacetalThioacetal Thioacetals are the sulphur analogue of acetals.... reaction with hydrazineHydrazine Hydrazine is the chemical compound with formula N2H4.... or derivativeDerivative In mathematics, the derivative is defined as the instantaneous rate of change of a function.... s of hydrazine gives hydrazoneHydrazone A hydrazone is a class of organic compounds with the structure R2C=NNR2.... s reaction with a metal hydride gives a metal alkoxide salt and then with water an alcoholAlcohol In chemistry, an alcohol is any organic compound in which a hydroxyl group is bound to a carbon atom of an alkyl or substit... reaction of an enolEnol Enol is an alkene with hydroxyl group on one of the carbon atoms of the double bond.... with halogenHalogen Overview The halogens are a chemical series.... s to form a-haloketoneHaloketone A haloketone in organic chemistry is a functional group consisting of a ketone group with a a-halogen substituent.... a reaction at an a-carbon is the reaction of a ketone with heavy waterHeavy water Heavy water is a loose term which usually refers to deuterium oxide, D2O or 2H2O.... to give a deuterated ketone-d. fragmentation in photochemical Norrish reactionNorrish reaction The Norrish reaction in organic chemistry describes the photochemical reactions taking place with ketones and aldehydes.... reaction with halogens and base of methyl ketones in the Haloform reactionHaloform reaction The haloform reaction is a chemical reaction where a haloform is produced by the multiple halogenation of a methyl ketone in... reaction of 1,4-aminodiketones to oxazoles by dehydration in the Robinson-Gabriel synthesisRobinson-Gabriel synthesis The Robinson-Gabriel synthesis is a chemical reaction that forms oxazoles by dehydration of 2-acylamino-ketones.... reaction of aryl alkyl ketones with sulfur and an amine to amides in the Willgerodt reaction Biochemistry AcetoneAcetone In chemistry, acetone is the simplest representative of the ketones.... , acetoacetate and beta-hydroxybutyrateFacts About Beta-hydroxybutyrate Beta-hydroxybutyrate, acetoacetate, and acetone collectively are called ketone bodies.... are ketones (or ketone bodiesKetone bodies Ketone bodies are three chemicals that are produced as by-products when fatty acids are broken down for energy.... ) generated from carbohydrateCarbohydrate Carbohydrates are chemical compounds that contain oxygen, hydrogen, and carbon atoms.... s, fatty acidFatty acid In chemistry, especially biochemistry, a fatty acid is a carboxylic acid , often with a long aliphatic tail , either saturat... s and amino acidAmino acid Summary In chemistry, an amino acid is any molecule that contains both amine and carboxyl functional groups.... s in humans and most vertebrateVertebrate Vertebrata is a subphylum of chordates, specifically, those with backbones or spinal columns.... s. Ketones are elevated in bloodBlood Blood is a highly specialised circulating tissue consisting of several types of cell suspended in a fluid medium known as pl... after fasting including a night of sleep, and in both blood and urineUrine Overview }Urine is liquid produced by an animal's kidney, collected in the bladder and excreted through the urethra.... in starvationStarvation Overview Symptoms Starved individuals lose substantial fat and muscle mass as the body breaks down these tissues for energy.... , hypoglycemiaHypoglycemia Hypoglycemia is a medical term referring to a pathologic state produced by a lower than normal amount of sugar in the bloo... due to causes other than hyperinsulinismHyperinsulinemic hypoglycemia Hyperinsulinemic hypoglycemia describes the condition and effects of low blood glucose caused by excessive insulin.... , various inborn errors of metabolismInborn error of metabolism Inborn errors of metabolism comprise a large class of genetic diseases involving disorders of metabolism.... , and ketoacidosisKetoacidosis Ketoacidosis is a type of metabolic acidosis which is caused by high concentrations of keto acids, formed by the deamination... (usually due to diabetes mellitusDiabetes mellitus Diabetes mellitus is a disease characterized by persistent hyperglycemia .... ). Although ketoacidosis is characteristic of decompensated or untreated type 1 diabetes, ketosis or even ketoacidosis can occur in type 2 diabetesDiabetes mellitus type 2 Diabetes mellitus type 2 is a metabolic disorder that is primarily characterized by insulin resistance, relative insulin def... in some circumstances as well. Acetoacetate and beta-hydroxybutyrate are an important fuel for many tissues, especially during fasting and starvation. The brain, in particular, relies heavily on ketone bodies as a substrate for lipidLipid Lipids are a class of hydrocarbon-containing organic compounds essential for the structure and function of living cells.... synthesis and for energy during times of reduced food intake. At the NIH, Dr. Richard Veech refers to ketones as "magic" in their ability to increase metabolic efficiency, while decreasing production of free radicals, the damaging byproducts of normal metabolism. His work has shown that ketone bodies may treat neurological diseases such as Alzheimer's and Parkinson's disease, and the heart and brain operate 25% more efficiently using ketones as a source of energy. Research has also shown ketones play a role in reducing epileptic siezures with the so-called high-fat, near-zero carbohydrate Ketogenic Diet. Applications Ketones are often used in perfumePerfume Perfume is a mixture of fragrant essential oils and aroma compounds, fixatives, and solvents used to give the human body, ob... s and paintPaint Paint is the general term for a family of products used to protect and add color to an object or surface by covering it with... s to stabilize the other ingredients so that they don't degrade as quickly over time. Other uses are as solvents and intermediates in chemical industry. Examples of ketones are acetoneAcetone In chemistry, acetone is the simplest representative of the ketones.... , acetophenoneAcetophenone Acetophenone is a crystalline ketone that is used as a solvent for cellulose ethers and esters in the manufacture of alcohol... , and methyl ethyl ketone. See also List of publications in organic chemistryList of publications in chemistry Some criteria for editing this page have been debated and are displayed on the .... KetosisKetosis Ketosis is a stage in metabolism occurring when the liver has been depleted of stored glycogen and switches to a chronic fas... Ketone bodiesKetone bodies Ketone bodies are three chemicals that are produced as by-products when fatty acids are broken down for energy.... (Medical term referring to all or either of the three ketones occurring in the body).