A ketone (pronounced as key tone) is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains a carbonyl group. In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions In Organic chemistry, a carbonyl group is a Functional group composed of a Carbon Atom double-bonded to an Oxygen Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. A ketone can be generally represented by the chemical formula:

R₁(CO)R₂. 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 Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the

A carbonyl carbon bonded to two carbon atoms distinguishes ketones from carboxylic acids, aldehydes, esters, amides, and other oxygen-containing compounds. Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H An aldehyde is an organic compound containing a terminal Carbonyl group. Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least In Chemistry, an amide is one of three kinds of Compounds (sometimes called acid amide the organic Functional group characterized Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The double-bond of the carbonyl group distinguishes ketones from alcohols and ethers. In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon Ether is a class of Organic compounds which contain an ether group — an Oxygen Atom connected to two (substituted Alkyl The simplest ketone is acetone (systematically named propan-2-one^[1]). Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable

The carbon atom adjacent to a carbonyl group is called the α-carbon. Hydrogens attached to this carbon are called α-hydrogens. In the presence of an acid catalyst the ketone is subjected to so-called keto-enol tautomerism. In Organic chemistry, keto-enol Tautomerism refers to a Chemical equilibrium between a keto form (a Ketone or an Aldehyde The reaction with a strong base gives the corresponding enolate. In Chemistry, a base is most commonly thought of as an aqueous substance that can accept Protons This refers to the Brønsted-Lowry theory of acids and Enols (also known as alkenols) are Alkenes with a Hydroxyl group affixed to one of the carbon atoms composing the Double bond. A diketone is a compound containing two ketone groups. A diketone is a molecule containing two Ketone groups The simpliest diketone is Diacetyl, also known as 23-butanedione

Contents 1 Nomenclature 2 Physical properties 3 Acidity 4 Spectroscopic properties 5 Synthesis 6 Reactions 7 Biochemistry 8 Applications 9 See also 10 References

Nomenclature

In general, ketones are named using IUPAC nomenclature by changing the suffix -e of the parent alkane to -one. Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general Alkanes, also known as Paraffins are Chemical compounds that consist only of the elements Carbon (C and Hydrogen (H (i For common ketones, some traditional names such as acetone and benzophenone predominate, and these are considered retained IUPAC names ^[2], although some introductory chemistry texts use names such as propanone. Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable Benzophenone is the Organic compound with the formula ( C 6 H 52C O, generally abbreviated Ph 2CO

Oxo is the formal IUPAC nomenclature for a ketone functional group. The International Union of Pure and Applied Chemistry ( IUPAC) (aɪjuːpæk or ay-yoo-pec) is an international Non-governmental organization In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions 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 group. In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions Oxo also refers to a single oxygen atom coordinated to a transition metal (a metal oxo).

Physical properties

A carbonyl group is polar. "Polar molecule" and "Non-polar" redirect here This makes ketones polar compounds. "Polar molecule" and "Non-polar" redirect here The carbonyl groups interact with water by hydrogen bonding, and ketones are soluble in water. A hydrogen bond results from a Dipole-dipole force between an Electronegative atom and a Hydrogen atom bonded to Nitrogen, Oxygen It is a hydrogen-bond acceptor, but not a hydrogen-bond donor, and cannot hydrogen-bond to itself. This makes ketones more volatile than alcohols and carboxylic acids of similar molecular weight. In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one

Acidity

The α-hydrogen of a ketone is far more acidic (pKa ≈ 20) than the hydrogen of a regular alkane (pKa ≈ 50). This is due to resonance stabilization of the enolate ion that is formed through dissociation. Enols (also known as alkenols) are Alkenes with a Hydroxyl group affixed to one of the carbon atoms composing the Double bond. The relative acidity of the α-hydrogen is important in the enolization reactions of ketones and other carbonyl compounds.

Spectroscopic properties

Spectroscopy is an important means for identifying ketones. Spectroscopy was originally the study of the interaction between Radiation and Matter as a function of Wavelength (λ Ketones and aldehydes will display a significant peak in infrared spectroscopy, at around 1700 cm⁻¹ (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 alcohols. Infrared spectroscopy (IR spectroscopy is the subset of Spectroscopy that deals with the Infrared region of the Electromagnetic spectrum. Wavenumber in most physical sciences is a Wave property inversely related to Wavelength, having SI units of reciprocal meters Redox (shorthand for reduction-oxidation reaction describes all Chemical reactions in which atoms have their Oxidation number ( Oxidation state In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon The process requires a strong oxidizing agent such as potassium permanganate, potassium dichromate or other agents containing Cr(VI). Organic reductions or organic oxidations or organic redox reactions are Redox reactions that take place with Organic compounds In Organic Potassium permanganate is the Chemical compound K[[manganese Mn]] O 4 Potassium dichromate, K2Cr2O7 is a common inorganic chemical reagent most commonly used as an Oxidizing agent in various laboratory Chromium (ˈkroʊmiəm is a Chemical element which has the symbol Cr and Atomic number 24 The alcohol is oxidized by heating under reflux in acidified solution. This article is about using reflux in chemical engineering and chemistry For example propan-2-ol is oxidised to acetone:

H₃C-CH(OH)-CH₃ → H₃C-CO-CH₃

Two atoms of hydrogen are removed, leaving a single oxygen atom double-bonded to a carbon atom. Isopropyl alcohol (also isopropanol, iso, isopro, Rubbing alcohol, or the abbreviation IPA) is a common name for Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable

• Ketones are also prepared by Gem halide hydrolysis. Geminal halide hydrolysis is an Organic reaction. The reactants are a Geminal dihalide and Water or a Hydroxide.
• Alkynes can be turned into enols through hydration in the presence of an acid and HgSO₄ , and subsequent enol-keto tautomerization gives a ketone. Enols (also known as alkenols) are Alkenes with a Hydroxyl group affixed to one of the carbon atoms composing the Double bond. Mercury(II sulfate, commonly called mercuric sulfate is the Chemical compound Hg[[Sulfur S]] O 4 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 reaction, the related Houben-Hoesch reaction and the Fries rearrangement. The Friedel-Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877. The Hösch reaction (also known as the Hoesch reaction or Houben-Hoesch reaction) is an Organic reaction in which a Nitrile reacts with an The Fries rearrangement, named for the German chemist Karl Theophil Fries, is a Rearrangement reaction of a Phenyl Ester to a Hydroxy
• In the Kornblum–DeLaMare rearrangement ketones are prepared from peroxides and base
• In the Ruzicka cyclization, cyclic ketones are prepared from dicarboxylic acids. The Kornblum–DeLaMare rearrangement is a Rearrangement reaction in Organic chemistry in which a primary or secondary Organic peroxide is converted to The Ruzicka large ring synthesis or Ruzicka reaction or Ruzicka cyclization is an Organic reaction in which a Dicarboxylic acid is converted
• In the Nef reaction, ketones form by hydrolysis of salts of secondary nitro compounds
• In the Fukuyama coupling, ketones form from a thioester and a organozinc compound
• Ketones are also prepeared by the reaction of acid chloride with organocadmium compounds or organocopper compounds. The Nef reaction is an Organic reaction describing the acid Hydrolysis of a salt of a primary or secondary Nitroalkane ( 1) to an The Fukuyama coupling is a Coupling reaction taking place between a Thioester and an Organozinc halide in the presence of a Palladium catalyst In Organic chemistry, an acyl chloride (or acid chloride) is an Organic compound which is a reactive derivative of a Carboxylic acid. An organocadmium compound is a Organometallic compound containing a Carbon to Cadmium Chemical bond. Organocopper compounds in Organometallic chemistry contain Carbon to Copper Chemical bonds Organocopper chemistry is the science of

Reactions

Ketones engage in many organic reactions:

• Nucleophilic addition. Organic reactions are Chemical reactions involving Organic compounds The basic Organic chemistry reaction types are Addition reactions Elimination In Organic chemistry, a nucleophilic addition reaction is an Addition reaction where in a Chemical compound a π bond is removed by the creation The reaction of a ketone with a nucleophile gives a tetrahedral carbonyl addition compound. In Chemistry, a nucleophile (literally nucleus lover as in nucleus and phile) is a Reagent that forms a Chemical bond to A tetrahedral carbonyl addition compound is an Organic compound formed by Nucleophilic addition to a Carbonyl compound such as an Aldehyde or
  • the reaction with the anion of a terminal alkyne gives a hydroxyalkyne
  • the reaction with ammonia or a primary amine gives an imine + water
  • the reaction with secondary amine gives an enamine + water
  • the reaction with a Grignard reagent gives a magnesium alkoxide and after aqueous workup a tertiary alcohol
  • the reaction with an organolithium reagent also gives a tertiary alcohol
  • the reaction with an alcohol, an acid or base gives a hemiketal + water and further reaction with an alcohol gives the ketal + water. An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge Alkynes are Hydrocarbons that have at least one Triple bond between two Carbon atoms with the formula CnH2n-2. Propargyl alcohol, or 2-propyn-1-ol is an Organic compound which is a simple Alcohol containing an Alkyne functional group. Ammonia is a compound with the formula N[[hydrogen H3]] It is normally encountered as a Gas with a characteristic pungent Odor Amines are Organic compounds and Functional groups that contain a basic Nitrogen Atom with a Lone pair. An imine is a Functional group or Chemical compound containing a Carbon – Nitrogen Double bond. Amines are Organic compounds and Functional groups that contain a basic Nitrogen Atom with a Lone pair. An enamine is an unsaturated compound derived by the reaction of an Aldehyde or Ketone with a Secondary amine followed by loss of H2O The Grignard reaction, named for the French chemist François Auguste Victor Grignard, is an organometallic Chemical reaction in which Alkyl - In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon An organolithium reagent is an Organometallic compound with a direct bond between a Carbon and a Lithium atom In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are In Chemistry, a base is most commonly thought of as an aqueous substance that can accept Protons This refers to the Brønsted-Lowry theory of acids and Hemiacetals and hemiketals are compounds of the general formula R1R2C(OHOR3 where R3 is not a hydrogen A ketal is a Functional group or Molecule containing the functional group of a Carbon bonded to two -OR groups where O is Oxygen This is a carbonyl-protecting reaction. In Organic chemistry, a carbonyl group is a Functional group composed of a Carbon Atom double-bonded to an Oxygen
  • reaction of RCOR' with sodium amide results in cleavage with formation of the amide RCONH2 and the alkane R'H, a reaction called the Haller-Bauer reaction (1909) ^[3]
• Electrophilic addition, reaction with an electrophile gives a resonance stabilized cation. Sodium amide, commonly called sodamide is the Chemical compound with the formula NaNH2 In Organic chemistry, an electrophilic addition reaction is an Addition reaction where in a Chemical compound, a Pi bond is removed by the creation In Chemistry, an electrophile (literally electron-lover) is a Reagent attracted to Electrons that participates in a chemical reaction by accepting
• the reaction with phosphonium ylides in the Wittig reaction gives alkenes
• reaction with water gives geminal diols
• reaction with thiols gives a thioacetal
• reaction with hydrazine or derivatives of hydrazine gives hydrazones
• reaction with a metal hydride gives a metal alkoxide salt and then with water an alcohol
• reaction of an enol with halogens to form α-haloketone
• a reaction at an α-carbon is the reaction of a ketone with heavy water to give a deuterated ketone-d. The Wittig reaction is a Chemical reaction of an Aldehyde or Ketone with a triphenyl phosphonium ylide (often called a Wittig reagent In Organic chemistry, an alkene, olefin, or olefine is an unsaturated Chemical compound containing at least one Carbon In Chemistry, the term geminal (from Latin gemini = twins refers to the relationship between two Functional groups that are attached to the same A diol or glycol is a Chemical compound containing two Hydroxyl groups (-OH groups Vicinal diols have hydroxyl groups attached to adjacent atoms In Organic chemistry, a thiol is a compound that contains the functional group composed of a Sulfur atom and a Hydrogen atom (-SH Thioacetals are the Sulfur analogue of Acetals They are prepared in a similar way to acetals by reacting a Thiol with an Aldehyde Hydrazine is a Chemical compound with the formula N2H4 It has an Ammonia -like odor and is derived from the same industrial chemistry In Calculus, a branch of mathematics the derivative is a measurement of how a function changes when the values of its inputs change A hydrazone is a class of Organic compounds with the structure R2C=NNR2 Hydride is the name given to the negative Ion of Hydrogen, H− In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon Enols (also known as alkenols) are Alkenes with a Hydroxyl group affixed to one of the carbon atoms composing the Double bond. Abundance Owing to their high Reactivity, the halogens are found in the environment only in compounds or as Ions Halide ions and oxoanions A haloketone in Organic chemistry is a Functional group consisting of a Ketone group or more general a Carbonyl group with a α- Halogen Heavy water is water which contains a higher proportion than normal of the Isotope Deuterium, as deuterium oxide, D2O or ²H2O
• fragmentation in photochemical Norrish reaction
• reaction with halogens and base of methyl ketones in the Haloform reaction
• reaction of 1,4-aminodiketones to oxazoles by dehydration in the Robinson-Gabriel synthesis
• reaction of aryl alkyl ketones with sulfur and an amine to amides in the Willgerodt reaction

Biochemistry

Acetone, acetoacetate and beta-hydroxybutyrate are ketones (or ketone bodies) generated from carbohydrates, fatty acids and amino acids in humans and most vertebrates. The Norrish reaction in Organic chemistry describes the Photochemical reactions taking place with Ketones and Aldehydes. The haloform reaction is a chemical reaction where a haloform (CHX3 where X is a Halogen) is produced by the exhaustive Halogenation of a methyl Ketone The Robinson-Gabriel synthesis is a Chemical reaction that forms Oxazoles by dehydration of 2-acylamino- Ketones Historically the dehydration The Willgerodt rearrangement or Willgerodt reaction is an Organic reaction converting an aryl alkyl Ketone to the corresponding Amide by reaction Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable Acetoacetic acid is the Organic compound with the formula CH3C(OCH2CO2H beta -Hydroxybutyric acid ( beta -hydroxybutyrate or 3-hydroxybutyric acid is a Ketone body. Ketone bodies are three water-soluble compounds that are produced as by-products when Fatty acids are broken down for energy in the Liver and Carbohydrates (from ' Hydrates of Carbon ' or saccharides ( Greek σάκχαρον meaning " Sugar " are the most In Chemistry, especially Biochemistry, a fatty acid is a Carboxylic acid often with a long unbranched Aliphatic tail ( chain) which In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this Vertebrates are members of the Subphylum Vertebrata, Chordates with backbones or spinal columns The grouping sometimes includes Ketones are elevated in blood after fasting including a night of sleep, and in both blood and urine in starvation, hypoglycemia due to causes other than hyperinsulinism, various inborn errors of metabolism, and ketoacidosis (usually due to diabetes mellitus). Blood is a specialized Bodily fluid that delivers necessary substances to the body's cells ��such as nutrients and oxygen—and transports Waste products Urine is a liquid waste product of the body secreted by the Kidneys by a process of filtration from Blood and Excreted through the Urethra. Starvation (also called inanition) is a severe reduction in Vitamin, Nutrient, and Energy intake and is the most extreme form of Hypoglycemia or hypoglycaemia is the medical term for a pathologic state produced by a lower than normal level of Glucose ( sugar) in the blood Hyperinsulinemic hypoglycemia describes the condition and effects of low blood Glucose caused by excessive Insulin. Inborn errors of metabolism comprise a large class of genetic Diseases involving disorders of Metabolism. Ketoacidosis is a type of metabolic Acidosis which is caused by high concentrations of Ketone bodies, formed by the Deamination of Amino acids Diabetes mellitus (ˌdaɪəˈbiːtiːz or /ˌdaɪəˈbiːtəs/ /məˈlaɪtəs/ or /ˈmɛlətəs/ often referred to simply as diabetes ( Ancient Greek: grc Although ketoacidosis is characteristic of decompensated or untreated type 1 diabetes, ketosis or even ketoacidosis can occur in type 2 diabetes in some circumstances as well. Diabetes mellitus type 1 (Type 1 diabetes Type I diabetes T1D T1DM IDDM juvenile diabetes is a form of Diabetes mellitus. Diabetes mellitus type 2 or Type 2 Diabetes (formerly called non - Insulin -dependent Diabetes mellitus (NIDDM or adult-onset diabetes is a metabolic 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 lipid synthesis and for energy during times of reduced food intake. Lipids are broadly defined as any fat- Soluble ( lipophilic) naturally-occurring Molecule, such as fats oils waxes cholesterol sterols fat-soluble At the NIH, Dr. "NIH" redirects here For other meanings of NIH see NIH (disambiguation. 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,^[4] and the heart and brain operate 25% more efficiently using ketones as a source of energy. ^[5]

Applications

Ketones are often used in perfumes and paints to stabilize the other ingredients so that they don't degrade as quickly over time. Perfume is a mixture of fragrant Essential oils and Aroma compounds Fixatives and Solvents used to give the human body animals objects and living Paint is any Liquid, liquifiable or mastic composition which after application to a substrate in a thin layer is converted to an opaque Solid Other uses are as solvents and intermediates in chemical industry. Examples of ketones are acetone, acetophenone, and methyl ethyl ketone. Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable Acetophenone is the Organic compound with the formula C6H5C(OCH3 Butanone is a manufactured organic chemical. It is a colorless liquid with a sharp sweet butterscotch odor reminiscent of Acetone.

See also

• List of publications in organic chemistry
• Ketosis
• Ketone bodies (Medical term referring to all or either of the three ketones occurring in the body). Some criteria for editing this page have been debated and are displayed Ketosis (kiːˈtoʊsɪs is a state in Metabolism occurring when the Liver excessively converts fat into fatty acids and Ketone Ketone bodies are three water-soluble compounds that are produced as by-products when Fatty acids are broken down for energy in the Liver and

References

1. ^ The position of the carbonyl group is usually denoted by a number; in propanone there can only be one position. While propanone or propan-2-one is how the molecule should be named according to systematic nomenclature, the name "acetone" is retained in official IUPAC nomenclature
2. ^ List of retained IUPAC names retained IUPAC names Link
3. ^ Haller-Bauer Reaction
4. ^ Y. Kashiwaya, T. Takeshima, N. Mori, K. Nakashima, K. Clarke and R. L. Veech (2000). "D-beta -Hydroxybutyrate protects neurons in models of Alzheimer's and Parkinson's disease". PNAS 97 (10): 5440-5444. The Proceedings of the National Academy of Sciences of the United States of America, usually referred to as PNAS, is the official journal of the United doi:10.1073/pnas.97.10.5440. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
5. ^ Y. Kashiwaya, K. Sato, N. Tsuchiya, S. Thomas, D. A. Fell, R. L. Veech and J. V. Passonneau (1994). "Control of glucose utilization in working perfused rat heart". J. Biol. Chem. 269 (41): 25502-25514. The Journal of Biological Chemistry (often abbreviated JBC) is a Scientific journal founded in 1905 and published since 1925 by the American Society  

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