Information about Enol
Enols (also known as alkenols) are alkenes with a hydroxyl group affixed to one of the carbon atoms composing the double bond. Enols and carbonyl compounds (such as ketones and aldehydes) are in fact isomers; this is called keto-enol tautomerism:
The enol form is shown on the left. It is usually unstable, does not survive long, and changes into the keto (ketone) form shown on the right. This is because oxygen is more electronegative than carbon and thus forms stronger multiple bonds. Hence, a carbon-oxygen (carbonyl) double bond is more than twice as strong as a carbon-oxygen single bond, but a carbon-carbon double bond is weaker than two carbon-carbon single bonds.
Only in 1,3-dicarbonyl and 1,3,5-tricarbonyl compounds does the (mono)enol form predominate. This is because the resonance and intermolecular hydrogen bonding that occurs in the enol form is not possible in the keto form. Thus, at equilibrium, over 99% of propanedial (OHCCH2CHO) molecules exist as the monoenol. The percentage is lower for 1,3-aldehyde ketones and diketones. Enols (and enolates) are important intermediates in many organic reactions.
The words enol and alkenol are portmanteaux of the words alkene (or just -ene, the suffix given to alkenes) and alcohol (which represents the enol's hydroxyl group).
Enolates can exist in quantitative amounts in strictly Brønsted acid free conditions, since they are generally very basic.
1,3-dicarbonyl and 1,3,5-tricarbonyl compounds are quite acidic because of the strong resonance stabilization created when one of the hydrogens is removed (from either the keto or enol forms). The resonance of the enol is exactly analogous to that used to explain the acidity of phenols and consists of the delocalisation of the enolate ion's negative charge to the alpha carbon. These enolate ions are very valuable in synthesis of complicated alcohols and carbonyl compounds (aldol additions). The synthetic value is due to the nucleophilicity of α-carbon of enolate group.
In ketones (a type of carbonyl) with acidic α-hydrogens on either side of the carbonyl carbon, selectivity of deprotonation may be achieved to generate the enolate directly from the ketone. At low temperatures (-78°C, i.e. dry ice bath), in aprotic solvents, and with bulky non-equilibrating bases (e.g. LDA) the "kinetic" proton may be removed. The "kinetic" proton is the one which is sterically most accessible. Under thermodynamic conditions (warmer temperatures, weak base, and protic solvent) equilibrium is established between the ketone and the two possible enolates, the enolate favoured is termed the "thermodynamic" enolate and is favoured because of its lower energy level than the other possible enolate. Thus, by choosing the "correct" conditions to generate an enolate, one can increase the yield of the desired product while minimizing formation of undesired products.
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The enol form is shown on the left. It is usually unstable, does not survive long, and changes into the keto (ketone) form shown on the right. This is because oxygen is more electronegative than carbon and thus forms stronger multiple bonds. Hence, a carbon-oxygen (carbonyl) double bond is more than twice as strong as a carbon-oxygen single bond, but a carbon-carbon double bond is weaker than two carbon-carbon single bonds.
Only in 1,3-dicarbonyl and 1,3,5-tricarbonyl compounds does the (mono)enol form predominate. This is because the resonance and intermolecular hydrogen bonding that occurs in the enol form is not possible in the keto form. Thus, at equilibrium, over 99% of propanedial (OHCCH2CHO) molecules exist as the monoenol. The percentage is lower for 1,3-aldehyde ketones and diketones. Enols (and enolates) are important intermediates in many organic reactions.
The words enol and alkenol are portmanteaux of the words alkene (or just -ene, the suffix given to alkenes) and alcohol (which represents the enol's hydroxyl group).
Enolate ion
When the hydroxyl group (−OH) in an enol loses a hydrogen ion (H+), a negative enolate ion is formed as shown here:)
Enolates can exist in quantitative amounts in strictly Brønsted acid free conditions, since they are generally very basic.
1,3-dicarbonyl and 1,3,5-tricarbonyl compounds are quite acidic because of the strong resonance stabilization created when one of the hydrogens is removed (from either the keto or enol forms). The resonance of the enol is exactly analogous to that used to explain the acidity of phenols and consists of the delocalisation of the enolate ion's negative charge to the alpha carbon. These enolate ions are very valuable in synthesis of complicated alcohols and carbonyl compounds (aldol additions). The synthetic value is due to the nucleophilicity of α-carbon of enolate group.
In ketones (a type of carbonyl) with acidic α-hydrogens on either side of the carbonyl carbon, selectivity of deprotonation may be achieved to generate the enolate directly from the ketone. At low temperatures (-78°C, i.e. dry ice bath), in aprotic solvents, and with bulky non-equilibrating bases (e.g. LDA) the "kinetic" proton may be removed. The "kinetic" proton is the one which is sterically most accessible. Under thermodynamic conditions (warmer temperatures, weak base, and protic solvent) equilibrium is established between the ketone and the two possible enolates, the enolate favoured is termed the "thermodynamic" enolate and is favoured because of its lower energy level than the other possible enolate. Thus, by choosing the "correct" conditions to generate an enolate, one can increase the yield of the desired product while minimizing formation of undesired products.
Natural occurrences
Vitamin C is a sugar acid containg an enol bond. It can lose a proton as pictured, which makes it an acid:)
Movement of electron pairs in deprotonation of ascorbic acid (vitamin C)
alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond. The simplest alkenes, with only one double bond and no other functional groups, form a homologous series of hydrocarbons with the general formula
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Hydroxyl in chemistry stands for a molecule consisting of an oxygen atom and a hydrogen atom connected by a covalent bond. The neutral form is a hydroxyl radical and the hydroxyl anion is called a hydroxide.
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Covalent bonding is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms, or between atoms and other covalent bonds.
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carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O.
The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g.
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The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g.
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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 this functional group.
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aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom which is bonded to a hydrogen atom and double-bonded to an oxygen atom (chemical formula O=CH-), is called the aldehyde group.
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In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of chemical bonds between atoms, but in which the atoms are arranged differently (analogous to a chemical anagram).
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In organic chemistry, keto-enol tautomerism refers to a chemical equilibrium between a keto form (a ketone or an aldehyde) and an enol. The enol and keto forms are said to be tautomers of each other.
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2, −1
(neutral oxide)
Electronegativity 3.44 (Pauling scale)
Ionization energies
(more) 1st: 1313.9 kJmol−1
2nd: 3388.3 kJmol−1
3rd: 5300.5 kJmol−1
Atomic radius 60 pm
Atomic radius (calc.
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(neutral oxide)
Electronegativity 3.44 (Pauling scale)
Ionization energies
(more) 1st: 1313.9 kJmol−1
2nd: 3388.3 kJmol−1
3rd: 5300.5 kJmol−1
Atomic radius 60 pm
Atomic radius (calc.
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Electronegativity, symbol χ, is a chemical property which describes the power of an atom (or, more rarely, a functional group) to attract electrons towards itself.[1] First proposed by Linus Pauling in 1932 as a development of valence bond theory,[2]
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4, 2
(mildly acidic oxide)
Electronegativity 2.55 (Pauling scale)
Ionization energies
(more) 1st: 1086.5 kJmol−1
2nd: 2352.6 kJmol−1
3rd: 4620.5 kJmol−1
Atomic radius 70 pm
Atomic radius (calc.
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(mildly acidic oxide)
Electronegativity 2.55 (Pauling scale)
Ionization energies
(more) 1st: 1086.5 kJmol−1
2nd: 2352.6 kJmol−1
3rd: 4620.5 kJmol−1
Atomic radius 70 pm
Atomic radius (calc.
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In chemistry, bond energy (E) is a measure of bond strength in a chemical bond. For example the carbon-hydrogen bond energy in methane E(C–H) is the enthalpy change involved with breaking up one molecule of methane into a carbon atom and 4 hydrogen radicals
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A chemical bond is the physical process responsible for the attractive interactions between atoms and molecules, and that which confers stability to diatomic and polyatomic chemical compounds.
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carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O.
The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g.
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The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g.
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For other uses, see Resonance (disambiguation).
Resonance in chemistry is a tool used to represent and model certain types of non-classical molecular structures...... Click the link for more information.
hydrogen bond is a special type of dipole-dipole bond that exists between an electronegative atom and a hydrogen atom bonded to another electronegative atom. This type of bond always involves a hydrogen atom, thus the name.
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A portmanteau (IPA: /pɔərtˈmæntoʊ/) is a word or morpheme that fuses two or more words or word parts to give a combined or loaded meaning.
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The suffix -ene is used in organic chemistry to form names of organic compounds where the -C=C- group has been attributed the highest priority according to the rules of organic nomenclature.
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alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond. The simplest alkenes, with only one double bond and no other functional groups, form a homologous series of hydrocarbons with the general formula
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alcohol is any organic compound in which a hydroxyl group (-OH) is bound to a carbon atom of an alkyl or substituted alkyl group. The general formula for a simple acyclic alcohol is CnH2n+1OH.
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In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group (-O H) attached to an aromatic hydrocarbon group. The simplest of the class is phenol (C6H5OH).
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The alpha carbon in organic chemistry refers to the first carbon after the carbon that attaches to the functional group (the carbon is attached at the first, or alpha, position).
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In chemistry, a nucleophile (literally nucleus lover as in nucleus and phile) is a reagent that forms a chemical bond to its reaction partner (the electrophile) by donating both bonding electrons.
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Lithium diisopropylamide is the chemical compound with the formula [(CH3)2CH]2NLi. Generally abbreviated LDA, it is a strong base, used in organic chemistry for the deprotonation of hydrocarbons.
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Steric effects arise from the fact that each atom within a molecule occupies a certain amount of space. If atoms are brought too close together, there is an associated cost in energy due to overlapping electron clouds (Pauli or Born repulsion), and this may affect the molecule's
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Vitamin C or L -ascorbate is an essential nutrient for higher primates, and a small number of other species. The presence of ascorbate is required for a range of essential metabolic reactions in all animals and in plants and is made internally by almost all organisms,
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ACID (Atomicity, Consistency, Isolation, Durability) is a set of properties that guarantee that database transactions are processed reliably. In the context of databases, a single logical operation on the data is called a transaction.
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