1.
Chemistry
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Chemistry is a branch of physical science that studies the composition, structure, properties and change of matter. Chemistry is sometimes called the science because it bridges other natural sciences, including physics. For the differences between chemistry and physics see comparison of chemistry and physics, the history of chemistry can be traced to alchemy, which had been practiced for several millennia in various parts of the world. The word chemistry comes from alchemy, which referred to a set of practices that encompassed elements of chemistry, metallurgy, philosophy, astrology, astronomy, mysticism. An alchemist was called a chemist in popular speech, and later the suffix -ry was added to this to describe the art of the chemist as chemistry, the modern word alchemy in turn is derived from the Arabic word al-kīmīā. In origin, the term is borrowed from the Greek χημία or χημεία and this may have Egyptian origins since al-kīmīā is derived from the Greek χημία, which is in turn derived from the word Chemi or Kimi, which is the ancient name of Egypt in Egyptian. Alternately, al-kīmīā may derive from χημεία, meaning cast together, in retrospect, the definition of chemistry has changed over time, as new discoveries and theories add to the functionality of the science. The term chymistry, in the view of noted scientist Robert Boyle in 1661, in 1837, Jean-Baptiste Dumas considered the word chemistry to refer to the science concerned with the laws and effects of molecular forces. More recently, in 1998, Professor Raymond Chang broadened the definition of chemistry to mean the study of matter, early civilizations, such as the Egyptians Babylonians, Indians amassed practical knowledge concerning the arts of metallurgy, pottery and dyes, but didnt develop a systematic theory. Greek atomism dates back to 440 BC, arising in works by such as Democritus and Epicurus. In 50 BC, the Roman philosopher Lucretius expanded upon the theory in his book De rerum natura, unlike modern concepts of science, Greek atomism was purely philosophical in nature, with little concern for empirical observations and no concern for chemical experiments. Work, particularly the development of distillation, continued in the early Byzantine period with the most famous practitioner being the 4th century Greek-Egyptian Zosimos of Panopolis. He formulated Boyles law, rejected the four elements and proposed a mechanistic alternative of atoms. Before his work, though, many important discoveries had been made, the Scottish chemist Joseph Black and the Dutchman J. B. English scientist John Dalton proposed the theory of atoms, that all substances are composed of indivisible atoms of matter. Davy discovered nine new elements including the alkali metals by extracting them from their oxides with electric current, british William Prout first proposed ordering all the elements by their atomic weight as all atoms had a weight that was an exact multiple of the atomic weight of hydrogen. The inert gases, later called the noble gases were discovered by William Ramsay in collaboration with Lord Rayleigh at the end of the century, thereby filling in the basic structure of the table. Organic chemistry was developed by Justus von Liebig and others, following Friedrich Wöhlers synthesis of urea which proved that organisms were, in theory
2.
Electron
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The electron is a subatomic particle, symbol e− or β−, with a negative elementary electric charge. Electrons belong to the first generation of the lepton particle family, the electron has a mass that is approximately 1/1836 that of the proton. Quantum mechanical properties of the include a intrinsic angular momentum of a half-integer value, expressed in units of the reduced Planck constant. As it is a fermion, no two electrons can occupy the same state, in accordance with the Pauli exclusion principle. Like all elementary particles, electrons exhibit properties of particles and waves, they can collide with other particles and can be diffracted like light. Since an electron has charge, it has an electric field. Electromagnetic fields produced from other sources will affect the motion of an electron according to the Lorentz force law, electrons radiate or absorb energy in the form of photons when they are accelerated. Laboratory instruments are capable of trapping individual electrons as well as electron plasma by the use of electromagnetic fields, special telescopes can detect electron plasma in outer space. Electrons are involved in applications such as electronics, welding, cathode ray tubes, electron microscopes, radiation therapy, lasers, gaseous ionization detectors. Interactions involving electrons with other particles are of interest in fields such as chemistry. The Coulomb force interaction between the positive protons within atomic nuclei and the negative electrons without, allows the composition of the two known as atoms, ionization or differences in the proportions of negative electrons versus positive nuclei changes the binding energy of an atomic system. The exchange or sharing of the electrons between two or more atoms is the cause of chemical bonding. In 1838, British natural philosopher Richard Laming first hypothesized the concept of a quantity of electric charge to explain the chemical properties of atoms. Irish physicist George Johnstone Stoney named this charge electron in 1891, electrons can also participate in nuclear reactions, such as nucleosynthesis in stars, where they are known as beta particles. Electrons can be created through beta decay of isotopes and in high-energy collisions. The antiparticle of the electron is called the positron, it is identical to the electron except that it carries electrical, when an electron collides with a positron, both particles can be totally annihilated, producing gamma ray photons. The ancient Greeks noticed that amber attracted small objects when rubbed with fur, along with lightning, this phenomenon is one of humanitys earliest recorded experiences with electricity. In his 1600 treatise De Magnete, the English scientist William Gilbert coined the New Latin term electricus, both electric and electricity are derived from the Latin ēlectrum, which came from the Greek word for amber, ἤλεκτρον
3.
Water
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Water is a transparent and nearly colorless chemical substance that is the main constituent of Earths streams, lakes, and oceans, and the fluids of most living organisms. Its chemical formula is H2O, meaning that its molecule contains one oxygen, Water strictly refers to the liquid state of that substance, that prevails at standard ambient temperature and pressure, but it often refers also to its solid state or its gaseous state. It also occurs in nature as snow, glaciers, ice packs and icebergs, clouds, fog, dew, aquifers, Water covers 71% of the Earths surface. It is vital for all forms of life. Only 2. 5% of this water is freshwater, and 98. 8% of that water is in ice and groundwater. Less than 0. 3% of all freshwater is in rivers, lakes, and the atmosphere, a greater quantity of water is found in the earths interior. Water on Earth moves continually through the cycle of evaporation and transpiration, condensation, precipitation. Evaporation and transpiration contribute to the precipitation over land, large amounts of water are also chemically combined or adsorbed in hydrated minerals. Safe drinking water is essential to humans and other even though it provides no calories or organic nutrients. There is a correlation between access to safe water and gross domestic product per capita. However, some observers have estimated that by 2025 more than half of the population will be facing water-based vulnerability. A report, issued in November 2009, suggests that by 2030, in developing regions of the world. Water plays an important role in the world economy, approximately 70% of the freshwater used by humans goes to agriculture. Fishing in salt and fresh water bodies is a source of food for many parts of the world. Much of long-distance trade of commodities and manufactured products is transported by boats through seas, rivers, lakes, large quantities of water, ice, and steam are used for cooling and heating, in industry and homes. Water is an excellent solvent for a variety of chemical substances, as such it is widely used in industrial processes. Water is also central to many sports and other forms of entertainment, such as swimming, pleasure boating, boat racing, surfing, sport fishing, Water is a liquid at the temperatures and pressures that are most adequate for life. Specifically, at atmospheric pressure of 1 bar, water is a liquid between the temperatures of 273.15 K and 373.15 K
4.
Nitrogen
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Nitrogen is a chemical element with symbol N and atomic number 7. It was first discovered and isolated by Scottish physician Daniel Rutherford in 1772, although Carl Wilhelm Scheele and Henry Cavendish had independently done so at about the same time, Rutherford is generally accorded the credit because his work was published first. Nitrogen is the lightest member of group 15 of the periodic table, the name comes from the Greek πνίγειν to choke, directly referencing nitrogens asphyxiating properties. It is an element in the universe, estimated at about seventh in total abundance in the Milky Way. At standard temperature and pressure, two atoms of the element bind to form dinitrogen, a colourless and odorless diatomic gas with the formula N2, dinitrogen forms about 78% of Earths atmosphere, making it the most abundant uncombined element. Nitrogen occurs in all organisms, primarily in amino acids, in the nucleic acids, the human body contains about 3% nitrogen by mass, the fourth most abundant element in the body after oxygen, carbon, and hydrogen. The nitrogen cycle describes movement of the element from the air, into the biosphere and organic compounds, many industrially important compounds, such as ammonia, nitric acid, organic nitrates, and cyanides, contain nitrogen. The extremely strong bond in elemental nitrogen, the second strongest bond in any diatomic molecule. Synthetically produced ammonia and nitrates are key industrial fertilisers, and fertiliser nitrates are key pollutants in the eutrophication of water systems. Apart from its use in fertilisers and energy-stores, nitrogen is a constituent of organic compounds as diverse as Kevlar used in high-strength fabric, Nitrogen is a constituent of every major pharmacological drug class, including antibiotics. Many notable nitrogen-containing drugs, such as the caffeine and morphine or the synthetic amphetamines. Nitrogen compounds have a long history, ammonium chloride having been known to Herodotus. They were well known by the Middle Ages, alchemists knew nitric acid as aqua fortis, as well as other nitrogen compounds such as ammonium salts and nitrate salts. The mixture of nitric and hydrochloric acids was known as aqua regia, celebrated for its ability to dissolve gold, the discovery of nitrogen is attributed to the Scottish physician Daniel Rutherford in 1772, who called it noxious air. Though he did not recognise it as a different chemical substance, he clearly distinguished it from Joseph Blacks fixed air. The fact that there was a component of air that does not support combustion was clear to Rutherford, Nitrogen was also studied at about the same time by Carl Wilhelm Scheele, Henry Cavendish, and Joseph Priestley, who referred to it as burnt air or phlogisticated air. Nitrogen gas was inert enough that Antoine Lavoisier referred to it as air or azote, from the Greek word άζωτικός. In an atmosphere of nitrogen, animals died and flames were extinguished
5.
Copper
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Copper is a chemical element with symbol Cu and atomic number 29. It is a soft, malleable, and ductile metal with high thermal and electrical conductivity. A freshly exposed surface of copper has a reddish-orange color. Copper is one of the few metals that occur in nature in directly usable metallic form as opposed to needing extraction from an ore and this led to very early human use, from c.8000 BC. Copper used in buildings, usually for roofing, oxidizes to form a green verdigris, Copper is sometimes used in decorative art, both in its elemental metal form and in compounds as pigments. Copper compounds are used as agents, fungicides, and wood preservatives. Copper is essential to all living organisms as a trace dietary mineral because it is a key constituent of the enzyme complex cytochrome c oxidase. In molluscs and crustaceans, copper is a constituent of the blood pigment hemocyanin, replaced by the hemoglobin in fish. In humans, copper is found mainly in the liver, muscle, the adult body contains between 1.4 and 2.1 mg of copper per kilogram of body weight. The filled d-shells in these elements contribute little to interatomic interactions, unlike metals with incomplete d-shells, metallic bonds in copper are lacking a covalent character and are relatively weak. This observation explains the low hardness and high ductility of single crystals of copper, at the macroscopic scale, introduction of extended defects to the crystal lattice, such as grain boundaries, hinders flow of the material under applied stress, thereby increasing its hardness. For this reason, copper is supplied in a fine-grained polycrystalline form. The softness of copper partly explains its high conductivity and high thermal conductivity. The maximum permissible current density of copper in open air is approximately 3. 1×106 A/m2 of cross-sectional area, Copper is one of a few metallic elements with a natural color other than gray or silver. Pure copper is orange-red and acquires a reddish tarnish when exposed to air, as with other metals, if copper is put in contact with another metal, galvanic corrosion will occur. A green layer of verdigris can often be seen on old structures, such as the roofing of many older buildings. Copper tarnishes when exposed to sulfur compounds, with which it reacts to form various copper sulfides. There are 29 isotopes of copper, 63Cu and 65Cu are stable, with 63Cu comprising approximately 69% of naturally occurring copper, both have a spin of 3⁄2
6.
Conjugate acid
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A conjugate acid, within the Brønsted–Lowry acid–base theory, is a species formed by the reception of a proton by a base—in other words, it is a base with a hydrogen ion added to it. On the other hand, a base is merely what is left after an acid has donated a proton in a chemical reaction. Hence, a base is a species formed by the removal of a proton from an acid. A proton is a particle with a unit positive electrical charge, it is represented by the symbol H+ because it constitutes the nucleus of a hydrogen atom, that is. A cation can be an acid, and an anion can be a conjugate base, depending on which substance is involved. In an acid-base reaction, an acid plus a base reacts to form a conjugate base plus a conjugate acid, refer to the following figure, We say that the water molecule is the conjugate acid of the hydroxide ion after the latter received the hydrogen proton donated by ammonium. On the other hand, ammonia is the base for the acid ammonium after ammonium has donated a hydrogen ion towards the production of the water molecule. The strength of an acid is directly proportional to its dissociation constant. If a conjugate acid is strong, its dissociation will have an equilibrium constant. The strength of a base can be seen as the tendency of the species to pull hydrogen protons towards itself. If a conjugate base is classified as strong, it will hold on to the hydrogen proton when in solution, if a chemical species is classified as a weak acid, its conjugate base will be strong in nature. This can be observed in ammonias reaction with water, the reaction proceeds until most of the ammonia has been transformed to ammonium. This shift to the right in the equilibrium of the reaction means that ammonium does not dissociate easily in water. On the other hand, if a species is classified as a strong acid, an example of this case would be the dissociation of Hydrochloric acid HCl in water. Since HCl is an acid, its conjugate base will be a weak conjugate base. Therefore, in system, most H+ will be in the form of a Hydronium ion H 3O+ instead of attached to a Cl anion. To summarize, the stronger the acid or base, the weaker the conjugate, the acid and conjugate base as well as the base and conjugate acid are known as conjugate pairs. When finding a conjugate acid or base, it is important to look at the reactants of the chemical equation, to identify the conjugate acid, look for the pair of compounds that are related
7.
Sarin
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Sarin, or GB, is a colorless, odorless liquid, used as a chemical weapon owing to its extreme potency as a nerve agent. It is generally considered a weapon of mass destruction, production and stockpiling of sarin was outlawed as of April 1997 by the Chemical Weapons Convention of 1993, and it is classified as a Schedule 1 substance. In June 1994, the UN Special Commission on Iraqi disarmament destroyed the nerve agent sarin under Security Council resolution 687 concerning the disposal of Iraqs weapons of mass destruction, Sarin is an organophosphorus compound with the formula CH3PF. People who absorb a non-lethal dose, but do not receive medical treatment. Sarin is a molecule because it has four chemically distinct substituents attached to the tetrahedral phosphorus center. The SP form is the active enantiomer due to its greater binding affinity to acetylcholinesterase. The P-F bond is broken by nucleophilic agents, such as water. At high pH, sarin decomposes rapidly to nontoxic phosphonic acid derivatives and it is usually manufactured and weaponized as a racemic mixture—an equal mixture of both enantiomeric forms, as this is a simpler process and provides an adequate weapon. A number of pathways can be used to create sarin. The final reaction typically involves attachment of the group to the phosphorus with an alcoholysis with isopropyl alcohol. Two variants of this process are common and this reaction also gives sarin, but hydrochloric acid as a byproduct instead. The Di-Di process was used by the United States for the production of its unitary sarin stockpile, the scheme below describes an example of Di-Di process. The selection of reagents is arbitrary and reaction conditions and product yield depend on the selected reagents, inert atmosphere and anhydrous conditions are used for synthesis of sarin and other organophosphates. As both reactions leave considerable acid in the product, bulk sarin produced without further treatment has a poor shelf life. Various methods have been tried to resolve these problems, triethylamine was added to UK sarin, with relatively poor success. The Aum Shinrikyo cult experimented with triethylamine as well, N, N-Diethylaniline was used by Aum Shinrikyo for acid reduction. N, N′-Diisopropylcarbodimide was added to sarin produced at Rocky Mountain Arsenal to combat corrosion, isopropylamine was included as part of the M687 155mm field artillery shell, which was a binary sarin weapon system developed by the US Army. Another byproduct of these two processes is diisopropyl methylphosphonate, formed when a second isopropyl alcohol reacts with the sarin itself
8.
Carbocation
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A carbocation is an ion with a positively charged carbon atom. Among the simplest examples are methenium CH+3, methanium CH+5, some carbocations may have two or more positive charges, on the same carbon atom or on different atoms, such as the ethylene dication C 2H2+4. Until the early 1970s, all carbocations were called carbonium ions and this nomenclature was proposed by G. A. Olah. One textbook retains the name of carbonium ion for carbenium ion to this day. The history of carbocations dates back to 1891 when G. Merling reported that he added bromine to tropylidene and then heated the product to obtain a crystalline, water-soluble material, C 7H 7Br. He did not suggest a structure for it, however, Doering and this ion is predicted to be aromatic by Hückels rule. In 1902, Norris and Kehrman independently discovered that colorless triphenylmethanol gives deep-yellow solutions in concentrated sulfuric acid, triphenylmethyl chloride similarly formed orange complexes with aluminium and tin chlorides. In 1902, Adolf von Baeyer recognized the character of the compounds formed. He dubbed the relationship between color and salt formation halochromy, of which green is a prime example. Carbocations are reactive intermediates in organic reactions. This idea, first proposed by Julius Stieglitz in 1899, was developed by Hans Meerwein in his 1922 study of the Wagner–Meerwein rearrangement. Carbocations were also found to be involved in the SN1 reaction, the E1 reaction, the chemical establishment was reluctant to accept the notion of a carbocation and for a long time the Journal of the American Chemical Society refused articles that mentioned them. The first NMR spectrum of a carbocation in solution was published by Doering et al. in 1958. It was the ion, made by treating hexamethylbenzene with methyl chloride. The stable 7-norbornadienyl cation was prepared by Story et al. in 1960 by reacting norbornadienyl chloride with silver tetrafluoroborate in sulfur dioxide at −80 °C, the NMR spectrum established that it was non-classically bridged. In 1962, Olah directly observed the tert-butyl carbocation by nuclear magnetic resonance as a species on dissolving tert-butyl fluoride in magic acid. The NMR of the norbornyl cation was first reported by Schleyer et al. the charged carbon atom in a carbocation is a sextet, i. e. it has only six electrons in its outer valence shell instead of the eight valence electrons that ensures maximum stability. Therefore, carbocations are often reactive, seeking to fill the octet of electrons as well as regain a neutral charge
9.
Benzene
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Benzene is an important organic chemical compound with the chemical formula C6H6. The benzene molecule is composed of 6 carbon atoms joined in a ring with 1 hydrogen atom attached to each, because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a constituent of crude oil and is one of the elementary petrochemicals. Because of the cyclic continuous pi bond between the atoms, benzene is classed as an aromatic hydrocarbon, the second -annulene. Benzene is a colorless and highly flammable liquid with a sweet smell and it is used primarily as a precursor to the manufacture of chemicals with more complex structure, such as ethylbenzene and cumene, of which billions of kilograms are produced. Because benzene has a high number, it is an important component of gasoline. Because benzene is a carcinogen, most non-industrial applications have been limited. The word benzene derives historically from gum benzoin, a resin known to European pharmacists. An acidic material was derived from benzoin by sublimation, and named flowers of benzoin, the hydrocarbon derived from benzoic acid thus acquired the name benzin, benzol, or benzene. Michael Faraday first isolated and identified benzene in 1825 from the oily residue derived from the production of illuminating gas, in 1833, Eilhard Mitscherlich produced it by distilling benzoic acid and lime. He gave the compound the name benzin, in 1845, Charles Mansfield, working under August Wilhelm von Hofmann, isolated benzene from coal tar. Four years later, Mansfield began the first industrial-scale production of benzene, gradually, the sense developed among chemists that a number of substances were chemically related to benzene, comprising a diverse chemical family. In 1855, Hofmann used the word aromatic to designate this family relationship, in 1997, benzene was detected in deep space. The empirical formula for benzene was known, but its highly polyunsaturated structure. In 1865, the German chemist Friedrich August Kekulé published a paper in French suggesting that the structure contained a ring of six carbon atoms with alternating single and double bonds, the next year he published a much longer paper in German on the same subject. Kekulés symmetrical ring could explain these facts, as well as benzenes 1,1 carbon-hydrogen ratio. Here Kekulé spoke of the creation of the theory and he said that he had discovered the ring shape of the benzene molecule after having a reverie or day-dream of a snake seizing its own tail. This vision, he said, came to him years of studying the nature of carbon-carbon bonds
10.
Chloride
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The chloride ion /ˈklɔəraɪd/ is the anion Cl−. It is formed when the element chlorine gains an electron or when a compound such as chloride is dissolved in water or other polar solvents. Chloride salts such as sodium chloride are often soluble in water. It is an essential electrolyte located in all body fluids responsible for maintaining acid/base balance, transmitting nerve impulses and regulating fluid in, less frequently, the word chloride may also form part of the common name of chemical compounds in which one or more chlorine atoms are covalently bonded. For example, methyl chloride, with the standard name chloromethane is a compound with a covalent C−Cl bond in which the chlorine is not an anion. A chloride ion is much larger than an atom,167 and 99 pm. The ion is colorless and diamagnetic, in aqueous solution, it is highly soluble in most cases, however, some chloride salts, such as silver chloride, lead chloride, and mercury chloride are slightly soluble in water. In aqueous solution, chloride is bound by the end of the water molecules. Some chloride-containing minerals include the chlorides of sodium, potassium, and magnesium, called serum chloride, the concentration of chloride in the blood is regulated by the kidneys. A chloride ion is a component of some proteins, e. g. it is present in the amylase enzyme. The chlor-alkali industry is a consumer of the worlds energy budget. This process converts sodium chloride into chlorine and sodium hydroxide, which are used to make many other materials and chemicals, in the petroleum industry, the chlorides are a closely monitored constituent of the mud system. An increase of the chlorides in the mud system may be an indication of drilling into a high-pressure saltwater formation and its increase can also indicate the poor quality of a target sand. Chloride is also a useful and reliable chemical indicator of river / groundwater fecal contamination, as chloride is a non-reactive solute, many water regulating companies around the world utilize chloride to check the contamination levels of the rivers and potable water sources. Chloride salts such as sodium chloride are used to preserve food, chloride is an essential electrolyte, trafficking in and out of cells through chloride channels and playing a key role in maintaining cell homeostasis and transmitting action potentials in neurons. Characteristic concentrations of chloride in model organisms are, in both E. coli and budding yeast are 10-200mM, in mammalian cell 5-100mM and in blood plasma 100mM, chloride can be oxidized but not reduced. The first oxidation, as employed in the process, is conversion to chlorine gas. Chlorine can be oxidized to other oxides and oxyanions including hypochlorite, chlorine dioxide, chlorate
11.
Nitrate
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Nitrate is a polyatomic ion with the molecular formula NO−3 and a molecular mass of 62.0049 g/mol. Nitrates also describe the functional group RONO2. These nitrate esters are a class of explosives. The anion is the base of nitric acid, consisting of one central nitrogen atom surrounded by three identically bonded oxygen atoms in a trigonal planar arrangement. The nitrate ion carries a charge of −1. This arrangement is used as an example of resonance. Like the isoelectronic carbonate ion, the ion can be represented by resonance structures. A common example of a nitrate salt is potassium nitrate. A rich source of nitrate in the human body comes from diets rich in leafy green foods, such as spinach. NO3- is the active component within beetroot juice and other vegetables. Nitrite and water are converted in the body to nitric oxide, nitrate salts are found naturally on earth as large deposits, particularly of nitratine, a major source of sodium nitrate. Nitrates are found in man-made fertilizers, as a byproduct of lightning strikes in earths nitrogen-oxygen rich atmosphere, nitric acid is produced when nitrogen dioxide reacts with water vapor. Nitrates are mainly produced for use as fertilizers in agriculture because of their solubility and biodegradability. The main nitrate fertilizers are ammonium, sodium, potassium, several million kilograms are produced annually for this purpose. The second major application of nitrates is as oxidizing agents, most notably in explosives where the oxidation of carbon compounds liberates large volumes of gases. Sodium nitrate is used to air bubbles from molten glass. Mixtures of the salt are used to harden some metals. Explosives and table tennis balls are made from celluloid, although nitrites are the nitrogen compound chiefly used in meat curing, nitrates are used in certain specialty curing processes where a long release of nitrite from parent nitrate stores is needed
12.
Phenol
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Phenol, also known as carbolic acid, is an aromatic organic compound with the molecular formula C6H5OH. It is a crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxyl group and it is mildly acidic and requires careful handling due to its propensity to cause chemical burns. Phenol was first extracted from tar, but today is produced on a large scale from petroleum. It is an important industrial commodity as a precursor to many materials and it is primarily used to synthesize plastics and related materials. Phenol and its derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides. Phenol is appreciably soluble in water, with about 84.2 g dissolving in 1000 mL, homogeneous mixtures of phenol and water at phenol to water mass ratios of ~2.6 and higher are possible. The sodium salt of phenol, sodium phenoxide, is far more water-soluble and it reacts completely with aqueous NaOH to lose H+, whereas most alcohols react only partially. One explanation for the increased acidity over alcohols is resonance stabilization of the anion by the aromatic ring. In this way, the charge on oxygen is delocalized on to the ortho. In another explanation, increased acidity is the result of orbital overlap between the lone pairs and the aromatic system. The pKa of the enol of acetone is 10.9, the acidities of phenol and acetone enol diverge in the gas phase owing to the effects of solvation. About 1⁄3 of the acidity of phenol is attributable to inductive effects. Phenolate esters are more stable toward hydrolysis than acid anhydrides and acyl halides but are sufficiently reactive under mild conditions to facilitate the formation of amide bonds, Phenol exhibits keto-enol tautomerism with its unstable keto tautomer cyclohexadienone, but only a tiny fraction of phenol exists as the keto form. The equilibrium constant for enolisation is approximately 10−13, meaning only one in every ten trillion molecules is in the keto form at any moment. The small amount of stabilisation gained by exchanging a C=C bond for a C=O bond is more than offset by the large destabilisation resulting from the loss of aromaticity, Phenol therefore exists essentially entirely in the enol form. Phenoxides are enolates stabilised by aromaticity, under normal circumstances, phenoxide is more reactive at the oxygen position, but the oxygen position is a hard nucleophile whereas the alpha-carbon positions tend to be soft. Phenol is highly reactive toward electrophilic aromatic substitution as the oxygen atoms pi electrons donate electron density into the ring, by this general approach, many groups can be appended to the ring, via halogenation, acylation, sulfonation, and other processes
