A chemical reaction is a process that leads to the chemical transformation of one set of

chemical substance A chemical substance is a form of matter having constant chemical composition and characteristic properties. Some references add that chemical substance cannot be separated into its constituent elements by physical separation methods, i.e., w ...

s to another. Classically,

chemical A chemical substance is a form of matter having constant chemical composition and characteristic properties. Some references add that chemical substance cannot be separated into its constituent elements by physical separation methods, i.e., w ...

reactions encompass changes that only involve the positions of

electron The electron ( or ) is a subatomic particle with a negative one elementary electric charge. Electrons belong to the first generation of the lepton particle family, and are generally thought to be elementary particles because they have no ...

s in the forming and breaking of

chemical bond A chemical bond is a lasting attraction between atoms or ions that enables the formation of molecules and crystals. The bond may result from the electrostatic force between oppositely charged ions as in ionic bonds, or through the sharing of ...

s between

atom Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons. Every solid, liquid, gas, ...

s, with no change to the nuclei (no change to the elements present), and can often be described by a

chemical equation A chemical equation is the symbolic representation of a chemical reaction in the form of symbols and chemical formulas. The reactant entities are given on the left-hand side and the product entities on the right-hand side with a plus sign between ...

Nuclear chemistry Nuclear chemistry is the sub-field of chemistry dealing with radioactivity, nuclear processes, and transformations in the nuclei of atoms, such as nuclear transmutation and nuclear properties. It is the chemistry of radioactive elements such as ...

is a sub-discipline of chemistry that involves the chemical reactions of

unstable In numerous fields of study, the component of instability within a system is generally characterized by some of the outputs or internal states growing without bounds. Not all systems that are not stable are unstable; systems can also be mar ...

and

radioactive Radioactive decay (also known as nuclear decay, radioactivity, radioactive disintegration, or nuclear disintegration) is the process by which an unstable atomic nucleus loses energy by radiation. A material containing unstable nuclei is consi ...

elements where both electronic and nuclear changes can occur. The substance (or substances) initially involved in a chemical reaction are called reactants or reagents. Chemical reactions are usually characterized by a

chemical change Chemical changes occur when a substance combines with another to form a new substance, called chemical synthesis or, alternatively, chemical decomposition into two or more different substances. These processes are called chemical reactions and, ...

, and they yield one or more

products Product may refer to: Business * Product (business), an item that serves as a solution to a specific consumer problem. * Product (project management), a deliverable or set of deliverables that contribute to a business solution Mathematics * Produ ...

, which usually have properties different from the reactants. Reactions often consist of a sequence of individual sub-steps, the so-called

elementary reaction An elementary reaction is a chemical reaction in which one or more chemical species react directly to form products in a single reaction step and with a single transition state. In practice, a reaction is assumed to be elementary if no reaction ...

s, and the information on the precise course of action is part of the reaction mechanism. Chemical reactions are described with

s, which symbolically present the starting materials, end products, and sometimes intermediate products and reaction conditions. Chemical reactions happen at a characteristic reaction rate at a given temperature and chemical concentration. Typically, reaction rates increase with increasing temperature because there is more

thermal energy The term "thermal energy" is used loosely in various contexts in physics and engineering. It can refer to several different well-defined physical concepts. These include the internal energy or enthalpy of a body of matter and radiation; heat, de ...

available to reach the activation energy necessary for breaking bonds between atoms. Reactions may proceed in the forward or reverse direction until they go to completion or reach equilibrium. Reactions that proceed in the forward direction to approach equilibrium are often described as spontaneous and reduce the free energy if they occur at constant temperature and pressure. Non-spontaneous reactions require an input of energy to go forward (examples include charging a battery driven by an external electrical power source, or photosynthesis driven by absorption of

electromagnetic radiation In physics, electromagnetic radiation (EMR) consists of waves of the electromagnetic (EM) field, which propagate through space and carry momentum and electromagnetic radiant energy. It includes radio waves, microwaves, infrared, (visible) li ...

usually in the form of sunlight). A reaction may be classified as

redox Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...

in which

oxidation Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...

and reduction occur or nonredox in which there is no oxidation and reduction occurring. Most simple redox reactions may be classified as a combination, decomposition, or single displacement reaction. Different chemical reactions are used during

chemical synthesis As a topic of chemistry, chemical synthesis (or combination) is the artificial execution of chemical reactions to obtain one or several products. This occurs by physical and chemical manipulations usually involving one or more reactions. In mod ...

in order to obtain the desired product. In

biochemistry Biochemistry or biological chemistry is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology and ...

, a consecutive series of chemical reactions (where the product of one reaction is the reactant of the next reaction) form

metabolic pathway In biochemistry, a metabolic pathway is a linked series of chemical reactions occurring within a cell. The reactants, products, and intermediates of an enzymatic reaction are known as metabolites, which are modified by a sequence of chemical reac ...

s. These reactions are often

catalyzed Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

by protein

enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products ...

s. Enzymes increase the rates of biochemical reactions, so that metabolic syntheses and decompositions impossible under ordinary conditions can occur at the temperature and concentrations present within a

cell Cell most often refers to: * Cell (biology), the functional basic unit of life Cell may also refer to: Locations * Monastic cell, a small room, hut, or cave in which a religious recluse lives, alternatively the small precursor of a monastery ...

. The general concept of a chemical reaction has been extended to reactions between entities smaller than atoms, including

nuclear reactions In nuclear physics and nuclear chemistry, a nuclear reaction is a process in which two nuclei, or a nucleus and an external subatomic particle, collide to produce one or more new nuclides. Thus, a nuclear reaction must cause a transformation o ...

, radioactive decays and reactions between

elementary particle In particle physics, an elementary particle or fundamental particle is a subatomic particle that is not composed of other particles. Particles currently thought to be elementary include electrons, the fundamental fermions ( quarks, leptons, a ...

s, as described by quantum field theory.

History

David - Portrait of Monsieur Lavoisier (cropped)

Chemical reactions such as combustion in fire, fermentation and the reduction of ores to metals were known since antiquity. Initial theories of transformation of materials were developed by Greek philosophers, such as the Four-Element Theory of

Empedocles Empedocles (; grc-gre, Ἐμπεδοκλῆς; , 444–443 BC) was a Greek pre-Socratic philosopher and a native citizen of Akragas, a Greek city in Sicily. Empedocles' philosophy is best known for originating the cosmogonic theory of the ...

stating that any substance is composed of the four basic elements – fire, water, air and earth. In the

Middle Ages In the history of Europe, the Middle Ages or medieval period lasted approximately from the late 5th to the late 15th centuries, similar to the post-classical period of global history. It began with the fall of the Western Roman Empire ...

, chemical transformations were studied by alchemists. They attempted, in particular, to convert

lead Lead is a chemical element with the symbol Pb (from the Latin ) and atomic number 82. It is a heavy metal that is denser than most common materials. Lead is soft and malleable, and also has a relatively low melting point. When freshly cu ...

into

gold Gold is a chemical element with the symbol Au (from la, aurum) and atomic number 79. This makes it one of the higher atomic number elements that occur naturally. It is a bright, slightly orange-yellow, dense, soft, malleable, and ductile me ...

, for which purpose they used reactions of lead and lead-copper alloys with sulfur. The artificial production of chemical substances already was a central goal for medieval alchemists. Examples include the synthesis of ammonium chloride from organic substances as described in the works (c. 850–950) attributed to Jābir ibn Ḥayyān, or the production of mineral acids such as sulfuric and

nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available nitri ...

s by later alchemists, starting from c. 1300. The production of mineral acids involved the heating of sulfate and nitrate minerals such as

copper sulfate Copper sulfate may refer to: * Copper(II) sulfate, CuSO4, a common compound used as a fungicide and herbicide * Copper(I) sulfate Copper(I) sulfate, also known as cuprous sulfate, is an inorganic compound with the chemical formula Cu2 SO4. It ...

, alum and

saltpeter Potassium nitrate is a chemical compound with the chemical formula . This alkali metal nitrate Salt (chemistry), salt is also known as Indian saltpetre (large deposits of which were historically mined in India). It is an ionic salt of potassium ...

. In the 17th century, Johann Rudolph Glauber produced

hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...

and sodium sulfate by reacting sulfuric acid and sodium chloride. With the development of the lead chamber process in 1746 and the Leblanc process, allowing large-scale production of sulfuric acid and sodium carbonate, respectively, chemical reactions became implemented into the industry. Further optimization of sulfuric acid technology resulted in the contact process in the 1880s, and the

Haber process The Haber process, also called the Haber–Bosch process, is an artificial nitrogen fixation process and is the main industrial procedure for the production of ammonia today. It is named after its inventors, the German chemists Fritz Haber and ...

was developed in 1909–1910 for

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous wa ...

synthesis. From the 16th century, researchers including

Jan Baptist van Helmont Jan Baptist van Helmont (; ; 12 January 1580 – 30 December 1644) was a chemist, physiologist, and physician from Brussels. He worked during the years just after Paracelsus and the rise of iatrochemistry, and is sometimes considered to b ...

Robert Boyle Robert Boyle (; 25 January 1627 – 31 December 1691) was an Anglo-Irish natural philosopher, chemist, physicist, alchemist and inventor. Boyle is largely regarded today as the first modern chemist, and therefore one of the founders of ...

, and

Isaac Newton Sir Isaac Newton (25 December 1642 – 20 March 1726/27) was an English mathematician, physicist, astronomer, alchemist, theologian, and author (described in his time as a " natural philosopher"), widely recognised as one of the grea ...

tried to establish theories of experimentally observed chemical transformations. The

phlogiston theory The phlogiston theory is a superseded scientific theory that postulated the existence of a fire-like element called phlogiston () contained within combustible bodies and released during combustion. The name comes from the Ancient Greek (''burni ...

was proposed in 1667 by

Johann Joachim Becher Johann Joachim Becher (; 6 May 1635 – October 1682) was a German physician, alchemist, precursor of chemistry, scholar and adventurer, best known for his development of the phlogiston theory of combustion, and his advancement of Austrian cameral ...

. It postulated the existence of a fire-like element called "phlogiston", which was contained within combustible bodies and released during

combustion Combustion, or burning, is a high-temperature exothermic redox chemical reaction between a fuel (the reductant) and an oxidant, usually atmospheric oxygen, that produces oxidized, often gaseous products, in a mixture termed as smoke. Combus ...

. This proved to be false in 1785 by

Antoine Lavoisier Antoine-Laurent de Lavoisier ( , ; ; 26 August 17438 May 1794),
CNRS (

Joseph Louis Gay-Lussac Joseph Louis Gay-Lussac (, , ; 6 December 1778 – 9 May 1850) was a French chemist and physicist. He is known mostly for his discovery that water is made of two parts hydrogen and one part oxygen (with Alexander von Humboldt), for two laws ...

recognized in 1808 that gases always react in a certain relationship with each other. Based on this idea and the atomic theory of John Dalton,

Joseph Proust Joseph Louis Proust (26 September 1754 – 5 July 1826) was a French chemist. He was best known for his discovery of the law of definite proportions in 1794, stating that chemical compounds always combine in constant proportions. Life Joseph L. ...

had developed the

law of definite proportions In chemistry, the law of definite proportions, sometimes called Proust's law, or law of constant composition states that a given chemical compound always contains its component elements in fixed ratio (by mass) and does not depend on its source an ...

, which later resulted in the concepts of stoichiometry and

s. Regarding the

organic chemistry Organic 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 carbon atoms.Clayden, ...

, it was long believed that compounds obtained from living organisms were too complex to be obtained synthetically. According to the concept of

vitalism Vitalism is a belief that starts from the premise that "living organisms are fundamentally different from non-living entities because they contain some non-physical element or are governed by different principles than are inanimate things." Wher ...

, organic matter was endowed with a "vital force" and distinguished from inorganic materials. This separation was ended however by the synthesis of

urea Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important ...

from inorganic precursors by Friedrich Wöhler in 1828. Other chemists who brought major contributions to organic chemistry include

Alexander William Williamson Prof Alexander William Williamson FRS FRSE PCS MRIA (1 May 18246 May 1904) was an English chemist. He is best known today for the Williamson ether synthesis. Life Williamson was born in 1824 in Wandsworth, London, the second of three childr ...

with his synthesis of

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be ...

s and

Christopher Kelk Ingold Sir Christopher Kelk Ingold (28 October 1893 – 8 December 1970) was a British chemist based in Leeds and London. His groundbreaking work in the 1920s and 1930s on reaction mechanisms and the electronic structure of organic compounds was resp ...

, who, among many discoveries, established the mechanisms of

substitution reaction A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. Substitution reactions ar ...

Characteristics

The general characteristics of chemical reactions are: * Evolution of a gas * Formation of a

precipitate In an aqueous solution, precipitation is the process of transforming a dissolved substance into an insoluble solid from a super-saturated solution. The solid formed is called the precipitate. In case of an inorganic chemical reaction leading ...

* Change in

temperature Temperature is a physical quantity that expresses quantitatively the perceptions of hotness and coldness. Temperature is measurement, measured with a thermometer. Thermometers are calibrated in various Conversion of units of temperature, temp ...

* Change in

state State may refer to: Arts, entertainment, and media Literature * ''State Magazine'', a monthly magazine published by the U.S. Department of State * ''The State'' (newspaper), a daily newspaper in Columbia, South Carolina, United States * ''Our S ...

Equations

Chemical equation A chemical equation is the symbolic representation of a chemical reaction in the form of symbols and chemical formulas. The reactant entities are given on the left-hand side and the product entities on the right-hand side with a plus sign between ...

s are used to graphically illustrate chemical reactions. They consist of

or structural formulas of the reactants on the left and those of the products on the right. They are separated by an arrow (→) which indicates the direction and type of the reaction; the arrow is read as the word "yields". The tip of the arrow points in the direction in which the reaction proceeds. A double arrow () pointing in opposite directions is used for equilibrium reactions. Equations should be balanced according to the stoichiometry, the number of atoms of each species should be the same on both sides of the equation. This is achieved by scaling the number of involved molecules (A, B, C and D in a schematic example below) by the appropriate integers ''a, b, c'' and ''d''. : More elaborate reactions are represented by reaction schemes, which in addition to starting materials and products show important intermediates or

transition state In chemistry, the transition state of a chemical reaction is a particular configuration along the reaction coordinate. It is defined as the state corresponding to the highest potential energy along this reaction coordinate. It is often marked ...

s. Also, some relatively minor additions to the reaction can be indicated above the reaction arrow; examples of such additions are water, heat, illumination, a

catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

, etc. Similarly, some minor products can be placed below the arrow, often with a minus sign. Baeyer-Villiger-Oxidation-V1

Retrosynthetic analysis Retrosynthetic analysis is a technique for solving problems in the planning of organic syntheses. This is achieved by transforming a target molecule into simpler precursor structures regardless of any potential reactivity/interaction with reagents. ...

can be applied to design a complex synthesis reaction. Here the analysis starts from the products, for example by splitting selected chemical bonds, to arrive at plausible initial reagents. A special arrow (⇒) is used in retro reactions.

Elementary reactions

The

is the smallest division into which a chemical reaction can be decomposed, it has no intermediate products. Most experimentally observed reactions are built up from many elementary reactions that occur in parallel or sequentially. The actual sequence of the individual elementary reactions is known as reaction mechanism. An elementary reaction involves a few molecules, usually one or two, because of the low probability for several molecules to meet at a certain time. Azobenzene isomerization de

The most important elementary reactions are unimolecular and bimolecular reactions. Only one molecule is involved in a unimolecular reaction; it is transformed by isomerization or a dissociation into one or more other molecules. Such reactions require the addition of energy in the form of heat or light. A typical example of a unimolecular reaction is the cis–trans

isomerization In chemistry, isomerization or isomerisation is the process in which a molecule, polyatomic ion or molecular fragment is transformed into an isomer with a different chemical structure. Enolization is an example of isomerization, as is tautomeriz ...

, in which the cis-form of a compound converts to the trans-form or vice versa. In a typical dissociation reaction, a bond in a molecule splits (ruptures) resulting in two molecular fragments. The splitting can be homolytic or heterolytic. In the first case, the bond is divided so that each product retains an electron and becomes a neutral radical. In the second case, both electrons of the chemical bond remain with one of the products, resulting in charged

ion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conve ...

s. Dissociation plays an important role in triggering

chain reaction A chain reaction is a sequence of reactions where a reactive product or by-product causes additional reactions to take place. In a chain reaction, positive feedback leads to a self-amplifying chain of events. Chain reactions are one way that sys ...

s, such as hydrogen–oxygen or

polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many fo ...

reactions. :AB -> A + B : Dissociation of a molecule AB into fragments A and B For bimolecular reactions, two molecules collide and react with each other. Their merger is called

or an

addition reaction In organic chemistry, an addition reaction is, in simplest terms, an organic reaction where two or more molecules combine to form a larger one (the adduct).. Addition reactions are limited to chemical compounds that have multiple bonds, such as ...

. :A + B -> AB Another possibility is that only a portion of one molecule is transferred to the other molecule. This type of reaction occurs, for example, in

and acid-base reactions. In redox reactions, the transferred particle is an electron, whereas in acid-base reactions it is a proton. This type of reaction is also called metathesis. :HA + B -> A + HB for example :NaCl + AgNO3 -> NaNO3 + AgCl(v)

Chemical equilibrium

Most chemical reactions are reversible; that is, they can and do run in both directions. The forward and reverse reactions are competing with each other and differ in reaction rates. These rates depend on the concentration and therefore change with the time of the reaction: the reverse rate gradually increases and becomes equal to the rate of the forward reaction, establishing the so-called chemical equilibrium. The time to reach equilibrium depends on parameters such as temperature, pressure, and the materials involved, and is determined by the minimum free energy. In equilibrium, the

Gibbs free energy In thermodynamics, the Gibbs free energy (or Gibbs energy; symbol G) is a thermodynamic potential that can be used to calculate the maximum amount of work that may be performed by a thermodynamically closed system at constant temperature and ...

must be zero. The pressure dependence can be explained with the Le Chatelier's principle. For example, an increase in pressure due to decreasing volume causes the reaction to shift to the side with fewer moles of gas. The reaction yield stabilizes at equilibrium but can be increased by removing the product from the reaction mixture or changed by increasing the temperature or pressure. A change in the concentrations of the reactants does not affect the equilibrium constant but does affect the equilibrium position.

Thermodynamics

Chemical reactions are determined by the laws of

thermodynamics Thermodynamics is a branch of physics that deals with heat, work, and temperature, and their relation to energy, entropy, and the physical properties of matter and radiation. The behavior of these quantities is governed by the four laws of th ...

. Reactions can proceed by themselves if they are exergonic, that is if they release free energy. The associated free energy change of the reaction is composed of the changes of two different thermodynamic quantities,

enthalpy Enthalpy , a property of a thermodynamic system, is the sum of the system's internal energy and the product of its pressure and volume. It is a state function used in many measurements in chemical, biological, and physical systems at a constant ...

and

entropy Entropy is a scientific concept, as well as a measurable physical property, that is most commonly associated with a state of disorder, randomness, or uncertainty. The term and the concept are used in diverse fields, from classical thermodynam ...

: :;

\Delta G = \Delta H - T \cdot \Delta S

. :: : free energy, : enthalpy, : temperature, : entropy, : difference (change between original and product) Reactions can be exothermic, where Δ''H'' is negative and energy is released. Typical examples of exothermic reactions are

precipitation In meteorology, precipitation is any product of the condensation of atmospheric water vapor that falls under gravitational pull from clouds. The main forms of precipitation include drizzle, rain, sleet, snow, ice pellets, graupel and hail. ...

and crystallization, in which ordered solids are formed from disordered gaseous or liquid phases. In contrast, in

endothermic In thermochemistry, an endothermic process () is any thermodynamic process with an increase in the enthalpy (or internal energy ) of the system.Oxtoby, D. W; Gillis, H.P., Butler, L. J. (2015).''Principle of Modern Chemistry'', Brooks Cole. ...

reactions, heat is consumed from the environment. This can occur by increasing the entropy of the system, often through the formation of gaseous or dissolved reaction products, which have higher entropy. Since the entropy term in the free-energy change increases with temperature, many endothermic reactions preferably take place at high temperatures. On the contrary, many exothermic reactions such as crystallization occur preferably at lower temperatures. A change in temperature can sometimes reverse the sign of the enthalpy of a reaction, as for the

carbon monoxide Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simple ...

reduction of molybdenum dioxide: :2CO(g) + MoO2(s) -> 2CO2(g) + Mo(s);

\Delta H^o = +21.86 \ \text

This reaction to form

carbon dioxide Carbon dioxide ( chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is trans ...

and molybdenum is endothermic at low temperatures, becoming less so with increasing temperature.Reaction Web
/ref> Δ''H''° is zero at , and the reaction becomes exothermic above that temperature. Changes in temperature can also reverse the direction tendency of a reaction. For example, the

water gas shift reaction Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a s ...

:CO(g) + H2O() <=> CO2(g) + H2(g) is favored by low temperatures, but its reverse is favored by high temperatures. The shift in reaction direction tendency occurs at . Reactions can also be characterized by their internal energy change, which takes into account changes in the entropy, volume and

chemical potential In thermodynamics, the chemical potential of a species is the energy that can be absorbed or released due to a change of the particle number of the given species, e.g. in a chemical reaction or phase transition. The chemical potential of a species ...

s. The latter depends, among other things, on the activities of the involved substances. :;

U = T\cdot S - p\cdot V + \mu\cdot n

:: : internal energy, : entropy, : pressure, : chemical potential, : number of molecules, : small change sign

Kinetics

The speed at which reactions take place is studied by reaction kinetics. The rate depends on various parameters, such as: *

Reactant In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...

concentrations, which usually make the reaction happen at a faster rate if raised through increased collisions per unit of time. Some reactions, however, have rates that are ''independent'' of reactant concentrations, due to a limited number of catalytic sites. These are called zero order reactions. * Surface area available for contact between the reactants, in particular solid ones in heterogeneous systems. Larger surface areas lead to higher reaction rates. *

Pressure Pressure (symbol: ''p'' or ''P'') is the force applied perpendicular to the surface of an object per unit area over which that force is distributed. Gauge pressure (also spelled ''gage'' pressure)The preferred spelling varies by country and e ...

– increasing the pressure decreases the volume between molecules and therefore increases the frequency of collisions between the molecules. *

Activation energy In chemistry and physics, activation energy is the minimum amount of energy that must be provided for compounds to result in a chemical reaction. The activation energy (''E''a) of a reaction is measured in joules per mole (J/mol), kilojoules p ...

, which is defined as the amount of energy required to make the reaction start and carry on spontaneously. Higher activation energy implies that the reactants need more energy to start than a reaction with lower activation energy. *

Temperature Temperature is a physical quantity that expresses quantitatively the perceptions of hotness and coldness. Temperature is measurement, measured with a thermometer. Thermometers are calibrated in various Conversion of units of temperature, temp ...

, which hastens reactions if raised, since higher temperature increases the energy of the molecules, creating more collisions per unit of time, * The presence or absence of a

. Catalysts are substances that make weak bonds with reactants or intermediates and change the pathway (mechanism) of a reaction which in turn increases the speed of a reaction by lowering the

activation energy In chemistry and physics, activation energy is the minimum amount of energy that must be provided for compounds to result in a chemical reaction. The activation energy (''E''a) of a reaction is measured in joules per mole (J/mol), kilojoules p ...

needed for the reaction to take place. A catalyst is not destroyed or changed during a reaction, so it can be used again. * For some reactions, the presence of

, most notably

ultraviolet light Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nanometer, nm (with a corresponding frequency around 30 Hertz, PHz) to 400 nm (750 Hertz, THz), shorter than that of visible light, but longer than ...

, is needed to promote the breaking of bonds to start the reaction. This is particularly true for reactions involving radicals. Several theories allow calculating the reaction rates at the molecular level. This field is referred to as reaction dynamics. The rate ''v'' of a first-order reaction, which could be the disintegration of a substance A, is given by: :

v= -\frac = k \cdot ce

Its integration yields: :

\ce(t) = \ce_ \cdot e^.

Here ''k'' is the first-order rate constant, having dimension 1/time, ''t'') is the concentration at a time ''t'' and sub>0 is the initial concentration. The rate of a first-order reaction depends only on the concentration and the properties of the involved substance, and the reaction itself can be described with a characteristic

half-life Half-life (symbol ) is the time required for a quantity (of substance) to reduce to half of its initial value. The term is commonly used in nuclear physics to describe how quickly unstable atoms undergo radioactive decay or how long stable at ...

. More than one time constant is needed when describing reactions of higher order. The temperature dependence of the rate constant usually follows the Arrhenius equation: :

k = k_0 e^

where ''E''_a is the activation energy and ''k''_B is the

Boltzmann constant The Boltzmann constant ( or ) is the proportionality factor that relates the average relative kinetic energy of particles in a gas with the thermodynamic temperature of the gas. It occurs in the definitions of the kelvin and the gas constant, ...

. One of the simplest models of reaction rate is the

collision theory Collision theory is a principle of chemistry used to predict the rates of chemical reactions. It states that when suitable particles of the reactant hit each other with correct orientation, only a certain amount of collisions result in a percept ...

. More realistic models are tailored to a specific problem and include the

transition state theory In chemistry, transition state theory (TST) explains the reaction rates of elementary chemical reactions. The theory assumes a special type of chemical equilibrium (quasi-equilibrium) between reactants and activated transition state complexes. T ...

, the calculation of the

potential energy surface A potential energy surface (PES) describes the energy of a system, especially a collection of atoms, in terms of certain parameters, normally the positions of the atoms. The surface might define the energy as a function of one or more coordinat ...

, the Marcus theory and the Rice–Ramsperger–Kassel–Marcus (RRKM) theory.

Reaction types

Four basic types

Synthesis

In a synthesis reaction, two or more simple substances combine to form a more complex substance. These reactions are in the general form: A + B->AB Two or more reactants yielding one product is another way to identify a synthesis reaction. One example of a synthesis reaction is the combination of

iron Iron () is a chemical element with Symbol (chemistry), symbol Fe (from la, Wikt:ferrum, ferrum) and atomic number 26. It is a metal that belongs to the first transition series and group 8 element, group 8 of the periodic table. It is, Abundanc ...

and sulfur to form

iron(II) sulfide Iron(II) sulfide or ferrous sulfide (Br.E. sulphide) is one of a family chemical compounds and minerals with the approximate formula . Iron sulfides are often iron-deficient non-stoichiometric. All are black, water-insoluble solids. Preparatio ...

: 8Fe + S8->8FeS Another example is simple hydrogen gas combined with simple oxygen gas to produce a more complex substance, such as water.To react or not to react?
Utah State Office of Education. Retrieved 4 June 2011.

Decomposition

A decomposition reaction is when a more complex substance breaks down into its more simple parts. It is thus the opposite of a synthesis reaction and can be written as AB->A + B One example of a decomposition reaction is the electrolysis of water to make

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as ...

and

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic ...

gas: 2H2O->2H2 + O2

Single displacement

In a

single displacement reaction A single-displacement reaction, also known as single replacement reaction or exchange reaction, is a chemical reaction in which one element is replaced by another in a compound. It can be represented generically as: :A + BC -> AC + B where eithe ...

, a single uncombined element replaces another in a compound; in other words, one element trades places with another element in a compound These reactions come in the general form of: A + BC->AC + B One example of a single displacement reaction is when

magnesium Magnesium is a chemical element with the symbol Mg and atomic number 12. It is a shiny gray metal having a low density, low melting point and high chemical reactivity. Like the other alkaline earth metals (group 2 of the periodic ta ...

replaces hydrogen in water to make

magnesium hydroxide Magnesium hydroxide is the inorganic compound with the chemical formula Mg(OH)2. It occurs in nature as the mineral brucite. It is a white solid with low solubility in water (). Magnesium hydroxide is a common component of antacids, such as milk ...

and hydrogen gas: Mg + 2H2O->Mg(OH)2 + H2 (^)

Double displacement

In a

double displacement reaction A salt metathesis reaction, sometimes called a double displacement reaction, is a chemical process involving the exchange of bonds between two reacting chemical species which results in the creation of products with similar or identical bonding a ...

, the anions and cations of two compounds switch places and form two entirely different compounds. These reactions are in the general form: AB + CD->AD + CB For example, when

barium chloride Barium chloride is an inorganic compound with the formula Ba Cl2. It is one of the most common water-soluble salts of barium. Like most other water-soluble barium salts, it is white, highly toxic, and imparts a yellow-green coloration to a flame. ...

(BaCl₂) and

magnesium sulfate Magnesium sulfate or magnesium sulphate (in English-speaking countries other than the US) is a chemical compound, a salt with the formula , consisting of magnesium cations (20.19% by mass) and sulfate anions . It is a white crystalline solid, ...

(MgSO₄) react, the SO₄²⁻ anion switches places with the 2Cl⁻ anion, giving the compounds BaSO₄ and MgCl₂. Another example of a double displacement reaction is the reaction of

lead(II) nitrate Lead(II) nitrate is an inorganic compound with the chemical formula Pb( NO3)2. It commonly occurs as a colourless crystal or white powder and, unlike most other lead(II) salts, is soluble in water. Known since the Middle Ages by the name plumbu ...

with

potassium iodide Potassium iodide is a chemical compound, medication, and dietary supplement. It is a medication used for treating hyperthyroidism, in radiation emergencies, and for protecting the thyroid gland when certain types of radiopharmaceuticals are u ...

to form

lead(II) iodide Lead(II) iodide or lead iodide is a chemical compound with the formula . At room temperature, it is a bright yellow odorless crystalline solid, that becomes orange and red when heated. It was formerly called plumbous iodide. The compound current ...

and

potassium nitrate Potassium nitrate is a chemical compound with the chemical formula . This alkali metal nitrate salt is also known as Indian saltpetre (large deposits of which were historically mined in India). It is an ionic salt of potassium ions K+ and nitr ...

: Pb(NO3)2 + 2KI->PbI2(v) + 2KNO3

Combustion

In a

reaction, an element or compound reacts with an oxidant, usually

, often producing energy in the form of

heat In thermodynamics, heat is defined as the form of energy crossing the boundary of a thermodynamic system by virtue of a temperature difference across the boundary. A thermodynamic system does not ''contain'' heat. Nevertheless, the term is ...

light Light or visible light is electromagnetic radiation that can be perceived by the human eye. Visible light is usually defined as having wavelengths in the range of 400–700 nanometres (nm), corresponding to frequencies of 750–420 te ...

. Combustion reactions frequently involve a

hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...

. For instance, the combustion of 1 mole (114 g) of octane in oxygen C8H18(l) + 25/2 O2(g)->8CO2 + 9H2O(l) releases 5500 kJ. A combustion reaction can also result from

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon mak ...

or sulfur reacting with oxygen. 2Mg(s) + O2->2MgO(s) S(s) + O2(g)->SO2(g)

Oxidation and reduction

Redox Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...

reactions can be understood in terms of the transfer of electrons from one involved species (

reducing agent In chemistry, a reducing agent (also known as a reductant, reducer, or electron donor) is a chemical species that "donates" an electron to an (called the , , , or ). Examples of substances that are commonly reducing agents include the Earth me ...

) to another (

oxidizing agent An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxi ...

). In this process, the former species is ''oxidized'' and the latter is ''reduced''. Though sufficient for many purposes, these descriptions are not precisely correct. Oxidation is better defined as an increase in

oxidation state In chemistry, the oxidation state, or oxidation number, is the hypothetical charge of an atom if all of its bonds to different atoms were fully ionic. It describes the degree of oxidation (loss of electrons) of an atom in a chemical compound. C ...

of atoms and reduction as a decrease in oxidation state. In practice, the transfer of electrons will always change the oxidation state, but there are many reactions that are classed as "redox" even though no electron transfer occurs (such as those involving

covalent A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms ...

bonds). In the following redox reaction, hazardous

sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable ...

metal reacts with toxic

chlorine Chlorine is a chemical element with the symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine i ...

gas to form the ionic compound sodium chloride, or common table salt: 2Na(s) + Cl2(g)->2NaCl(s) In the reaction, sodium metal goes from an oxidation state of 0 (as it is a pure element) to +1: in other words, the sodium lost one electron and is said to have been oxidized. On the other hand, the chlorine gas goes from an oxidation of 0 (it is also a pure element) to −1: the chlorine gains one electron and is said to have been reduced. Because the chlorine is the one reduced, it is considered the electron acceptor, or in other words, induces oxidation in the sodium – thus the chlorine gas is considered the oxidizing agent. Conversely, the sodium is oxidized or is the electron donor, and thus induces a reduction in the other species and is considered the ''reducing agent''. Which of the involved reactants would be a reducing or oxidizing agent can be predicted from the

electronegativity Electronegativity, symbolized as , is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. An atom's electronegativity is affected by both its atomic number and the ...

of their elements. Elements with low electronegativities, such as most metals, easily donate electrons and oxidize – they are reducing agents. On the contrary, many oxides or ions with high oxidation numbers of their non-oxygen atoms, such as , , , , or , can gain one or two extra electrons and are strong oxidizing agents. For some

main-group element In chemistry and atomic physics, the main group is the group of elements (sometimes called the representative elements) whose lightest members are represented by helium, lithium, beryllium, boron, carbon, nitrogen, oxygen, and fluorine as arrange ...

s the number of electrons donated or accepted in a redox reaction can be predicted from the electron configuration of the reactant element. Elements try to reach the low-energy

noble gas The noble gases (historically also the inert gases; sometimes referred to as aerogens) make up a class of chemical elements with similar properties; under standard conditions, they are all odorless, colorless, monatomic gases with very low ch ...

configuration, and therefore alkali metals and halogens will donate and accept one electron, respectively. Noble gases themselves are chemically inactive. The overall redox reaction can be balanced by combining the oxidation and reduction half-reactions multiplied by coefficients such that the number of electrons lost in the oxidation equals the number of electrons gained in the reduction. An important class of redox reactions are the electrolytic

electrochemical Electrochemistry is the branch of physical chemistry concerned with the relationship between electrical potential difference, as a measurable and quantitative phenomenon, and identifiable chemical change, with the potential difference as an outc ...

reactions, where electrons from the power supply at the negative electrode are used as the reducing agent and electron withdrawal at the positive electrode as the oxidizing agent. These reactions are particularly important for the production of chemical elements, such as

aluminium Aluminium (aluminum in American and Canadian English) is a chemical element with the symbol Al and atomic number 13. Aluminium has a density lower than those of other common metals, at approximately one third that of steel. I ...

. The reverse process, in which electrons are released in redox reactions and chemical energy is converted to electrical energy, is possible and used in batteries.

Complexation

In complexation reactions, several

ligand In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...

s react with a metal atom to form a

coordination complex A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as '' ligands'' or complexing agents. ...

. This is achieved by providing lone pairs of the ligand into empty orbitals of the metal atom and forming dipolar bonds. The ligands are Lewis bases, they can be both ions and neutral molecules, such as carbon monoxide, ammonia or water. The number of ligands that react with a central metal atom can be found using the 18-electron rule, saying that the

valence shell In chemistry and physics, a valence electron is an electron in the outer shell associated with an atom, and that can participate in the formation of a chemical bond if the outer shell is not closed. In a single covalent bond, a shared pair forms ...

s of a

transition metal In chemistry, a transition metal (or transition element) is a chemical element in the d-block of the periodic table (groups 3 to 12), though the elements of group 12 (and less often group 3) are sometimes excluded. They are the elements that ca ...

will collectively accommodate 18

s, whereas the symmetry of the resulting complex can be predicted with the crystal field theory and

ligand field theory Ligand field theory (LFT) describes the bonding, orbital arrangement, and other characteristics of coordination complexes. It represents an application of molecular orbital theory to transition metal complexes. A transition metal ion has nine valen ...

. Complexation reactions also include ligand exchange, in which one or more ligands are replaced by another, and redox processes which change the oxidation state of the central metal atom.

Acid–base reactions

In the Brønsted–Lowry acid–base theory, an acid–base reaction involves a transfer of protons (H⁺) from one species (the acid) to another (the base). When a proton is removed from an acid, the resulting species is termed that acid's

conjugate base A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a ...

. When the proton is accepted by a base, the resulting species is termed that base's conjugate acid. In other words, acids act as proton donors and bases act as proton acceptors according to the following equation: \underset + \underset <=> \underset + \underset The reverse reaction is possible, and thus the acid/base and conjugated base/acid are always in equilibrium. The equilibrium is determined by the acid and base dissociation constants (''K''_a and ''K''_b) of the involved substances. A special case of the acid-base reaction is the neutralization where an acid and a base, taken at the exact same amounts, form a neutral

salt Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quant ...

. Acid-base reactions can have different definitions depending on the acid-base concept employed. Some of the most common are: * Arrhenius definition: Acids dissociate in water releasing H₃O⁺ ions; bases dissociate in water releasing OH⁻ ions. * Brønsted–Lowry definition: Acids are proton (H⁺) donors, bases are proton acceptors; this includes the Arrhenius definition. *

Lewis Lewis may refer to: Names * Lewis (given name), including a list of people with the given name * Lewis (surname), including a list of people with the surname Music * Lewis (musician), Canadian singer * "Lewis (Mistreated)", a song by Radiohead ...

definition: Acids are electron-pair acceptors, and bases are electron-pair donors; this includes the Brønsted-Lowry definition.

Precipitation

Precipitation In meteorology, precipitation is any product of the condensation of atmospheric water vapor that falls under gravitational pull from clouds. The main forms of precipitation include drizzle, rain, sleet, snow, ice pellets, graupel and hail. ...

is the formation of a solid in a solution or inside another solid during a chemical reaction. It usually takes place when the concentration of dissolved ions exceeds the

solubility In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solub ...

limit and forms an insoluble salt. This process can be assisted by adding a precipitating agent or by the removal of the solvent. Rapid precipitation results in an amorphous or microcrystalline residue and a slow process can yield single

crystal A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macro ...

s. The latter can also be obtained by recrystallization from microcrystalline salts.

Solid-state reactions

Reactions can take place between two solids. However, because of the relatively small

diffusion Diffusion is the net movement of anything (for example, atoms, ions, molecules, energy) generally from a region of higher concentration to a region of lower concentration. Diffusion is driven by a gradient in Gibbs free energy or chemica ...

rates in solids, the corresponding chemical reactions are very slow in comparison to liquid and gas phase reactions. They are accelerated by increasing the reaction temperature and finely dividing the reactant to increase the contacting surface area.

Reactions at the solid/gas interface

The reaction can take place at the solid, gas interface, surfaces at very low pressure such as ultra-high vacuum. Via

scanning tunneling microscopy A scanning tunneling microscope (STM) is a type of microscope used for imaging surfaces at the atomic level. Its development in 1981 earned its inventors, Gerd Binnig and Heinrich Rohrer, then at IBM Zürich, the Nobel Prize in Physics in 1986. ...

, it is possible to observe reactions at the solid, gas interface in real space, if the time scale of the reaction is in the correct range. Reactions at the solid, gas interface are in some cases related to catalysis.

Photochemical reactions

photochemical reactions Organic photochemistry encompasses organic reactions that are induced by the action of light. The absorption of ultraviolet light by organic molecules often leads to reactions. In the earliest days, sunlight was employed, while in more modern times ...

, atoms and molecules absorb energy (

photon A photon () is an elementary particle that is a quantum of the electromagnetic field, including electromagnetic radiation such as light and radio waves, and the force carrier for the electromagnetic force. Photons are massless, so they a ...

s) of the illumination light and convert it into an excited state. They can then release this energy by breaking chemical bonds, thereby producing radicals. Photochemical reactions include hydrogen–oxygen reactions,

radical polymerization In polymer chemistry, free-radical polymerization (FRP) is a method of polymerization by which a polymer forms by the successive addition of free-radical building blocks ( repeat units). Free radicals can be formed by a number of different mechani ...

s and rearrangement reactions. Many important processes involve photochemistry. The premier example is

photosynthesis Photosynthesis is a process used by plants and other organisms to convert light energy into chemical energy that, through cellular respiration, can later be released to fuel the organism's activities. Some of this chemical energy is stored i ...

, in which most plants use solar energy to convert

and water into

glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, u ...

, disposing of

as a side-product. Humans rely on photochemistry for the formation of vitamin D, and

vision Vision, Visions, or The Vision may refer to: Perception Optical perception * Visual perception, the sense of sight * Visual system, the physical mechanism of eyesight * Computer vision, a field dealing with how computers can be made to gain und ...

is initiated by a photochemical reaction of rhodopsin. In

fireflies The Lampyridae are a family of elateroid beetles with more than 2,000 described species, many of which are light-emitting. They are soft-bodied beetles commonly called fireflies, lightning bugs, or glowworms for their conspicuous production ...

, an

in the abdomen catalyzes a reaction that results in bioluminescence. Many significant photochemical reactions, such as ozone formation, occur in the Earth atmosphere and constitute

atmospheric chemistry Atmospheric chemistry is a branch of atmospheric science in which the chemistry of the Earth's atmosphere and that of other planets is studied. It is a multidisciplinary approach of research and draws on environmental chemistry, physics, meteorol ...

Catalysis

catalysis Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

, the reaction does not proceed directly, but through a reaction with a third substance known as

. Although the catalyst takes part in the reaction, forming weak bonds with reactants or intermediates, it is returned to its original state by the end of the reaction and so is not consumed. However, it can be inhibited, deactivated or destroyed by secondary processes. Catalysts can be used in a different phase ( heterogeneous) or in the same phase ( homogeneous) as the reactants. In heterogeneous catalysis, typical secondary processes include coking where the catalyst becomes covered by

polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...

ic side products. Additionally, heterogeneous catalysts can dissolve into the solution in a solid-liquid system or evaporate in a solid–gas system. Catalysts can only speed up the reaction – chemicals that slow down the reaction are called inhibitors. Substances that increase the activity of catalysts are called promoters, and substances that deactivate catalysts are called catalytic poisons. With a catalyst, a reaction that is kinetically inhibited by high activation energy can take place in the circumvention of this activation energy. Heterogeneous catalysts are usually solids, powdered in order to maximize their surface area. Of particular importance in heterogeneous catalysis are the

platinum group The platinum-group metals (abbreviated as the PGMs; alternatively, the platinoids, platinides, platidises, platinum group, platinum metals, platinum family or platinum-group elements (PGEs)) are six noble, precious metallic elements clustered t ...

metals and other transition metals, which are used in

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organ ...

catalytic reforming Catalytic reforming is a chemical process used to convert petroleum refinery naphthas distilled from crude oil (typically having low octane ratings) into high-octane liquid products called reformates, which are premium blending stocks for high-oc ...

and in the synthesis of commodity chemicals such as

and

. Acids are an example of a homogeneous catalyst, they increase the nucleophilicity of

carbonyl In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containi ...

s, allowing a reaction that would not otherwise proceed with electrophiles. The advantage of homogeneous catalysts is the ease of mixing them with the reactants, but they may also be difficult to separate from the products. Therefore, heterogeneous catalysts are preferred in many industrial processes.

Reactions in organic chemistry

In organic chemistry, in addition to oxidation, reduction or acid-base reactions, a number of other reactions can take place which involves covalent bonds between carbon atoms or carbon and

heteroatom In chemistry, a heteroatom () is, strictly, any atom that is not carbon or hydrogen. Organic chemistry In practice, the term is usually used more specifically to indicate that non-carbon atoms have replaced carbon in the backbone of the molecula ...

s (such as oxygen, nitrogen, halogens, etc.). Many specific reactions in organic chemistry are

name reaction A name reaction is a chemical reaction named after its discoverers or developers. Among the tens of thousands of organic reactions that are known, hundreds of such reactions are well-known enough to be named after people. Well-known examples include ...

s designated after their discoverers.

Substitution

In a

, a

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the re ...

in a particular

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

is replaced by another group. These reactions can be distinguished by the type of substituting species into a

nucleophilic In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...

, electrophilic or radical substitution. In the first type, a nucleophile, an atom or molecule with an excess of electrons and thus a negative charge or

partial charge A partial charge is a non-integer charge value when measured in elementary charge units. Partial charge is more commonly called net atomic charge. It is represented by the Greek lowercase letter 𝛿, namely 𝛿− or 𝛿+. Partial charges are c ...

, replaces another atom or part of the "substrate" molecule. The electron pair from the nucleophile attacks the substrate forming a new bond, while the

leaving group In chemistry, a leaving group is defined by the IUPAC as an atom or group of atoms that detaches from the main or residual part of a substrate during a reaction or elementary step of a reaction. However, in common usage, the term is often limited ...

departs with an electron pair. The nucleophile may be electrically neutral or negatively charged, whereas the substrate is typically neutral or positively charged. Examples of nucleophiles are

hydroxide Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. I ...

ion, alkoxides,

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen Hydrogen is the chemical element wi ...

s and halides. This type of reaction is found mainly in aliphatic hydrocarbons, and rarely in

aromatic hydrocarbon Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past groupin ...

. The latter have high electron density and enter

nucleophilic aromatic substitution A nucleophilic aromatic substitution is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring. Aromatic rings are usually nucleophilic, but some aromatic compou ...

only with very strong electron withdrawing groups. Nucleophilic substitution can take place by two different mechanisms, S_N1 and S_N2. In their names, S stands for substitution, N for nucleophilic, and the number represents the kinetic order of the reaction, unimolecular or bimolecular. The S_N1 reaction proceeds in two steps. First, the

is eliminated creating a carbocation. This is followed by a rapid reaction with the nucleophile. In the S_N2 mechanisms, the nucleophile forms a transition state with the attacked molecule, and only then the leaving group is cleaved. These two mechanisms differ in the stereochemistry of the products. S_N1 leads to the non-stereospecific addition and does not result in a chiral center, but rather in a set of

geometric isomers Geometry (; ) is, with arithmetic, one of the oldest branches of mathematics. It is concerned with properties of space such as the distance, shape, size, and relative position of figures. A mathematician who works in the field of geometry is ca ...

(''cis/trans''). In contrast, a reversal (

Walden inversion Walden inversion is the inversion of a stereogenic center in a chiral molecule in a chemical reaction. Since a molecule can form two enantiomers around a stereogenic center, the Walden inversion converts the configuration of the molecule fro ...

) of the previously existing stereochemistry is observed in the S_N2 mechanism. Electrophilic substitution is the counterpart of the nucleophilic substitution in that the attacking atom or molecule, an

electrophile In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carrie ...

, has low electron density and thus a positive charge. Typical electrophiles are the carbon atom of

carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containi ...

s, carbocations or sulfur or nitronium cations. This reaction takes place almost exclusively in aromatic hydrocarbons, where it is called

electrophilic aromatic substitution Electrophilic aromatic substitution is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced by an electrophile. Some of the most important electrophilic aromatic substitutions are aromatic n ...

. The electrophile attack results in the so-called σ-complex, a transition state in which the aromatic system is abolished. Then, the leaving group, usually a proton, is split off and the aromaticity is restored. An alternative to aromatic substitution is electrophilic aliphatic substitution. It is similar to the nucleophilic aliphatic substitution and also has two major types, S_E1 and S_E2 Electrophilic aromatic substitution

In the third type of substitution reaction, radical substitution, the attacking particle is a radical. This process usually takes the form of a

, for example in the reaction of alkanes with halogens. In the first step, light or heat disintegrates the halogen-containing molecules producing radicals. Then the reaction proceeds as an avalanche until two radicals meet and recombine. :;X. + R-H -> X-H + R. :;R. + X2 -> R-X + X. :: Reactions during the chain reaction of radical substitution

Addition and elimination

The addition and its counterpart, the elimination, are reactions that change the number of substituents on the carbon atom, and form or cleave multiple bonds. Double and

triple bond A triple bond in chemistry is a chemical bond between two atoms involving six bonding electrons instead of the usual two in a covalent single bond. Triple bonds are stronger than the equivalent single bonds or double bonds, with a bond order o ...

s can be produced by eliminating a suitable leaving group. Similar to the nucleophilic substitution, there are several possible reaction mechanisms that are named after the respective reaction order. In the E1 mechanism, the leaving group is ejected first, forming a carbocation. The next step, the formation of the double bond, takes place with the elimination of a proton (

deprotonation Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.Henry Jakubowski, Biochemistry Online Chapter 2A3, https://employees.csbsju. ...

). The leaving order is reversed in the E1cb mechanism, that is the proton is split off first. This mechanism requires the participation of a base. Because of the similar conditions, both reactions in the E1 or E1cb elimination always compete with the S_N1 substitution. E2-mechanism

The E2 mechanism also requires a base, but there the attack of the base and the elimination of the leaving group proceed simultaneously and produce no ionic intermediate. In contrast to the E1 eliminations, different stereochemical configurations are possible for the reaction product in the E2 mechanism, because the attack of the base preferentially occurs in the anti-position with respect to the leaving group. Because of the similar conditions and reagents, the E2 elimination is always in competition with the S_N2-substitution. HBr-addition

The counterpart of elimination is an addition where double or triple bonds are converted into single bonds. Similar to substitution reactions, there are several types of additions distinguished by the type of the attacking particle. For example, in the

electrophilic addition In organic chemistry, an electrophilic addition reaction is an addition reaction where a chemical compound containing a double or triple bond has a π bond broken, with the formation of two new σ bonds.March, Jerry; (1985). Advanced Organic Che ...

of hydrogen bromide, an electrophile (proton) attacks the double bond forming a carbocation, which then reacts with the nucleophile (bromine). The carbocation can be formed on either side of the double bond depending on the groups attached to its ends, and the preferred configuration can be predicted with the Markovnikov's rule. This rule states that "In the heterolytic addition of a polar molecule to an alkene or alkyne, the more electronegative (nucleophilic) atom (or part) of the polar molecule becomes attached to the carbon atom bearing the smaller number of hydrogen atoms." If the addition of a functional group takes place at the less substituted carbon atom of the double bond, then the electrophilic substitution with acids is not possible. In this case, one has to use the

hydroboration–oxidation reaction Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been. Hydroboration–oxidation is an ...

, wherein the first step, the boron atom acts as electrophile and adds to the less substituted carbon atom. In the second step, the nucleophilic hydroperoxide or halogen

anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conve ...

attacks the boron atom. While the addition to the electron-rich alkenes and alkynes is mainly electrophilic, the nucleophilic addition plays an important role in the carbon-heteroatom multiple bonds, and especially its most important representative, the carbonyl group. This process is often associated with elimination so that after the reaction the carbonyl group is present again. It is, therefore, called an addition-elimination reaction and may occur in carboxylic acid derivatives such as chlorides, esters or anhydrides. This reaction is often catalyzed by acids or bases, where the acids increase the electrophilicity of the carbonyl group by binding to the oxygen atom, whereas the bases enhance the nucleophilicity of the attacking nucleophile. H-Add-El

Nucleophilic addition of a carbanion or another nucleophile to the double bond of an alpha, beta-unsaturated carbonyl compound can proceed via the Michael reaction, which belongs to the larger class of

conjugate addition Nucleophilic conjugate addition is a type of organic reaction. Ordinary nucleophilic additions or 1,2-nucleophilic additions deal mostly with additions to carbonyl compounds. Simple alkene compounds do not show 1,2 reactivity due to lack of polari ...

s. This is one of the most useful methods for the mild formation of C–C bonds. Some additions which can not be executed with nucleophiles and electrophiles can be succeeded with free radicals. As with the free-radical substitution, the

radical addition In organic chemistry, free-radical addition is an addition reaction which involves free radicals. The addition may occur between a radical and a non-radical, or between two radicals. The basic steps with examples of the free-radical addition ( ...

proceeds as a chain reaction, and such reactions are the basis of the free-radical polymerization.

Other organic reaction mechanisms

In a rearrangement reaction, the carbon skeleton of a

molecule A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bioche ...

is rearranged to give a structural isomer of the original molecule. These include

hydride shift A sigmatropic reaction in organic chemistry is a pericyclic reaction wherein the net result is one σ-bond is changed to another σ-bond in an uncatalyzed intramolecular reaction. The name ''sigmatropic'' is the result of a compounding of the lon ...

reactions such as the Wagner-Meerwein rearrangement, where a

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloa ...

aryl In organic chemistry, an aryl is any functional group or substituent derived from an aromaticity, aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar ...

group migrates from one carbon to a neighboring carbon. Most rearrangements are associated with the breaking and formation of new carbon-carbon bonds. Other examples are

sigmatropic reaction A sigmatropic reaction in organic chemistry is a pericyclic reaction wherein the net result is one σ-bond is changed to another σ-bond in an uncatalyzed intramolecular reaction. The name ''sigmatropic'' is the result of a compounding of the lo ...

such as the

Cope rearrangement The Cope rearrangement is an extensively studied organic reaction involving the ,3sigmatropic rearrangement of 1,5-dienes. It was developed by Arthur C. Cope and Elizabeth Hardy. For example, 3-methyl-hexa-1,5-diene heated to 300 °C yield ...

. Cyclic rearrangements include

cycloaddition In organic chemistry, a cycloaddition is a chemical reaction in which "two or more unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity". T ...

s and, more generally, pericyclic reactions, wherein two or more double bond-containing molecules form a cyclic molecule. An important example of cycloaddition reaction is the Diels–Alder reaction (the so-called +2cycloaddition) between a conjugated

diene In organic chemistry a diene ( ) (diolefin ( ) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alk''ene'' units, with the standard prefix ''di'' of systematic nomenclature. ...

and a substituted

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

to form a substituted cyclohexene system. Whether a certain cycloaddition would proceed depends on the electronic orbitals of the participating species, as only orbitals with the same sign of

wave function A wave function in quantum physics is a mathematical description of the quantum state of an isolated quantum system. The wave function is a complex-valued probability amplitude, and the probabilities for the possible results of measurements ...

will overlap and interact constructively to form new bonds. Cycloaddition is usually assisted by light or heat. These perturbations result in a different arrangement of electrons in the excited state of the involved molecules and therefore in different effects. For example, the +2Diels-Alder reactions can be assisted by heat whereas the +2cycloaddition is selectively induced by light. Because of the orbital character, the potential for developing stereoisomeric products upon cycloaddition is limited, as described by the

Woodward–Hoffmann rules The Woodward–Hoffmann rules (or the pericyclic selection rules), devised by Robert Burns Woodward and Roald Hoffmann, are a set of rules used to rationalize or predict certain aspects of the stereochemistry and activation energy of pericyclic rea ...

Biochemical reactions

Biochemical reactions are mainly controlled by enzymes. These

protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, res ...

s can specifically

catalyze Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

a single reaction so that reactions can be controlled very precisely. The reaction takes place in the active site, a small part of the enzyme which is usually found in a cleft or pocket lined by

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha a ...

residues, and the rest of the enzyme is used mainly for stabilization. The catalytic action of enzymes relies on several mechanisms including the molecular shape ("induced fit"), bond strain, proximity and orientation of molecules relative to the enzyme, proton donation or withdrawal (acid/base catalysis), electrostatic interactions and many others. The biochemical reactions that occur in living organisms are collectively known as

metabolism Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run c ...

. Among the most important of its mechanisms is the anabolism, in which different DNA and enzyme-controlled processes result in the production of large molecules such as

s and carbohydrates from smaller units. Bioenergetics studies the sources of energy for such reactions. Important energy sources are

and

, which can be produced by plants via

or assimilated from food and air, respectively. All organisms use this energy to produce

adenosine triphosphate Adenosine triphosphate (ATP) is an organic compound that provides energy to drive many processes in living cells, such as muscle contraction, nerve impulse propagation, condensate dissolution, and chemical synthesis. Found in all known forms o ...

(ATP), which can then be used to energize other reactions.

Applications

Chemical reactions are central to

chemical engineering Chemical engineering is an engineering field which deals with the study of operation and design of chemical plants as well as methods of improving production. Chemical engineers develop economical commercial processes to convert raw materials int ...

, where they are used for the synthesis of new compounds from natural raw materials such as

petroleum Petroleum, also known as crude oil, or simply oil, is a naturally occurring yellowish-black liquid mixture of mainly hydrocarbons, and is found in geological formations. The name ''petroleum'' covers both naturally occurring unprocessed crud ...

, mineral

ore Ore is natural rock or sediment that contains one or more valuable minerals, typically containing metals, that can be mined, treated and sold at a profit.Encyclopædia Britannica. "Ore". Encyclopædia Britannica Online. Retrieved 7 Apr ...

s, and

in air. It is essential to make the reaction as efficient as possible, maximizing the yield and minimizing the number of reagents, energy inputs and waste.

Catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

s are especially helpful for reducing the energy required for the reaction and increasing its reaction rate. Some specific reactions have their niche applications. For example, the

thermite Thermite () is a pyrotechnic composition of metal powder and metal oxide. When ignited by heat or chemical reaction, thermite undergoes an exothermic reduction-oxidation (redox) reaction. Most varieties are not explosive, but can create brie ...

reaction is used to generate light and heat in pyrotechnics and

welding Welding is a fabrication process that joins materials, usually metals or thermoplastics, by using high heat to melt the parts together and allowing them to cool, causing fusion. Welding is distinct from lower temperature techniques such as bra ...

. Although it is less controllable than the more conventional

oxy-fuel welding Principle of burn cutting Oxy-fuel welding (commonly called oxyacetylene welding, oxy welding, or gas welding in the United States) and oxy-fuel cutting are processes that use fuel gases (or liquid fuels such as gasoline or petrol, diesel, ...

arc welding Arc welding is a welding process that is used to join metal to metal by using electricity to create enough heat to melt metal, and the melted metals, when cool, result in a binding of the metals. It is a type of welding that uses a welding powe ...

and

flash welding Flash welding is a type of resistance welding that does not use any filler metals. The pieces of metal to be welded are set apart at a predetermined distance based on material thickness, material composition, and desired properties of the finish ...

, it requires much less equipment and is still used to mend rails, especially in remote areas.

Monitoring

Mechanisms of monitoring chemical reactions depend strongly on the reaction rate. Relatively slow processes can be analyzed in situ for the concentrations and identities of the individual ingredients. Important tools of real-time analysis are the measurement of pH and analysis of optical absorption (color) and emission spectra. A less accessible but rather efficient method is the introduction of a radioactive isotope into the reaction and monitoring how it changes over time and where it moves to; this method is often used to analyze the redistribution of substances in the human body. Faster reactions are usually studied with ultrafast laser spectroscopy where utilization of femtosecond

laser A laser is a device that emits light through a process of optical amplification based on the stimulated emission of electromagnetic radiation. The word "laser" is an acronym for "light amplification by stimulated emission of radiation". The fi ...

s allows short-lived transition states to be monitored at a time scaled down to a few femtoseconds. Atkins, p. 987

References

Bibliography

* * * * * {{DEFAULTSORT:Chemical Reaction Chemistry Change

History

Characteristics

Equations

Elementary reactions

Chemical equilibrium

Thermodynamics

Kinetics

Reaction types

Four basic types

Synthesis

Decomposition

Single displacement

Double displacement

Combustion

Oxidation and reduction

Complexation

Acid–base reactions

Precipitation

Solid-state reactions

Reactions at the solid/gas interface

Photochemical reactions

Catalysis

Reactions in organic chemistry

Substitution

Addition and elimination

Other organic reaction mechanisms

Biochemical reactions

Applications

Monitoring

See also

References

Bibliography