Organic reaction

Source: Wikipedia, the free encyclopedia.

Organic reactions are

fabrics
depend on organic reactions.

The oldest organic reactions are combustion of organic fuels and saponification of fats to make soap. Modern organic chemistry starts with the Wöhler synthesis in 1828. In the history of the Nobel Prize in Chemistry awards have been given for the invention of specific organic reactions such as the Grignard reaction in 1912, the Diels–Alder reaction in 1950, the Wittig reaction in 1979 and olefin metathesis in 2005.

The Claisen rearrangement

Classifications

Organic chemistry has a strong tradition of naming a specific reaction to its inventor or inventors and a long

CBS reduction. The number of reactions hinting at the actual process taking place is much smaller, for example the ene reaction or aldol reaction
.

Another approach to organic reactions is by type of

organic reagent, many of them inorganic, required in a specific transformation. The major types are oxidizing agents such as osmium tetroxide, reducing agents such as lithium aluminium hydride, bases such as lithium diisopropylamide and acids such as sulfuric acid
.

Finally, reactions are also classified by mechanistic class. Commonly these classes are (1) polar, (2) radical, and (3) pericyclic. Polar reactions are characterized by the movement of electron pairs from a well-defined source (a nucleophilic bond or lone pair) to a well-defined sink (an electrophilic center with a low-lying antibonding orbital). Participating atoms undergo changes in charge, both in the formal sense as well as in terms of the actual electron density. The vast majority of organic reactions fall under this category. Radical reactions are characterized by species with unpaired electrons (radicals) and the movement of single electrons. Radical reactions are further divided into chain and nonchain processes. Finally, pericyclic reactions involve the redistribution of chemical bonds along a cyclic transition state. Although electron pairs are formally involved, they move around in a cycle without a true source or sink. These reactions require the continuous overlap of participating orbitals and are governed by orbital symmetry considerations. Of course, some chemical processes may involve steps from two (or even all three) of these categories, so this classification scheme is not necessarily straightforward or clear in all cases. Beyond these classes, transition-metal mediated reactions are often considered to form a fourth category of reactions, although this category encompasses a broad range of elementary organometallic processes, many of which have little in common and very specific.

Fundamentals

Factors governing organic reactions are essentially the same as that of any chemical reaction. Factors specific to organic reactions are those that determine the stability of reactants and products such as conjugation, hyperconjugation and aromaticity and the presence and stability of reactive intermediates such as free radicals, carbocations and carbanions.

An organic compound may consist of many

Zaitsev's rule
.

Organic reactions are important in the production of

functional group interconversions
.

By mechanism

There is no limit to the number of possible organic reactions and mechanisms.[5][6] However, certain general patterns are observed that can be used to describe many common or useful reactions. Each reaction has a stepwise reaction mechanism that explains how it happens, although this detailed description of steps is not always clear from a list of reactants alone. Organic reactions can be organized into several basic types. Some reactions fit into more than one category. For example, some substitution reactions follow an addition-elimination pathway. This overview isn't intended to include every single organic reaction. Rather, it is intended to cover the basic reactions.

Reaction type Subtype Comment
Addition reactions electrophilic addition include such reactions as halogenation, hydrohalogenation and hydration.
nucleophilic addition
radical addition
Elimination reaction include processes such as
Substitution reactions nucleophilic aliphatic substitution with SN1, SN2 and SNi reaction mechanisms
nucleophilic aromatic substitution
nucleophilic acyl substitution
electrophilic substitution
electrophilic aromatic substitution
radical substitution
Organic redox reactions are
redox reactions specific to organic compounds
and are very common.
Rearrangement reactions 1,2-rearrangements
pericyclic reactions
metathesis

In

addition polymerizations and step-growth polymerizations
.

In general the stepwise progression of reaction mechanisms can be represented using arrow pushing techniques in which curved arrows are used to track the movement of electrons as starting materials transition to intermediates and products.

By functional groups

Organic reactions can be categorized based on the type of functional group involved in the reaction as a reactant and the functional group that is formed as a result of this reaction. For example, in the Fries rearrangement the reactant is an ester and the reaction product an alcohol.

An overview of functional groups with their preparation and reactivity is presented below:

Functional group Preparation Reactions
Acid anhydride preparation reactions
Acyl halides preparation reactions
Acyloins preparation reactions
Alcohols preparation reactions
Aldehydes preparation reactions
Alkanes
preparation
reactions
Alkenes
preparation
reactions
Alkyl halides
preparation
reactions
Alkyl nitrites
preparation
reactions
Alkynes
preparation
reactions
Amides preparation reactions
Amine oxide preparation reactions
Amines preparation reactions
Arene compounds
preparation
reactions
Azides preparation reactions
Aziridines preparation reactions
Carboxylic acids
preparation
reactions
Cyclopropanes preparation reactions
Diazo compounds preparation reactions
Diols preparation reactions
Esters preparation reactions
Ethers preparation reactions
Epoxide preparation reactions
Haloketones
preparation
reactions
Imines preparation reactions
Isocyanates preparation reactions
Ketones preparation reactions
Lactams preparation reactions
Lactones preparation reactions
Nitriles preparation reactions
Nitro compounds preparation reactions
Phenols preparation reactions
Thiols preparation reactions

Other classification

In

ring-closing reactions
.

Organic reactions can also be classified by the type of bond to carbon with respect to the element involved. More reactions are found in

organosilicon chemistry, organosulfur chemistry, organophosphorus chemistry and organofluorine chemistry. With the introduction of carbon-metal bonds the field crosses over to organometallic chemistry
.

See also

References

  1. ^ J. Clayden, N. Greeves & S. Warren "Organic Chemistry" (Oxford University Press, 2012)
  2. ^ Robert T. Morrison, Robert N. Boyd, and Robert K. Boyd, Organic Chemistry, 6th edition, Benjamin Cummings, 1992

External links