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Concept
Regioselectivity
Summary
In chemistry, regioselectivity is the preference of chemical bonding or breaking in one direction over all other possible directions. It can often apply to which of many possible positions a reagent will affect, such as which proton a strong base will abstract from an organic molecule, or where on a substituted benzene ring a further substituent will be added.
A specific example is a halohydrin formation reaction with 2-propenylbenzene:
Because of the preference for the formation of one product over another, the reaction is selective. This reaction is regioselective because it selectively generates one constitutional isomer rather than the other.
Various examples of regioselectivity have been formulated as rules for certain classes of compounds under certain conditions, many of which are named. Among the first introduced to chemistry students are Markovnikov's rule for the addition of protic acids to alkenes, and the Fürst-Plattner rule for the addition of nucleophiles to derivatives of cyclohexene, especially epoxide derivatives.
Regioselectivity in ring-closure reactions is subject to Baldwin's rules. If there are two or more orientations that can be generated during a reaction, one of them is dominant (e.g., Markovnikov/anti-Markovnikov addition across a double bond)
Regioselectivity can also be applied to specific reactions such as addition to pi ligands.
Selectivity also occurs in carbene insertions, for example in the Baeyer-Villiger reaction. In this reaction, an oxygen is regioselectively inserted near an adjacent carbonyl group. In ketones, this insertion is directed toward the carbon which is more highly substituted (i.e. according to Markovnikov's rule). For example, in a study involving acetophenones, this oxygen was preferentially inserted between the carbonyl and the aromatic ring to give acetyl aromatic esters instead of methyl benzoates.
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Cyclic compound
A cyclic compound (or ring compound) is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon (i.e., are carbocycles), none of the atoms are carbon (inorganic cyclic compounds), or where both carbon and non-carbon atoms are present (heterocyclic compounds with rings containing both carbon and non-carbon).
Benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon.
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. The driving force for this reaction is the formation of an electrophile X+ that forms a covalent bond with an electron-rich, unsaturated C=C bond. The positive charge on X is transferred to the carbon-carbon bond, forming a carbocation during the formation of the C-X bond.
Related courses (1)
CH-234: Organic functions and reactions II
To develop basic understanding of the reactivity of aromatic and heteroaromatic compounds. To develop a knowledge of a class of pericyclic reactions. To apply them in the context of the synthesis.