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A 1,2-rearrangement or 1,2-migration or 1,2-shift or Whitmore 1,2-shift [1] is an organic reaction where a substituent moves from one atom to another atom in a chemical compound. In a 1,2 shift the movement involves two adjacent atoms but moves over larger distances are possible. In the example below the substituent R moves from carbon atom C 2 ...
In organic chemistry, a rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. [1] Often a substituent moves from one atom to another atom in the same molecule, hence these reactions are usually intramolecular.
When a pinacol is not symmetrical, there is a choice for which hydroxyl group will leave and which alkyl shift will occur. The selectivity will be determined by the stability of the carbocations. In this case although both choices are tertiary, the phenyl groups result in significantly higher stabilization of the positive charge through resonance.
In organic chemistry, an alkyl group is an alkane missing one hydrogen. [1] The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of −C n H 2n+1. A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula −C n H ...
Thermal alkyl [1,3] shifts, similar to [1,3] hydride shifts, must proceed antarafacially. Here the geometry of the transition state is prohibitive, but an alkyl group , due to the nature of its orbitals, can invert its geometry, form a new bond with the back lobe of its sp 3 orbital, and therefore proceed via a suprafacial shift.
Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). [1] Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation.
A Wagner–Meerwein rearrangement is a class of carbocation 1,2-rearrangement reactions in which a hydrogen, alkyl or aryl group migrates from one carbon to a neighboring carbon. [ 1 ] [ 2 ] They can be described as cationic [1,2]- sigmatropic rearrangements, proceeding suprafacially and with stereochemical retention.
Industrially, most alkylations are typically conducted using alcohols, not alkyl halides. Alcohols are less expensive than alkyl halides and their alkylation does not produce salts, the disposal of which can be problematic. Key to the alkylation of alcohols is the use of catalysts that render the hydroxyl group a good leaving group.