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Rearrangement Reactions of Alkyl Carbocation

Carbocation rearrangements can be defined as the movement of the carbocation from an unstable state to a more stable state by making use of different structural reorganisational shifts within the molecule. Alkyl carbocation is a carbocation comprising an alkyl group. They are the most common carbocation.

For example,

Alkyl Carbocation

Carbocation Rearrangement

Carbocation rearrangement occurs when the alcohols are converted into several carbocations, and this phenomenon is termed carbocation rearrangement. In simple, carbocation comprises +ve charge in a molecule that is connected to 3 more groups and holds a sextet. Carbocation rearrangement can be carried out to a reaction that does not involve alcohol. There are 2 types of carbocation rearrangements, namely alkyl and hybrid shift.

Alkyl Shift

An alkyl shift occurs when a carbocation does not contain a hydrogen atom that is present on the adjacent carbon atom that is readily available for rearrangement. There are some cases where a hybrid shift does not lead to a stable carbocation. For instance, consider the following case:

Alkyl Carbocation

When the alkyl group migrates, there would be a chance for the formation of tertiary carbocation that is more stable.

Alkyl Carbocation

When a carbon attached to four carbons is present adjacent to secondary carbocation, then there would be a possibility for the occurrence of an alkyl shift.

Alkyl Carbocation

This alkyl occurs when a carbon-carbon bond donates a pair of electrons to the empty p-orbital on the carbocation. It can occur potentially at any time when carbocation is formed.

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