ORGANIC CHEMISTRY PRESENTATION

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ORGANIC CHEMISTRY PRESENTATION

ALKYL HALIDES AND SN1 REACTIONS

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REARRANGEMENTS IN SN1 REACTIONS

Carbocations undergo rearrangements frequently to form more stable ions An arrangement may occur after a carbocation has formed or it may occur as the leaving group is leaving.

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Hydride shift

This is the movement of a hydrogen atom and its bonding pair of electrons. The symbol “~h“ represents a hydride shift. This hydride shift converts the initially formed secondary carbocation to a more stable tertiary carbocation. An attack by the solvent gives the rearranged product.

I, 2 - Hydride shift: a common rearrangement reaction - Br- Loss of L G OH 3 O 1 2 20 O 3 30 Rearrangement 1, 2 - Hydride shift H20 : Nucleophilic attack Expected product OH Major Product Deprotonation