Allylic rearrangement

An allylic rearrangement or allylic shift is an organic reaction in which the double bond in an allyl chemical compound shifts to the next carbon atom. It is encountered in nucleophilic substitution.

In reaction conditions that favor a S_N1 reaction mechanism the intermediate is a carbocation for which several resonance structures are possible. This explains the product distribution (or product spread) after recombination with nucleophile Y. This type of process is called an S_N1' substitution.