Chemistry Reference
In-Depth Information
This is a solvolysis reaction where the alcohol is protonated and water leaves, gen-
erating a carbocation. The resulting carbocation then joins with acetic acid or
migrates through the double bond (note the arrow pushing). The migrated carbo-
cation then joins with acetic acid. In both cases, the resulting acetates are cleaved
with sodium hydroxide generating a mixture of two alcohols—regenerated starting
material and 3-hydroxy-1-pentene.
Like the previous example, this is a solvolysis reaction. Initial protonation of the
alcohol followed by water leaving generates a primary carbocation. The bromide
can then add to this carbocation generating neopentyl bromide. Since, for this
carbocation, 1,2-hydride shifts cannot occur, a 1,2-alkyl shift generates a more
stable tertiary carbocation. This new carbocation is not subject to possible 1,2-
hydride shifts because any such transformation would generate either a less stable
