Carbocation Intermediate Rearrangements Practice Problems
The pinacol rearrangement begins with an acid-catalyzed ionization to give a carbocation. The carbocation then undergoes rearrangement to give a resonance-stabilized cation, which will give the product of the reaction after the loss of a proton. Draw a mechanism for the reaction shown below.
In acidic medium, 1-propanol can undergo isomerization to 2-propanol. Write a plausible mechanism for this reaction and explain why this isomerization is energetically feasible.
Does the following carbocation undergo rearrangement? If so, illustrate the resulting carbocation and provide the corresponding mechanism.
Determine whether the following carbocation is likely to undergo rearrangement. If rearrangement is expected, draw the resulting carbocation and the mechanism by which the rearrangement occurs.
Identify the carbocations from the given options that are most likely to undergo rearrangement during a reaction.
Start with the given molecule and predict the product formed after undergoing a pinacol rearrangement.
Identify which of the given carbocation species is most likely to undergo rearrangement.