Carbocation Intermediate Rearrangements Practice Problems

Identify the carbocations from the given options that are most likely to undergo rearrangement during a reaction.

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.

Consider the two pathways for the reaction:

Does the following reaction coordinate for the boxed portion of the two pathways rationalize pathway B as the one that produces the major product?

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.

Identify which of the given carbocation species is most likely to undergo rearrangement.

Select the carbocation(s) that is/are expected to undergo rearrangement.

Show how the following carbocations rearrange to more stable carbocations.

In the following partial reactions below, it shows the possibility of 1,2-alkyl and 1,2-hydride shifts. Which is expected to occur? Explain your answer.

Determine if the carbocation below is expected to rearrange. If so, provide the rearranged form and the arrow-pushing mechanism.

Determine if the carbocation below is expected to rearrange. If so, draw the rearranged form and the arrow-pushing mechanism.

Determine if the carbocation below is expected to rearrange. If so, draw the rearranged structure and the arrow-pushing mechanism.

Is the following carbocation expected to undergo rearrangement? If so, provide the mechanism for the formation of the expected carbocation.

Consider the proposed stepwise mechanism for a hydride shift:

Does the following reaction coordinate diagram illustrate this mechanism? Is this mechanism more likely than a concerted mechanism? Why?