By the end of this chapter you should be familiar with
- How we can change the connectivity of an existing organic backbone by using reactions that result in skeletal rearrangements.
- Participation: nucleophiles are more efficient if they are already part of the molecule.
- Participation means acceleration and retention of stereochemistry and may mean rearrangement. Participating groups can have lone pairs of π electrons.
- Types of rearrangement. Carbocations often rearrange by alkyl migration.
- The mechanisms of rearrangements.
- Ring expansion and contraction by rearrangement and controlling rearrangements.
- Insertion of O, N, or C next to a ketone.
There are two types of rearrangements: ...