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Advanced Organic Chemistry by Maya Shankar Singh

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7

Molecular Rearrangements

LEARNING OBJECTIVES

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.
7.1 INTRODUCTION

There are two types of rearrangements: ...

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