Custom eBook for Organic Chemistry
Custom eBook for Organic Chemistry
2nd Edition
ISBN: 9798214171104
Author: Straumanis
Publisher: Cengage Custom
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Chapter 8, Problem 7E
Interpretation Introduction

Interpretation: The most likely hydride shift that will occur for each of the below carbocations should be depicted with curved arrow and reason behind lowered potential energy for thus newly formed carbocation should be explained.

  Custom eBook for Organic Chemistry, Chapter 8, Problem 7E , additional homework tip  1

Concept introduction: Carbocation is a general term employed for a postively charged carbon irrespective of valency of carbon. In carbocation, carbon is bonded to 3 atoms or groups and has only sextet of electrons so it behaves as an electron-deficient species. It is sp2 hybridized with a vacant p orbital and has a planar geometry.

The order of relative stability of various possible carbocation species is as follows:

  Custom eBook for Organic Chemistry, Chapter 8, Problem 7E , additional homework tip  2

Thus, whenever possibility to attain lower energy by rearrangement is there hydride or alkyl shift may occurs and results in more stable carbocation. This type of rearrangement is highly favorable in polar solvents.

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