Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter D, Problem D.4P
Interpretation Introduction

Interpretation:

It is to be determined whether the proton transfer between OH and HCl is allowed if OH were to approach HCl from the same end as Cl. Whether you would expect that elementary step to take place or not is to be justified.

Concept introduction:

An elementary step in which a proton is transferred from an electron-poor site to an electron-rich site and one bond is broken and another is formed simultaneously is called proton transfer step.

In an elementary step, the flow of electrons is from an electron rich group to an electron poor atom. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) must have axial overlap or parallel overlap. The axial overlap between HOMO and LUMO has substantial net overlap, so this reaction is allowed. If the HOMO and LUMO do not have a substantial overlap, this reaction is forbidden.

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