EBK GET READY FOR ORGANIC CHEMISTRY
EBK GET READY FOR ORGANIC CHEMISTRY
2nd Edition
ISBN: 9780321787989
Author: KARTY
Publisher: PEARSON CO
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Chapter 12, Problem 12.5YT
Interpretation Introduction

Interpretation:

The mechanism for the reaction in Equation 12-17 is as follows, but the curved arrows have been omitted. The mechanism by drawing in the curved arrows is to be completed and the name of each elementary step is to be written. Also, label the chloronium ion intermediate.

Concept introduction:

Cl2 does not appear to possess an electron–poor atom. Br2 behave as an electrophile once before in the SN2 chlorination of enols and enolate anions. As the electron-rich π bond approaches Cl2, the Cl2 molecule becomes polarized, temporarily making one of the Cl atoms electron-poor. The mechanism proceeds through a chromium ion intermediate. The curved arrow from the π bond to Cl represents the flow of electrons from an electron-rich site to an electron-poor site. A lone pair of electrons on Cl forms a bond back to one of the alkene C atoms to avoid breaking the C atom’s octet, resulting in a three-membered ring. The weak Cl-Cl bond breaks and one of the atoms leaves as Cl-.

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EBK GET READY FOR ORGANIC CHEMISTRY

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