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 11, Problem 11.50P
Interpretation Introduction

Interpretation:

The three electrophilic addition steps for the formation of cholesterol from squalene as per Equation 11-38 are to be drawn using curved arrow notation.

Concept introduction:

An electrophilic addition reaction step is one in which an electron-rich species attacks an electron-poor species to form a σ bond with it. An electron-rich species (nucleophiles) may be an atom with a lone pair, with or without a negative charge, or a π bond pair. Highly electronegative atoms like O and N that possess at least one lone pair can act as nucleophiles. An electron-poor species (electrophile) is an atom with an incomplete octet and a positive charge. These are typically a carbocation or a carbon attached to a highly electronegative atom like oxygen.

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In the partial mechanism for the formation of cholesterol from squalene (Equation 11-38, p. 593), the steps for the following transformation were not shown explicitly. As indicated, the transformation involves three electrophilic addition steps. Draw each step and its curved arrow notation explicitly. H -H CH3 CH3 Three electrophilic addition steps CH3 H HO HO A Protosterol cation
Complete the following reaction diagram by giving either the reaction conditions or the missing products. The reaction mechanisms are not required.
Supply the missing reagent for the following reactions.

Chapter 11 Solutions

EBK GET READY FOR ORGANIC CHEMISTRY

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