ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
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Chapter 8, Problem 65P
Interpretation Introduction

Interpretation:The best structure for substrate A should be chosen.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 65P , additional homework tip  1

Concept introduction:The carbonyl bond is polar with partial postive charge on carbon and partial negative charge on oxygen as illustrated below.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 65P , additional homework tip  2

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include NaBH4 , LiAlH4 .The boron and lithium in these reagents tend to push the electron of B-H bond towards carbonyl carbon as illustrated below.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 65P , additional homework tip  3

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