ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
Question
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Chapter 8, Problem 39P

(a)

Interpretation Introduction

Interpretation: The mechanism for formation of product in indicated reaction should be written.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 39P , additional homework tip  1

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

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 39P , 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 aluminum and lithium in these reagents such as LiAlH4 tend to push the electron of Al-H bond towards carbonyl carbon. The work up finally yields alcohol as illustrated below:

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 39P , additional homework tip  3

(b)

Interpretation Introduction

Interpretation:The mechanism for formation of product in indicated reaction should be written.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 39P , additional homework tip  4

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

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 39P , additional homework tip  5

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 aluminum and lithium in these reagents such as LiAlH4 tend to push the electron of Al-H bond towards carbonyl carbon. The work up finally yields alcohol as illustrated below:

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 39P , additional homework tip  6

(c)

Interpretation Introduction

Interpretation:The mechanism for formation of product in indicated reaction should be written.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 39P , additional homework tip  7

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

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 39P , additional homework tip  8

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain regents that are useful for such hydride addition at carbonyl carbon include NaBH4 , LiAlH4 .

(d)

Interpretation Introduction

Interpretation:The mechanism for formation of product in indicated reaction should be written.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 39P , additional homework tip  9

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 39P , additional homework tip  10

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 aluminum and lithium in these reagents such as LiAlH4 tend to push the electron of Al-H bond towards carbonyl carbon.

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