ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
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Chapter 8.5, Problem 8.8E

(a)

Interpretation Introduction

Interpretation:The expected product of NaBH4 reduction of below compound should be determined and its chirality or achirality should be identified.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8.5, Problem 8.8E , 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 8.5, Problem 8.8E , 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 sodium borohydride, lithium aluminum hydride. 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 8.5, Problem 8.8E , additional homework tip  3

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(b)

Interpretation Introduction

Interpretation: The expected product of NaBH4 reduction of below compound should be determinedand its chirality or achirality should be identified.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8.5, Problem 8.8E , 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 8.5, Problem 8.8E , 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 sodium borohydride, lithium aluminum hydride. 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 8.5, Problem 8.8E , additional homework tip  6

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(c)

Interpretation Introduction

Interpretation: The expected product of NaBH4 reduction of below compound should be determinedand its chirality or achirality should be identified.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8.5, Problem 8.8E , 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 8.5, Problem 8.8E , additional homework tip  8

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 sodium borohydride, lithium aluminum hydride. 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 8.5, Problem 8.8E , additional homework tip  9

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(d)

Interpretation Introduction

Interpretation: The expected product of NaBH4 reduction of below compound should be determinedand its chirality or achirality should be identified.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8.5, Problem 8.8E , additional homework tip  10

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 8.5, Problem 8.8E , additional homework tip  11

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 sodium borohydride, lithium aluminum hydride. 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 8.5, Problem 8.8E , additional homework tip  12

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(e)

Interpretation Introduction

Interpretation: The expected product of NaBH4 reduction of below compound should be determinedand its chirality or achirality should be identified.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8.5, Problem 8.8E , additional homework tip  13

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 8.5, Problem 8.8E , additional homework tip  14

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 sodium borohydride, lithium aluminum hydride. 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 8.5, Problem 8.8E , additional homework tip  15

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

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