ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
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Chapter 8, Problem 53P

(a)

Interpretation Introduction

Interpretation:The best method for synthesis of indicated ketone from appropriate alcohol should be outlined.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 53P , additional homework tip  1

Concept introduction:Chromium reagents such as CrO3 , pyridiniumchlorochromate or sodium and potassium chromate that has chromium present in high oxidation state Cr(VI) are useful oxidizing reagent for primary or secondary alcohols. The tertiary alcohols have no hydrogen so it cannot be oxidized.

Aqueous sodium dichromate is the reagent added for oxidation of 2° alcohol to a ketone. The reagent is written as NaCr2O7/H2SO4 and has Cr(VI) that transforms to Cr(III) while it acts as oxidizing agent.

(b)

Interpretation Introduction

Interpretation:The best method for synthesis of indicated acid from appropriate alcohol should be devised.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 53P , additional homework tip  2

Concept introduction:Chromium reagents such as CrO3 , pyridiniumchlorochromateor sodium and potassium chromate that has chromium present in high oxidation state Cr(VI) are useful oxidizing reagent for primary or secondary alcohols. The tertiary alcohols have no hydrogen so it cannot be oxidized.

Since aldehydes in water tend to remain in equilibrium with the diols, one of the two hydroxyl functional group presents may further react with chromium regent to form carboxylic acid as final oxidation product. This is known as overoxidation without the formation of intermediate oxidized product aldehyde. The regent for direct conversion of alcohol to acid is K2Cr2O7 , H2SO4 and H2O .

(c)

Interpretation Introduction

Interpretation: The best method for synthesis of indicated aldehyde from appropriate alcohol should be devised.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 53P , additional homework tip  3

Concept introduction:PCC is useful for selective oxidation of primary alcohol to corresponding aldehydes. The tertiary alcohols have no hydrogen so it cannot be oxidized. The structure of pyridinium chlorochromate is as follows:

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 53P , additional homework tip  4

(d)

Interpretation Introduction

Interpretation: The best method for synthesis of indicated ketone from appropriate alcohol should be outlined.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 53P , additional homework tip  5

Concept introduction:Chromium reagents such as CrO3 , pyridiniumchlorochromate or sodium and potassium chromate that has chromium present in high oxidation state Cr(VI) are useful oxidizing reagent for primary or secondary alcohols. The tertiary alcohols have no hydrogen so it cannot be oxidized.

Aqueous sodium dichromate is the reagent added for oxidation of 2° alcohol to a ketone. The reagent is written as NaCr2O7/H2SO4 and has Cr(VI) that transforms to Cr(III) while it acts as oxidizing agent.

(e)

Interpretation Introduction

Interpretation: The best method for synthesis of indicated aldehyde from appropriate alcohol should be devised.

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 53P , additional homework tip  6

Concept introduction: PCC is pyridinium chlorochromate is useful for selective oxidation of primary alcohol to corresponding aldehydes. The tertiary alcohols have no hydrogen so it cannot be oxidized. The structure of pyridinium chlorochromate is as follows:

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 8, Problem 53P , additional homework tip  7

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