Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 10.8, Problem 10.11P

(a)

Interpretation Introduction

Interpretation:

The product formed in the reaction of 1-Hexanol with chromic acid has to be drawn.

Concept Introduction:

Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions.

Chromic acid Oxidation of an Alcohol:

Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium.

Organic Chemistry, Chapter 10.8, Problem 10.11P , additional homework tip  1

Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

Organic Chemistry, Chapter 10.8, Problem 10.11P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation:

The product formed in the reaction of 2-Hexanol with chromic acid has to be drawn.

Concept Introduction:

Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions.

Chromic acid Oxidation of an Alcohol:

Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium.

Organic Chemistry, Chapter 10.8, Problem 10.11P , additional homework tip  3

Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

Organic Chemistry, Chapter 10.8, Problem 10.11P , additional homework tip  4

(c)

Interpretation Introduction

Interpretation:

The product formed in the reaction of Cyclohexanol with chromic acid has to be drawn.

Concept Introduction:

Oxidation of alcohols: Oxidation of primary alcohol gives an aldehyde or a carboxylic acid, depending on experimental conditions.

Chromic acid Oxidation of an Alcohol:

Step 1: Reaction of alcohol and chromic acid gives an alkyl chromate. No change in oxidation state of both Carbon and Chromium.

Organic Chemistry, Chapter 10.8, Problem 10.11P , additional homework tip  5

Step 2: Take a proton away and simultaneously break bonds to give stable molecules or ions. Reaction of the alkyl chromate with a base (here water molecule) results in cleavage of a C-H bond, formation of the carbonyl groups, and reduction of Chromium (VI) to Chromium (IV).

Organic Chemistry, Chapter 10.8, Problem 10.11P , additional homework tip  6

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Chapter 10 Solutions

Organic Chemistry

Ch. 10.7 - Prob. AQCh. 10.7 - Prob. BQCh. 10.7 - Prob. CQCh. 10.7 - Prob. DQCh. 10.7 - Which step in the reaction would you expect to be...Ch. 10.7 - Prob. FQCh. 10.7 - Prob. GQCh. 10.8 - Prob. 10.11PCh. 10.8 - Prob. AQCh. 10.8 - Prob. BQCh. 10.8 - Prob. CQCh. 10.8 - Why does nature use a reagent as complex as NAD+...Ch. 10.8 - -Hydroxyketones and -hydroxyaldehydes are also...Ch. 10.9 - Write IUPAC names for these thiols.Ch. 10 - Which are secondary alcohols?Ch. 10 - Name each compound.Ch. 10 - Prob. 10.16PCh. 10 - Name and draw structural formulas for the eight...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Prob. 10.20PCh. 10 - Prob. 10.21PCh. 10 - Arrange the compounds in each set in order of...Ch. 10 - Prob. 10.23PCh. 10 - The decalinols A and B can be equilibrated using...Ch. 10 - Prob. 10.25PCh. 10 - Select the stronger acid from each pair and...Ch. 10 - Prob. 10.27PCh. 10 - In each equilibrium, label the stronger acid, the...Ch. 10 - Write equations for the reaction of 1-butanol with...Ch. 10 - Write equations for the reaction of 2-butanol with...Ch. 10 - Prob. 10.31PCh. 10 - When (R)-2-butanol is left standing in aqueous...Ch. 10 - Two diastereomeric sets of enantiomers, A/B and...Ch. 10 - Acid-catalyzed dehydration of 3-methyl-2-butanol...Ch. 10 - Show how you might bring about the following...Ch. 10 - Propose a mechanism for the following pinacol...Ch. 10 - Prob. 10.37PCh. 10 - Show how each alcohol or diol can be prepared from...Ch. 10 - Dihydropyran is synthesized by treating...Ch. 10 - Show how to convert propene to each of these...Ch. 10 - Prob. 10.41PCh. 10 - Prob. 10.42PCh. 10 - The tosylate of a primary alcohol normally...Ch. 10 - Prob. 10.44PCh. 10 - Show how to convert cyclohexene to each compound...Ch. 10 - Prob. 10.46PCh. 10 - Ethanol (CH3CH2OH) and dimethyl ether (CH3OCH3)...Ch. 10 - Prob. 10.48PCh. 10 - Prob. 10.49PCh. 10 - Prob. 10.50PCh. 10 - Write the products of the following sequences of...Ch. 10 - Alcohols are important for organic synthesis,...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59P
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