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

Concept explainers

Question
100%
Book Icon
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

Blurred answer
Students have asked these similar questions
(a) Draw the products formed when propane is heated with Br2.  (b) Label major and minor products and explain with an energy diagram.
Which of (a)-(d) is the correct IUPAC name of the following compound? * HO O 3-methyl-1-phenyl-1-pentanol ○ 3-methyl-5-phenyl-5-pentanol ○ 3-methyl-1-benzene-1-pentanol O 1-phenyl-1-hexanol
(a) Draw two different enol tautomers of 2-methylcyclohexanone. (b) Draw two constitutional isomers that are not tautomers, but contain a C=C and an OH group. 2-methylcyclohexanone

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
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning