Introduction to General, Organic and Biochemistry
Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
bartleby

Concept explainers

Question
Book Icon
Chapter 14, Problem 14.29P
Interpretation Introduction

(a)

Interpretation:

State True or false.

The two most important reactions of alcohols are their acid-catalyzed dehydration to give alkenes and their oxidation to aldehydes, ketones and carboxylic acid.

Concept Introduction:

Chemical reaction is the procedure to transform the chemical substance in the new substance. During this procedure sometimes, acid is involved which is the substance which could either accept electron pairs or donate protons in the reactions.

A catalyst is the molecule which is used to speed up the chemical reaction, not being consumed within the procedure. Acids are used as catalysts are needed for an acid catalyzed hydration.

A dehydration reaction is aeration when any organic substance loses the water molecule to form an alkene.

Expert Solution
Check Mark

Answer to Problem 14.29P

True.

Explanation of Solution

Alcohols are organic compounds containing -OH group. It undergoes in the presence of acid to form an alkene. Dehydration is the removal of water from alcohol.

Introduction to General, Organic and Biochemistry, Chapter 14, Problem 14.29P , additional homework tip  1

Alcohols undergo oxidation to yield aldehyde, ketone, and carboxylic acid. The primary alcohol in an acid catalyzed oxidation gives an aldehyde and further acid catalyzed oxidation gives a corresponding acid.

Introduction to General, Organic and Biochemistry, Chapter 14, Problem 14.29P , additional homework tip  2

The secondary alcohol in an acid catalyzed oxidation fives a ketone.

Introduction to General, Organic and Biochemistry, Chapter 14, Problem 14.29P , additional homework tip  3

Therefore, this statement is True.

Interpretation Introduction

(b)

Interpretation:

State True or false.

The acidity of alcohols is comparable to that of water.

Concept Introduction:

Chemical reaction is the procedure to transform the chemical substance in the new substance. During this procedure sometimes, acid is involved which is the substance which could either accept electron pairs or donate protons in the reactions.

A catalyst is the molecule which is used to speed up the chemical reaction, not being consumed within the procedure. Acids are used as catalysts are needed for an acid catalyzed hydration.

A dehydration reaction is aeration when any organic substance loses the water molecule to form an alkene.

Expert Solution
Check Mark

Answer to Problem 14.29P

True.

Explanation of Solution

The strength of an acid can be measured by the acid dissociation constant Ka while the pKa value is logarithmic value of the acid dissociation constant. So, the alcohol has the nearly same pKa value as of water.

Therefore, this statement is True.

Interpretation Introduction

(c)

Interpretation:

State True or false.

Water-insoluble alcohols and water-insoluble phenols react with string bases to give water soluble salts.

Concept Introduction:

Chemical reaction is the procedure to transform the chemical substance in the new substance. During this procedure sometimes, acid is involved which is the substance which could either accept electron pairs or donate protons in the reactions.

A catalyst is the molecule which is used to speed up the chemical reaction, not being consumed within the procedure. Acids are used as catalysts are needed for an acid catalyzed hydration.

A dehydration reaction is aeration when any organic substance loses the water molecule to form an alkene.

Expert Solution
Check Mark

Answer to Problem 14.29P

False.

Explanation of Solution

Alcohol is a water-soluble compound. It is soluble in water because of the hydrogen bonding between oxygen and hydrogen atoms of water and alcohol molecules. Phenol is also water soluble because of hydrogen bonding. Water-soluble alcohol and water-insoluble phenol react with string bases to form water-soluble salt.

Therefore, this statement is False.

Interpretation Introduction

(d)

Interpretation:

State True or false.

Acid catalyzed dehydration of cyclohexanol gives cyclohexene.

Concept Introduction:

Chemical reaction is the procedure to transform the chemical substance in the new substance. During this procedure sometimes, acid is involved which is the substance which could either accept electron pairs or donate protons in the reactions.

A catalyst is the molecule which is used to speed up the chemical reaction, not being consumed within the procedure. Acids are used as catalysts are needed for an acid catalyzed hydration.

A dehydration reaction is aeration when any organic substance loses the water molecule to form an alkene.

Expert Solution
Check Mark

Answer to Problem 14.29P

False.

Explanation of Solution

Acid-catalyzed dehydration of cyclohexanol gives corresponding alkene. In the presence of sulfuric acid, cyclohexanol gives cyclohexene.

Introduction to General, Organic and Biochemistry, Chapter 14, Problem 14.29P , additional homework tip  4

Therefore, this statement is False.

Interpretation Introduction

(e)

Interpretation:

State True or false.

When the acid-catalyzed dehydration of an alkene can yield isomeric alkenes, the alkene with the greater number of hydrogens in the carbons of the double bond generally predominates.

Concept Introduction:

Chemical reaction is the procedure to transform the chemical substance in the new substance. During this procedure sometimes, acid is involved which is the substance which could either accept electron pairs or donate protons in the reactions.

A catalyst is the molecule which is used to speed up the chemical reaction, not being consumed within the procedure. Acids are used as catalysts are needed for an acid catalyzed hydration.

A dehydration reaction is aeration when any organic substance loses the water molecule to form an alkene.

Expert Solution
Check Mark

Answer to Problem 14.29P

False.

Explanation of Solution

Acid-catalyzed dehydration of an alcohol gives an isomeric alkene. The isomeric alkene, which has a lower number of hydrogen atoms in the double bond, has a grater yield. Hence, when butanol undergoes an acid-catalyzed dehydration, 2-butene is the major product.

Introduction to General, Organic and Biochemistry, Chapter 14, Problem 14.29P , additional homework tip  5

Therefore, this statement is False.

Interpretation Introduction

(f)

Interpretation:

State True or false.

The acid-catalyzed dehydration of 2-butanol gives predominantly 1-butene.

Concept Introduction:

Chemical reaction is the procedure to transform the chemical substance in the new substance. During this procedure sometimes, acid is involved which is the substance which could either accept electron pairs or donate protons in the reactions.

A catalyst is the molecule which is used to speed up the chemical reaction, not being consumed within the procedure. Acids are used as catalysts are needed for an acid catalyzed hydration.

A dehydration reaction is aeration when any organic substance loses the water molecule to form an alkene.

Expert Solution
Check Mark

Answer to Problem 14.29P

False.

Explanation of Solution

An acid catalyzed dehydration of butanol gives predominantly 2-butene. The yield of 1-butene is approximately because in the acid-catalyzed dehydration reaction of an alcohol, the major product has the lower number of hydrogen atoms attached to the carbon atoms with double bonds. Thus, 2-Butene is the major product.

Introduction to General, Organic and Biochemistry, Chapter 14, Problem 14.29P , additional homework tip  6

Therefore, this statement is False.

Interpretation Introduction

(g)

Interpretation:

State True or false.

The oxidation of a primary alcohol gives either an aldehyde or a carboxylic acid depending on experimental conditions.

Concept Introduction:

Chemical reaction is the procedure to transform the chemical substance in the new substance. During this procedure sometimes, acid is involved which is the substance which could either accept electron pairs or donate protons in the reactions.

A catalyst is the molecule which is used to speed up the chemical reaction, not being consumed within the procedure. Acids are used as catalysts are needed for an acid catalyzed hydration.

A dehydration reaction is aeration when any organic substance loses the water molecule to form an alkene.

Expert Solution
Check Mark

Answer to Problem 14.29P

True.

Explanation of Solution

The oxidation of the primary alcohols gives either aldehyde or carboxylic acid, depending on the experimental condition. For illustration, the primary alcohol in an acid catalyzed oxidation gives an aldehyde and further acid catalyzed oxidation gives a corresponding acid.

Introduction to General, Organic and Biochemistry, Chapter 14, Problem 14.29P , additional homework tip  7

Therefore, this statement is True.

Interpretation Introduction

(h)

Interpretation:

State True or false.

The oxidation of a secondary alcohol gives a carboxylic acid.

Concept Introduction:

Chemical reaction is the procedure to transform the chemical substance in the new substance. During this procedure sometimes, acid is involved which is the substance which could either accept electron pairs or donate protons in the reactions.

A catalyst is the molecule which is used to speed up the chemical reaction, not being consumed within the procedure. Acids are used as catalysts are needed for an acid catalyzed hydration.

A dehydration reaction is aeration when any organic substance loses the water molecule to form an alkene.

Expert Solution
Check Mark

Answer to Problem 14.29P

False.

Explanation of Solution

The secondary alcohol in an acid-catalyzed oxidation gives ketone. The oxidation of the secondary alcohol gives ketone in the presence of potassium chromate as an oxidizing agent. It does not produce carboxylic acid because it lacks a hydrogen atom.

Introduction to General, Organic and Biochemistry, Chapter 14, Problem 14.29P , additional homework tip  8

Therefore, this statement is false.

Interpretation Introduction

(i)

Interpretation:

State True or false.

Acetic acid, CH3 COOH, can be prepared from ethylene, CH2 =CH2, by treatment of ethylene with H2 O/H2 SO4, followed by treatment with K2 Cr2 O7 /H2 SO4.

Concept Introduction:

Chemical reaction is the procedure to transform the chemical substance in the new substance. During this procedure sometimes, acid is involved which is the substance which could either accept electron pairs or donate protons in the reactions.

A catalyst is the molecule which is used to speed up the chemical reaction, not being consumed within the procedure. Acids are used as catalysts are needed for an acid catalyzed hydration.

A dehydration reaction is aeration when any organic substance loses the water molecule to form an alkene.

Expert Solution
Check Mark

Answer to Problem 14.29P

True.

Explanation of Solution

Ethylene undergoes acid catalyzed hydration to produce ethanol. This, ethanol, in further treatment with potassium dichromate, undergoes oxidation to form acetic acid. The reaction is.

Introduction to General, Organic and Biochemistry, Chapter 14, Problem 14.29P , additional homework tip  9

Introduction to General, Organic and Biochemistry, Chapter 14, Problem 14.29P , additional homework tip  10

Therefore, this statement is True.

Interpretation Introduction

(j)

Interpretation:

State True or false.

Treatment of propene, CH3 CH=CH2, with H2 O/H2 SO4, followed by treatment with K2 Cr2 O7 /H2 SO4 gives propanoic acid.

Concept Introduction:

Chemical reaction is the procedure to transform the chemical substance in the new substance. During this procedure sometimes, acid is involved which is the substance which could either accept electron pairs or donate protons in the reactions.

A catalyst is the molecule which is used to speed up the chemical reaction, not being consumed within the procedure. Acids are used as catalysts are needed for an acid catalyzed hydration.

A dehydration reaction is aeration when any organic substance loses the water molecule to form an alkene.

Expert Solution
Check Mark

Answer to Problem 14.29P

False.

Explanation of Solution

The hydration of propene with water in the presence of sulfuric acid produces propanol. It is a secondary alcohol. Propanol undergoes oxidation in the presence of potassium chromate and produces propanone. There is no hydrogen atom present in propanone. So, it does not produce propanoic acid in oxidation.

Therefore, this statement is false.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
What are the chemical reactions for the alcohol?  Choices Oxidation of primary alcoholOxidation of secondary alcoholOxidation of tertiary alcoholHydration of alkeneIntramolecular dehydrationIntermolecular dehydrationCombustionHalogenation with hydrogen halidesHalogenation with phosphorus trihalides
Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. ROH, H+ OH OR Aldehyde/ketone Alcohol ROH, H+ Draw the structural formulas for the hemiacetal and the acetal formed between the following compounds: OH OH OR OR • Use the wedge/hash bond tools to indicate stereochemistry where it exists. + H₂O
Terpineol has 5 isomers. Write their structures and describe why chemically (optically) they receive those names. Number the carbons for a better description.

Chapter 14 Solutions

Introduction to General, Organic and Biochemistry

Ch. 14 - 14-11 Which of the alcohols in Problem 14-10 are...Ch. 14 - 14-12 Write the 1UPAC name of each compound. (e)...Ch. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - 14-15 Both alcohols and phenols contain an —OH...Ch. 14 - Prob. 14.16PCh. 14 - 14-17 Explain in terms of noncovalent interactions...Ch. 14 - Prob. 14.18PCh. 14 - Prob. 14.19PCh. 14 - 14-20 Show hydrogen bonding between methanol and...Ch. 14 - 14-21 Show hydrogen bonding between the oxygen of...Ch. 14 - 14-22 Arrange these compounds in order of...Ch. 14 - 14-23 Arrange these compounds in order of...Ch. 14 - 14-24 2-Propanol (isopropyl alcohol) is commonly...Ch. 14 - 14-25 Explain why glycerol is much thicker (more...Ch. 14 - Prob. 14.26PCh. 14 - Prob. 14.27PCh. 14 - 14-28 Give the structural formula of an alkene or...Ch. 14 - Prob. 14.29PCh. 14 - 14-30 Show how to distinguish between cyclohexanol...Ch. 14 - 14-31 Compare the acidity of alcohols and phenols,...Ch. 14 - 14-32 Both 2,6-diisopropylcyclohexanol and the...Ch. 14 - 14-33 Write equations for the reaction of...Ch. 14 - 14-34 Write equations for the reaction of...Ch. 14 - 14-35 Write equations for the reaction of each of...Ch. 14 - 14-36 Show how to convert cyclohexanol to these...Ch. 14 - Prob. 14.37PCh. 14 - Prob. 14.38PCh. 14 - 14-39 Name two important alcohols derived from...Ch. 14 - 14-40 Name two important alcohols derived from...Ch. 14 - Prob. 14.41PCh. 14 - 14-42 Write the common name for each ether. ch3...Ch. 14 - Prob. 14.43PCh. 14 - 14-44 Answer true or false. (a) The functional...Ch. 14 - Prob. 14.45PCh. 14 - Prob. 14.46PCh. 14 - 14-47 Following are structural formulas for...Ch. 14 - 14-48 Explain why methanethiol, CH3SH, has a lower...Ch. 14 - 14-49 Answer true or false. Today, the major...Ch. 14 - Prob. 14.50PCh. 14 - 14-51 (Chemical Connections 14B) When was...Ch. 14 - 14-52 (Chemical Connections 14B) What was Alfred...Ch. 14 - Prob. 14.53PCh. 14 - 14-54 (Chemical Connections 14C) What is the color...Ch. 14 - 14-55 (Chemical Connections 140 The legal...Ch. 14 - 14-56 (Chemical Connections 14D) What does it mean...Ch. 14 - 14-57 (Chemical Connections 14E) What are the...Ch. 14 - Prob. 14.58PCh. 14 - Prob. 14.59PCh. 14 - 14-60 Write a balanced equation for the complete...Ch. 14 - 14-61 Knowing what you do about electronegativity,...Ch. 14 - 14-62 Draw structural formulas and write IUPAC...Ch. 14 - Prob. 14.63PCh. 14 - 14-64 Explain why the boiling point of ethylene...Ch. 14 - Prob. 14.65PCh. 14 - 14-66 1,4-Butanediol, hexane, and 1-pentanol have...Ch. 14 - 14-67 Of the three compounds given in Problem...Ch. 14 - Prob. 14.68PCh. 14 - 14-69 Show how to prepare each compound from...Ch. 14 - 14-70 Show how to prepare each compound from...Ch. 14 - 14-71 The mechanism of the acid-catalyzed...Ch. 14 - Prob. 14.72PCh. 14 - 14-73 Lipoic acid is a growth factor for many...Ch. 14 - 14-74 Following is a structural formula for the...Ch. 14 - Prob. 14.75PCh. 14 - Prob. 14.76PCh. 14 - Prob. 14.77PCh. 14 - 14-78 Consider alkenes A, B, and C. each of which...Ch. 14 - Prob. 14.79P
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
    Introduction to General, Organic and Biochemistry
    Chemistry
    ISBN:9781285869759
    Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning