The mechanism for the reaction of tert-butyl alcohol and 1-butanol under the reaction conditions in the experiment needs to be explained. Concept Introduction : Generally, alcohols do not react in simple nucleophilic displacement reactions. If alcohols are attracted directly by nucleophile, hydroxide ion which is a strong base can be displaced easily from the alcohol. But the reaction is not energetically favorable and cannot occur to an extent. To avoid this, the nucleophilic substitution reaction of alcohol takes place in acidic medium. Initially, protonation of alcohol takes place followed by the removal of water molecule. The reaction is energetically stable. This is represented as follows:

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Answer 1

Question

Chapter 20, Problem 1Q

Interpretation Introduction

Interpretation:

The mechanism for the reaction of tert-butyl alcohol and 1-butanol under the reaction conditions in the experiment needs to be explained.

Concept Introduction:

Generally, alcohols do not react in simple nucleophilic displacement reactions. If alcohols are attracted directly by nucleophile, hydroxide ion which is a strong base can be displaced easily from the alcohol. But the reaction is not energetically favorable and cannot occur to an extent.

To avoid this, the nucleophilic substitution reaction of alcohol takes place in acidic medium. Initially, protonation of alcohol takes place followed by the removal of water molecule. The reaction is energetically stable.

This is represented as follows:

Expert Solution & Answer

Explanation of Solution

This reaction examines the capability of two halides to replace an alcohol bynucleophilic substitution.

Initially, suppose the reaction of bromide and chloride ions with tert-butyl alcohol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 2

Now suppose, reaction of bromide and chloride ions with 1-butanol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 3

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Students have asked these similar questions

1-pentanol + NaBr/H2SO4 -> 1-bromopentane Is this substitution reaction reversible? In other words, would one expect to obtain an equilibrium mixture of the alcohol and bromoalkene at the end of the reaction of would one expect this reaction to go to completion? Justify your answer?

Imagine that phenol (“hydroxybenzene”) and nitrobenzene are reacted (in separate beakers) with a hot solution containing both concentrated sulfuric acid and concentrated nitric acid. A) Phenol reacts much more quickly than benzene, and benzene reacts much more quickly that nitrobenzene. Explain this observation, using at least one appropriate reaction coordinate diagram as part of your answer (be sure to label your reaction diagram with appropriate structures). You do not need to include any complete mechanisms, but you may wish to use portions of mechanisms as part of your discussion.

Draw complete mechanisms that explain the resultant product distributions observed for the reactions of tert-butyl alcohol and 1-butanol under the reaction conditions of this experiment.

Answer 2

Question

Chapter 20, Problem 1Q

Interpretation Introduction

Interpretation:

The mechanism for the reaction of tert-butyl alcohol and 1-butanol under the reaction conditions in the experiment needs to be explained.

Concept Introduction:

Generally, alcohols do not react in simple nucleophilic displacement reactions. If alcohols are attracted directly by nucleophile, hydroxide ion which is a strong base can be displaced easily from the alcohol. But the reaction is not energetically favorable and cannot occur to an extent.

To avoid this, the nucleophilic substitution reaction of alcohol takes place in acidic medium. Initially, protonation of alcohol takes place followed by the removal of water molecule. The reaction is energetically stable.

This is represented as follows:

Expert Solution & Answer

Explanation of Solution

This reaction examines the capability of two halides to replace an alcohol bynucleophilic substitution.

Initially, suppose the reaction of bromide and chloride ions with tert-butyl alcohol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 2

Now suppose, reaction of bromide and chloride ions with 1-butanol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 3

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Answer 3

Question

Chapter 20, Problem 1Q

Interpretation Introduction

Interpretation:

The mechanism for the reaction of tert-butyl alcohol and 1-butanol under the reaction conditions in the experiment needs to be explained.

Concept Introduction:

Generally, alcohols do not react in simple nucleophilic displacement reactions. If alcohols are attracted directly by nucleophile, hydroxide ion which is a strong base can be displaced easily from the alcohol. But the reaction is not energetically favorable and cannot occur to an extent.

To avoid this, the nucleophilic substitution reaction of alcohol takes place in acidic medium. Initially, protonation of alcohol takes place followed by the removal of water molecule. The reaction is energetically stable.

This is represented as follows:

Expert Solution & Answer

Explanation of Solution

This reaction examines the capability of two halides to replace an alcohol bynucleophilic substitution.

Initially, suppose the reaction of bromide and chloride ions with tert-butyl alcohol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 2

Now suppose, reaction of bromide and chloride ions with 1-butanol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 3

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Answer 4

Question

Chapter 20, Problem 1Q

Interpretation Introduction

Interpretation:

The mechanism for the reaction of tert-butyl alcohol and 1-butanol under the reaction conditions in the experiment needs to be explained.

Concept Introduction:

Generally, alcohols do not react in simple nucleophilic displacement reactions. If alcohols are attracted directly by nucleophile, hydroxide ion which is a strong base can be displaced easily from the alcohol. But the reaction is not energetically favorable and cannot occur to an extent.

To avoid this, the nucleophilic substitution reaction of alcohol takes place in acidic medium. Initially, protonation of alcohol takes place followed by the removal of water molecule. The reaction is energetically stable.

This is represented as follows:

Expert Solution & Answer

Explanation of Solution

This reaction examines the capability of two halides to replace an alcohol bynucleophilic substitution.

Initially, suppose the reaction of bromide and chloride ions with tert-butyl alcohol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 2

Now suppose, reaction of bromide and chloride ions with 1-butanol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 3

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Chapter 20, Problem 1Q

Interpretation Introduction

Interpretation:

The mechanism for the reaction of tert-butyl alcohol and 1-butanol under the reaction conditions in the experiment needs to be explained.

Concept Introduction:

Generally, alcohols do not react in simple nucleophilic displacement reactions. If alcohols are attracted directly by nucleophile, hydroxide ion which is a strong base can be displaced easily from the alcohol. But the reaction is not energetically favorable and cannot occur to an extent.

To avoid this, the nucleophilic substitution reaction of alcohol takes place in acidic medium. Initially, protonation of alcohol takes place followed by the removal of water molecule. The reaction is energetically stable.

This is represented as follows:

Expert Solution & Answer

Explanation of Solution

This reaction examines the capability of two halides to replace an alcohol bynucleophilic substitution.

Initially, suppose the reaction of bromide and chloride ions with tert-butyl alcohol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 2

Now suppose, reaction of bromide and chloride ions with 1-butanol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 3

Answer 6

Chapter 20, Problem 1Q

Interpretation Introduction

Interpretation:

The mechanism for the reaction of tert-butyl alcohol and 1-butanol under the reaction conditions in the experiment needs to be explained.

Concept Introduction:

Generally, alcohols do not react in simple nucleophilic displacement reactions. If alcohols are attracted directly by nucleophile, hydroxide ion which is a strong base can be displaced easily from the alcohol. But the reaction is not energetically favorable and cannot occur to an extent.

To avoid this, the nucleophilic substitution reaction of alcohol takes place in acidic medium. Initially, protonation of alcohol takes place followed by the removal of water molecule. The reaction is energetically stable.

This is represented as follows:

Expert Solution & Answer

Explanation of Solution

This reaction examines the capability of two halides to replace an alcohol bynucleophilic substitution.

Initially, suppose the reaction of bromide and chloride ions with tert-butyl alcohol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 2

Now suppose, reaction of bromide and chloride ions with 1-butanol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 3

Answer 7

Chapter 20, Problem 1Q

Interpretation Introduction

Interpretation:

The mechanism for the reaction of tert-butyl alcohol and 1-butanol under the reaction conditions in the experiment needs to be explained.

Concept Introduction:

Generally, alcohols do not react in simple nucleophilic displacement reactions. If alcohols are attracted directly by nucleophile, hydroxide ion which is a strong base can be displaced easily from the alcohol. But the reaction is not energetically favorable and cannot occur to an extent.

To avoid this, the nucleophilic substitution reaction of alcohol takes place in acidic medium. Initially, protonation of alcohol takes place followed by the removal of water molecule. The reaction is energetically stable.

This is represented as follows:

Answer 8

Expert Solution & Answer

Explanation of Solution

This reaction examines the capability of two halides to replace an alcohol bynucleophilic substitution.

Initially, suppose the reaction of bromide and chloride ions with tert-butyl alcohol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 2

Now suppose, reaction of bromide and chloride ions with 1-butanol. Below possible reaction will take place:

EBK A SMALL SCALE APPROACH TO ORGANIC L, Chapter 20, Problem 1Q , additional homework tip 3

Answer 9

Expert Solution & Answer

Answer 10

Expert Solution & Answer

Answer 11

Ch. 20 - Prob. 1Q Ch. 20 - Prob. 2Q Ch. 20 - Prob. 3Q Ch. 20 - Prob. 4Q Ch. 20 - Prob. 5Q Ch. 20 - Prob. 6Q Ch. 20 - Prob. 7Q Ch. 20 - Prob. 8Q Ch. 20 - Prob. 9Q

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