Essential Organic Chemistry (3rd Edition)
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 9.4, Problem 10P

(a)

Interpretation Introduction

Interpretation:

The major elimination product obtained when the given alcohol is heated in the presence of sulphuric acid has to be has to be drawn.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction of alcohol with strong acid like sulfuric acid is known as dehydration reaction.

Essential Organic Chemistry (3rd Edition), Chapter 9.4, Problem 10P , additional homework tip  1

E1 dehydration reaction of secondary and tertiary alcohols:

The alcohols react with acids like hydrochloric acid or hydrobromic which yield the corresponding stable carbocation intermediate. The elimination of hydrogen from the beta carbon results in the alkene product. Thus the removal of water molecule occurs in the dehydration process and the major product of the acid-catalysed dehydration reaction will be the more substituted product.

Carbocation: It is carbon ion that bears a positive charge on it.

The increasing stability order of carbocation is as follows,

Primary carbocation < secondary carbocation < tertiary carbocation

(b)

Interpretation Introduction

Interpretation:

The major elimination product obtained when the given alcohol is heated in the presence of sulphuric acid has to be has to be drawn.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction of alcohol with strong acid like sulfuric acid is known as dehydration reaction.

Essential Organic Chemistry (3rd Edition), Chapter 9.4, Problem 10P , additional homework tip  2

E1 dehydration reaction of secondary and tertiary alcohols:

The alcohols react with acids like hydrochloric acid or hydrobromic which yield the corresponding stable carbocation intermediate. The elimination of hydrogen from the beta carbon results in the alkene product. Thus the removal of water molecule occurs in the dehydration process and the major product of the acid-catalysed dehydration reaction will be the more substituted product.

Carbocation: It is carbon ion that bears a positive charge on it.

The increasing stability order of carbocation is as follows,

Primary carbocation < secondary carbocation < tertiary carbocation

(c)

Interpretation Introduction

Interpretation:

The major elimination product obtained when the given alcohol is heated in the presence of sulphuric acid has to be has to be drawn.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction of alcohol with strong acid like sulfuric acid is known as dehydration reaction.

Essential Organic Chemistry (3rd Edition), Chapter 9.4, Problem 10P , additional homework tip  3

E2 dehydration of primary alcohols:

Due to the unstability of the primary carbocation, the dehydration of primary alcohol is an E2 reaction.

In the E2 reaction, protonation of the most basic atom occurs and then base will remove a proton from the beta carbon.

(d)

Interpretation Introduction

Interpretation:

The major elimination product obtained when the given alcohol is heated in the presence of sulphuric acid has to be has to be drawn.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction of alcohol with strong acid like sulfuric acid is known as dehydration reaction.

Essential Organic Chemistry (3rd Edition), Chapter 9.4, Problem 10P , additional homework tip  4

E1 dehydration reaction of secondary and tertiary alcohols:

The alcohols react with acids like hydrochloric acid or hydrobromic which yield the corresponding stable carbocation intermediate. The elimination of hydrogen from the beta carbon results in the alkene product. Thus the removal of water molecule occurs in the dehydration process and the major product of the acid-catalysed dehydration reaction will be the more substituted product.

Carbocation: It is carbon ion that bears a positive charge on it.

The increasing stability order of carbocation is as follows,

Primary carbocation < secondary carbocation < tertiary carbocation

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Chapter 9 Solutions

Essential Organic Chemistry (3rd Edition)

Ch. 9.4 - Prob. 13PCh. 9.5 - What product will be obtained from the reaction of...Ch. 9.5 - Prob. 15PCh. 9.6 - a. What is each ethers systematic name? 1....Ch. 9.8 - Draw the structure of the following: a....Ch. 9.8 - Prob. 20PCh. 9.8 - Would you expect the reactivity of a five-membered...Ch. 9.9 - Explain why the two arene oxides in Problem 22...Ch. 9.9 - Which compound is more likely to be...Ch. 9.11 - The following three nitrogen mustards were studied...Ch. 9 - What are the common and systematic names of the...Ch. 9 - Prob. 28PCh. 9 - Prob. 29PCh. 9 - Prob. 30PCh. 9 - Prob. 31PCh. 9 - What is the major product obtained from the...Ch. 9 - Draw structures for the following: a....Ch. 9 - Prob. 34PCh. 9 - Prob. 35PCh. 9 - Prob. 36PCh. 9 - Prob. 37PCh. 9 - Ethylene oxide reacts readily with HO.because of...Ch. 9 - Propose a mechanism for each of the following...Ch. 9 - Which of the following ethers would be obtained in...Ch. 9 - Show how each of the following syntheses could be...Ch. 9 - Prob. 42PCh. 9 - Prob. 43PCh. 9 - Prob. 44PCh. 9 - Propose a mechanism for each of the following...Ch. 9 - a. Propose a mechanism for the following reaction:...Ch. 9 - Three arene oxides can be obtained from...Ch. 9 - Prob. 48PCh. 9 - The following reaction takes place several times...Ch. 9 - Show how each of the following compounds could be...Ch. 9 - Propose a mechanism for the following reaction:Ch. 9 - Propose a mechanism for the following reaction:Ch. 9 - What alkenes would you expect to be obtained from...Ch. 9 - Triethylenemelamine (TEM) is an antitumor agent....Ch. 9 - When a diol that has OH groups on adjacent carbons...Ch. 9 - What product is obtained when...Ch. 9 - Prob. 58P
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