EBK ESSENTIAL ORGANIC CHEMISTRY
EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 9780100659469
Author: Bruice
Publisher: YUZU
Question
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Chapter 9, Problem 31P

(a)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

SN1 reaction:

The reaction of alcohols with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes SN1 substitution reaction.

(b)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

SN2 reaction:

The alcohols are reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding substitution product. Primary alcohol undergoes SN2 substitution reaction than secondary alcohol than tertiary alcohol because SN2 reaction is simultaneous reaction.

(c)

Interpretation Introduction

Interpretation:

The major product has to be identified.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction, the alcohol is treated with strong acid like sulfuric acid.

EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 9, Problem 31P , additional homework tip  1

The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary and primary.

(d)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

SN1 reaction:

The alcohols is reaction with acids like hydrochloric acid or hydrobromic which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergoes SN1 substitution reaction.

(e)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 9, Problem 31P , additional homework tip  2

In the presence of acid catalyst, this reaction takes place through partial SN1 and partial SN2 pathway. Epoxides are reactive, Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 9, Problem 31P , additional homework tip  3

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product.

(f)

Interpretation Introduction

Interpretation:

The major product should be identified.

Concept introduction:

EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 9, Problem 31P , additional homework tip  4

In the presence of acid catalyst, this reaction takes place through partial SN1 and partial SN2 pathway. It is not a pure SN1 reaction because a carbocation is not formed fully and not a pure SN2 reaction because the leaving group begins to depart before the compound is attacked by the nucleophile. Epoxides are reactive; Epoxides get protonated followed by alcohol attacks to the stable carbocation and form the product.

EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 9, Problem 31P , additional homework tip  5

Epoxides are reactive, methoxide ion attacks the Epoxides in a less sterically hindered position which forms the alkoxide ion, and then it gets proton from alcohol which form the product. When a nucleophile attacks an unprotonated epoxide, the reaction is a pure SN2 reaction.

Note: Under acidic conditions, the nucleophile preferentially attacks the more substuituted ring carbon. Under Basic conditions, the nucleophile preferentially attacks the less substuituted ring carbon.

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Chapter 9 Solutions

EBK ESSENTIAL ORGANIC CHEMISTRY

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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