Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
Question
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Chapter 11.1, Problem 5P

(a)

Interpretation Introduction

Interpretation:

The major product of the given reaction should be given.

Concept introduction:

SN1reaction:

In the nucleophilic substitution reaction, the rate of reaction depends only on one reactant, which is involved in reaction is called unimolecular nucleophilic substitution reaction.

In SN1 reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

The rate determination step is formation of carbocation.

The stability order of carbocation is,

Tertiary > Secondary > Primary

Therefore, 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 of the given reaction should be given.

Concept introduction:

SN1reaction:

In the nucleophilic substitution reaction, the rate of reaction depends only on one reactant, which is involved in reaction is called unimolecular nucleophilic substitution reaction.

In SN1 reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

The rate determination step is formation of carbocation.

The stability order of carbocation is,

Tertiary > Secondary > Primary

Therefore, 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.

(c)

Interpretation Introduction

Interpretation:

The major product of the given reaction should be given.

Concept introduction:

SN1reaction:

In the nucleophilic substitution reaction, the rate of reaction depends only on one reactant, which is involved in reaction is called unimolecular nucleophilic substitution reaction.

In SN1 reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

The rate determination step is formation of carbocation.

The stability order of carbocation is,

Tertiary > Secondary > Primary

Therefore, 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.

(d)

Interpretation Introduction

Interpretation:

The major product of the given reaction should be given.

Concept introduction:

SN1reaction:

In the nucleophilic substitution reaction, the rate of reaction depends only on one reactant, which is involved in reaction is called unimolecular nucleophilic substitution reaction.

In SN1 reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

The rate determination step is formation of carbocation.

The stability order of carbocation is,

Tertiary > Secondary > Primary

Therefore, 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 of the given reaction should be given.

Concept introduction:

SN1reaction:

In the nucleophilic substitution reaction, the rate of reaction depends only on one reactant, which is involved in reaction is called unimolecular nucleophilic substitution reaction.

In SN1 reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

The rate determination step is formation of carbocation.

The stability order of carbocation is,

Tertiary > Secondary > Primary

Therefore, 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.

(f)

Interpretation Introduction

Interpretation:

The major product of the given reaction should be given.

Concept introduction:

SN1reaction:

In the nucleophilic substitution reaction, the rate of reaction depends only on one reactant, which is involved in reaction is called unimolecular nucleophilic substitution reaction.

In SN1 reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

The rate determination step is formation of carbocation.

The stability order of carbocation is,

Tertiary > Secondary > Primary

Therefore, 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.

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Chapter 11 Solutions

Organic Chemistry

Ch. 11.4 - Draw the product of each of the following...Ch. 11.4 - Explain why the following alcohols, when heated...Ch. 11.4 - What stereoisomers are formed in the following...Ch. 11.4 - Prob. 18PCh. 11.4 - What alcohol would you treat with phosphorus...Ch. 11.5 - Prob. 20PCh. 11.6 - Prob. 22PCh. 11.7 - Prob. 24PCh. 11.7 - Would you expect the reactivity of a five-membered...Ch. 11.7 - Prob. 26PCh. 11.7 - What products are obtained from the reaction of...Ch. 11.7 - Prob. 28PCh. 11.7 - Prob. 29PCh. 11.7 - Prob. 30PCh. 11.8 - Prob. 31PCh. 11.8 - Prob. 32PCh. 11.8 - How do the major products obtained from...Ch. 11.8 - Explain why the two arene oxides in Problem 38...Ch. 11.8 - Three arene oxides can be obtained from...Ch. 11.9 - Explain why the half-life (the time it takes for...Ch. 11.10 - Prob. 38PCh. 11.10 - Prob. 39PCh. 11.10 - Prob. 40PCh. 11.10 - Prob. 41PCh. 11.10 - Prob. 42PCh. 11.11 - Using an alkyl halide and a thiol as starting...Ch. 11.11 - The following three nitrogen mustards were studied...Ch. 11.11 - Why is melphalan a good cancer drug?Ch. 11.11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Which compound is more likely to be carcinogenic?Ch. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Write the appropriate reagent over each arrow.Ch. 11 - What alkenes would you expect to be obtained from...Ch. 11 - Prob. 54PCh. 11 - When heated with H2SO4, both...Ch. 11 - What is the major product obtained from the...Ch. 11 - When deuterated phenanthrene oxide undergoes a...Ch. 11 - An unknown alcohol with a molecular formula of...Ch. 11 - Prob. 59PCh. 11 - Prob. 60PCh. 11 - Propose a mechanism for the following reaction:Ch. 11 - What product would be formed if the four-membered...Ch. 11 - Which of the following ethers would be obtained in...Ch. 11 - Using the given starting material any necessary...Ch. 11 - Prob. 65PCh. 11 - When 3-methyl-2-butanol is heated with...Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - How could you synthesize isopropyl propyl ether,...Ch. 11 - When the following seven-membered ring alcohol is...Ch. 11 - Ethylene oxide reacts readily with HO because of...Ch. 11 - Prob. 71PCh. 11 - Propose a mechanism for each of the following...Ch. 11 - Explain why the acid-catalyzed dehydration of an...Ch. 11 - Triethylene glycol is one of the products obtained...Ch. 11 - Prob. 75PCh. 11 - Prob. 76PCh. 11 - When ethyl ether is heated with excess HI for...Ch. 11 - Propose a mechanism for the following reaction:Ch. 11 - Prob. 79PCh. 11 - An ion with a positively charged nitrogen atom in...Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - Prob. 82PCh. 11 - The following reaction takes place several times...Ch. 11 - A vicinal diol has OH groups on adjacent carbons....Ch. 11 - Prob. 85PCh. 11 - Prob. 86PCh. 11 - Two stereoisomers are obtained from the reaction...Ch. 11 - Propose a mechanism for each or the following...Ch. 11 - Triethylenemelamine (TEM) is an antitumor agent....
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