Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 7, Problem 47P

(a)

Interpretation Introduction

Interpretation: The major product and mechanism needs to be determined in the reaction between 2-bromo-2methylpropane and KCl in DMF.

Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.

(b)

Interpretation Introduction

Interpretation: The major product and mechanism needs to be determined in the reaction between 2-bromo-2methylpropane with KI in DMF.

Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.

(c)

Interpretation Introduction

Interpretation: The major product and mechanism needs to be determined in the reaction between 2-bromo-2methylpropane with KCl in CH3NO2.

Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.

(d)

Interpretation Introduction

Interpretation: The major product and mechanism needs to be determined in the reaction between 2-bromo-2methylpropane with NH3 in CH3CH2OH.

Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.

(e)

Interpretation Introduction

Interpretation: The major product and mechanism needs to be determined in the reaction between 2-bromo-2methylpropane with NaOCH2CH3 in CH3CH2OH.

Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.

(f)

Interpretation Introduction

Interpretation: The major product and mechanism needs to be determined in the reaction between 2-bromo-2methylpropane with CH3CH2OH.

Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.

(g)

Interpretation Introduction

Interpretation: The major product and mechanism needs to be determined in the reaction between 2-bromo-2methylpropane with KOC(CH3)3 in (CH3)3COH.

Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.

(h)

Interpretation Introduction

Interpretation: The major product and mechanism needs to be determined in the reaction between 2-bromo-2methylpropane with (CH3)3P.

Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.

(i)

Interpretation Introduction

Interpretation: The major product and mechanism needs to be determined in the reaction between 2-bromo-2methylpropane with CH3COOH.

Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.

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Br Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:
b) Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. OMe HO + OMe + OH HO + CH; OH
Provide the curved-arrow mechanism to account for the following nucleophilic addition reaction. H20 EN NaOH NH2
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