Among the given reactions, the reaction takes place more rapidly has to be identified. Concept Introduction: The S N 2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S N 2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration. The configuration of the product is inverted relative to the configuration of the reactant. Steric effect is the effect due to the groups occupies a certain volume of space. Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

Question

Given a 1,3-dicarbonyl compound, state the (condensed) formula of the compound obtaineda) if I add hydroxylamine (NH2OH) to give an isooxazole.b) if I add thiosemicarbazide (NH2-CO-NH-NH2) to give an isothiazole.

Answer 1

Question

Chapter 9, Problem 48P

(a)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

(b)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

(c)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

(d)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism.

The stronger base is always a better nucleophile in an aprotic solvent.

Protic solvent are polar solvent molecules which have hydrogen bonded to oxygen to nitrogen.

The stronger base is always a better nucleophile in an aprotic solvent.

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Given a 1,3-dicarbonyl compound, state the (condensed) formula of the compound obtaineda) if I add hydroxylamine (NH2OH) to give an isooxazole.b) if I add thiosemicarbazide (NH2-CO-NH-NH2) to give an isothiazole.

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Answer 2

Question

Chapter 9, Problem 48P

(a)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

(b)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

(c)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

(d)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism.

The stronger base is always a better nucleophile in an aprotic solvent.

Protic solvent are polar solvent molecules which have hydrogen bonded to oxygen to nitrogen.

The stronger base is always a better nucleophile in an aprotic solvent.

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Answer 3

Question

Chapter 9, Problem 48P

(a)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

(b)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

(c)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

(d)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism.

The stronger base is always a better nucleophile in an aprotic solvent.

Protic solvent are polar solvent molecules which have hydrogen bonded to oxygen to nitrogen.

The stronger base is always a better nucleophile in an aprotic solvent.

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Answer 4

Question

Chapter 9, Problem 48P

(a)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

(b)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

(c)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

(d)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism.

The stronger base is always a better nucleophile in an aprotic solvent.

Protic solvent are polar solvent molecules which have hydrogen bonded to oxygen to nitrogen.

The stronger base is always a better nucleophile in an aprotic solvent.

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Answer 5

Chapter 9, Problem 48P

(a)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

(b)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

(c)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

(d)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism.

The stronger base is always a better nucleophile in an aprotic solvent.

Protic solvent are polar solvent molecules which have hydrogen bonded to oxygen to nitrogen.

The stronger base is always a better nucleophile in an aprotic solvent.

Answer 6

Chapter 9, Problem 48P

(a)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

Answer 7

Chapter 9, Problem 48P

(a)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

Answer 8

(b)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

Answer 9

(b)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

Answer 10

(c)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

Answer 11

(c)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

Answer 12

(d)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism.

The stronger base is always a better nucleophile in an aprotic solvent.

Protic solvent are polar solvent molecules which have hydrogen bonded to oxygen to nitrogen.

The stronger base is always a better nucleophile in an aprotic solvent.

Answer 13

(d)

Interpretation Introduction

Interpretation:

Among the given reactions, the reaction takes place more rapidly has to be identified.

Concept Introduction:

The S_N2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. S_N2 is a kind of nucleophilic substitution reaction mechanism.

The stronger base is always a better nucleophile in an aprotic solvent.

Protic solvent are polar solvent molecules which have hydrogen bonded to oxygen to nitrogen.

The stronger base is always a better nucleophile in an aprotic solvent.

Answer 14

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Answer 15

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Answer 25

Ch. 9.1 - Prob. 3P Ch. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.2 - Prob. 8P Ch. 9.2 - Prob. 9P Ch. 9.2 - Prob. 10P Ch. 9.2 - Prob. 11P Ch. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 14P Ch. 9.2 - Prob. 16P

Solution Summary: The author explains that the S N 2 reaction is a kind of nucleophilic substitution reaction mechanism.

Chapter 9 Solutions