Chapter 6, Problem 45P

(a)

Interpretation Introduction

Interpretation:The product of the reaction of $1\text{-bromopropane}$ with water as nucleophile should be listed if the reaction is possible.

Concept introduction: Bimolecular substitution or ${\text{S}}_{\text{N}}2$ proceeds via the single-step mechanism. Thus it is well known as the concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general ${\text{S}}_{\text{N}}2$ reaction mechanistic pathway is illustrated below:

  

${\text{S}}_{\text{N}}2$ pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to an inverted S stereoisomer and vice versa. Thus the outcome is the rear side displacement of the leaving group.

A nucleophile is an electron-rich species with high electron density that can be donated to another electron-deficient species called electrophile. For effective ${\text{S}}_{\text{N}}2$ reaction nucleophilic should be strong enough but not hindered or bulky.

(b)

Interpretation Introduction

Interpretation: The product of the reaction of $1\text{-bromopropane}$ with sulphuric acid as nucleophile should be listed if the reaction is possible.

Concept introduction:Bimolecular substitution or ${\text{S}}_{\text{N}}2$ proceeds via the single-step mechanism. Thus it is well known as the concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general ${\text{S}}_{\text{N}}2$ reaction mechanistic pathway is illustrated below:

  

${\text{S}}_{\text{N}}2$ pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to an inverted S stereoisomer and vice versa. Thus the outcome is the rear side displacement of the leaving group.

A nucleophile is an electron-rich species with high electron density that can be donated to another electron-deficient species called electrophile. For effective ${\text{S}}_{\text{N}}2$ reaction nucleophilic should be strong enough but not hindered or bulky.

(c)

Interpretation Introduction

Interpretation: The product of the reaction of $1\text{-bromopropane}$ with potassium hydroxide as nucleophile should be listed if the reaction is possible.

Concept introduction:Bimolecular substitution or ${\text{S}}_{\text{N}}2$ proceeds via the single-step mechanism. Thus it is well known as the concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general ${\text{S}}_{\text{N}}2$ reaction mechanistic pathway is illustrated below:

  

${\text{S}}_{\text{N}}2$ pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to an inverted S stereoisomer and vice versa. Thus the outcome is the rear side displacement of the leaving group.

A nucleophile is an electron-rich species with high electron density that can be donated to another electron-deficient species called electrophile. For effective ${\text{S}}_{\text{N}}2$ reaction nucleophilic should be strong enough but not hindered or bulky.

(d)

Interpretation Introduction

Interpretation: The product of the reaction of $1\text{-bromopropane}$ with cesium iodide as nucleophile should be listed if the reaction is possible.

Concept introduction:Bimolecular substitution or ${\text{S}}_{\text{N}}2$ proceeds via the single-step mechanism. Thus it is well known as the concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general ${\text{S}}_{\text{N}}2$ reaction mechanistic pathway is illustrated below:

  

${\text{S}}_{\text{N}}2$ pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to an inverted S stereoisomer and vice versa. Thus the outcome is the rear side displacement of the leaving group.

A nucleophile is an electron-rich species with high electron density that can be donated to another electron-deficient species called electrophile. For effective ${\text{S}}_{\text{N}}2$ reaction nucleophilic should be strong enough but not hindered or bulky.

(e)

Interpretation Introduction

Interpretation: The product of the reaction of $1\text{-bromopropane}$ with sodium cyanide as nucleophile should be listed if the reaction is possible.

Concept introduction:Bimolecular substitution or ${\text{S}}_{\text{N}}2$ proceeds via the single-step mechanism. Thus it is well known as the concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general ${\text{S}}_{\text{N}}2$ reaction mechanistic pathway is illustrated below:

  

${\text{S}}_{\text{N}}2$ pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to an inverted S stereoisomer and vice versa. Thus the outcome is the rear side displacement of the leaving group.

A nucleophile is an electron-rich species with high electron density that can be donated to another electron-deficient species called electrophile. For effective ${\text{S}}_{\text{N}}2$ reaction nucleophilic should be strong enough but not hindered or bulky.

(f)

Interpretation Introduction

Interpretation: The product of the reaction of $1\text{-bromopropane}$ with $\text{HCl}$ as nucleophile should be listed if the reaction is possible.

Concept introduction:Bimolecular substitution or ${\text{S}}_{\text{N}}2$ proceeds via the single-step mechanism. Thus it is well known as the concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general ${\text{S}}_{\text{N}}2$ reaction mechanistic pathway is illustrated below:

  

${\text{S}}_{\text{N}}2$ pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to an inverted S stereoisomer and vice versa. Thus the outcome is the rear side displacement of the leaving group.

A nucleophile is an electron-rich species with high electron density that can be donated to another electron-deficient species called electrophile. For effective ${\text{S}}_{\text{N}}2$ reaction nucleophilic should be strong enough but not hindered or bulky.

(g)

Interpretation Introduction

Interpretation: The product of the reaction of $1\text{-bromopropane}$ with dimethyl sulfide as nucleophile should be listed if the reaction is possible.

Concept introduction:Bimolecular substitution or ${\text{S}}_{\text{N}}2$ proceeds via the single-step mechanism. Thus it is well known as the concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general ${\text{S}}_{\text{N}}2$ reaction mechanistic pathway is illustrated below:

  

${\text{S}}_{\text{N}}2$ pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to an inverted S stereoisomer and vice versa. Thus the outcome is the rear side displacement of the leaving group.

A nucleophile is an electron-rich species with high electron density that can be donated to another electron-deficient species called electrophile. For effective ${\text{S}}_{\text{N}}2$ reaction nucleophilic should be strong enough but not hindered or bulky.

(h)

Interpretation Introduction

Interpretation: The product of the reaction of $1\text{-bromopropane}$ with ammonia as nucleophile should be listed if the reaction is possible.

Concept introduction:Bimolecular substitution or ${\text{S}}_{\text{N}}2$ proceeds via the single-step mechanism. Thus it is well known as the concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general ${\text{S}}_{\text{N}}2$ reaction mechanistic pathway is illustrated below:

  

${\text{S}}_{\text{N}}2$ pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to an inverted S stereoisomer and vice versa. Thus the outcome is the rear side displacement of the leaving group.

A nucleophile is an electron-rich species with high electron density that can be donated to another electron-deficient species called electrophile. For effective ${\text{S}}_{\text{N}}2$ reaction nucleophilic should be strong enough but not hindered or bulky.

(i)

Interpretation Introduction

Interpretation: The product of the reaction of $1\text{-bromopropane}$ with ${\text{Cl}}_{\text{2}}$ as nucleophile should be listed if the reaction is possible.

Concept introduction:Bimolecular substitution or ${\text{S}}_{\text{N}}2$ proceeds via the single-step mechanism. Thus it is well known as the concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general ${\text{S}}_{\text{N}}2$ reaction mechanistic pathway is illustrated below:

  

${\text{S}}_{\text{N}}2$ pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to an inverted S stereoisomer and vice versa. Thus the outcome is the rear side displacement of the leaving group.

A nucleophile is an electron-rich species with high electron density that can be donated to another electron-deficient species called electrophile. For effective ${\text{S}}_{\text{N}}2$ reaction nucleophilic should be strong enough but not hindered or bulky.

(j)

Interpretation Introduction

Interpretation: The product of the reaction of $1\text{-bromopropane}$ with potassium fluoride as nucleophile should be listed if the reaction is possible.

Concept introduction:Bimolecular substitution or ${\text{S}}_{\text{N}}2$ proceeds via the single-step mechanism. Thus it is well known as the concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general ${\text{S}}_{\text{N}}2$ reaction mechanistic pathway is illustrated below:

  

${\text{S}}_{\text{N}}2$ pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to an inverted S stereoisomer and vice versa. Thus the outcome is the rear side displacement of the leaving group.

A nucleophile is an electron-rich species with high electron density that can be donated to another electron-deficient species called electrophile. For effective ${\text{S}}_{\text{N}}2$ reaction nucleophilic should be strong enough but not hindered or bulky.