Chapter 9, Problem 9.45P

Draw a structural formula for the major organic product of each reaction and specify the most likely mechanism by which each is formed.

(g) ${\text{CH}}_3{\text{CH}}_2{\text{O}}^{-}{\text{Na}}^{+}{\text{+ CH}}_2={\text{CHCH}}_2\text{Cl}\underset{\text{ethanol}}{\to }$

Interpretation Introduction

Interpretation:

The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.

Concept Introduction:

${\text{S}}_{\text{N}}\text{1}$ reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as ${\text{S}}_{\text{N}}1$ unimolecular nucleophilic substitution.

The first step of ${\text{S}}_{\text{N}}1$ is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]$

Nucleophile attacks the both front and back side of carbocation in ${\text{S}}_{\text{N}}1$ reaction therefore result of this racemic product where formed.

Order of the substrate that favored in ${\text{S}}_{\text{N}}1$ reaction is $3°>2°>1°$

${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.

$\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$

Elimination:

An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.

In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.

The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.

E1 elimination fallows saytzeff rule (more substituted alkene is formed).

Explanation of Solution

Methanol is a polar protic solvent, moderate nucleophile and alkyl halide forms allyl cation, it is stable cation.

Hence, the given reaction is takes place in both ${\text{S}}_{\text{N}}1$ and E1 mechanisms and the products are,

Interpretation Introduction

Interpretation:

The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.

Concept Introduction:

${\text{S}}_{\text{N}}\text{1}$ reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as ${\text{S}}_{\text{N}}1$ unimolecular nucleophilic substitution.

The first step of ${\text{S}}_{\text{N}}1$ is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]$

Nucleophile attacks the both front and back side of carbocation in ${\text{S}}_{\text{N}}1$ reaction therefore result of this racemic product where formed.

Order of the substrate that favored in ${\text{S}}_{\text{N}}1$ reaction is $3°>2°>1°$

${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.

$\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$

Elimination:

An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.

In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.

The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.

E1 elimination fallows saytzeff rule (more substituted alkene is formed).

Explanation of Solution

The given alkyl halide is a tertiary halide, sodium hydroxide is strong base and water is polar solvent hence, the given reaction is takes place in $\text{E2}$ mechanism,

Interpretation Introduction

Interpretation:

The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.

Concept Introduction:

${\text{S}}_{\text{N}}\text{1}$ reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as ${\text{S}}_{\text{N}}1$ unimolecular nucleophilic substitution.

The first step of ${\text{S}}_{\text{N}}1$ is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]$

Nucleophile attacks the both front and back side of carbocation in ${\text{S}}_{\text{N}}1$ reaction therefore result of this racemic product where formed.

Order of the substrate that favored in ${\text{S}}_{\text{N}}1$ reaction is $3°>2°>1°$

${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.

$\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$

Elimination:

An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.

In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.

The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.

E1 elimination fallows saytzeff rule (more substituted alkene is formed).

Explanation of Solution

The given alkyl halide is a secondary halide, sodium acetate is strong neucleophile and DMSO is polar aprotic solvent hence, the given reaction is takes place in ${\text{S}}_{\text{N}}\text{2}$ mechanism,

Interpretation Introduction

Interpretation:

The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.

Concept Introduction:

${\text{S}}_{\text{N}}\text{1}$ reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as ${\text{S}}_{\text{N}}1$ unimolecular nucleophilic substitution.

The first step of ${\text{S}}_{\text{N}}1$ is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]$

Nucleophile attacks the both front and back side of carbocation in ${\text{S}}_{\text{N}}1$ reaction therefore result of this racemic product where formed.

Order of the substrate that favored in ${\text{S}}_{\text{N}}1$ reaction is $3°>2°>1°$

${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.

$\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$

Elimination:

An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.

In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.

The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.

E1 elimination fallows saytzeff rule (more substituted alkene is formed).

Explanation of Solution

The given alkyl halide is a secondary halide, sodium methoxide is strong base and methonal is polar solvent hence, the given reaction is takes place in $\text{E2}$ mechanism,

Interpretation Introduction

Interpretation:

The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.

Concept Introduction:

${\text{S}}_{\text{N}}\text{1}$ reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as ${\text{S}}_{\text{N}}1$ unimolecular nucleophilic substitution.

The first step of ${\text{S}}_{\text{N}}1$ is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]$

Nucleophile attacks the both front and back side of carbocation in ${\text{S}}_{\text{N}}1$ reaction therefore result of this racemic product where formed.

Order of the substrate that favored in ${\text{S}}_{\text{N}}1$ reaction is $3°>2°>1°$

${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.

$\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$

Elimination:

An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.

In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.

The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.

E1 elimination fallows saytzeff rule (more substituted alkene is formed).

Explanation of Solution

The given alkyl halide is a secondary halide, iodide is strong nucleophile and acetone is polar solvent hence, the given reaction is takes place in ${\text{S}}_{\text{N}}\text{2}$ mechanism,

Interpretation Introduction

Interpretation:

The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.

Concept Introduction:

${\text{S}}_{\text{N}}\text{1}$ reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as ${\text{S}}_{\text{N}}1$ unimolecular nucleophilic substitution.

The first step of ${\text{S}}_{\text{N}}1$ is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]$

Nucleophile attacks the both front and back side of carbocation in ${\text{S}}_{\text{N}}1$ reaction therefore result of this racemic product where formed.

Order of the substrate that favored in ${\text{S}}_{\text{N}}1$ reaction is $3°>2°>1°$

${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.

$\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$

Elimination:

An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.

In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.

The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.

E1 elimination fallows saytzeff rule (more substituted alkene is formed).

Explanation of Solution

The given alkyl halide is a secondary halide, formic acid  is moderate nucleophile and is polar solvent hence, the given reaction is takes place in both ${\text{S}}_{\text{N}}\text{1}$ and E1 mechanism,

Interpretation Introduction

Interpretation:

The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.

Concept Introduction:

${\text{S}}_{\text{N}}\text{1}$ reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as ${\text{S}}_{\text{N}}1$ unimolecular nucleophilic substitution.

The first step of ${\text{S}}_{\text{N}}1$ is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  $\text{Rate}\text{= k}\left[\text{alkylhalide}\right]$

Nucleophile attacks the both front and back side of carbocation in ${\text{S}}_{\text{N}}1$ reaction therefore result of this racemic product where formed.

Order of the substrate that favored in ${\text{S}}_{\text{N}}1$ reaction is $3°>2°>1°$

${\text{S}}_{\text{N}}2$ reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.

$\text{Rate}\text{= k}\left[\text{alkylhalide}\right]\text{×}\left[\text{nucleophile}\right]$

Elimination:

An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.

In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.

The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.

E1 elimination fallows saytzeff rule (more substituted alkene is formed).

Explanation of Solution

The given alkyl halide is a allyl  halide, sodium ethoxide  is strong base and ethanol  is polar solvent hence, the given reaction is takes place in ${\text{S}}_{\text{N}}\text{2}$ mechanism,