Chapter 10, Problem 58P

(a)

Interpretation Introduction

Interpretation:

Synthesis of (S)-1-deutrino-1-propanol should be explained.

Concept introduction:

${\text{S}}_{\text{N}}\text{2}$ reaction:

In the nucleophilic substitution reaction, the rate of reaction depends on reactant as well as nucleophile, which are involved in reaction is called bimolecular nucleophilic substitution reaction.

In ${\text{S}}_{\text{N}}2$ reaction, the reliving of leaving group from reactant and nucleophilic of attack takes place simultaneously.

Reactant and nucleophile are present at the rate determination step.

The order of species involving in ${\text{S}}_{\text{N}}2$ reaction is,

Tertiary < Secondary < Primary

Example:

Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again ${\text{S}}_{\text{N}}\text{2}$ type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

(b)

Interpretation Introduction

Interpretation:

(S)-1-deutrino-1-methoxypropane should be synthesized.

Concept introduction:

${\text{S}}_{\text{N}}\text{2}$ reaction:

In the nucleophilic substitution reaction, the rate of reaction depends on reactant as well as nucleophile, which are involved in reaction is called bimolecular nucleophilic substitution reaction.

In ${\text{S}}_{\text{N}}2$ reaction, the reliving of leaving group from reactant and nucleophilic of attack takes place simultaneously.

Reactant and nucleophile are present at the rate determination step.

The order of species involving in ${\text{S}}_{\text{N}}2$ reaction is,

Tertiary < Secondary < Primary

Example:

Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again ${\text{S}}_{\text{N}}\text{2}$ type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

(c)

Interpretation Introduction

Interpretation:

(R)-1-deutrino-1-methoxypropane should be synthesized.

Concept introduction:

${\text{S}}_{\text{N}}\text{2}$ reaction:

In the nucleophilic substitution reaction, the rate of reaction depends on reactant as well as nucleophile, which are involved in reaction is called bimolecular nucleophilic substitution reaction.

In ${\text{S}}_{\text{N}}2$ reaction, the reliving of leaving group from reactant and nucleophilic of attack takes place simultaneously.

Reactant and nucleophile are present at the rate determination step.

The order of species involving in ${\text{S}}_{\text{N}}2$ reaction is,

Tertiary < Secondary < Primary

Example:

Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again ${\text{S}}_{\text{N}}\text{2}$ type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,