Chapter 11.14, Problem 11.38P

(a)

Interpretation Introduction

Interpretation:

The synthesis of given compound with the use of cyclopentanol, alcohols that have no more than four carbon atoms as starting materials and any common reagents and solvents is to be stated.

Concept introduction:

The sulphuric acid catalyzed dehydration reaction is used to convert alcohols into respective alkenes. The reaction of an alkene with $m\text{-CPBA}$ followed by hydrolysis leads to the formation of diol with inversion of configuration.

(b)

Interpretation Introduction

Interpretation:

The synthesis of given compound with the use of cyclopentanol, alcohols that have no more than four carbon atoms as starting materials and any common reagents and solvents is to be stated.

Concept introduction:

The reaction of secondary alcohols with PCC leads to the formation of ketone. The Wittig reaction of ketone through phosphorous ylides leads to the addition of double bond (alkene). The reaction of an alkene with halogen acids leads to the addition of halogen group.

(c)

Interpretation Introduction

Interpretation:

The synthesis of given compound with the use of cyclopentanol, alcohols that have no more than four carbon atoms as starting materials and any common reagents and solvents is to be stated.

Concept introduction:

The reaction of secondary alcohols with PCC leads to the formation of ketone. The Wittig reaction of ketone through phosphorous ylides leads to the addition of double bond (alkene). The reaction of an alkene with $m\text{-CPBA}$ in the presence of $\text{DCM}$ leads to the formation of epoxide.

(d)

Interpretation Introduction

Interpretation:

The synthesis of given compound with the use of cyclopentanol, alcohols that have no more than four carbon atoms as starting materials and any common reagents and solvents is to be stated.

Concept introduction:

The reaction of secondary alcohols with $\text{PCC}$ leads to the formation of ketone.

The conversion of an alcohol into an alkyl bromide is done by ${\text{PBr}}_3$. The formation of Grignard reagent is done by reaction of an alkyl halide with $\text{Mg}/\text{THF}$.

The reaction of Grignard reagent with ketone yields an alcohol. The reaction of an alcohol with $\text{TsCl}/\text{Pyridine}$ leads to the addition of tosyl group (tosylate ester). The reaction of tosylate ester with sodium methoxide yields ether.

(e)

Interpretation Introduction

Interpretation:

The synthesis of given compound with the use of cyclopentanol, alcohols that have no more than four carbon atoms as starting materials and any common reagents and solvents is to be stated.

Concept introduction:

The conversion of an alcohol into an alkyl bromide is done by ${\text{PBr}}_3$. The conversion of bromine into cyano group is done by $\text{NaCN}\text{or}\text{CuCN}/\text{Pyridine}$. The hydrolysis (acidic or basic of) cyano group leads to the formation of carboxylic acid. The conversion of carboxylic acid into acyl chloride is done by ${\text{SOCl}}_{\text{2}}\text{or}{\text{PCl}}_{\text{3}}$. The reduction of acyl chloride into ${\text{R-CH}}_{\text{2}}\text{-OH}$ is done by ${\text{LiAlH}}_{\text{4}}/\text{ether}$ followed by hydrolysis. The reaction of primary alcohols with PCC leads to the formation of an aldehyde. The reaction of Grignard reagent with an aldehyde yields an alcohol.

The reaction of an alcohol with $\text{TsCl}/\text{Pyridine}$ leads to the addition of tosyl group (tosylate ester). The reaction of tosylate ester with sodium ethoxide yields ether.

(f)

Interpretation Introduction

Interpretation:

The synthesis of given compound with the use of cyclopentanol, alcohols that have no more than four carbon atoms as starting materials and any common reagents and solvents is to be stated.

Concept introduction:

The reaction of secondary alcohols with PCC leads to the formation of ketone. The conversion of an alcohol into an alkyl iodide is done by $\text{HI}$. The conversion of alkyl halide into alkyl nitrile is done by $\text{KCN}$. The conversion of bromine into cyano group is done by $\text{KCN}$. The hydrolysis (acidic or basic ) of cyano group leads to the formation of carboxylic acid. The conversion of carboxylic acid into acyl chloride is done by ${\text{SOCl}}_{\text{2}}\text{or}{\text{PCl}}_{\text{3}}$. The reduction of acyl chloride into ${\text{R-CH}}_{\text{2}}\text{-OH}$ is done by ${\text{LiAlH}}_{\text{4}}/\text{ether}$ followed by hydrolysis. The reaction of primary alcohols with PCC leads to the formation of an aldehyde. The reaction of Grignard reagent with an aldehyde yields an alcohol. The conversion of an alcohol into an alkyl bromide is done by ${\text{PBr}}_3$. The reaction of an alcohol with $\text{TsCl}/\text{Pyridine}$ leads to the addition of tosyl group (tosylate ester). The reaction of tosylate ester with sodium methoxide yields ether.