Chapter 22, Problem 22.75P

Devise a synthesis of each labeled compound using ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only sources of labeled starting materials. You may use any other unlabeled organic compounds and inorganic reagents.

a. b. c. d.

Interpretation Introduction

(a)

Interpretation:

The synthesis of given compound by the use of ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only source of labeled staring materials is to be stated.

Concept introduction:

The replacement or substitution of one functional group with another functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons is known as a nucleophile. In nucleophilc acyl substitution reaction, a nucleophile takes the position of a leaving group.

Answer to Problem 22.75P

The synthesis of given compound by the use of ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only source of labeled staring materials is,

Explanation of Solution

An ester is formed by the reaction of carboxylic acid with alcohol. This reaction is known as Fischer Esterification. During this reaction, bond formation between carbon and oxygen takes place and water removes as a byproduct. In the synthesis of given compound, acetic acid is used as the source of unlabeled carbon atom and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the source of labeled carbon atom as shown in Figure 1.

Figure 1

Conclusion

The synthesis of given compound by the use of ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only source of labeled staring materials is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The synthesis of given compound by the use of ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only source of labeled staring materials is to be stated.

Concept introduction:

The replacement or substitution of one functional group with another functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons is known as a nucleophile. In nucleophilc acyl substitution reaction, a nucleophile takes the position of a leaving group.

Answer to Problem 22.75P

The synthesis of given compound by the use of ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only source of labeled staring materials is,

Explanation of Solution

An ester is formed by the reaction of carboxylic acid with alcohol. This reaction is known as Fischer Esterification. During this reaction, bond formation between carbon and oxygen takes place and water removes as a byproduct. In the synthesis of given compound, ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ is first converted to ${\text{CH}}_{\text{3}}{}^{\text{13}}\text{COOH}$ in the presence of ${\text{Na}}_{\text{2}}{\text{Cr}}_2{\text{O}}_7$. Ethanol on reaction with ${\text{CH}}_{\text{3}}{}^{\text{13}}\text{COOH}$ leads to the formation of desired compound as shown in Figure 2.

Figure 2

Conclusion

The synthesis of given compound by the use of ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only source of labeled staring materials is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The synthesis of given compound by the use of ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only source of labeled staring materials is to be stated.

Concept introduction:

The replacement or substitution of one functional group with another functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons is known as a nucleophile. In nucleophilc acyl substitution reaction, a nucleophile takes the position of a leaving group.

Answer to Problem 22.75P

The synthesis of given compound by the use of ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only source of labeled staring materials is,

Explanation of Solution

An ester is formed by the reaction of carboxylic acid with alcohol. This reaction is known as Fischer Esterification. During this reaction, bond formation between carbon and oxygen takes place and water removes as a byproduct. In the synthesis of given compound, diethylether is first hydrolyzed to give ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{}^{\text{18}}\text{OH}$. Acetic acid undergoes Esterification with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{}^{\text{18}}\text{OH}$ and leads to the formation of desired compound as shown in Figure 3.

Figure 3

Conclusion

The synthesis of given compound by the use of ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only source of labeled staring materials is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The synthesis of given compound by the use of ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only source of labeled staring materials is to be stated.

Concept introduction:

The replacement or substitution of one functional group with another functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons is known as a nucleophile. In nucleophilc acyl substitution reaction, a nucleophile takes the position of a leaving group.

Answer to Problem 22.75P

The synthesis of given compound by the use of ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only source of labeled staring materials is,

Explanation of Solution

An ester is formed by the reaction of carboxylic acid with alcohol. This reaction is known as Fischer Esterification. During this reaction, bond formation between carbon and oxygen takes place and water removes as a byproduct. In the synthesis of given compound, ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ is first convert to ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}{}^{\text{18}}\text{OH}$ in a two step reaction. This product is then converted to ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{C}}^{\text{18}}\text{OOH}$ which undergoes Esterification reaction with unlabeled ethanol to give desired product as shown below.

Figure 4

Conclusion

The synthesis of given compound by the use of ${\text{H}}_{\text{2}}{}^{\text{18}}\text{O}$ and ${\text{CH}}_{\text{3}}{}^{\text{13}}{\text{CH}}_{\text{2}}\text{OH}$ as the only source of labeled staring materials is shown in Figure 4.