Chapter 25, Problem 25.63P

Interpretation Introduction

(a)

Interpretation:

The reagents that are needed to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are to be predicted.

Concept introduction:

The structural representation of sugar molecule in cyclic form is known as Haworth projection. A compound in which the hydroxyl group of first and sixth carbon atom is on the same side is known as $\text{β}$ anomer, otherwise it is called it is called $\text{α}$ anomer.

Answer to Problem 25.63P

The reagent that is required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound is ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{NH}$ in the presence of acid.

Explanation of Solution

The given compound is shown below.

Figure 1

Carbonyl compounds react with secondary amines in the presence of acid to form enamine. Therefore, the reaction that shows the conversion of acetophenone into the given compound is shown below.

Figure 2

Thus, the reagent that is required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound is ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{NH}$ in the presence of acid.

Conclusion

The reagent that is required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound is ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{NH}$ in the presence of acid.

Interpretation Introduction

(b)

Interpretation:

The reagents that are needed to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are to be predicted.

Concept introduction:

The structural representation of sugar molecule in cyclic form is known as Haworth projection. A compound in which the hydroxyl group of first and sixth carbon atom is on the same side is known as $\text{β}$ anomer, otherwise it is called $\text{α}$ anomer.

Answer to Problem 25.63P

The reagent that is required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound is ${\text{CH}}_3{\text{CH}}_2{\text{CH}}_2{\text{NH}}_2$ in the presence of mild acid.

Explanation of Solution

The given compound is shown below.

Figure 3

Carbonyl compounds react with primary amines in the presence of mild acid to form imine. Therefore, the reaction that shows the conversion of acetophenone into the given compound is shown below.

Figure 4

Thus, the reagent that is required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound is ${\text{CH}}_3{\text{CH}}_2{\text{CH}}_2{\text{NH}}_2$ in the presence of mild acid.

Conclusion

The reagent that is required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound is ${\text{CH}}_3{\text{CH}}_2{\text{CH}}_2{\text{NH}}_2$ in the presence of mild acid.

Interpretation Introduction

(c)

Interpretation:

The reagents that are needed to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are to be predicted.

Concept introduction:

The structural representation of sugar molecule in cyclic form is known as Haworth projection. A compound in which the hydroxyl group of first and sixth carbon atom is on the same side is known as $\text{β}$ anomer, otherwise it is called $\text{α}$ anomer.

Answer to Problem 25.63P

he reagents that are required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are ${\text{NH}}_{\text{3}}$ and ${\text{NaBH}}_{\text{3}}\text{CN}$.

Explanation of Solution

The given compound is shown below.

Figure 5

Carbonyl compounds react with ammonia to form imine. The conversion of imine to amines takes place by using selective reducing agent called sodium cyanoborohydride. Therefore, the reaction that shows the conversion of acetophenone into the given compound is shown below.

Figure 6

Thus, reagent that is required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound is ${\text{NH}}_{\text{3}}$ and ${\text{NaBH}}_{\text{3}}\text{CN}$.

Conclusion

The reagents that are required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are ${\text{NH}}_{\text{3}}$ and ${\text{NaBH}}_{\text{3}}\text{CN}$.

Interpretation Introduction

(d)

Interpretation:

The reagents that are needed to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are to be predicted.

Concept introduction:

The structural representation of sugar molecule in cyclic form is known as Haworth projection. A compound in which the hydroxyl group of first and sixth carbon atom is on the same side is known as $\text{β}$ anomer, otherwise it is called $\text{α}$ anomer.

Answer to Problem 25.63P

The reagents that are required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are ${\text{NaBH}}_{\text{4}}/{\text{CH}}_{\text{3}}\text{OH}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$.

Explanation of Solution

The given compound is shown below.

Figure 7

The reaction that shows the conversion of acetophenone into the given compound is shown below.

Figure 8

The given reaction is a two step process. The first step involves reduction of carbonyl compounds into alcohol by using sodium borohydride. This results in the formation of $1-\text{phenylethanol}$. In the next step, dehydration of alcohol takes place to give alkenes. This results in the formation of desired product.

Thus, the reagents that are required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are ${\text{NaBH}}_{\text{4}}/{\text{CH}}_{\text{3}}\text{OH}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$.

Conclusion

The reagents that are required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are ${\text{NaBH}}_{\text{4}}/{\text{CH}}_{\text{3}}\text{OH}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$.

Interpretation Introduction

(e)

Interpretation:

The reagents that are needed to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are to be predicted.

Concept introduction:

The structural representation of sugar molecule in cyclic form is known as Haworth projection. A compound in which the hydroxyl group of first and sixth carbon atom is on the same side is known as $\text{β}$ anomer, otherwise it is called $\text{α}$ anomer.

Answer to Problem 25.63P

The reagents that are required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are ${\text{NaBH}}_{\text{4}}/{\text{CH}}_{\text{3}}\text{OH}$, ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$, m-CPBA, and ${\text{CH}}_{\text{3}}{\text{NH}}_{\text{2}}$.

Explanation of Solution

The given compound is shown below.

Figure 9

The reaction that shows the conversion of acetophenone into the given compound is shown below.

Figure 10

The first step involves reduction of carbonyl compounds into alcohol by using sodium borohydride. This results in the formation of $1-\text{phenylethanol}$. In the next step, dehydration of alcohol takes place to give alkenes. This results in the formation of styrene. The next step is the formation of epoxidation by reacting meta-chloroperbenzoic acid with styrene. This results in the formation of $2-\text{phenyloxirane}$. In the next step, $2-\text{phenyloxirane}$ reacts with methylamine to give the final product.

Thus, the reagents that are required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are ${\text{NaBH}}_{\text{4}}/{\text{CH}}_{\text{3}}\text{OH}$, ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$, m-CPBA, and ${\text{CH}}_{\text{3}}{\text{NH}}_{\text{2}}$.

Conclusion

The reagents that are required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are ${\text{NaBH}}_{\text{4}}/{\text{CH}}_{\text{3}}\text{OH}$, ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$, m-CPBA, and ${\text{CH}}_{\text{3}}{\text{NH}}_{\text{2}}$.

Interpretation Introduction

(f)

Interpretation:

The reagents that are needed to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound are to be predicted.

Concept introduction:

The structural representation of sugar molecule in cyclic form is known as Haworth projection. A compound in which the hydroxyl group of first and sixth carbon atom is on the same side is known as $\text{β}$ anomer, otherwise it is called $\text{α}$ anomer.

Answer to Problem 25.63P

The reagent that is required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound is ${\text{Br}}_{\text{2}}/{\text{CH}}_{\text{3}}\text{COOH}$ and ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$.

Explanation of Solution

The given compound is shown below.

Figure 11

The reaction that shows the conversion of acetophenone into the given compound is shown below.

Figure 12

The first step is the bromination step which results in the formation of $1-\text{bromo}-1-\text{phenylethanone}$. In the next step, $1-\text{bromo}-1-\text{phenylethanone}$ reacts with butylamine to give the final product.

Thus, reagent that is required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound is ${\text{Br}}_{\text{2}}/{\text{CH}}_{\text{3}}\text{COOH}$ and ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$.

Conclusion

The reagent that is required to convert acetophenone $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{COCH}}_{\text{3}}\right)$ into the given compound is ${\text{Br}}_{\text{2}}/{\text{CH}}_{\text{3}}\text{COOH}$ and ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$.