Chapter 23, Problem 23.46AP

Interpretation Introduction

(a)

Interpretation:

The product obtained in the reaction of isopropylamine with dilute ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and it also has the ability to accept the proton in water.

Answer to Problem 23.46AP

The product $\text{propan}-2-\text{ammonium}\text{sulfate}$ is obtained in the reaction of isopropylamine with dilute ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$. The reaction is shown below.

Explanation of Solution

The reaction of amines with dilute ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ result in the formation of sulfate salts of corresponding amines. When isopropylamine reacts with dilute ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$, it results in the formation of $\text{propan}-2-\text{ammonium}\text{sulfate}$. The reaction is shown below.

Figure 1

Conclusion

The product obtained in the reaction of isopropylamine with dilute ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ is $\text{propan}-2-\text{ammonium}\text{sulfate}$ and its reaction is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The product obtained in the reaction of isopropylamine with a dilute $\text{NaOH}$ solution is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and it also has the ability to accept the proton in water.

Answer to Problem 23.46AP

The reaction does not form any product. The reaction is shown below.

Explanation of Solution

When isopropylamine reacts with a dilute $\text{NaOH}$ solution, it does not form any product because both $\text{NaOH}$ and amine are basic in nature. The reaction is shown below.

Figure 2

Conclusion

No product is obtained in the reaction of isopropylamine with a dilute $\text{NaOH}$ solution and its reaction is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The product obtained in the reaction of isopropylamine with butyllithium in $\text{THF}$ at $-78°\text{C}$ is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and it also has the ability to accept the proton in water.

Answer to Problem 23.46AP

The product lithium isopropylamide is obtained in the reaction of isopropylamine with butyllithium in $\text{THF}$ at $-78°\text{C}$. The reaction is shown below.

Explanation of Solution

The organolithium base butyllithium in $\text{THF}$ $-78°\text{C}$ abstracts a proton from isopropylamine results in the formation of lithium isopropylamide with butane. The reaction is shown below.

Figure 3

Conclusion

The product obtained in the reaction of isopropylamine with butyllithium in $\text{THF}$ at $-78°\text{C}$ is lithium isopropylamide and its reaction is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The product obtained in the reaction of isopropylamine with acetyl chloride and pyridine is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and it also has the ability to accept the proton in water.

Answer to Problem 23.46AP

The product, $N-\text{isopropylacetamide}$ is obtained in the reaction of isopropylamine with acetyl chloride and pyridine. The reaction is shown below.

Explanation of Solution

The acid chloride is a very reactive compound. When it reacts with amines it forms amides. The reaction of isopropylamine with acetyl chloride in pyridine results in the formation of $N-\text{isopropylacetamide}$. This reaction is similar to amide formation from a carboxylic acid. The reaction is shown below

Figure 4

Conclusion

The product obtained in the reaction of isopropylamine with acetyl chloride and pyridine is $N-\text{isopropylacetamide}$ and its reaction is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

The product obtained in the reaction of isopropylamine with ${\text{NaNO}}_{\text{2}}$ and aqueous $\text{HBr}$ at $0°\text{C}$ is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. The formation of diazonium salt from aromatic amines takes place using sodium nitrite and hydrohalide at low temperatures. Aryl diazonium salts undergo a variety of specific substitution reactions in which the incoming Z group replaces (a very good leaving group) to form corresponding products.

Answer to Problem 23.46AP

The product, $\text{propane}-2-\text{diazonium}\text{chloride}$ is obtained in the reaction of isopropylamine with ${\text{NaNO}}_{\text{2}}$ and aqueous $\text{HBr}$ at $0°\text{C}$. The reaction is shown below.

Explanation of Solution

The reaction is an example of a diazotization reaction. When isopropylamine reacts with ${\text{NaNO}}_{\text{2}}$ and aqueous $\text{HBr}$ at $0°\text{C}$ it undergoes diazotization reaction and results in the formation of $\text{propane}-2-\text{diazonium}\text{chloride}$. The reaction is shown below.

Figure 5

Conclusion

The product that obtained in the reaction of isopropylamine with ${\text{NaNO}}_{\text{2}}$ and aqueous $\text{HBr}$ at $0°\text{C}$ is $\text{propane}-2-\text{diazonium}\text{chloride}$ and its reaction is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

The product obtained in the reaction of isopropylamine with acetone and ${\text{H}}_{\text{2}}$, $\text{Pd}/\text{C}$ is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and it also has the ability to accept the proton in water.

Answer to Problem 23.46AP

Explanation of Solution

When acetone reacts with isopropylamine, it forms enamine, with double bonds. It is then hydrogenated by ${\text{H}}_{\text{2}}$ in presence of $\text{Pd}/\text{C}$. As a result, it forms diisopropylamine as the final product. The reaction is shown below.

Figure 6

Conclusion

The product obtained in the reaction of isopropylamine with acetone and ${\text{H}}_{\text{2}}$, $\text{Pd}/\text{C}$ is diisopropylamine and its reaction is shown in Figure 6.

Interpretation Introduction

(g)

Interpretation:

The product obtained in the reaction of isopropylamine with excess ${\text{CH}}_{\text{3}}\text{I}$, heat is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Hofmann elimination reaction occurs as an anti-elimination reaction. In this reaction, the starting material is quaternary ammonium hydroxide. When quaternary ammonium hydroxide is heated, $\text{β}$ elimination occurs to form an alkene, amines act as a leaving group.

Answer to Problem 23.46AP

The product, $N,N,N-\text{trimethylpropan}-2-\text{ammonium}\text{iodide}$ is obtained in the reaction of isopropylamine with excess ${\text{CH}}_{\text{3}}\text{I}$ in presence of heat. The reaction is shown below.

Explanation of Solution

Hofmann elimination reaction occurs as an anti-elimination reaction. In this reaction, the starting material is isopropylamine. When it reacts with an excess of ${\text{CH}}_{\text{3}}\text{I}$ in presence of heat, it forms $N,N,N-\text{trimethylpropan}-2-\text{ammonium}\text{iodide}$ salt only. The reaction is shown below.

Figure 7

Conclusion

The product obtained in the reaction of isopropylamine with excess ${\text{CH}}_{\text{3}}\text{I}$ in presence of heat is $N,N,N-\text{trimethylpropan}-2-\text{ammonium}\text{iodide}$ and its reaction is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation:

The product obtained in the reaction of isopropylamine with benzoic acid at $25°\text{C}$ is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and it also has the ability to accept the proton in water.

Answer to Problem 23.46AP

The product $N-\text{isopropylamide}$ is obtained in the reaction of isopropylamine with benzoic acid at $25°\text{C}$. The reaction is shown below.

Explanation of Solution

In this reaction, benzoic acid is a reactive compound. When it reacts with amine it results in the formation of an amide. This reaction is similar to the conversion of carboxylic acid to amides. The reaction is shown below.

Figure 8

Conclusion

The product obtained in the reaction of isopropylamine with benzoic acid at $25°\text{C}$ is $N-\text{isopropylamide}$ and its reaction is shown in Figure 8.

Interpretation Introduction

(i)

Interpretation:

The product obtained in the reaction of isopropylamine with formaldehyde, ${\text{NaBH}}_{\text{3}}\text{CN}$ and $\text{EtOH}$ is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and it also has the ability to accept the proton in water.

Answer to Problem 23.46AP

The product $N-\text{methylpropan}-2-\text{amine}$ is obtained in the reaction of isopropylamine with formaldehyde, ${\text{NaBH}}_{\text{3}}\text{CN}$ and $\text{EtOH}$. The reaction is shown below.

Explanation of Solution

This reaction is an example of a reductive amination reaction. Reductive amination reaction is the conversion of the carbonyl group to the amine or it converts one amine to newer amine. In this reaction, when isopropylamine reacts formaldehyde, ${\text{NaBH}}_{\text{3}}\text{CN}$ and $\text{EtOH}$ results in the formation of $N-\text{methylpropan}-2-\text{amine}$. The reaction is shown below.

Figure 9

Conclusion

The product that obtained in the reaction of isopropylamine with formaldehyde, ${\text{NaBH}}_{\text{3}}\text{CN}$ and $\text{EtOH}$ is $N-\text{methylpropan}-2-\text{amine}$ and its reaction is shown in Figure 9.

Interpretation Introduction

(j)

Interpretation:

The product obtained in the reaction of isopropylamine with $2,4-\text{dinitrochlorobenzene}$, ${\text{K}}^{\text{+}}t-\text{BuO}$, and a $\text{Pd}\left(\text{0}\right)$ catalyst is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and it also has the ability to accept the proton in water.

Answer to Problem 23.46AP

The product $N-\text{isopropyl}-2,4-\text{dimethylaniline}$ is obtained in the reaction of isopropylamine with $2,4-\text{dinitrochlorobenzene}$, ${\text{K}}^{\text{+}}t-\text{BuO}$, and a $\text{Pd}\left(\text{0}\right)$ catalyst. The reaction is shown below.

Explanation of Solution

This reaction is an example of a Buchwald-Hartwig reaction. Buchwald Hartwig reaction is used for $\text{C}-\text{N}$ bond formation and is a palladium-catalyzed reaction. In this reaction, when isopropylamine reacts with $2,4-\text{dinitrochlorobenzene}$, ${\text{K}}^{\text{+}}t-\text{BuO}$, and a $\text{Pd}\left(\text{0}\right)$ catalyst, it results in the formation of $N-\text{isopropyl}-2,4-\text{dimethylaniline}$. The reaction is shown below.

Figure 10

Conclusion

The product obtained in the reaction of isopropylamine with $2,4-\text{dinitrochlorobenzene}$, ${\text{K}}^{\text{+}}t-\text{BuO}$, and a $\text{Pd}\left(\text{0}\right)$ catalyst is $N-\text{isopropyl}-2,4-\text{dimethylaniline}$ and its reaction is shown in Figure 10.

Interpretation Introduction

(k)

Interpretation:

The product obtained in the reaction of isopropylamine with a product of part (g) +${\text{Ag}}_{\text{2}}\text{O}$, then heat is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Hofmann elimination reaction occurs as an anti-elimination reaction. In this reaction, the starting material is quaternary ammonium hydroxide. When quaternary ammonium hydroxide is heated, $\text{β}$ elimination occurs to form an alkene, amines act as a leaving group.

Answer to Problem 23.46AP

The product $N,N,N-\text{trimethylpropan}-2-\text{ammonium}\text{hydroxide}$ is obtained in the reaction of a product of part (g) $+$ ${\text{Ag}}_{\text{2}}\text{O}$, then heat. The reaction is shown below.

Explanation of Solution

When isopropylamine undergoes Hofmann elimination reaction with a product of part (g) $+$ ${\text{Ag}}_{\text{2}}\text{O}$, then heat. The only substitution of iodide ion by hydroxide ion takes place in this reaction and forms $N,N,N-\text{trimethylpropan}-2-\text{ammonium}\text{hydroxide}$. The reaction is shown below.

Figure 11

Conclusion

The product obtained in the reaction of isopropylamine with a product of part (g) $+$ ${\text{Ag}}_{\text{2}}\text{O}$, then heat is $N,N,N-\text{trimethylpropan}-2-\text{ammonium}\text{hydroxide}$ and its reaction is shown in Figure 11.

Interpretation Introduction

(l)

Interpretation:

The product obtained in the reaction of isopropylamine with a product of part (d) with ${\text{LiAlH}}_{\text{4}}$, then ${\text{H}}_{\text{3}}{\text{O}}^{\text{+}}$ and then ${}^{-}\text{OH}$ is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and it also has the ability to accept the proton in water.

Answer to Problem 23.46AP

The product, $N-\text{ethylpropan}-2-\text{amine}$ is obtained in the reaction of a product of part (d) with ${\text{LiAlH}}_{\text{4}}$, then ${\text{H}}_{\text{3}}{\text{O}}^{\text{+}}$ and then ${}^{-}\text{OH}$. The reaction is shown below.

Explanation of Solution

When $N-\text{isopropylacetamide}$ undergoes reduction reaction with a product of part (d) with ${\text{LiAlH}}_{\text{4}}$, then ${\text{H}}_{\text{3}}{\text{O}}^{\text{+}}$ and then ${}^{-}\text{OH}$, it results in the formation of $N-\text{ethylpropan}-2-\text{amine}$. The reaction is shown below.

Figure 12

Conclusion

The product obtained in the reaction of isopropylamine with a product of part (d) with ${\text{LiAlH}}_{\text{4}}$, then ${\text{H}}_{\text{3}}{\text{O}}^{\text{+}}$ and then ${}^{-}\text{OH}$ is $N-\text{ethylpropan}-2-\text{amine}$ and its reaction is shown in Figure 12.