Chapter 25, Problem 25.53P

Interpretation Introduction

(a)

Interpretation: The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$; [3] $\Delta$ are to be drawn and the major product is to be identified.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of molecules with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 25.53P

The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$; [3] $\Delta$ and the major product is shown below.

Explanation of Solution

The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$ are shown below.

Figure 1

It is conferred from the above reaction that $\text{octan}-2-\text{amine}$ reacts with ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$ to form quaternary ammonium salt (compound X), which again reacts with ${\text{Ag}}_{\text{2}}\text{O}$ to form ammonium hydroxide compound (compound Y).

The products formed by heating of compound Y are shown below.

Figure 2

Compound Y on heating undergoes elimination reaction. In the above reaction, base removes ${\text{H}}^{+}$ ion from less substituted carbon and $\text{β-}$ carbon of the compound. The major product is labeled in the above figure.

Interpretation Introduction

(b)

Interpretation: The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$; [3] $\Delta$ are to be drawn and the major product is to be identified.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of molecules with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 25.53P

The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$; [3] $\Delta$ and the major product is shown below.

Explanation of Solution

The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$ are shown below.

Figure 3

It is conferred from the above reaction that $N\text{-}$ ethylpropan $\text{-2-}$ amine reacts with ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$ to form quaternary ammonium salt (compound X), which again reacts with ${\text{Ag}}_{\text{2}}\text{O}$ to form ammonium hydroxide compound (compound Y).

The products formed by heating of compound Y are shown below.

Figure 4

Compound Y on heating undergoes elimination reaction. In the above reaction, base removes ${\text{H}}^{+}$ ion from less substituted carbon and $\text{β-}$ carbon of the compound to form two products. The major product is labeled in the above figure.

Conclusion

The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$; [3] $\Delta$ are drawn in Figure 3 and Figure 4. The major product is shown in Figure 4.

Interpretation Introduction

(c)

Interpretation: The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$; [3] $\Delta$ are to be drawn. The major product is to be identified.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of molecules with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 25.53P

The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$; [3] $\Delta$ and the major product is shown below.

Explanation of Solution

The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$ are shown below.

Figure 5

It is conferred from the above reaction that $1,2\text{-}$ dimethylcyclopentanamine reacts with ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$ to form quaternary ammonium salt (compound X), which again reacts with ${\text{Ag}}_{\text{2}}\text{O}$ to form ammonium hydroxide compound (compound Y).

The products formed by heating of compound Y are shown below.

Figure 6

Compound Y on heating undergoes elimination reaction. In the above reaction, base removes ${\text{H}}^{+}$ ion from less substituted carbon and $\text{β-}$ carbon of the compound to form the products. The major product is labeled in the above figure.

Conclusion

The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$; [3] $\Delta$ are drawn in Figure 5 and Figure 6. The major product is shown in Figure 6.

Interpretation Introduction

(d)

Interpretation: The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$; [3] $\Delta$ are to be drawn. The major product is to be identified.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of molecules with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer to Problem 25.53P

The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$; [3] $\Delta$ and the major product is shown below.

Explanation of Solution

The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$ are shown below.

Figure 7

It is conferred from the above reaction that $2\text{-}$ propylpiperidine reacts with ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$ to form quaternary ammonium salt (compound X), which again reacts with ${\text{Ag}}_{\text{2}}\text{O}$ to form ammonium hydroxide compound (compound Y).

The products formed by heating of compound Y are shown below.

Figure 8

Compound Y on heating undergoes elimination reaction. In the above reaction, base removes ${\text{H}}^{+}$ ion from less substituted carbon and $\text{β-}$ carbon of the compound to form the products. The major product is labeled in the above figure.

Conclusion

The products formed when the given amine reacts with [1] ${\text{CH}}_{\text{3}}\text{I}\left(\text{excess}\right)$; [2] ${\text{Ag}}_{\text{2}}\text{O}$; [3] $\Delta$ are drawn in Figure 7 and Figure 8. The major product is shown in Figure 8.