Chapter 25, Problem 25.60P

Draw the products formed when $p\text{-}$ methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ is treated with each reagent.

a. $\text{HCl}$

b. ${\text{CH}}_{\text{3}}\text{COCl}$

c. ${\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}$

d. excess ${\text{CH}}_{\text{3}}\text{I}$

e. ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}-\text{O}$

f. ${\text{CH}}_{\text{3}}\text{COCl,}{\text{AlCl}}_{\text{3}}$

g. ${\text{CH}}_{\text{3}}{\text{CO}}_{\text{2}}\text{H}$

h. ${\text{NaNO}}_{\text{2}}\text{,}\text{HCl}$

i. Part (b), then ${\text{CH}}_{\text{3}}\text{COCl,}{\text{AlCl}}_3$

j. ${\text{CH}}_{\text{3}}\text{CHO,}{\text{NaBH}}_{\text{3}}\text{CN}$

Interpretation Introduction

(a)

Interpretation: The product formed by the treatment of $p\text{-}$ methylaniline with $\text{HCl}$ is to be drawn.

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 25.60P

The product formed by the treatment of $p\text{-}$ methylaniline with $\text{HCl}$ is shown below.

Explanation of Solution

The product formed by the treatment of $p\text{-}$ methylaniline with $\text{HCl}$ is shown below.

Figure 1

In the above reaction, hydrochloric acid attacks on nitrogen atom of $p\text{-}$ methylaniline to form the final product. The starting material of the reaction behaves as basic compound due to the presence of $-{\text{NH}}_{\text{2}}$ group.

Conclusion

The product formed by the treatment of $p\text{-}$ methylaniline with $\text{HCl}$ is drawn in Figure 1.

Interpretation Introduction

(b)

Interpretation: The products formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{COCl}$ are to be drawn.

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 25.60P

The products formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{COCl}$ are drawn below.

Explanation of Solution

The products formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{COCl}$ are shown below.

Figure 2

The above reaction indicates that $-{\text{COCH}}_{\text{3}}$ part of acetyl chloride reacts with $-{\text{NH}}_{\text{2}}$ of $p\text{-}$ methylaniline to form the final product. The other product formed in the reaction is $\text{HCl}$.

Conclusion

The products formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{COCl}$ are drawn in Figure 2.

Interpretation Introduction

(c)

Interpretation: The products formed by the treatment of $p\text{-}$ methylaniline with ${\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}$ are to be drawn.

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 25.60P

The products formed by the treatment of $p\text{-}$ methylaniline with ${\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}$ are shown in Figure 3.

Explanation of Solution

The products formed by the treatment of $p\text{-}$ methylaniline with ${\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}$ are shown below.

Figure 3

The above reaction implies that $-{\text{COCH}}_{\text{3}}$ part of ${\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}$ reacts with $-{\text{NH}}_{\text{2}}$ of $p\text{-}$ methylaniline to form the final product. The other product formed in the reaction is ${\text{CH}}_{\text{3}}\text{COOH}$.

Conclusion

The products formed by the treatment of $p\text{-}$ methylaniline with ${\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}$ are drawn in Figure 3.

Interpretation Introduction

(d)

Interpretation: The products formed by the treatment of $p\text{-}$ methylaniline with excess ${\text{CH}}_{\text{3}}\text{I}$ are to be drawn.

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 25.60P

The products formed by the treatment of $p\text{-}$ methylaniline with excess ${\text{CH}}_{\text{3}}\text{I}$ are drawn in Figure 4.

Explanation of Solution

The products formed by the treatment of $p\text{-}$ methylaniline with excess ${\text{CH}}_{\text{3}}\text{I}$ are shown below.

Figure 4

The above reaction indicates that excess of methyl iodide reacts with $-{\text{NH}}_{\text{2}}$ of $p\text{-}$ methylaniline to form the quaternary ammonium salt.

Conclusion

The products formed by the treatment of $p\text{-}$ methylaniline with excess ${\text{CH}}_{\text{3}}\text{I}$ are drawn in Figure 4.

Interpretation Introduction

(e)

Interpretation: The products formed by the treatment of $p\text{-}$ methylaniline with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}=\text{O}$ are to be drawn.

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 25.60P

The products formed by the treatment of $p\text{-}$ methylaniline with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}=\text{O}$ are drawn in Figure 5.

Explanation of Solution

The products formed by the treatment of $p\text{-}$ methylaniline with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}=\text{O}$ are shown below.

Figure 5

Water gets removed when ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}=\text{O}$ reacts with $p\text{-}$ methylaniline and the final product is formed.

Conclusion

The products formed by the treatment of $p\text{-}$ methylaniline with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}-\text{O}$ are drawn in Figure 5.

Interpretation Introduction

(f)

Interpretation: The products formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{COCl,}{\text{AlCl}}_{\text{3}}$ are to be drawn.

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 25.60P

The products formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{COCl,}{\text{AlCl}}_{\text{3}}$ are shown below.

Explanation of Solution

The products formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{COCl,}{\text{AlCl}}_{\text{3}}$ are shown below.

Figure 6

The above reaction indicates that $p\text{-}$ methylaniline reacts with ${\text{CH}}_{\text{3}}\text{COCl}$ in the presence of ${\text{AlCl}}_{\text{3}}$ to form the final product. The $-{\text{NH}}_{\text{2}}$ group has positive inductive effect due to which $-{\text{COCH}}_{\text{3}}$ attached to ortho position with respect to $-{\text{NH}}_{\text{2}}$ group.

Interpretation Introduction

(g)

Interpretation: The product formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}{\text{CO}}_{\text{2}}\text{H}$ is to be drawn.

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 25.60P

The product formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}{\text{CO}}_{\text{2}}\text{H}$ is drawn below.

Explanation of Solution

The product formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}{\text{CO}}_{\text{2}}\text{H}$ is shown below.

Figure 7

The above reaction indicates that $p\text{-}$ methylaniline reacts with ${\text{CH}}_{\text{3}}{\text{CO}}_{\text{2}}\text{H}$ to form the final product. The product is formed by the acid-base reaction.

Conclusion

The product formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{CHO,}{\text{NaBH}}_{\text{3}}\text{CN}$ is drawn in Figure 7.

Interpretation Introduction

(h)

Interpretation: The products formed by the treatment of $p\text{-}$ methylaniline with ${\text{NaNO}}_{\text{2}}\text{,}\text{HCl}$ are to be drawn.

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 25.60P

The product formed by the treatment of $p\text{-}$ methylaniline with ${\text{NaNO}}_{\text{2}}\text{,}\text{HCl}$ is drawn below.

Explanation of Solution

The product formed by the treatment of $p\text{-}$ methylaniline with ${\text{NaNO}}_{\text{2}}\text{,}\text{HCl}$ is shown below.

Figure 8

In the above reaction $p\text{-}$ methylaniline reacts with ${\text{NaNO}}_{\text{2}}$ in the presence of $\text{HCl}$ to form diazonium compound.

Conclusion

The product formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{CHO,}{\text{NaBH}}_{\text{3}}\text{CN}$ is drawn in Figure 8.

Interpretation Introduction

(i)

Interpretation: The product formed by the treatment of $p\text{-}$ methylaniline with Part (b), then ${\text{CH}}_{\text{3}}\text{COCl,}{\text{AlCl}}_3$ is to be drawn.

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 25.60P

The product formed by the treatment of $p\text{-}$ methylaniline with Part (b), then ${\text{CH}}_{\text{3}}\text{COCl,}{\text{AlCl}}_3$ is shown below.

Explanation of Solution

The product formed by the treatment of $p\text{-}$ methylaniline with Part (b), then ${\text{CH}}_{\text{3}}\text{COCl,}{\text{AlCl}}_3$ is shown below.

Figure 9

The product formed in part (b) is used as a reactant in the above reaction. It again reacts with ${\text{CH}}_{\text{3}}\text{COCl}$ in the presence of ${\text{AlCl}}_{\text{3}}$ to form the desired product.

Conclusion

The product formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{CHO,}{\text{NaBH}}_{\text{3}}\text{CN}$ is drawn in Figure 9.

Interpretation Introduction

(j)

Interpretation: The product formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{CHO,}{\text{NaBH}}_{\text{3}}\text{CN}$ is to be drawn.

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 25.60P

The product formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{CHO,}{\text{NaBH}}_{\text{3}}\text{CN}$ is shown below.

Explanation of Solution

The product formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{CHO,}{\text{NaBH}}_{\text{3}}\text{CN}$ is to shown below.

Figure 10

In the above reaction, $p\text{-}$ methylaniline reacts with ${\text{CH}}_{\text{3}}\text{CHO}$ in the presence of ${\text{NaBH}}_{\text{3}}\text{CN}$ to form the final product.

Conclusion

The product formed by the treatment of $p\text{-}$ methylaniline with ${\text{CH}}_{\text{3}}\text{CHO,}{\text{NaBH}}_{\text{3}}\text{CN}$ is drawn in Figure 10.