Chapter 6, Problem 6.46P

Interpretation Introduction

(a)

Interpretation:

It is to be determined whether the given reactant is suitable for a reaction involving ethanamine (${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$) as a solvent with respect to leveling effect.

Concept introduction:

Leveling effect refers to the effect of a solvent on the properties of acids and bases. For an acid-base reaction, the strength of the strong acid is limited or leveled by the basicity of the solvent. Similarly, the strength of the strong base is leveled by the acidity of the solvent. With respect to the leveling effect, a solvent is unsuitable for a particular reactant R if R is a stronger acid that the solvent’s conjugate acid (i.e., R has the lower pKa) or if R is a stronger base than the solvent’s conjugate base (i.e., the conjugate acid of R has a higher pKa than the solvent).

Answer to Problem 6.46P

With respect to the leveling effect, ethanamine is a suitable solvent for a reaction involving the chloride ion ${\text{Cl}}^{\text{Θ}}$ as a reactant.

Explanation of Solution

The reaction of chloride ion ${\text{Cl}}^{\text{Θ}}$ with ethanamine is shown below:

Hydrochloric acid, $\text{HCl}$ ($\text{pKa = -7}$), is a stronger acid than ethanamine, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$ ($\text{pKa = }\sim \text{10}\text{.8}$). The reactant side of the reaction is most favored because the stronger acid, $\text{HCl}$, is on the product side. Chloride ion ${\text{Cl}}^{\text{Θ}}$ changes the properties of ethanamine. Therefore, ethanamine (${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$) is a suitable solvent for ${\text{Cl}}^{\text{Θ}}$ because the equilibrium lies to the reactant side.

Conclusion

The solvent effect on the reactant is determined with respect to the leveling effect.

Interpretation Introduction

(b)

Interpretation:

It is to be determined whether the given reactant is suitable for a reaction involving ethanamine (${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$) as a solvent with respect to leveling effect.

Concept introduction:

Leveling effect refers to the effect of a solvent on the properties of acids and bases. For an acid-base reaction, the strength of the strong acid is limited or leveled by the basicity of the solvent. Similarly, the strength of the strong base is leveled by the acidity of the solvent. With respect to the leveling effect, a solvent is unsuitable for a particular reactant R if R is a stronger acid that the solvent’s conjugate acid (i.e., R has the lower pKa) or if R is a stronger base than the solvent’s conjugate base (i.e., the conjugate acid of R has a higher pKa than the solvent).

Answer to Problem 6.46P

With respect to the leveling effect, ethanamine is a not suitable solvent for a reaction involving $\text{HCl}$ as a reactant.

Explanation of Solution

The reaction of $\text{HC}\equiv {\text{C:}}^{\text{Θ}}$ with ethanamine is shown below:

Hydrochloric acid, $\text{HCl}$ ($\text{pKa = -7}$), is a stronger acid than ethanamine, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$ ($\text{pKa = }\sim \text{10}\text{.8}$). The product side of the reaction is most favored because the stronger acid, $\text{HCl}$, is on the reactant side. $\text{HCl}$ changes the properties of ethanamine. Therefore, ethanamine (${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$) is not a suitable solvent for $\text{HCl}$ because the equilibrium lies to the product side.

Conclusion

The solvent effect on the reactant is determined with respect to the leveling effect.

Interpretation Introduction

(c)

Interpretation:

It is to be determined whether the given reactant is suitable for a reaction involving ethanamine (${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$) as a solvent with respect to leveling effect.

Concept introduction:

Leveling effect refers to the effect of a solvent on the properties of acids and bases. For an acid-base reaction, the strength of the strong acid is limited or leveled by the basicity of the solvent. Similarly, the strength of the strong base is leveled by the acidity of the solvent. With respect to the leveling effect, a solvent is unsuitable for a particular reactant R if R is a stronger acid that the solvent’s conjugate acid (i.e., R has the lower pKa) or if R is a stronger base than the solvent’s conjugate base (i.e., the conjugate acid of R has a higher pKa than the solvent).

Answer to Problem 6.46P

With respect to the leveling effect, ethanamine is not a suitable solvent for a reaction involving ${\text{H}}_{\text{3}}{\text{C:}}^{\text{Θ}}$ as a reactant.

Explanation of Solution

The reaction of ${\text{H}}_{\text{3}}{\text{C:}}^{\text{Θ}}$ with ethanamine is shown below:

Ethanamine, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$ ($\text{pKa = }\sim \text{10}\text{.8}$), is a stronger acid than methane, ${\text{CH}}_{\text{4}}$ ($\text{pKa = 48}$). The product side of the reaction is most favored because the stronger acid, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$, is on the reactant side. ${\text{H}}_{\text{3}}{\text{C:}}^{\text{Θ}}$ does not change the properties of ethanamine. Therefore, ethanamine (${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$) is not a suitable solvent for ${\text{H}}_{\text{3}}{\text{C:}}^{\text{Θ}}$ because the equilibrium lies to the product side.

Conclusion

The solvent effect on the reactant is determined with respect to the leveling effect.

Interpretation Introduction

(d)

Interpretation:

It is to be determined whether the given reactant is suitable for a reaction involving ethanamine (${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$) as a solvent with respect to leveling effect.

Concept introduction:

Leveling effect refers to the effect of a solvent on the properties of acids and bases. For an acid-base reaction, the strength of the strong acid is limited or leveled by the basicity of the solvent. Similarly, the strength of the strong base is leveled by the acidity of the solvent. With respect to the leveling effect, a solvent is unsuitable for a particular reactant R if R is a stronger acid that the solvent’s conjugate acid (i.e., R has the lower pKa) or if R is a stronger base than the solvent’s conjugate base (i.e., the conjugate acid of R has a higher pKa than the solvent).

Answer to Problem 6.46P

With respect to the leveling effect, ethanamine is not a suitable solvent for a reaction involving ${}^{\text{Θ}}{\text{NH}}_{\text{2}}$ as a reactant.

Explanation of Solution

The reaction of ${}^{\text{Θ}}{\text{NH}}_{\text{2}}$ with ethanamine is shown below:

Ethanamine, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$ ($\text{pKa = }\sim \text{10}\text{.8}$), is a stronger acid than ammonia, ${\text{NH}}_{\text{3}}$ ($\text{pKa = 36}$). The product side of the reaction is most favored because the stronger acid, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$, is on the reactant side. ${}^{\text{Θ}}{\text{NH}}_{\text{2}}$ does not change the properties of ethanamine. Therefore, ethanamine (${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$) is not a suitable solvent for ${}^{\text{Θ}}{\text{NH}}_{\text{2}}$ because the equilibrium lies to the product side.

Conclusion

The solvent effect on the reactant is determined with respect to the leveling effect.

Interpretation Introduction

(e)

Interpretation:

It is to be determined whether the given reactant is suitable for a reaction involving ethanamine (${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$) as a solvent with respect to leveling effect.

Concept introduction:

Leveling effect refers to the effect of a solvent on the properties of acids and bases. For an acid-base reaction, the strength of the strong acid is limited or leveled by the basicity of the solvent. Similarly, the strength of the strong base is leveled by the acidity of the solvent. With respect to the leveling effect, a solvent is unsuitable for a particular reactant R if R is a stronger acid that the solvent’s conjugate acid (i.e., R has the lower pKa) or if R is a stronger base than the solvent’s conjugate base (i.e., the conjugate acid of R has a higher pKa than the solvent).

Answer to Problem 6.46P

With respect to the leveling effect, ethanamine is not a suitable solvent for a reaction involving ${}^{\oplus }{\text{NH}}_{\text{4}}$ as a reactant.

Explanation of Solution

The reaction of ${}^{\oplus }{\text{NH}}_{\text{4}}$ with ethanamine is shown below:

Ethanamine, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$ ($\text{pKa = }\sim \text{10}\text{.8}$), is a stronger acid than ammonia, ${\text{NH}}_{\text{3}}$ ($\text{pKa = 36}$). The product side of the reaction is most favored because the stronger acid, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$, is on the reactant side. ${}^{\oplus }{\text{NH}}_{\text{4}}$ does not change the properties of ethanamine. Therefore, ethanamine (${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$) is not a suitable solvent for ${}^{\oplus }{\text{NH}}_{\text{4}}$ because the equilibrium lies to the product side.

Conclusion

The solvent effect on the reactant is determined with respect to the leveling effect.

Interpretation Introduction

(f)

Interpretation:

It is to be determined whether the given reactant is suitable for a reaction involving ethanamine ( ) as a solvent with respect to leveling effect.

Concept introduction:

Leveling effect refers to the effect of a solvent on the properties of acids and bases. For an acid-base reaction, the strength of the strong acid is limited or leveled by the basicity of the solvent. Similarly, the strength of the strong base is leveled by the acidity of the solvent. With respect to the leveling effect, a solvent is unsuitable for a particular reactant R if R is a stronger acid that the solvent’s conjugate acid (i.e., R has the lower pKa) or if R is a stronger base than the solvent’s conjugate base (i.e., the conjugate acid of R has a higher pKa than the solvent).

Answer to Problem 6.46P

With respect to the leveling effect, ethanamine is not a suitable solvent for a reaction involving ${}^{\text{Θ}}\text{OH}$ as a reactant.

Explanation of Solution

The reaction of hydroxide ion ${}^{\text{Θ}}\text{OH}$ with ethanamine is shown below:

Ethanamine, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$ ($\text{pKa = }\sim \text{10}\text{.8}$), is a stronger acid than water, ${\text{H}}_{\text{2}}\text{O}$ ($\text{pKa = 15}\text{.7}$). The product side of the reaction is most favored because the stronger acid, ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$, is on the reactant side. ${}^{\text{Θ}}\text{OH}$ does not change the properties of ethanamine. Therefore, ethanamine (${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$) is not a suitable solvent for ${}^{\text{Θ}}\text{OH}$ because the equilibrium lies to the product side.

Conclusion

The solvent effect on the reactant is determined with respect to the leveling effect.