Chapter 6, Problem 6.64P

Interpretation Introduction

(a)

Interpretation:

The stronger base from the given pair of species is to be predicted.

Concept introduction:

According to the Bronsted Lowry theory, a base is the species that accepts a proton by donating its lone pair of electrons. A negatively charged species is less stable than uncharged species; hence the negatively charged species is more basic. The negative charge on the less electronegative atom makes it a stronger base. Resonance can stabilize a negatively charged species and make it a weaker base. Electron donating group, which is less electronegative than hydrogen, stabilizes the positive charge but destabilizes a nearby negative charge and makes the species more basic. The neutral species may easily abstract protons due to the lone pair and may become more basic than the positively charged species. A positive charge is energetically favored on the atom with the lower effective electronegativity, i.e., ${\text{sp}}^{\text{3}}{\text{ > sp}}^{\text{2}}\text{ > sp}$.

Answer to Problem 6.64P

The stronger base in the given pair of species is

Explanation of Solution

The given pair of species is

The second species has negative charge whereas the first species is uncharged. A negatively charged species is less stable than the uncharged species; hence the negatively charged species is more basic than the uncharged species. Therefore, the stronger base in given pair of species is

Conclusion

The stronger base from the given pair of species is predicted on the basis of factors affecting charge stability.

Interpretation Introduction

(b)

Interpretation:

The stronger base from the given pair of species is to be predicted.

Concept introduction:

According to the Bronsted Lowry theory, a base is the species that accepts a proton by donating its lone pair of electrons. A negatively charged species is less stable than uncharged species; hence the negatively charged species is more basic. The negative charge on the less electronegative atom makes it a stronger base. Resonance can stabilize a negatively charged species and make it a weaker base. Electron donating group, which is less electronegative than hydrogen, stabilizes the positive charge but destabilizes a nearby negative charge and makes the species more basic. The neutral species may easily abstract protons due to the lone pair and may become more basic than the positively charged species. A positive charge is energetically favored on the atom with the lower effective electronegativity, i.e., ${\text{sp}}^{\text{3}}{\text{ > sp}}^{\text{2}}\text{ > sp}$.

Answer to Problem 6.64P

The stronger base in the given pair of species is

Explanation of Solution

The given pair of species is

The first species is neutral, and the second is positively charged. The neutral species can easily abstract protons as it has two lone pairs whereas the second species has no lone pair to abstract a proton. Therefore, the stronger base in the given pair of species is

Conclusion

The stronger base from the given pair of species is predicted on the basis of factors affecting charge stability.

Interpretation Introduction

(c)

Interpretation:

The stronger base from the given pair of species is to be predicted.

Concept introduction:

According to the Bronsted Lowry theory, a base is the species that accepts a proton by donating its lone pair of electrons. A negatively charged species is less stable than uncharged species; hence the negatively charged species is more basic. The negative charge on the less electronegative atom makes it a stronger base. Resonance can stabilize a negatively charged species and make it a weaker base. Electron donating group, which is less electronegative than hydrogen, stabilizes the positive charge but destabilizes a nearby negative charge and makes the species more basic. The neutral species may easily abstract protons due to the lone pair and may become more basic than the positively charged species. A positive charge is energetically favored on the atom with the lower effective electronegativity, i.e., ${\text{sp}}^{\text{3}}{\text{ > sp}}^{\text{2}}\text{ > sp}$.

Answer to Problem 6.64P

The stronger base in the given pair of species is

Explanation of Solution

The given pair of species is

In the first species, the negative charge is on the ${\text{sp}}^{\text{2}}$ hybridized carbon whereas in the second species, a negative charge is on the $\text{sp}$ hybridized carbon. A positive charge is energetically favored on the atom with the lower effective electronegativity, i.e., ${\text{sp}}^{\text{3}}{\text{ > sp}}^{\text{2}}\text{ > sp}$. Hence, the species having a negatively charged ${\text{sp}}^{\text{2}}$ hybridized carbon is more basic than the species having a negatively charged $\text{sp}$ hybridized carbon. Therefore, the stronger base in the given pair of species is

Conclusion

The stronger base from the given pair of species is predicted on the basis of factors affecting charge stability.

Interpretation Introduction

(d)

Interpretation:

The stronger base from the given pair of species is to be predicted.

Concept introduction:

According to the Bronsted Lowry theory, a base is the species that accepts a proton by donating its lone pair of electrons. A negatively charged species is less stable than uncharged species; hence the negatively charged species is more basic. The negative charge on the less electronegative atom makes it a stronger base. Resonance can stabilize a negatively charged species and make it a weaker base. Electron donating group, which is less electronegative than hydrogen, stabilizes the positive charge but destabilizes a nearby negative charge and makes the species more basic. The neutral species may easily abstract protons due to the lone pair and may become more basic than the positively charged species. A positive charge is energetically favored on the atom with the lower effective electronegativity, i.e., ${\text{sp}}^{\text{3}}{\text{ > sp}}^{\text{2}}\text{ > sp}$.

Answer to Problem 6.64P

The stronger base in the given pair of species is

Explanation of Solution

The given pair of species is

The first species has an oxygen atom and second species has an N atom. The nitrogen atom is less electronegative than oxygen and can easily donate a lone pair. Therefore, the stronger base in the given pair of species is

Conclusion

The stronger base from the given pair of species is predicted on the basis of factors affecting charge stability.

Interpretation Introduction

(e)

Interpretation:

The stronger base from the given pair of species is to be predicted.

Concept introduction:

According to the Bronsted Lowry theory, a base is the species that accepts a proton by donating its lone pair of electrons. A negatively charged species is less stable than uncharged species; hence the negatively charged species is more basic. The negative charge on the less electronegative atom makes it a stronger base. Resonance can stabilize a negatively charged species and make it a weaker base. Electron donating group, which is less electronegative than hydrogen, stabilizes the positive charge but destabilizes a nearby negative charge and makes the species more basic. The neutral species may easily abstract protons due to the lone pair and may become more basic than the positively charged species. A positive charge is energetically favored on the atom with the lower effective electronegativity, i.e., ${\text{sp}}^{\text{3}}{\text{ > sp}}^{\text{2}}\text{ > sp}$.

Answer to Problem 6.64P

The stronger base in the given pair of species is

Explanation of Solution

The given pair of species is

The first species has a negatively charged nitrogen atom whereas the second species has a negatively charged P atom. The phosphorus atom is less electronegative than nitrogen. The species having a negative charge on less electronegative atom is more basic. Therefore, the stronger base in the given pair of species is

Conclusion

The stronger base from the given pair of species is predicted on the basis of factors affecting charge stability.

Interpretation Introduction

(f)

Interpretation:

The stronger base from the given pair of species is to be predicted.

Concept introduction:

According to the Bronsted Lowry theory, a base is the species that accepts a proton by donating its lone pair of electrons. A negatively charged species is less stable than uncharged species; hence the negatively charged species is more basic. The negative charge on the less electronegative atom makes it a stronger base. Resonance can stabilize a negatively charged species and make it a weaker base. Electron donating group, which is less electronegative than hydrogen, stabilizes the positive charge but destabilizes a nearby negative charge and makes the species more basic. The neutral species may easily abstract protons due to the lone pair and may become more basic than the positively charged species. A positive charge is energetically favored on the atom with the lower effective electronegativity, i.e., ${\text{sp}}^{\text{3}}{\text{ > sp}}^{\text{2}}\text{ > sp}$.

Answer to Problem 6.64P

The stronger base in the given pair of species is

Explanation of Solution

The given pair of species is

The first species is more stable due to resonance; it shows the delocalization of the negative charge and makes the species more acidic, whereas, the second species does not show the resonance effect, making it more basic than the first species. Therefore, the stronger base in the given pair of species is

Conclusion

The stronger base from the given pair of species is predicted on the basis of factors affecting charge stability.

Interpretation Introduction

(g)

Interpretation:

The stronger base from the given pair of species is to be predicted.

Concept introduction:

According to the Bronsted Lowry theory, a base is the species that accepts a proton by donating its lone pair of electrons. A negatively charged species is less stable than uncharged species; hence the negatively charged species is more basic. The negative charge on the less electronegative atom makes it a stronger base. Resonance can stabilize a negatively charged species and make it a weaker base. Electron donating group, which is less electronegative than hydrogen, stabilizes the positive charge but destabilizes a nearby negative charge and makes the species more basic. The neutral species may easily abstract protons due to the lone pair and may become more basic than the positively charged species. A positive charge is energetically favored on the atom with the lower effective electronegativity, i.e., ${\text{sp}}^{\text{3}}{\text{ > sp}}^{\text{2}}\text{ > sp}$.

Answer to Problem 6.64P

The stronger base in the given pair of species is

Explanation of Solution

The given pair of species is

The first species is more stable due to resonance; it shows the delocalization of the negative charge and makes the species more acidic, whereas the second species does not show resonance effect, making it more basic than the first species. Therefore, the stronger base in the given pair of species is

Conclusion

The stronger base from the given pair of species is predicted on the basis of factors affecting charge stability.

Interpretation Introduction

(h)

Interpretation:

The stronger base from the given pair of species is to be predicted.

Concept introduction:

According to the Bronsted Lowry theory, a base is the species that accepts a proton by donating its lone pair of electrons. A negatively charged species is less stable than uncharged species; hence the negatively charged species is more basic. The negative charge on the less electronegative atom makes it a stronger base. Resonance can stabilize a negatively charged species and make it a weaker base. Electron donating group, which is less electronegative than hydrogen, stabilizes the positive charge but destabilizes a nearby negative charge and makes the species more basic. The neutral species may easily abstract protons due to the lone pair and may become more basic than the positively charged species. A positive charge is energetically favored on the atom with the lower effective electronegativity, i.e., ${\text{sp}}^{\text{3}}{\text{ > sp}}^{\text{2}}\text{ > sp}$.

Answer to Problem 6.64P

The stronger base in the given pair of species is

Explanation of Solution

The given pair of species is

Both the species have the resonance effect but presence of five electronegative F atoms in the second species makes it more stable and therefore more acidic than the first species. Therefore, the stronger base in the given pair of species is

Conclusion

The stronger base from the given pair of species is predicted on the basis of factors affecting charge stability.

Interpretation Introduction

(i)

Interpretation:

The stronger base from the given pair of species is to be predicted.

Concept introduction:

According to the Bronsted Lowry theory, a base is the species that accepts a proton by donating its lone pair of electrons. A negatively charged species is less stable than uncharged species; hence the negatively charged species is more basic. The negative charge on the less electronegative atom makes it a stronger base. Resonance can stabilize a negatively charged species and make it a weaker base. Electron donating group, which is less electronegative than hydrogen, stabilizes the positive charge but destabilizes a nearby negative charge and makes the species more basic. The neutral species may easily abstract protons due to the lone pair and may become more basic than the positively charged species. A positive charge is energetically favored on the atom with the lower effective electronegativity, i.e., ${\text{sp}}^{\text{3}}{\text{ > sp}}^{\text{2}}\text{ > sp}$.

Answer to Problem 6.64P

The stronger base in the given pair of species is

Explanation of Solution

The given pair of species is

The negative charge on the first species is in complete conjugation, making it more stable and increasing the acidity. The negative charge on the second species shows conjugation, but there is no aromaticity, which makes it less stable and hence more basic. Therefore, the stronger base in the given pair of species is

Conclusion

The stronger base from the given pair of species is predicted on the basis of factors affecting charge stability.