Chapter 16, Problem 16.6P

Interpretation Introduction

(a)

Interpretation: The second resonance structure for given species and its hybrid is to be drawn. The two resonance structure and the hybrid are to be ranked in order of increasing stability.

Concept introduction: Most of the organic structures cannot be represented using single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. These are the hypothetical structures and do not specify the exact structure. These resonance structure combine together to give resonance hybrid that is lower in energy and is the most stable structure.

The delocalization of electrons results in the formation resonance structure.

Answer to Problem 16.6P

The second resonance structure for given species and its hybrid are,

The increasing order of stability for the given resonance structure is $\text{I}<\text{II}<\text{III}$.

Explanation of Solution

The given species is shown below.

Figure 1

Delocalization of electrons from one position to the other position result in the formation of resonance structure. Resonance hybrid is the combination of all resonating structures. Thus, resonance structures and resonance hybrid for the given species is shown below.

Figure 2

Better resonance structure is the one which has major contribution in the hybrid and others are minor contributors. Major contributor is the resonance structure which possesses more bonds and fewer charges.

The Figure 2 shows that the structure $\text{I}$ does not contain double bond. Thus, the stability of structure $\text{I}$ is less than the structure $\text{II}$.

Therefore, the increasing order of stability for the given resonance structure is $\text{I}<\text{II}<\text{III}$.

Conclusion

The second resonance structure for given species and its hybrid is shown in Figure 2. The increasing order of stability for the given resonance structure is is $\text{I}<\text{II}<\text{III}$.

Interpretation Introduction

(b)

Interpretation: The second resonance structure for given species and its hybrid is to be drawn. The two resonance structure and the hybrid are to be ranked in order of increasing stability.

Concept introduction: Most of the organic structures cannot be represented using single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. These are the hypothetical structures and do not specify the exact structure. These resonance structure combine together to give resonance hybrid that is lower in energy and is the most stable structure.

The delocalization of electrons results in the formation resonance structure.

Answer to Problem 16.6P

The second resonance structure for given species and its hybrid are,

The increasing order of stability for the given resonance structure is $\text{I}<\text{II}<\text{III}$.

Explanation of Solution

The given species is shown below.

Figure 3

Delocalization of electrons from one position to the other position result in the formation of resonance structure. Resonance hybrid is the combination of all resonating structures. Thus, resonance structures and resonance hybrid for the given species is shown below.

Figure 4

Better resonance structure is the one which has major contribution in the hybrid and others are minor contributors. Major contributor is the resonance structure in which negative charge is on more electronegative atom. The electronegativity of oxygen is more than nitrogen.

The Figure 4 shows that structure $\text{I}$, negative charge is on nitrogen atom, whereas in structure $\text{II}$, negative charge is on oxygen atom. Thus, the stability of structure $\text{I}$ is less than the structure $\text{II}$.

Therefore, the increasing order of stability for the given resonance structure is $\text{I}<\text{II}<\text{III}$.

Conclusion

The second resonance structure for given species and its hybrid is shown in Figure 4. The increasing order of stability for the given resonance structure is is $\text{I}<\text{II}<\text{III}$.

Interpretation Introduction

(c)

Interpretation: The second resonance structure for given species and its hybrid is to be drawn. The two resonance structure and the hybrid are to be ranked in order of increasing stability.

Concept introduction: Most of the organic structures cannot be represented using single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. These are the hypothetical structures and do not specify the exact structure. These resonance structure combine together to give resonance hybrid that is lower in energy and is the most stable structure.

The delocalization of electrons results in the formation resonance structure.

Answer to Problem 16.6P

The second resonance structure for given carbocation and its hybrid are,

The increasing order of stability for the given resonance structure is,

Explanation of Solution

The given species is shown below.

Figure 5

Delocalization of electrons from one position to the other position result in the formation of resonance structure. The resonance structure for the given species is shown below.

Figure 6

Resonance hybrid is the combination of all resonating structures. Thus, resonance hybrid for the given species is shown below.

Figure 7

Better resonance structure is the one which has major contribution in the hybrid and others are minor contributors. Major contributor is the resonance structure which possesses more bonds and fewer charges.

Therefore, the increasing order of stability for the given resonance structure is shown below.

Figure 8

Conclusion

The second resonance structure for given carbocation and its hybrid is shown in Figure 6 and 7. The increasing order of stability for the given resonance structure is shown in Figure 8.

Interpretation Introduction

(d)

Interpretation: The second resonance structure for given species and its hybrid is to be drawn. The two resonance structure and the hybrid are to be ranked in order of increasing stability.

Concept introduction: Most of the organic structures cannot be represented using single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. These are the hypothetical structures and do not specify the exact structure. These resonance structure combine together to give resonance hybrid that is lower in energy and is the most stable structure.

The delocalization of electrons results in the formation resonance structure.

Answer to Problem 16.6P

The second resonance structure for given carbocation and its hybrid are,

The increasing order of stability for the given resonance structure is,

Explanation of Solution

The given species is shown below.

Figure 9

Delocalization of electrons from one position to the other position result in the formation of resonance structure. The resonance structure for the given species is shown below.

Figure 10

Resonance hybrid is the combination of all resonating structures. Thus, resonance hybrid for the given species is shown below.

Figure 11

Better resonance structure is the one which has major contribution in the hybrid and others are minor contributors. Major contributor is the resonance structure which possesses more bonds and fewer charges.

The given Figure 2 shows that the left side structure does not contain double bond. Thus, the stability of left side structure is less than the right side structure.

Therefore, the increasing order of stability for the given resonance structure is shown below.

Figure 12

Conclusion

The second resonance structure for given carbocation and its hybrid is shown in Figure 10 and 11. The increasing order of stability for the given resonance structure is shown in Figure 12.