Chemistry
Chemistry
4th Edition
ISBN: 9780393919370
Author: Thomas R. Gilbert
Publisher: NORTON
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Chapter 8, Problem 8.88QP

(a)

Interpretation Introduction

To determine: The lewis structure for CH3NO2 .

(a)

Expert Solution
Check Mark

Answer to Problem 8.88QP

Solution

The lewis structure for CH3NO2 is shown in Figure 1.

Explanation of Solution

Explanation

Number of valence electrons in hydrogen is 1 , number of valence electrons in nitrogen is 5 and number of valence electrons in carbon is 4 . There is one carbon atom, three hydrogen atoms, one nitrogen atom and two oxygen atoms present in CH3NO2 , therefore the total valence electrons are =4+(3×1)+5+(2×6)=24

Carbon is bonded to three hydrogen atoms and nitrogen atom by single bond. With one oxygen, nitrogen is bonded by single bond while with other oxygen, it is bonded by double bond. Lone pairs of electrons present on oxygen atoms are delocalized which results in the formation of another lewis structure. Hence the lewis structure of CH3NO2 is,

Chemistry, Chapter 8, Problem 8.88QP , additional homework tip  1

Figure 1

(b)

Interpretation Introduction

To determine: The lewis structure for. CNNO2 ; formal charge on each atom of CNNO2 and the structure more likely to exist.

(b)

Expert Solution
Check Mark

Answer to Problem 8.88QP

Solution

The lewis structures for. CNNO2 is shown in Figure 4 and Figure 5. The formal charge on each atom of CNNO2 is calculated. Both the resonating structures are preferred.

Explanation of Solution

Explanation

The two given possible skeletal for CNNO2 are,

Chemistry, Chapter 8, Problem 8.88QP , additional homework tip  2

Figure 2

Chemistry, Chapter 8, Problem 8.88QP , additional homework tip  3

Figure 3

In the first skeletal, the nitrogen of CN group is bonded with NO2 group while in the second skeletal, carbon of CN group is bonded with NO2 group.

Number of valence electrons in carbon is 4 , number of valence electrons in nitrogen is 5 and number of valence electrons in oxygen is 6 . There is one carbon atom, two nitrogen atom and two oxygen atoms present in first skeletal ( CNNO2 ), therefore the total valence electrons are =4+(5×2)+(6×2)=26

With one oxygen atom, nitrogen is bonded by single bond while with other oxygen; it is bonded by double bond. Lone pairs of electrons present on oxygen atoms are delocalized which results in the formation of another lewis structure. Hence the lewis structure of CNNO2 is,

Chemistry, Chapter 8, Problem 8.88QP , additional homework tip  4

Figure 4

The formal charge on each atom of resonating structure (I) of CNNO2 is calculated by the formula,

Formal charge is calculated as,

Formalcharge=(Valenceelectrons(Lonepairelectrons+12Bondpairelectrons)) (1)

Number of valence electrons in first nitrogen is 5 .

Number of lone pair electrons in first nitrogen is 0 .

Number of bond pair electrons in first nitrogen is 8 .

To calculate the formal charge on first nitrogen, substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=5(0+12(8))=+1

Number of valence electrons in carbon is 4 .

Number of lone pair electrons in carbon is 2 .

Number of bond pair electrons in carbon is 6 .

To calculate the formal charge on carbon, substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=4(2+12(6))=1

Number of valence electrons in second nitrogen is 5 .

Number of lone pair electrons in second nitrogen is 0 .

Number of bond pair electrons in second nitrogen is 8 .

To calculate the formal charge on second nitrogen, substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=5(0+12(8))=+1

Number of valence electrons in oxygen (1) is 6 .

Number of lone pair electrons in oxygen (1) is 4 .

Number of bond pair electrons in oxygen (1) is 4 .

To calculate the formal charge on oxygen (1), substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=6(4+12(4))=0

Number of valence electrons in oxygen (2) is 6 .

Number of lone pair electrons in oxygen (2) is 6 .

Number of bond pair electrons in oxygen (2) is 2 .

To calculate the formal charge on oxygen (2), substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=6(6+12(2))=1

The formal charge on each atom of resonating structure (II) of CNNO2 is calculated as,

Number of valence electrons in first nitrogen is 5 .

Number of lone pair electrons in first nitrogen is 0 .

Number of bond pair electrons in first nitrogen is 8 .

To calculate the formal charge on first nitrogen, substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=5(0+12(8))=+1

Number of valence electrons in carbon is 4 .

Number of lone pair electrons in carbon is 2 .

Number of bond pair electrons in carbon is 6 .

To calculate the formal charge on carbon, substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=4(2+12(6))=1

Number of valence electrons in second nitrogen is 5 .

Number of lone pair electrons in second nitrogen is 0 .

Number of bond pair electrons in second nitrogen is 8 .

To calculate the formal charge on second nitrogen, substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=5(0+12(8))=+1

Number of valence electrons in oxygen (1) is 6 .

Number of lone pair electrons in oxygen (1) is 6 .

Number of bond pair electrons in oxygen (1) is 2 .

To calculate the formal charge on oxygen (1), substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=6(6+12(2))=1

Number of valence electrons in oxygen (2) is 6 .

Number of lone pair electrons in oxygen (2) is 4 .

Number of bond pair electrons in oxygen (2) is 4 .

To calculate the formal charge on oxygen (2), substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=6(4+12(4))=0

Number of valence electrons in carbon is 4 , number of valence electrons in nitrogen is 5 and number of valence electrons in oxygen is 6 . There is one carbon atom, two nitrogen atom and two oxygen atoms present in first skeletal ( NCNO2 ), therefore the total valence electrons are 4+5×2+6×2=26 . With one oxygen atom, nitrogen is bonded by single bond while with other oxygen; it is bonded by double bond. Lone pairs of electrons present on oxygen atoms are delocalized which results in the formation of another lewis structure. Hence the lewis structure of NCNO2 is,

Chemistry, Chapter 8, Problem 8.88QP , additional homework tip  5

Figure 5

The formal charge on each atom of resonating structure (I) of NCNO2 is calculated as,

Number of valence electrons in first nitrogen is 5 .

Number of lone pair electrons in first nitrogen is 2 .

Number of bond pair electrons in first nitrogen is 6 .

To calculate the formal charge on first nitrogen, substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=5(2+12(6))=0

Number of valence electrons in carbon is 4 .

Number of lone pair electrons in carbon is 0 .

Number of bond pair electrons in carbon is 8 .

To calculate the formal charge on carbon, substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=4(0+12(8))=0

Number of valence electrons in second nitrogen is 5 .

Number of lone pair electrons in second nitrogen is 0 .

Number of bond pair electrons in second nitrogen is 8 .

To calculate the formal charge on second nitrogen, substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=5(0+12(8))=+1

Number of valence electrons in oxygen (1) is 6 .

Number of lone pair electrons in oxygen (1) is 4 .

Number of bond pair electrons in oxygen (1) is 4 .

To calculate the formal charge on oxygen (1), substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=6(4+12(4))=0

Number of valence electrons in oxygen (2) is 6 .

Number of lone pair electrons in oxygen (2) is 6 .

Number of bond pair electrons in oxygen (2) is 2 .

To calculate the formal charge on oxygen (2), substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=6(6+12(2))=1

The formal charge on each atom of resonating structure (II) of NCNO2 is calculated as,

Number of valence electrons in first nitrogen is 5 .

Number of lone pair electrons in first nitrogen is 2 .

Number of bond pair electrons in first nitrogen is 6 .

To calculate the formal charge on first nitrogen, substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=5(2+12(6))=0

Number of valence electrons in carbon is 4 .

Number of lone pair electrons in carbon is 0 .

Number of bond pair electrons in carbon is 8 .

To calculate the formal charge on carbon, substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=4(0+12(8))=0

Number of valence electrons in second nitrogen is 5 .

Number of lone pair electrons in second nitrogen is 0 .

Number of bond pair electrons in second nitrogen is 8 .

To calculate the formal charge on second nitrogen, substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=5(0+12(8))=+1

Number of valence electrons in oxygen (1) is 6 .

Number of lone pair electrons in oxygen (1) is 6 .

Number of bond pair electrons in oxygen (1) is 2 .

To calculate the formal charge on oxygen (1), substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=6(6+12(2))=1

Number of valence electrons in oxygen (2) is 6 .

Number of lone pair electrons in oxygen (2) is 4 .

Number of bond pair electrons in oxygen (2) is 4 .

To calculate the formal charge on oxygen (2), substitute the value of valence electrons, lone pair electrons and bond pair electrons in the equation (1).

Formalcharge=6(4+12(4))=0

The resonating structure which possesses zero or minimum formal charge is preferred. The distribution of formal charges on both the molecules CNNO2 and NCNO2 is same. Hence both the resonating structures are preferred.

(c)

Interpretation Introduction

To determine: Whether the given two structures of CNNO2 are resonance forms of each other.

(c)

Expert Solution
Check Mark

Answer to Problem 8.88QP

Solution

The two structures of CNNO2 are not resonance forms of each other.

Explanation of Solution

Explanation

In the resonating forms, the postion of atoms remains same. But in the two structures of CNNO2 , the postion of carbon and nitrogen is not same. Hence the two structures of CNNO2 are not resonance forms of each other.

Conclusion

The two structures of CNNO2 are not resonance forms of each other.

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Chapter 8 Solutions

Chemistry

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