Chemistry & Chemical Reactivity
Chemistry & Chemical Reactivity
10th Edition
ISBN: 9781337399074
Author: John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher: Cengage Learning
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Chapter 8, Problem 33PS

Three resonance structures are possible for dinitrogen monoxide, N2O.

  1. (a) Draw the three resonance structures.
  2. (b) Calculate the formal charge on each atom in each resonance structure.
  3. (c) Based on formal charges and electronegativity, predict which resonance structure is the most reasonable.

(a)

Expert Solution
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Interpretation Introduction

Interpretation:

The three resonance structure of N2O has to be drawn.

Concept Introduction:

Resonance structures: A molecule or ion which show more than structure but none of them are accurately correct show the known property of that molecule, and can lie between the canonical structure is known as resonance or canonical or contributing structure.

Explanation of Solution

The three resonance structure is drawn

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  1

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

Formal charge on each atom in each resonance structure has to be calculated.

Concept Introduction:

Formal charge: It is the electrostatic charge that would reside on an atom in a molecule or polyatomic ion if all bonding electron are shared equally between pairs of atoms.

Formal charge calculation: The formal charge for atom in a molecule or ion is calculated based on the Lewis structure of the molecule or ion by following the given equation below:

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  2

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  3- Number of valence electrons

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  4- Number of non-bonding electrons

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  5- Number of bonding electrons

Explanation of Solution

The formal charges can be calculated as follows.

For resonance structure A is given below,

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  6

Formal charge on nitrogen1 can be calculated as follows.

FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onN(1)=5Number of nonbonding electrons=4Number of bonding electrons=4

FormalCharge=Nvalence-Nnon-bond-Nbond2=5-4-42=1

Formal charge on nitrogen2 can be calculated as follows.

 FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onN(2)=5Number of nonbonding electrons=0Number of bonding electrons=8

FormalCharge=Nvalence-Nnon-bond-Nbond2=5-0-82=+1

Formal charge on oxygen can be calculated as follows.

FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onO=6Number of nonbonding electrons=4Number of bonding electrons=4

FormalCharge=Nvalence-Nnon-bond-Nbond2=6-4-42=0

For resonance structure B is given below,

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  7

Formal charge on nitrogen1 can be calculated as follows.

FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onN(1)=5Number of nonbonding electrons=2Number of bonding electrons=6

FormalCharge=Nvalence-Nnon-bond-Nbond2=5-2-62=0

Formal charge on nitrogen2 can be calculated as follows.

 FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onN(2)=5Number of nonbonding electrons=0Number of bonding electrons=8

FormalCharge=Nvalence-Nnon-bond-Nbond2=5-0-82=+1

Formal charge on oxygen can be calculated as follows.

FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onO=6Number of nonbonding electrons=6Number of bonding electrons=2

FormalCharge=Nvalence-Nnon-bond-Nbond2=6-6-22=1

For resonance structure C, is given below,

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  8

Formal charge on nitrogen1 can be calculated as follows.

FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onN(1)=5Number of nonbonding electrons=6Number of bonding electrons=2

FormalCharge=Nvalence-Nnon-bond-Nbond2=5-6-22=2

Formal charge on nitrogen2 can be calculated as follows.

 FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onN(2)=5Number of nonbonding electrons=0Number of bonding electrons=8

FormalCharge=Nvalence-Nnon-bond-Nbond2=5-0-82=+1

Formal charge on oxygen can be calculated as follows.

FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onO=6Number of nonbonding electrons=2Number of bonding electrons=6

FormalCharge=Nvalence-Nnon-bond-Nbond2=6-2-62=+1

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

From the resonance structure drawn, the most reasonable structure has to be identified.

Concept Introduction:

Formal charge: It is the electrostatic charge that would reside on an atom in a molecule or polyatomic ion if all bonding electron are shared equally between pairs of atoms.

Formal charge calculation: The formal charge for atom in a molecule or ion is calculated based on the Lewis structure of the molecule or ion by following the given equation below:

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  9

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  10- Number of valence electrons

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  11- Number of non-bonding electrons

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  12- Number of bonding electrons

Resonance structures:

A molecule or ion which show more than structure but none of them are accurately correct show the known property of that molecule, and can lie between the canonical structure is known as resonance or canonical or contributing structure.

Explanation of Solution

The three resonance structure is drawn

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  13

  1. (a) The formal charges can be calculated as follows.

For resonance structure A

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  14

Formal charge on nitrogen1 can be calculated as follows.

FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onN(1)=5Number of nonbonding electrons=4Number of bonding electrons=4

FormalCharge=Nvalence-Nnon-bond-Nbond2=5-4-42=1

Formal charge on nitrogen2 can be calculated as follows.

 FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onN(2)=5Number of nonbonding electrons=0Number of bonding electrons=8

FormalCharge=Nvalence-Nnon-bond-Nbond2=5-0-82=+1

Formal charge on oxygen can be calculated as follows.

FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onO=6Number of nonbonding electrons=4Number of bonding electrons=4

FormalCharge=Nvalence-Nnon-bond-Nbond2=6-4-42=0

For resonance structure B

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  15

Formal charge on nitrogen1 can be calculated as follows.

FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onN(1)=5Number of nonbonding electrons=2Number of bonding electrons=6

FormalCharge=Nvalence-Nnon-bond-Nbond2=5-2-62=0

Formal charge on nitrogen2 can be calculated as follows.

 FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onN(2)=5Number of nonbonding electrons=0Number of bonding electrons=8

FormalCharge=Nvalence-Nnon-bond-Nbond2=5-0-82=+1

Formal charge on oxygen can be calculated as follows.

FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onO=6Number of nonbonding electrons=6Number of bonding electrons=2

FormalCharge=Nvalence-Nnon-bond-Nbond2=6-6-22=1

For resonance structure C

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  16

Formal charge on nitrogen1 can be calculated as follows.

FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onN(1)=5Number of nonbonding electrons=6Number of bonding electrons=2

FormalCharge=Nvalence-Nnon-bond-Nbond2=5-6-22=2

Formal charge on nitrogen2 can be calculated as follows.

 FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onN(2)=5Number of nonbonding electrons=0Number of bonding electrons=8

FormalCharge=Nvalence-Nnon-bond-Nbond2=5-0-82=+1

Formal charge on oxygen can be calculated as follows.

FormalCharge=Nvalence-Nnon-bond-Nbond2

Number of valence electrons onO=6Number of nonbonding electrons=2Number of bonding electrons=6

FormalCharge=Nvalence-Nnon-bond-Nbond2=6-2-62=+1

Thus from the formal charge given above, the Structure B is most reasonable

Chemistry & Chemical Reactivity, Chapter 8, Problem 33PS , additional homework tip  17

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