ORGANIC CHEMISTRY-OWL V2 ACCESS
ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582422
Author: Brown
Publisher: CENGAGE L
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Chapter 1, Problem 1.28P

Write Lewis structures for these ions. Show all valence electrons and all formal charges.

  1. (a) Amide ion, NH2
  2. (b) Bicarbonate ion, HCO3
  3. (c) Carbonate ion, CO32−
  4. (d) Nitrate ion, NO3
  5. (e) Formate ion, HCOO
  6. (f) Acetate ion, CH3COO

(a)

Expert Solution
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Interpretation Introduction

Interpretation:

Lewis structure of the ions, valence electron and formal charge has to be identified.

Concept introduction:

Lewis structure: The Lewis structure is based on the concept of the octet rule so that the electrons shared in each atom should have 8 electrons in its outer shell. Sometimes the chemical bonding of a molecule cannot be represented using a single Lewis structure. In these cases, the chemical bonding are described by delocalization of electrons and is known as resonance. All the possible resonance structures are imaginary whereas the resonance hybrid is real. These structures will differ only in the arrangement of the electrons not in the relative position of the atomic nuclei.

Valence shell:

The outer most shell of the element is called as valence shell.

Valence electron:

The electrons present in the outer shell are called valence electron.

For example:

Nitrogen element has seven electrons and it has two shells, the second shell is the valence shell and it has five electrons in the valence shell. The five electrons are called as valence electrons.

Formal charge:

The charge on an atom in a molecule is called its formal charge.

Formal charge can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Explanation of Solution

The given ion is amide ion,

NH2-

First the skeletal structure for the given molecule is drawn then the total number of valence electrons for all atoms present in the molecule is determined. The next step is to subtract the electrons present in the total number of bonds present in the skeletal structure of the molecule with the total valence electrons such that considering each bond contains two electrons with it. Finally, the electrons which got after subtractions have to be equally distributed such that each atom contains eight electrons in its valence shell.

The valence electron for the hydrogen atom is one, the valence electron for the nitrogen is five, therefore, and the Lewis structure of the ion is given below,

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 1, Problem 1.28P , additional homework tip  1

Formal charge can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Formal charge= 5[2 + 2]Formal charge= 1

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The Lewis structure of the ions, valence electron and formal charge has to be identified.

Concept introduction:

Lewis structure: The Lewis structure is based on the concept of the octet rule so that the electrons shared in each atom should have 8 electrons in its outer shell. Sometimes the chemical bonding of a molecule cannot be represented using a single Lewis structure. In these cases, the chemical bonding are described by delocalization of electrons and is known as resonance. All the possible resonance structures are imaginary whereas the resonance hybrid is real. These structures will differ only in the arrangement of the electrons not in the relative position of the atomic nuclei.

Valence shell:

The outer most shell of the element is called as valence shell.

Valence electron:

The electrons present in the outer shell are called valence electron.

For example:

Nitrogen element has seven electrons and it has two shells, the second shell is the valence shell and it has five electrons in the valence shell. The five electrons are called as valence electrons.

Formal charge:

The charge on an atom in a molecule is called its formal charge.

Formal charge can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Explanation of Solution

The given ion is bicarbonate ion,

HCO3-

First the skeletal structure for the given molecule is drawn then the total number of valence electrons for all atoms present in the molecule is determined. The next step is to subtract the electrons present in the total number of bonds present in the skeletal structure of the molecule with the total valence electrons such that considering each bond contains two electrons with it. Finally, the electrons which got after subtractions have to be equally distributed such that each atom contains eight electrons in its valence shell.

The valence electron for the hydrogen atom is one, the valence electron for the carbon is four and valence electron of oxygen is six, therefore, and the Lewis structure of the ion is given below,

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 1, Problem 1.28P , additional homework tip  2

Formal charge can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Formal charge= 6[6 + 1]Formal charge= 1

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The Lewis structure of the ions, valence electron and formal charge has to be identified.

Concept introduction:

Lewis structure: The Lewis structure is based on the concept of the octet rule so that the electrons shared in each atom should have 8 electrons in its outer shell. Sometimes the chemical bonding of a molecule cannot be represented using a single Lewis structure. In these cases, the chemical bonding are described by delocalization of electrons and is known as resonance. All the possible resonance structures are imaginary whereas the resonance hybrid is real. These structures will differ only in the arrangement of the electrons not in the relative position of the atomic nuclei.

Valence shell:

The outer most shell of the element is called as valence shell.

Valence electron:

The electrons present in the outer shell are called valence electron.

For example:

Nitrogen element has seven electrons and it has two shells, the second shell is the valence shell and it has five electrons in the valence shell. The five electrons are called as valence electrons.

Formal charge:

The charge on an atom in a molecule is called its formal charge.

Formal charge can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Explanation of Solution

The given ion is carbonate ion,

CO32-

First the skeletal structure for the given molecule is drawn then the total number of valence electrons for all atoms present in the molecule is determined. The next step is to subtract the electrons present in the total number of bonds present in the skeletal structure of the molecule with the total valence electrons such that considering each bond contains two electrons with it. Finally, the electrons which got after subtractions have to be equally distributed such that each atom contains eight electrons in its valence shell.

The valence electron the carbon is four and valence electron of oxygen is six, therefore, and the Lewis structure of the ion is given below,

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 1, Problem 1.28P , additional homework tip  3

Formal charge can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Formal charge= 2×6[2(6 + 1)]Formal charge= 2

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The Lewis structure of the ions, valence electron and formal charge has to be identified.

Concept introduction:

Lewis structure: The Lewis structure is based on the concept of the octet rule so that the electrons shared in each atom should have 8 electrons in its outer shell. Sometimes the chemical bonding of a molecule cannot be represented using a single Lewis structure. In these cases, the chemical bonding are described by delocalization of electrons and is known as resonance. All the possible resonance structures are imaginary whereas the resonance hybrid is real. These structures will differ only in the arrangement of the electrons not in the relative position of the atomic nuclei.

Valence shell:

The outer most shell of the element is called as valence shell.

Valence electron:

The electrons present in the outer shell are called valence electron.

For example:

Nitrogen element has seven electrons and it has two shells, the second shell is the valence shell and it has five electrons in the valence shell. The five electrons are called as valence electrons.

Formal charge:

The charge on an atom in a molecule is called its formal charge.

Formal charge can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Explanation of Solution

The given ion is nitrate ion,

NO3-

First the skeletal structure for the given molecule is drawn then the total number of valence electrons for all atoms present in the molecule is determined. The next step is to subtract the electrons present in the total number of bonds present in the skeletal structure of the molecule with the total valence electrons such that considering each bond contains two electrons with it. Finally, the electrons which got after subtractions have to be equally distributed such that each atom contains eight electrons in its valence shell.

The valence electron for the nitrogen atom is five, the valence electron for the carbon is four and valence electron of oxygen is six, therefore, and the Lewis structure of the ion is given below,

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 1, Problem 1.28P , additional homework tip  4

Formal charge for nitrogen atom can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Formal charge= 5[0 + 4]Formal charge= 1

Formal charge for oxygen can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Formal charge= 2×6[2(6 + 1)]Formal charge= 2

(e)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The Lewis structure of the ions, valence electron and formal charge has to be identified.

Concept introduction:

Lewis structure: The Lewis structure is based on the concept of the octet rule so that the electrons shared in each atom should have 8 electrons in its outer shell. Sometimes the chemical bonding of a molecule cannot be represented using a single Lewis structure. In these cases, the chemical bonding are described by delocalization of electrons and is known as resonance. All the possible resonance structures are imaginary whereas the resonance hybrid is real. These structures will differ only in the arrangement of the electrons not in the relative position of the atomic nuclei.

Valence shell:

The outer most shell of the element is called as valence shell.

Valence electron:

The electrons present in the outer shell are called valence electron.

For example:

Nitrogen element has seven electrons and it has two shells, the second shell is the valence shell and it has five electrons in the valence shell. The five electrons are called as valence electrons.

Formal charge:

The charge on an atom in a molecule is called its formal charge.

Formal charge can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Explanation of Solution

The given ion is formate ion,

HCO2-

First the skeletal structure for the given molecule is drawn then the total number of valence electrons for all atoms present in the molecule is determined. The next step is to subtract the electrons present in the total number of bonds present in the skeletal structure of the molecule with the total valence electrons such that considering each bond contains two electrons with it. Finally, the electrons which got after subtractions have to be equally distributed such that each atom contains eight electrons in its valence shell.

The valence electron for the hydrogen atom is one, the valence electron for the carbon is four and valence electron of oxygen is six, therefore, and the Lewis structure of the ion is given below,

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 1, Problem 1.28P , additional homework tip  5

Formal charge can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Formal charge= 6[6 + 1]Formal charge= 1

(f)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The Lewis structure of the ions, valence electron and formal charge has to be identified.

Concept introduction:

Lewis structure: The Lewis structure is based on the concept of the octet rule so that the electrons shared in each atom should have 8 electrons in its outer shell. Sometimes the chemical bonding of a molecule cannot be represented using a single Lewis structure. In these cases, the chemical bonding are described by delocalization of electrons and is known as resonance. All the possible resonance structures are imaginary whereas the resonance hybrid is real. These structures will differ only in the arrangement of the electrons not in the relative position of the atomic nuclei.

Valence shell:

The outer most shell of the element is called as valence shell.

Valence electron:

The electrons present in the outer shell are called valence electron.

For example:

Nitrogen element has seven electrons and it has two shells, the second shell is the valence shell and it has five electrons in the valence shell. The five electrons are called as valence electrons.

Formal charge:

The charge on an atom in a molecule is called its formal charge.

Formal charge can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Explanation of Solution

The given ion is acetate ion,

CH3CO2-

First the skeletal structure for the given molecule is drawn then the total number of valence electrons for all atoms present in the molecule is determined. The next step is to subtract the electrons present in the total number of bonds present in the skeletal structure of the molecule with the total valence electrons such that considering each bond contains two electrons with it. Finally, the electrons which got after subtractions have to be equally distributed such that each atom contains eight electrons in its valence shell.

The valence electron for the hydrogen atom is one, the valence electron for the carbon is four and valence electron of oxygen is six, therefore, and the Lewis structure of the ion is given below,

ORGANIC CHEMISTRY-OWL V2 ACCESS, Chapter 1, Problem 1.28P , additional homework tip  6

Formal charge can be calculated by using following formula,

 Number of valence electrons in the neutral, unboned atomFormal charge=                                            -[All unshared electrons shared electrons + One half of all shared electrons]

Formal charge= 6[6 + 1]Formal charge= 1

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Chapter 1 Solutions

ORGANIC CHEMISTRY-OWL V2 ACCESS

Ch. 1.3 - Prob. 1.11PCh. 1.3 - Prob. 1.12PCh. 1.4 - Predict all bond angles for these molecules. (a)...Ch. 1.5 - The geometry of carbon in diamond is tetrahedral,...Ch. 1.5 - Because of their spherical shape, C60 molecules...Ch. 1.5 - What best describes the CCC bond angles in C60? 1....Ch. 1.5 - Prob. 1.14PCh. 1.7 - Describe the bonding in these molecules in terms...Ch. 1.8 - Prob. 1.16PCh. 1.8 - Prob. 1.17PCh. 1.8 - Prob. 1.18PCh. 1.9 - Draw three contributing structures of the...Ch. 1.9 - What is the hybridization state of the circled...Ch. 1.9 - The molecule shown on the right in the example in...Ch. 1.9 - Prob. CQCh. 1.9 - The following structure is called imidazolium....Ch. 1 - Write the ground-state electron configuration for...Ch. 1 - Identify the atom that has each ground-state...Ch. 1 - Define valence shell and valence electron.Ch. 1 - How many electrons are in the valence shell of...Ch. 1 - Prob. 1.24PCh. 1 - Prob. 1.25PCh. 1 - Prob. 1.26PCh. 1 - Write Lewis structures for these compounds. Show...Ch. 1 - Write Lewis structures for these ions. Show all...Ch. 1 - Prob. 1.29PCh. 1 - Some of these structural formulas are incorrect...Ch. 1 - Following the rule that each atom of carbon,...Ch. 1 - Following are several Lewis structures showing all...Ch. 1 - Which statements are true about electronegativity?...Ch. 1 - Why does fluorine, the element in the upper right...Ch. 1 - Arrange the single covalent bonds within each set...Ch. 1 - Using the values of electronegativity given in...Ch. 1 - Prob. 1.37PCh. 1 - Use VSEPR to predict bond angles about each...Ch. 1 - Use VSEPR to predict bond angles about each atom...Ch. 1 - Use VSEPR to predict the geometry of these ions....Ch. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - What is the meaning of the term tertiary (3) when...Ch. 1 - What is the meaning of the term tertiary (3) when...Ch. 1 - Draw structural formulas for (a) The four primary...Ch. 1 - Draw structural formulas for the three tertiary...Ch. 1 - Prob. 1.47PCh. 1 - Identify the functional groups in each compound.Ch. 1 - Draw a three-dimensional representation for each...Ch. 1 - Tetrafluoroethylene, C2F4, is the starting...Ch. 1 - Which statements are true about resonance...Ch. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Are the structures in each set valid contributing...Ch. 1 - State the orbital hybridization of each...Ch. 1 - Describe each highlighted bond in terms of the...Ch. 1 - Following is a structural formula of the...Ch. 1 - Draw a Lewis structure for methyl isocyanate,...Ch. 1 - What is the hybridization of the highlighted atoms...Ch. 1 - Using cartoon representations, draw a molecular...Ch. 1 - In what kind of orbitals do the lone-pair...Ch. 1 - Draw the delocalized molecular orbitals for the...Ch. 1 - Prob. 1.64APCh. 1 - Each compound contains both ions and covalent...Ch. 1 - Predict whether the carbon-metal bond in these...Ch. 1 - Prob. 1.67APCh. 1 - Phosphorus is immediately under nitrogen in the...Ch. 1 - Draw a Lewis structure for the azide ion, N3. (The...Ch. 1 - Cyanic acid, HOCN, and isocyanic acid, HNCO,...Ch. 1 - In Chapter 6, we study a group of organic cations...Ch. 1 - Many reactions involve a change in hybridization...Ch. 1 - Following is a structural formula of benzene,...Ch. 1 - Following are three contributing structures for...Ch. 1 - (a) Draw a Lewis structure for the ozone molecule,...Ch. 1 - The following two compounds are isomers; that is,...Ch. 1 - In future chapters, we will encounter...Ch. 1 - Prob. 1.78AP
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