Lecture Presentation

Chapter 8

Basic Concepts of
Chemical Bonding

James F. Kirby
Quinnipiac University
Hamden, CT
© 2015 Pearson Education, Inc.
 LEARNING OBJECTIVES
1. Lewis Symbols and the Octet Rule Learn about the three main
types of chemical bonds: ionic, covalent, and metallic. In evaluating
bonding, Lewis symbols provide a useful shorthand for keeping
track of valence electrons. We learn that atoms usually follow the
octet rule.
2. Ionic Bonding Explore ionic substances, substances in which atoms
are held together by the electrostatic attractions between ions of
opposite charge. Analyze the energetics of forming ionic
substances and describe the lattice energy of these substances.
3. Covalent Bonding Examine the bonding in molecular substances, in
which atoms bond by sharing one or more electron pairs. In general,
the electrons are shared in such a way that each atom attains an
octet of electrons.
 LEARNING OBJECTIVES
4. Bond Polarity and Electronegativity Learn that electronegativity is
the ability of an atom in a compound to attract electrons to itself. In
general, electron pairs are shared unequally between atoms with
different electronegativities, leading to polar covalent bonds.
5. Drawing Lewis Structures Learn that Lewis structures are a simple
yet powerful way of predicting covalent bonding patterns in molecules.
In addition to the octet rule, see how the concept of formal charge can
be used to identify the dominant Lewis structure.
6. Resonance Structures Learn that in some cases, more than one
equivalent Lewis structure can be drawn for a molecule or polyatomic
ion. The bonding description in such cases is a blend of two or more
resonance structures.
 LEARNING OBJECTIVES
7. Exceptions to the Octet Rule Recognize that the octet rule is
more of a guideline than an absolute rule. Exceptions to the rule
include molecules with an odd number of electrons, molecules where
large differences in electronegativity prevent an atom from
completing its octet, and molecules where an element from period 3
or below in the periodic table attains more than an octet of
electrons.
8. Strengths and Lengths of Covalent Bonds Observe that bond
strengths and lengths vary with the number of shared electron
pairs as well as other factors.
 Chemical Bonds

Three basic types of bonds:

Ionic
Electrostatic attraction between ions

Covalent
Sharing of electrons

Metallic
Metal atoms bonded to several other atom

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 Lewis Symbols

▪ G. N. Lewis developed a method to denote potential bonding electrons by

using one dot for every valence electron around the element symbol.

Basic Concept s
▪ When forming compounds, atoms tend to gain, lose, or share electrons until
of Chemical
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they are surrounded by eight valence electrons (the octet rule).
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 Ionic Formation
Atoms tend to lose (metals) or gain (nonmetals) electrons to make
them iso-electronic to the noble gases.

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 Lattice Energy is the energy required to break apart an ionic solid and
convert its component atoms into gaseous ions.

This definition causes the value for the lattice energy to always be
positive, since this will always be an endothermic reaction.

NaCl(s) → Na+(g) + Cl-(g) ∆H = Lattice Energy

Endothermic Reaction

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 Energetics of Ionic Bonding-
Born-Haber Cycle
Many factors affect the energy of ionic bonding.
Start with the metal & nonmetal elements:
Na(s) and Cl2(g

Make gaseous atoms:

Na(g) and Cl(g)

Make ions:
Na+(g) and Cl–(g)
Combine the ions: NaCl(s) Basic C oncepts
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 Energetics of Ionic Bonding
▪ We already discussed making ions (ionization energy and electron
affinity).

▪ It takes energy to convert the elements to gaseous atoms

(endothermic)

▪ It takes energy to create a cation (endothermic).

▪ Energy is released by making the anion (exothermic).

▪ The formation of the solid releases a huge amount of energy

(exothermic).

▪ This makes the formation of salts from the elements exothermic.

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 Lattice Energy
▪ That huge, exothermic transition is the reverse of the lattice energy
the energy required to completely separate a mole of a solid ionic
compound into its gaseous ions.

▪ The energy associated with electrostatic interactions is governed

by Coulomb’s law:

 Q 1 Q 2
Eel =
d

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 Lattice Energy
Lattice energy increases ↑ with:

▪ increasing charge on the ions↑

▪ decreasing size of ions↓

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 Ionic Bonding and Transition Metals

I1 < I2 < I3: up to 3 electrons can be lost and compensated by

lattice energy of the compounds
So most of the cations in ionic compounds have +1, +2 and +3
charges.

Transition metals can lose > 3 electrons: because they have electrons in d
orbitals 1 B group elements : Cu, Ag, Au
Ag: [Kr] 4d10 5s1
Lose one electron in 5s shell and becomes completely d subshell.

Transition metals do not form ions in noble gas configuration

Basic Concepts
so octet rule does not apply to transition metals of C hemical
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 Ionic Bonding and Transition Metals

Remember chapter 7 !!
Electrons are lost from higher orbitals: shell with highest value of n

in forming ions, transition metals lose the valence-shell s electrons first,

then as many d electrons as required to reach the charge of the ion.

Fe: [Ar]3d64s2
Fe2+ : [Ar] 3d 6
Fe3+: [Ar]3d5

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 Basic Concepts
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 Covalent Bonding

In covalent bonds, atoms share electrons.

There are several electrostatic interactions

in these bonds:

▪ attractions between electrons and nuclei

▪ repulsions between electrons

▪ repulsions between nuclei

For a bond to form, the attractions must be

greater than the repulsions. Basic Concepts
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Chemical Bonds
 Questions
Label the following as either ionic or covalent bonded molecules.
F2 :
LiBr :
CH3CH3 :
NaNH2 :
How many bonds are predicted for each atom.
O:
Al:
Br:
 Lewis Structures
▪ Sharing electrons to make covalent bonds can be demonstrated
using Lewis structures.

▪ Give each atom the same number of electrons as the nearest

noble gas by sharing electrons.

▪ The simplest examples are for hydrogen, H2, and chlorine, Cl2, shown
below.

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 Electrons on Lewis Structures
▪ Lone pairs: electrons located on only one atom in a Lewis
structure
▪ Bonding pairs: shared electrons in a Lewis structure; they can
be represented by two dots or one line

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 Multiple Bonds
▪ Some atoms share only one pair of electrons. These bonds are called
single bonds
▪ Sometimes, two pairs of electrons need to be shared. These are
called double bonds

▪ There are even cases where three pair of electrons are shared
between two atoms. These are called triple bonds

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 Polar Covalent Bonds
The electrons in a covalent bond are not always shared equally.
▪ Fluorine pulls harder on the electrons it shares with hydrogen than
hydrogen does.
▪ Therefore, the fluorine end of the molecule has more electron
density than the hydrogen end

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 Electronegativity
❖ Electronegativity is the ability of an atom in a molecule to attract
electrons to itself.

❖ The greater an atom’s electronegativity the greater its ability to

attract electrons itself.
❖ Electronegativity is related with
➢ ionization energy
➢ electron affinity

An atom with a very high negative electron affinity and a high

ionization energy both attracts electrons from other atoms and
resists having its electrons attracted away; therefore it is highly
electronegative. Basic Concepts
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 Electronegativity

❖ On the periodic table, electronegativity generally increases as you go

➢ from left to right across a period
➢ from the bottom to the top of a group

Ionization energies decrease↓ with increasing ↑ atomic number electron

affinities do not change very much in a group

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▪ Know the trends !! Bonding
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 Electronegativity and Polar Covalent Bonds

▪ When two atoms share electrons unequally, a polar covalent bond

results.

▪ Electrons tend to spend more time around the more electronegative

atom. The result is a partial negative charge (not a complete
transfer of charge). It is represented by δ–.

▪ The other atom is “more positive,” or δ+.

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 Polar Covalent Bonds

Going down group:

▪ Electronegativity difference decrease ↓
▪ Bond length increases ↑
▪ HI less polar than HF

The greater the difference in electronegativity, the more

Basic Concepts
polar is the bond. of Chemical
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 Dipoles
▪ When two equal, but opposite charges are separated by a distance,
a dipole forms.
▪ A dipole moment, , produced by two equal but opposite charges
separated by a distance, r, is calculated:
▪  = Qr
▪ It is measured in debyes (D).

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 Dipoles
▪ Polar covalent bond: electronegativity difference
▪ Electron density: toward flourine atom
▪ Crossed arrow: plus sign
▪ Polarity: properties of atoms at macroscopic level in laboratory
and every day life

▪ Interactions of liquids, solids and solutions

Alignment of polar molecules

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 Is a Compound Ionic or Covalent?
Metal + Nonmetal : ionic
Simple Approach :
Non-metal + Non-metal : covalent

▪ Electronegativity difference can be used

▪ Properties of compounds are often best: Lower melting
points mean covalent bonding
▪ Electrolyte: Ionic, Non-electrolyte: Covalent

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 Writing Lewis Structures
(Covalent Molecules)

1. Sum the valence electrons from all atoms, taking into account
overall charge.

✓ If it is an anion, add one electron for each negative charge.

✓ If it is a cation, substract one electron for each positive charge.

Keep track of the electrons:

PCl3
5 + 3(7) = 26

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 Writing Lewis Structures
2. Write the symbols for the atoms, show which atoms are attached
to which, and connect them with a single bond (a line
representing two electrons).

Keep track of the electrons:

26 − 6 = 20

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 Writing Lewis Structures
3. Complete the octets around all atoms bonded to the central atom.

Keep track of the electrons:

26 − 6 = 20
20 − 18 = 2

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 Writing Lewis Structures
4. Place any leftover electrons on the central atom.

Keep track of the electrons:

26 − 6 = 20
20 − 18 = 2
2−2=0

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 Writing Lewis Structures
5. If there are not enough electrons to give the central atom an
octet, try multiple bonds.

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 Writing Lewis Structures
6. Assign formal charges.
Formal charge: charge an atom would have if all of the electrons in a
covalent bond were shared equally.

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 Writing Lewis Structures
▪ The dominant Lewis Structure
✓ is the one in which atoms have formal charges closest to zero
✓ puts a negative formal charge on the most electro-negative atom

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 The Best Lewis Structure?
▪ Following our rules, this is the Lewis structure we would draw for
ozone, O3.

▪ However, it doesn’t agree with what is observed in nature: Both

O to O connections are the same.

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 Homework
Write the Lewis formulas for each of the following structures containing
double or triple bonds.
a) Cl2CO
b) C2Cl4
c) C3H4O
d) C2H4O2
e) CH3NH2
f) CH3F
 Formal Charge
• Formal charge is the charge assigned to individual atoms in a Lewis
structure.
• By calculating formal charge, we determine how the number of electrons
around a particular atom compares to its number of valence electrons.
Formal charge is calculated as follows:

• The number of electrons “owned” by an atom is determined by its number

of bonds and lone pairs.
• An atom “owns” all of its unshared electrons and half of its shared
electrons.
 Formal Charge

• The number of electrons “owned” by different atoms is indicated in the

following examples:
Formal Charge
Formal Charge
 Formal Charge

• Draw the Lewis structure for CH5N.

• Arrange H’s around periphery.
• Count valence electrons.
• 1C x 4 e-s = 4
• 5H x 1 e- = 5
• 1N x 5 e-s = 5
• total e-s = 14
• Assign 2 e-s to each bond to hydrogen and fill the octets of the other atoms
 Formal Charge

• Draw the Lewis structure for HCN.

• Arrange H’s around periphery. H C N
• Count valence electrons.
• 1C x 4 e-s = 4
• 1H x 1 e- = 1
• 1N x 5 e-s = 5
• total e-s = 10
• Assign 2 e-s to each bond to hydrogen and fill the octets of the other atoms
 Formal Charge
1. Draw the Lewis structure for Nitronium, NO2+, ion.
2. Draw the Lewis structure for Nitrosyl chloride, NOCl.
 Isomers
In drawing a Lewis structure for a molecule with several atoms, sometimes
more than one arrangement of atoms is possible for a given molecular
formula.

Both are valid Lewis structures and both molecules exist. These two
compounds are called isomers. Isomers are different molecules having the
same molecular formula. Ethanol and dimethyl ether are constitutional
isomers.
 Isomers
C4H10’s constitutional isomers:
CH3
ǀ
CH3CH2CH2CH3 CH3CHCH3
Butane, bp: -0.5°C Metylpropane, bp: -12°C

OH
ǀ
CH3CH2CH2OH CH3CHCH3
1-propanol, bp: 97°C 2-propanol, bp: 82°C

CH2=CHCH2CH3 CH2CH=CHCH3
1-butene, bp: -6.3°C 2-butene, bp: 3.7°C
 Isomers
Which of the following compounds represent isomers of each other?
 Isomers
Which of the following pairs of formulas represent isomers and which
represent the same compound?
 Resonance

▪ One Lewis structure cannot accurately depict

a molecule like ozone.

▪ We use multiple structures, resonance

structures to describe the molecule.

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 Resonance
▪ The organic compound benzene (C6H6) has two resonance
structures.

▪ It is commonly depicted as a hexagon with a circle inside to signify

the delocalized electrons in the ring.

▪ Localized electrons: are specifically on one atom or shared between

two atoms Basic Concepts
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▪ Delocalized electrons: shared by multiple atoms. Bonding
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 Resonance
All contributing structures must
1. have the same number of valence electrons
2. obey the rules of covalent bonding
–no more than 2 electrons in the valence shell of H
–no more than 8 electrons in the valence shell of a 2nd period
element
–3rd period elements, such as P and S, may have up to 12
electrons in their valence shells
3. differ only in distribution of valence electrons; the position of
all nuclei must be the same
4. have the same number of paired and unpaired electrons
 Resonance
The carbonate ion, for example
–a hybrid of three equivalent contributing structures
–the negative charge is distributed equally among the three
oxygens
 Resonance
Preference 1:filled valence shells
structures in which all atoms have filled valence shells
contribute more than those with one or more unfilled valence
shells.
 Resonance
Preference 2: maximum number of covalent bonds
structures with a greater number of covalent bonds contribute
more than those with fewer covalent bonds
 Resonance
Preference 3:least separation of unlike charge
structures with separation of unlike charges contribute less than
those with no charge separation
 Resonance
Preference 4: negative charge on the more electronegative atom
structures that carry a negative charge on the more
electronegative atom contribute more than those with the
negative charge on the less electronegative atom
Resonance
Resonance
 Resonance Hybrids

•A resonance hybrid is a composite of all possible resonance

structures. In the resonance hybrid, the electron pairs drawn in
different locations in individual resonance forms are
delocalized.
•When two resonance structures are different, the hybrid looks
more like the “better” resonance structure. The “better”
resonance structure is called the major contributor to the
hybrid, and all others are minor contributors.
•The hybrid is a weighted average of the contributing
resonance structures.
 Resonance Hybrids

A “better” resonance structure is one that has more bonds and

fewer charges.
Resonance Hybrids
Resonance Hybrids
Resonance Hybrids
 Resonance Hybrids

1. Which of the following resonance structures contributes

more to the real structure?

2. Are the following structures isomers or resonances?

 Resonance Hybrids
• 2. Which of the following is not a resonance form of the 1,3-butadiene
molecule?

a. b.

c. d.

e.
 Resonance Hybrids
• 3. In which option is the resonance structure that will result from the
movement of electrons, as indicated by the curved arrows, given
correctly?

• a. b.

• c. d.

• e.
Resonance Hybrids

• 4.

• Which of the following is a structural isomer of the above molecule?

• a. b. c.

• d. e.
 Exceptions to the Octet Rule

There are three types of ions or molecules that do not follow the octet
rule:

▪ ions or molecules with an odd number of electrons

▪ ions or molecules with less than an octet
▪ ions or molecules with more than eight valence electrons (an
expanded octet).

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 Odd Number of Electrons
Though relatively rare and usually quite unstable and reactive,
there are ions and molecules with an odd number of electrons.

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 Fewer Than Eight Electrons
Elements in the second period before carbon can make stable
compounds with fewer than eight electrons.

Consider BF3
▪ Giving boron a filled octet places a negative charge on the boron and a
positive charge on fluorine.
▪ This would not be an accurate picture of the distribution of electrons in BF3.

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 Fewer Than Eight Electrons
The lesson is: If filling the octet of the central atom results in a
negative charge on the central atom and a positive charge on the
more electronegative outer atom, don’t fill the octet of the central
atom.

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 More Than Eight Electrons
Elements in period 3, 5 and etc: use d-orbitals to make > 4 bonds
Examples: PF5 and phosphate below
(Note: Phosphate will actually have four resonance structures with five
bonds on the P atom!)

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 Covalent Bond Strength

Bond Enthalpy : energy is required to break the bond

Bond strengths are measured by determining the bond enthalpies

▪ The bond enthalpy for a Cl - Cl bond, D(Cl- Cl), is measured to be

242 kJ/mol.
▪ We write out reactions for breaking one mole of those bonds:
Cl - Cl → 2 Cl•

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 Average Bond Enthalpies
Average bond enthalpies : + Bond Breaking : Endothermic Process

▪ Note that these are averages

over many different
compounds

▪ Not every bond in nature for a

pair of atoms has exactly the
same bond energy.

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 Using Bond Enthalpies to Estimate
Enthalpy of Reaction

H for a reaction
▪ The bond enthalpies of bonds broken
▪ The bond enthalpies of the new bonds formed

Energy is added to break bonds and released when

making bonds.

Hrxn =

 (bond enthalpies of all bonds broken)

−  (bond enthalpies of all bonds formed)
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 Basic Concepts
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 Example
CH4(g) + Cl2(g) ⎯⎯→ CH3Cl(g) + HCl(g)

one C—H bond and one Cl—Cl bond are broken

one C—Cl and one H—Cl bond are formed

Answer
H = [D(C—H) + D(Cl—Cl)] − [D(C—Cl) + D(H—Cl)]

= [(413 kJ) + (242 kJ)] − [(328 kJ) + (431 kJ)]

= (655 kJ) − (759 kJ)

= −104 kJ Basic Concepts

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 Bond Enthalpy & Length
▪ We can also measure an average bond length for different bond
types
▪ As the number of bonds between two atoms increases, the bond
length decreases↓

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Basic Concepts
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 Basic Concept s
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 Homework
Calculate the formal charge of each atom in the structures given below.
.. ..
a) H:O:N::O
..

H
..
b) H:C::N::N

..
H
.. .. O
..
..

.. ..
c) H:C:O:S:O:H
.. .. .. ..
H O
..
..

..
 Questions
In which option are the formal charges of Nitrogen atoms numbered 1, 2, 3, 4
and 5 in the structure given below given correctly?

•a) -1, -1, 0, +1, 0

•b) +1, +1, 0, +1, 0
•c) -1, +1, 0, -1, 0
•d) -1, +1, 0, +1, 0
•e) -1, +1, -1, +1, -1