Module On Character of Covalent Bond

ORGANIC CHEMISTRY Module on Character of Covalent Bond
Introduction
Covalent bonds are the most important means of bonding in organic chemistry. The formation of
a covalent bond is the result of atoms sharing some electrons. The bond is created by the
overlapping of two atomic orbitals. Since majority of the organic compounds are covalently
bonded, it is important that you are familiar with the characteristics of covalent bond. This
module will discuss the character of covalent bond such as, bond polarity, bond length, bond
strength, bond order and bond angle. The factors affecting the mentioned properties will likewise
be discussed here.
Learning Objectives
At the end of this module, the students are expected to:
1. Identify the characteristics of a covalent bond

2. Summarize the factors that affect the character of covalent bond
3. Apply the aforementioned factors in predicting properties of a specific covalent bond or
compound
CHARACTER OF COVALENT BOND
I. Bond Polarity (BP)
 Separation of charges in a bond
 Results from the unequal distribution of electrons between two atoms sharing a bond due
to differences in their electronegativity.
 Identical non-metallic atoms have identical electronegativities and form non-polar

covalent bonds since the bonding electrons will be shared equally between the atoms in
the molecule. Ex: Cl2, F2, O2 (all these are non-polar covalent molecules; they are also
called homonuclear diatomic molecules)
 When atoms are different (electronegativity difference < ~1.7) , the more electronegative
atom has a greater share of the bonding electrons than the less electronegative atom. The
more electronegative atom has a partial negative charge, and the less electronegative
atom has a partial positive charge. The resulting covalent bond is called a polar covalent
bond.
 Non-metals are more electronegative than metals. When an extremely electronegative

atom, like fluorine, bonds with an electropositive atom, like sodium, the resulting bond is
ionic due to the huge difference in electronegativity (difference > ~1.7). The
electronegative atom's pull on the bonding electrons is so strong that it pulls the bonding
electron off the electropositive atom resulting in two oppositely charged ions which are
held together by electrostatic attraction (an ionic bond).
1 |7 P a g e
Factors Affecting Bond Polarity
1. Electronegativity difference (ED)
Order of electronegativity of common elements found in organic compounds:
F>O>N=Cl>Br>I=C>H
2. Formal Charge (FC)
2 |7 P a g e
It can be noted that the FC of of N in Ammonia (NH3) is 0 while the Fc of N in ammonium ion
(NH4+1 ) is =1. The lone pair electron cloud overlaps with the empty s –orbital of a hydrogen ion,
and the N-H bond in ammonium ion will be more polar than the N-H bond in ammonia.
Conclusion: Bond tends to be more polar as the FC is increased
3. Nature of adjacent atom
The polarity of identical bonds may differ as a result of varied nature of adjacent atoms. For
instance, the C-H of chloroform (CHCl3) has been shown to be more polar than the C-H bond in
methane. Each bond is an sp3-s bond type, an sp3 orbital of carbon overlaps with an s orbital of
hydrogen. In chloroform, adjacent atoms are chlorine atoms which possess greater electron
attracting capacity than the hydrogen atoms in methane. As a result, the three chlorines will
attact electrons from hydrogen increasing the partial positive charge on this atom. This makes the
C-H bond of chloroform more polar than the bond of methane.
4. Difference in hybridization
Difference in hybridization of two identical atoms may also affect the polarity of a bond. For
instance, the C-H bond in acetylene is more polar than the C-H bond in ethylene. The C-H bond
in ethylene is more polar than the C-H bond in methane. This is a consequence of sp hybrids of
the carbon of acetylene, involvement of sp 2 hybrids of ethylene and sp3 hybrid of methane. An sp
hybrid has ½ or 50% s character, sp2 has a 1/3 or 33 % s character while an sp3 hybrid has ¼ or
25% s character.
The s character of the hybrid orbital is the measure of the electro-attracting capacity of an atom.
This electron-attracting capacity as a result of s character of the bond is called the orbital
electronegativity. On the basis of orbital electronegativity, The C_H bond in acetylene is more
3 |7 P a g e
polar than the C_H bond in ethylene. The C-H bond in methane is the least polar among the
three.
II. Bond Length
The average distance between the centre of the nuclei of the two bonded atoms is called bond
length
Factors affecting bond length
1. Bond polarity
 Polar bond length is usually smaller than the theoretical non-polar bond length.
It can be seen here that bond polarity is inversely related to bond length which means that
the bonds tend to be shortened as polarity is increased
2. Multiplicity of the bond
 The bond length decreases with the multiplicity of the bond. Thus, bond length of
carbon–carbon bonds are in the order, C ≡ C < C = C < C – C.
3. Orbital electronegativity
The greater the s-character of the hybrid orbital, the shorter is the bond length.
For example, sp3 C – H > sp2 C – H > sp C – H
4. Nature of Adjacent Group or atom
4 |7 P a g e
5. Pi and Sigma Electron Delocalization
III. Bond Energy

 The amount of energy necessary to break one mole of bonds in a substance, dissociating
the substance in the gaseous state into atoms of its elements in the gaseous state.
Factors Affecting Bond Energy
1. Bond polarity
2. Orbital electronegativity
3. Bond order
IV. Bond Order
 Bond order is a measurement of the number of electrons involved in bonds

between two atoms in a molecule.
 Most of the time, bond order is equal to the number of bonds between two
atoms.
Total bond order (tbo) = no. of sigma bonds + number of pi bonds
Mobile bond order (mbo) = no of pi bonds only
Ex. for acetylene: CH2=CH2 tbo = 2 mbo = 1
5 |7 P a g e
V. Bond Angle
 The angle that is formed between two adjacent bonds on the same atom
 Bond angle of 109o 28’ would be expected if sp3 hybrids are utilized, 120o if sp2
hybrids and 180o of sp hybridized
Factors Affecting Bond Angle
1. Hybridization of central atom
2. Interelectronic repulsion or repulsion of electron clouds
6 |7 P a g e
Exercise No ____
Character of Covalent Bond
1. Explain the following observations:
a. C-Cl bond in vinyl chloride is stronger than C-Cl bond in ethyl chloride
b. N=N is stronger than C=C
c. O-H is stronger than N-H
2. In the following formula, encircle the:

a. strongest bond
b. weakest bond
c. biggest bond angle
d. smallest bond angle?
7 |7 P a g e

Module On Character of Covalent Bond

Uploaded by

Copyright:

Available Formats

Module On Character of Covalent Bond

Uploaded by

Document Information

Original Description:

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Module On Character of Covalent Bond

Uploaded by

Copyright:

Available Formats

ORGANIC CHEMISTRY Module on Character of Covalent Bond

At the end of this module, the students are expected to:

1. Identify the characteristics of a covalent bond

CHARACTER OF COVALENT BOND

I. Bond Polarity (BP)

 Separation of charges in a bond

 Identical non-metallic atoms have identical electronegativities and form non-polar

 Non-metals are more electronegative than metals. When an extremely electronegative

Factors Affecting Bond Polarity

1. Electronegativity difference (ED)

Order of electronegativity of common elements found in organic compounds:

2. Formal Charge (FC)

Conclusion: Bond tends to be more polar as the FC is increased

3. Nature of adjacent atom

II. Bond Length

Factors affecting bond length

2. Multiplicity of the bond

For example, sp3 C – H > sp2 C – H > sp C – H

4. Nature of Adjacent Group or atom

5. Pi and Sigma Electron Delocalization

III. Bond Energy

Factors Affecting Bond Energy

IV. Bond Order

 Bond order is a measurement of the number of electrons involved in bonds

Total bond order (tbo) = no. of sigma bonds + number of pi bonds

Mobile bond order (mbo) = no of pi bonds only

Ex. for acetylene: CH2=CH2 tbo = 2 mbo = 1

Factors Affecting Bond Angle

1. Hybridization of central atom

2. Interelectronic repulsion or repulsion of electron clouds

1. Explain the following observations:

2. In the following formula, encircle the:

You might also like