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Covalent Bond Characteristics Explained

The document discusses resonance contributors and hybrids, focusing on polycentric molecular orbitals and resonance structures. It outlines the characteristics of covalent bonds, including factors affecting bond polarity, length, energy, and angle. Specific examples and comparisons of bond types and lengths are provided to illustrate these concepts.

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Galen Nifas
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42 views14 pages

Covalent Bond Characteristics Explained

The document discusses resonance contributors and hybrids, focusing on polycentric molecular orbitals and resonance structures. It outlines the characteristics of covalent bonds, including factors affecting bond polarity, length, energy, and angle. Specific examples and comparisons of bond types and lengths are provided to illustrate these concepts.

Uploaded by

Galen Nifas
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

Resonance contributor vs.

Resonance Hybrid
Polycentric MO
- covers more than one atom, associated with
conjugated systems of polyenes
Resonance Structures
Examples: Draw resonance and hybrid structures
for the following compounds:

O
H3C C NH2 CH2
NH2

O
N
O
Characteristics of Covalent Bond
1. Bond Polarity
- results from unequal sharing of electrons
between bonded atoms
Factors affecting bond polarity:
a. Difference in electronegativity of the atoms
forming the bond
Characteristics of Covalent Bond

Factors affecting bond polarity:

b. Formal Charge

c. Nature of the adjacent atom


d. Orbital electronegativity
- electron-attracting tendency arising from the
high s character of the hybrid orbital used by an
atom in bond formation
Characteristics of Covalent Bond
2. Bond Length
- internuclear distance

Factors affecting bond length


a. atomic size or radius
b. bond polarity
c. number of pi bonds
d. pi electron delocalization
Characteristics of Covalent Bond
Factors affecting bond length

Compound Structural Bond Type Bond


Formula Length

Ethane CH3 –CH3 sp3 – sp3 1.538


Propylene CH3 - CH = CH2 sp3 – sp2 1.501
Methylacetylene CH3 – C≡ CH sp3 – sp 1.459
Ethylene CH2 = CH2 sp2– sp2 ; p-p 1.339
Acetylene H–C≡C–H sp2– sp2 ; p-p; p-p 1.207
Characteristics of Covalent Bond
Factors affecting bond length

Comparison of Three types of sp-sp bonds

Bond Type Bond Length


≡C–C≡ sp – sp 1.38

=C=C= sp – sp ; p – p 1.28

-C≡C- sp – sp ; p-p; p-p 1.20


Characteristics of Covalent Bond
Factors affecting bond length

Effect of Adjacent Atom

Compound Bond Length


H–C≡C–H 1.207
F–C≡C–H 1.198
CH3 –CH3 1.538
F – CH2 –CH3 1.533
Characteristics of Covalent Bond
Factors affecting bond length

Effect of p electron delocalization


Compound Bond Type Bond Length
Vinyl chloride C – Cl 1.726
Methyl chloride C – Cl 1.781
Vinyl flouride C–F 1.347
Methyl fluoride C–F 1.384
Urea C=O 1.26
Formaldehyde C=O 1.21
Characteristics of Covalent Bond
Factors affecting bond length

Effect of hyperconjugation (C – C bond)

Compound Bond length


CH3 – CH2 – CH3 1.538
CH3 – CH = CH3 1.488
CH3 – CH3 1.538
CH3 – CH = O 1.498
CF3 – CH = O 1.538
Characteristics of Covalent Bond
3. Bond Energy (Bond Strength)
- energy necessary to break a bond

Factors affecting bond energy


a. bond length
b. angle/angular strain
- forced bending of the bonds in small cyclic
structures resulting in the compression of the C-C-C
bond angle far below the normal value
Bond Length and Bond Strength
Characteristics of Covalent Bond
4. Bond Angle
- angel made by any two bonds in a molecule

Deviations from normal bond angles:


a. electron pair repulsion
b. angular strain

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