Unit 2

Bonding and Structure

At the end of the unit, the students must:
1. Recognize the bonding characteristics of covalent compounds
2. Draw Lewis structures for covalent compounds
3. Draw resonance structures for some ions and molecules
4. Determine the molecular shape
5. Differentiate and draw the different ways of drawing structural
formulas
6. Understand the concept of hybridization
7. Study ethane, ethylene, and acetylene
8. Study bond length and bond strength
9. Use electronegativity to determine whether a bond is polar or
nonpolar
10.Determine whether a molecule is polar or non-polar
❑ Common elements encountered in Organic Chemistry
❑Structure of the Atom:
▪ Protons, Neutrons, Electrons
▪ Isotopes
▪ Cations vs Anions

❑Distribution of electrons
▪ Electron configuration
▪ Quantum numbers
▪ Orbitals: s, p, d, f
▪ Valence shell, valence
electrons
❑ Atomic Bonding

▪ Through bonding, atoms attain a complete

outer shell of valence electrons
▪ Through bonding, atoms attain a stable
noble gas configuration of electrons. (octet
rule)
 Na1+ Cl1-

Ionic Bond
Ideally, the electron clouds of each ion do not overlap.
Electron transfer occurs from metal to nonmetal and
the resulting ions attract only by electrostatic
attraction.
 Ionic Compounds
have a rigid and strong
crystal lattice structure
in which the ions are
arranged in an orderly,
repeating pattern.
Cl - ion
Na+ ion
 Covalent Bond
Electrons are shared between two or more nonmetal
atoms in a molecule.
Most Covalent Substances Have a
Molecular Form
Electronegativity – A measure of the ability of an
atom to attract shared electrons in a chemical
 EN > 2.1
Ionic Bond – Electron Transfer Between 2 Atoms

EN = 0.4 to 2.1

Polar Covalent Bond – Unequal Sharing of the
Shared Electrons Between 2 Atoms

EN < 0.4

Pure Covalent Bond (Nonpolar Covalent) –
Essentially equal Sharing of the Shared Electrons
Between 2 Atoms
 Examples
Predict the Bond Type based on EN:
Ca=1.0, O=3.5, C=2.5, H=2.1, Al=1.5, Cl=2.1,
Mg=1.2, S=2.5

1) Na and Cl EN = 0.9 – 3.0 = 2.1, polar covalent bond

2) Ca and O
3) C and H
4) Al and Cl
5) Mg and H
6) S and O
 Polar Covalent vs. Pure Covalent Bonds
2.1 2.1
The O-H bond (EN = 1.4) in H O H
water is a polar covalent bond.
3.5

2.8 2.5
The Br-I bond (EN = 0.3) in
bromine iodide is a pure covalent Br I
(nonpolar) bond.
Covalent Bonds are Like Springs!

• The atoms can vibrate back and forth to some

extent without the bond breaking.
• The strength of a bond is related to its length,
which is in turn related to the radii of the
bonding atoms.
 CHY 32
Organic Chemistry

February 10, 2023

Hannah Jean V. Esteban, RCh
❑ Drawing Lewis Structure
STEPS:
1. Count the total number of valence electrons
2. Arrange atoms with least electronegative at the center,
surrounded by the usual number of bonds it is expected to
form. Connect them with single bonds
3. Deduct the electrons used to make single bonds from the total
valence electrons.
4. Distribute the remaining electrons as lone pairs in the structure
to complete octet of the atoms. Start with the most electron
negative. Draw double bonds when necessary by sharing a lone
pair.
5. Assign formal charges.
❑ Drawing Lewis Structure
• General Rules for Organic Compounds Lewis structures
❑ Assignment! Drawing Lewis Structure
❑ Formal Charge

1. For neutral molecules, a Lewis structure in which there are no formal

charges is preferable to one in which formal charges are present.
2. Lewis structures with large formal charges are less possible than those
with small formal charges.
3. Among Lewis structures having similar distributions of formal charges, the
most possible structure is the one in which negative formal charges are
placed on the more electronegative atoms.

Which is the most likely Lewis structure for CH2O?

❑ Formal Charge

formal charge total number

total number
on an atom in of valence
a Lewis
= electrons in - of nonbonding - # of bonds
electrons
structure the free atom
❑ Formal Charge
❑ Formal Charge

SEATWORK – ½ sheet

Assign formal charge for the second row elements in

each of the structures above
 • ISOMERS
➢Isomers are different molecules having the same
molecular formula.

Ethanol and dimethyl ether are constitutional isomers because they have the
same molecular formula, but the connectivity of their atoms is different
• ISOMERS
 CHY 32
Organic Chemistry

February 15, 2023 (Virtual Make-Up Class)

Hannah Jean V. Esteban, RCh
• Resonance
➢ • Resonance structures are two Lewis structures
having the same placement of atoms but a different
arrangement of electrons.
• Resonance

• Resonance structures are not real

• Resonance structures are not in equilibrium with each other.
• Resonance structures are not isomers.
• Resonance

Resonance forms

Isomers
 • Drawing Resonance Structures
Rule [1] Two resonance structures differ in the position of multiple bonds
and nonbonded electrons. The placement of atoms and single bonds
always stays the same.
 • Drawing Resonance Structures
Rule [2] Two resonance structures must have the same number of
unpaired electrons.
 • Drawing Resonance Structures
Rule [3] Resonance structures must be valid Lewis structures. Hydrogen
must have two electrons and no second-row element can have more than
eight electrons.
 • Drawing Resonance Structures
Curved arrow notation is a convention that shows how electron position
differs between the two resonance forms.
• Drawing Resonance Structures
 The curved arrow notation shows the movement of an
electron pair. The tail of the arrow always begins at an
electron pair, either in a bond or lone pair. The head points
to where the electron pair “moves.”
When do we draw a resonance structure?
When do we draw a resonance structure?
The Resonance Hybrid

• the composite of all possible resonance structures

• the electron pairs drawn in different locations in individual
resonance structures are delocalized
• The resonance hybrid is more stable than any resonance
structure because it delocalizes electron density over a larger
volume.
• The “better” resonance structure is called the major
contributor to the hybrid, and all others are minor
contributors
The Resonance Hybrid
• A “better” resonance structure is one that
has more bonds and fewer charges
The Resonance Hybrid
Assignment:
Draw resonance structure/s of nitrous acid (Lewis structure given). Label the
structure as major or minor or equal contributor.
Determining Molecular Shape (Bond Length and Bond Angle)
• Bond Length - the average distance between the centers of
two bonded nuclei
SUMMARY on GEOMETRY
 EXERCISE:
• Enanthotoxin is a poisonous compound isolated from a common variety
of hemlock grown in England. Predict the geometry, indicate angles,
around the indicated atoms in enanthotoxin.
Drawing chemical structures
Convert each condensed formula to a Lewis structure.
• Draw a complete structure for vanillin showing all H
atoms and lone pairs. Vanillin is the principal component
of the extract of the vanilla bean.
Seatwork:

Draw the skeletal or bond line structure of the first molecule, while give
the expanded (dash) and condensed structure of the second molecule
• Skeletal Structures with Charged Carbon Atoms
• Skeletal Structures with Charged Carbon Atoms
• A sigma bond concentrates electron density on the axis that joins
two nuclei. All single bonds are r bonds.

• This lowest energy arrangement of electrons for an atom is called

its ground state.
• Carbon would form two different types of bonds: three with 2p
orbitals and one with a 2s orbital. But experimental evidence points
to carbon forming four identical bonds in methane.
• These hybrid orbitals are called sp3 hybrids because they are
formed from one s orbital and three p orbitals.
Other Hybridization Patterns—sp and sp2 Hybrid Orbitals
• The number of groups (atoms and nonbonded electron pairs)
corresponds to the number of atomic orbitals that must be
hybridized to form the hybrid orbitals.
Ethane, Ethylene, and Acetylene
• As the number of electrons between two nuclei increases, bonds
become shorter and stronger.