STRUCTURE AND BONDING

EDUC 705 Organic Chemistry | First Semester

ATOMIC STRUCTURE THE PERIODIC TABLE

• Schematic of an Ion • Elements in the same row = similar in size
o Has same number of shells
• Elements in the same column = similar electronic and
chemical properties
• Column = groups

ATOMIC ORBITALS
• S orbital
o o Sphere of electron density
▪ Quantum Mechanical model o Lower in energy than other orbitals of the same shell
▪ Most accurate model o Has one orbital and can hold up to two electrons
o Nucleus
▪ Contains protons (positively charged) &
neutrons (uncharged or neutral)
• Atomic Number
o Number of protons in the neutron o
• P orbital
o Number of electrons in the surrounding
o Dumbbell shaped
• Mass number
o Contains a node (no electron density) at nucleus
o Number of protons + neutrons in nucleus
o Higher in energy than S orbital
o Mass number = atomic number + atomic weight
o Has three orbitals and can hold up to six electrons
• In a neutral atom
o Number of protons = number of neutrons
• Atomic Weight
o Weighted average of the mass of all of its isotopes
reported in atomic mass unit (amu; g/mol)
o
• Electron configuration table

•
• Neutrons = mass number – number of protons

IONS
• Cation o
o Positively charged • Elements in the first row of the periodic table
o Has fewer electrons than protons o Has only one orbital
• Anion o Each shell can hold a maximum of two electrons
o Negatively charged o Two elements: H and He
o Has more electrons • Elements in the second row of the periodic table
o Has four orbitals
o Available to accept additional electrons
ISOTOPES
o One 2s orbital and three 2p orbitals
• Two atoms of same element having different number of
neutrons
• Have different mass numbers
• Most isotope of carbon have 6 protons and 6 neutrons

•
o

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 TRANS: Structure and Bonding

BONDING • General Rules

• Joining of two atoms in a stable arrangement o Draw only the valence electrons
• Attain electron configuration of noble gas closest to them o Give every second-row element no more than eight
• Makes it lower in energy electrons
o Give each hydrogen two electrons
IONIC BONDING
• Transfer of electrons from one element to another HOW TO DRAW LEWIS STRUCTURES
• Metal to nonmetal elements • Arrange atoms next to each other
• Usually, elements on far-left side combined with elements o Always place hydrogen and halogens on periphery;
on far-right side (ignoring noble gases) they form only one bond each
• Positively charged cation formed from element on left side
(metal loses an electron) attracts negatively anion formed
from element on the right side (nonmetal gains an electron)

COVALENT BONDING ▪
o Place no more atoms around an atom than the number
• Sharing of electrons between two nuclei of bonds it usually forms
• Nonmetal or metalloid to nonmetal elements
• Can be between two of the same elements from sides of a
table
• A two-electron bond
• A compound with covalent bonds = molecule ▪
• Bonding in molecular hydrogen (H2) • Count the electrons
o Forms one covalent bond o Count the number of valence electrons from all atoms
o Two hydrogen atoms joined in a bond each has filled o Add one electron for each negative charge
valence shell of two electrons o Subtract one electron for each positive charge
o Give total number of electrons that must be used
• Arrange electron around atoms
o Place bond between every two atoms; giving two
electrons to each H and no more than eight to any
o second-row atom
o Use all remaining electrons to fill the octet with lone
VALENCE ELECTRONS pairs
• Second row elements can have no more than eight o If all valence electrons are used and atom does not
electrons around them have octet = forms multiple bonds
• For neutral atoms
o Atoms with 1, 2, 3, and 4 valence electrons have 1, 2,
3, and 4 bonds respectively
o Atoms with five or more valence electrons form enough ▪
▪ To give both Cs octet = change one lone pair into
bonds to give an octet
one bonding pair between two Cs to form a double
▪ Example:
bond
• NH3 – predicted number of bonds = 8 –
• Assign formal charges to all atoms
number of valence electrons
o Charge assigned to individual atoms
o N – has 5 valence electrons
o Formal charge = number of valence electrons –
– 8 – 5 = 3 bonds
number of electrons an atom “owns”
o Number of electrons “owned” = number of bonds +
NONBONDED ELECTRONS number of lone pairs
• When second row elements form fewer than four bonds o Atom “owns” all of its unshared electrons and half of its
their octet consist of both bonding (shared) and nonbonding shared electrons
(unshared) electrons o Table No. 2: Formal charge observed with common
• Unshared electrons = lone pairs bonding patterns
• Table No. 1: Nonbonded Electrons Number Formal Formal Formal
l .. .. .. Atom of Charge Charge Charge
-H -C- -N- -O- -X: valence +1 0 -1
l .. .. electrons
Number of C + l ..-
1 4 2 2 1 4 -C- -C- -C-
bonds
Number of 0 0 1 2 3 l l l
nonbonded N 5 l+ .. ..-
electron pairs -N- -N- -N-
o X = F, Cl, Br, I l l ..
• !!! Carbon should only have a maximum of four bonds O 6 ..+ .. ..-
-O- -O- - O:
LEWIS STRUCTURE l .. ..
• Electron dot representations for a molecules
• A solid line = indicates a two-electron covalent bond

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EXEPTIONS TO THE OCTET RULE • resonance stabilized = Molecule with two or more
• Elements in groups 2A and 3A resonance forms
o Four electrons around Be
▪ H — Be — H RESONANCE THEORY
o Six electrons around B • Resonance structures are not real
o Individual resonance structure does not represent
structure of a molecule or ion
o Only resonance hybrid does
• Resonance structure are not equilibrium with each
▪
• Elements in the third row other
o Dimethyl sulfide (DMSO) o No movement of electrons from one form to another
• Resonance structures are not isomers
o Isomers = arrangement of both atoms and electrons
o Resonance = only in arrangement of electrons
▪
▪ 10 electrons around S DRAWING RESONANCE STRUCTURES
o Sulfuric Acid
• Two resonance structure differ in positions of multiple
bonds and nonbonded election placement of atoms and
single bonds always stays the same
▪
▪ 12 electrons around S
o Alendronic acid

o
▪ Position of double bond is different
▪ ▪ Position of lone pair is different
▪ 10 electrons around each P
• Two resonance structure must have same number of
unpair electrons
ISOMERS
• More than one arrangement of atom is possible for
given molecular formula
• Different molecules having the same molecular formula
• Example o
o C2H6O ▪ This is not a resonance structure of A (or C)
• Resonance structures must be valid Lewis structures
o Hydrogen must have two electrons and second-row
element can have more than eight electrons

▪
▪ These are called constitutional isomers
o
RESONANCE ▪ Not a valid resonance structure of A
• Some molecules cannot be adequately represented by a ▪ It must follow the octet rule
single Lewis structure
o Example CURVED ARROW NOTATION
• A convention
• Shows that electron position differs between two resonance
forms
• Shows the movement of an electron pair
• Tail of the arrow = begin at the electron pair; whether
▪
• These structures are called resonance structures or bond or lone pair
resonance forms • Head of the arrow = points to where electron pair moves
• Double-headed arrow = separates the two-resonance • Examples
structure
• Has two Lewis structures
• Has the same placement of atoms but different
arrangement of electrons (delocalization) o
• Neither resonance is an accurate representation for
(HCOCH)- (see example above)
• True structures = composite of both resonance forms =
resonance hybrid
o Hybrid shows characteristics of both structures o
• It allows certain electron pairs to delocalize over two or
more atoms
o This adds stability to the atom

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ATOMS WITHOUT OCTET • Increases down a column of periodic table as size of

• Resonance structure can have an atom with fewer than 8 atom increases
electrons

o
• Table No. 3: Average bond length
o Bond Length (pm)
• Resonance can never have a second-row element with H—H 74
more than 8 electrons C—H 109
N—H 101
O—H 96
C—F 133
C — Cl 177
o C — Br 194
C—I 213
OCCURRENCE OF RESONANCE
• Two different structures can be drawn when lone pair is MOLECULAR GEOMETRY
located on atom directly bonded to a double bond • Number of groups surrounding a particular atom
• Group is either an atom or a lone pair of electrons
• Most stable arrangement keeps these groups as far way
from each other as possible
• Exemplified by Valence Shell Electron Pair Repulsion
o (VSEPR) Theory
▪ Position of double bond changes • Table No. 3:
▪ Location of lone pair changes Numbe Geometr Bond Example Ball & stick
r of y angle model
RESONANCE HYBRID groups
• “Better” resonance structure is one that has more 2 Linear 180°
bonds and fewer charges

3 Trigonal 120°
planar

o
▪ X = has more bonds and fewer charges
4 Tetrahedr 109.5
X = major contributor
al °
▪ Y = minor contributor
• Individual resonance structures to resonance hybrid
structures
Square
planar does
not occur

o •
o Resonance hybrid = the (-) charge delocalized on N &
O; double bond is delocalized on O, C, & N
o If C & N has the double bond = O has the charge
o If C & O has the double bond = N has the charge
o Dashed line on resonance hybrid = temporary double
bond
DETERMINING MOLECULAR SHAPE
• Two variables define a molecule’s structure = bond length
and bond angle
DRAWING 3D STRUCTURE
Solid line = bond in the plane
• Wedge = bond in front of the plane
• Dashed line = bond behind the plane
•
• Equivalent representations of methane
o Molecule can be turned in many different ways
generating equivalent representations

BOND LENGTH
• Decreases across row of periodic table as sized of atom o
decreases o Has same number of lines and wedges

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WEDGES AND DASHED WEDGES

• Used for groups that are really aligned one behind
another
• Does not matter in the following two diagrams whether
wedge or dash is skewed to the left or right:

o
▪ The wedge can be skewed to the left or right of the
dashed wedge

NONBONDED PAIR OF ELECTRONS IS COUNTED

AS A GROUP
• Example: NH3
o One of the four groups attached to central N atom is a
lone pair
o Group geometry = tetrahedron
o Molecular shape = trigonal pyramidal

o
• Example: H2O
o Two four groups attached to O are lone pairs
o Geometry = tetrahedron
o Molecular shape = bent

o
• Varying bond angles
o Both NH3 and H2O
▪ Bond angle is smaller than theoretical tetrahedral
bond angle
▪ Because of repulsion of lone pairs
o Bonded atoms are composed into a smaller space with
similar bond angles

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