• Lecturer: Assist. Prof. Tuğçe N.

Gevrek-Civan
CHEM 106: • Email: tcivan@gtu.edu.tr
Organic Chemistry • Office: Chemistry-139 Thu 14:00-16:00

Book: Organic Chemistry, T.W.Graham SOLOMONS, Craig B. FRYHLE, Scott Synder 12th ed
 Course Outline
Date Topics

27.09.2022 General Introduction, Chemical Bonds and Molecular Structures

04.10.2022 Resonance Theory, Atomic and Molecular Orbitals, Hybridizations

11.10.2022 Functional Groups, Intermolecular Forces

18.10.2022 An Introduction to Organic Reactions and Their Mechanism

25.10.2022 Nomenclature and Conformation of Alkanes

01.11.2022 Nomenclature and Conformation of Cycloalkanes

08.11.2022 Stereochemistry

15.11.2022 Midterm Exam

Course Outline

Date Topics

22.11.2022 Nucleophilic Substitution Reactions of Alkyl Halides

29.11.2022 Elimination Reactions of Alkyl Halides

06.12.2022 Properties and Synthesis of Alkenes,

13.12.2022 Properties and Synthesis of Alkynes

20.12.2022 Aromatic Compounds

27.12.2022 Genereal Review-Problem Session

11.01.2023 Final Exam

 The Basics
Bonding and Molecular
Structure

Created by
Professor William Tam & Dr. Phillis Chang
We will consider:

❖ What kinds of atoms make up organic

molecules

❖ The principles that determine how the

atoms in organic molecules are bound
together

❖ How best to depict organic molecules

Life & the Chemistry of Carbon
Compounds

CH3-CH2-OH

Vitamin C Glucose Ethanol

O
C
H 3C CH 3

Acetylsalicylic acid Acetone PVC TEFLON

(Aspirin)
 Atomic Structure
❖ Atomic number (Z) = number
of protons in nucleus

❖ Valence shell, is the

outermost shell

❖ The number of electrons in the valence shell

(called valence electrons) is equal to the
group number of the atom

❖ e.g. Carbon → group IVA → 4 valence electrons

 Chemical Bonds: The Octet Rule
❖ Ionic bonds are formed by the transfer of
electrons from one atom to another to create
ions

❖ Covalent bonds result when atoms share

electrons

❖ Octet Rule
In forming compounds, they gain, lose, or
share electrons to give a stable electron
configuration characterized by 8 valence
electrons Ne: 1s2[2s22p6] → 8 e-s in outer shell
Ionic Bonds
❖ Atoms may gain or lose electrons and
form charged particles called ions

● An ionic bond is an attractive force

between oppositely charged ions
 give 1 e- to
Na Cl
1s2 2s2 2p6 3s1 1s2 2s2 2p6 3s2 3p5
(1 e- in outermost shell) (7 e- in outermost shell)

ionic bonding
+ –
Na Cl
1s2 2s2 2p6 1s2 2s2 2p6 3s2 3p6
8 8
❖ Electronegativity (EN)
● The intrinsic ability of an atom to
attract electrons
element H
(EN) (2.1)
Li Be B C N O F
……..………
(1.0) (1.6) (2.0) (2.5) (3.0) (3.5) (4.0)
Na Mg Si P S Cl
………………...……
(0.9) (1.2) (1.8) (2.1) (2.5) (3.0)
K Br
………………………..…………………………………
(0.8) (2.8)
Rb I
………………………………………………..…………
(0.8) (2.5)
Cs
……………………………………………………………………
(0.7)
Covalent Bonds & Lewis Structures
❖ Covalent bonds form by sharing of
electrons between atoms of similar
electronegativities

:Cl. . Cl:
: :

: :
[Ne] 3s2 3p5 [Ne] 3s2 3p5
shared electrons covalent bonding
(bond pair e-s)
: :
unshared electrons
: :
(lone pair e-s) :Cl—Cl:
 How to Write Lewis Structures
1. Determine the total number of valence electrons in the structure.
❖ For a negative ion, add one electron for each negative charge and for a
positive ion, subtract one electron for each positive charge.

2. Identify the central atom (the atom with the lowest EN) and terminal atoms.
❖ Hydrogen atoms are always terminal atoms.
❖ Carbon atoms are always central atoms.

3. Write the skeleton structure, and join the atoms in this structure by single covalent
bonds.

4. For each single bond in the skeletal structure, subtract two from the total number
of valence electrons.

5. With the valence electrons remaining, first complete the octets of the terminal
atoms. Then, to the extent possible, complete the octets of the central atom(s).

6. At this point, if the central atom lacks an octet, form multiple covalent bonds by
converting unshared (lone pair) electrons from terminal atoms into bond pairs.
 How to Write Lewis Structures

❖ Lewis structure of CH3Br

1. Determine the total number of valence electrons
in the structure.
● Total number of all valence electrons:

C H Br

4 + 1 x 3 + 7 = 14
Lewis structure H
of CH3Br 2. Identify the central
atom.
H C Br
3. Write the skeleton
structure, and join the
4. For each single bond in the
H atoms in this structure by
skeletal structure, subtract single covalent bonds.
two from the total number of
valence electrons.
H
H C Br
8 H
valence
electrons
Lewis structure
of CH3Br
5. With the valence electrons
remaining, first complete the
octets of the terminal atoms.
Then, to the extent possible,
complete the octets of the
central atom(s).

: :
H C Br:
8 H remaining
valence 6 valence
electrons electrons
(2) Lewis structure of methylamine
(CH3NH2)

● Total number of all valence

electrons:

C H N

4 + 1 x 5 + 5 = 14
● CH3NH2 H
H C N H
H H
2 valence
● electrons left
H

:
H C N H
12 valence H H
electrons
Exceptions to the Octet Rule
❖ Expanded Octet: Elements in the 3rd row in the
periodic table have d orbitals that can be used for
bonding and may not obey the Octet Rule

❖ Incomplete Octet: Some highly reactive molecules

or ions have atoms with fewer than eight electrons
in their outer shell F
B
F F
 Formal Charges and How to
Calculate Them
❖ Formal charge = number of valence electrons
– 1/2 number of shared electrons
– number of unshared electrons

or F = Z - S /2 - U

F : formal charge
Z : group number of the element
S : number of shared electrons
U : number of unshared electrons
General rules to determine the plausibility of a Lewis
structure based on its formal charge.

❖ The sum of the formal charges in a Lewis structure

must equal zero for a neutral molecule and
must equal the magnitude of the charge for an ion.

❖ Where formal charges are required, they should be

as small as possible.

❖ Negative formal charges usually appear on the

most EN atoms; positive formal charges, on the
least EN atoms.
❖ Examples
(1) The Ammonium ion (NH4+)
H
H NH Recall: F = Z - S /2 - U
H

Formal charge of H:
= 1 – 2/2 – 0 = 0
group number number of
number of shared unshared
of H electrons electrons
 Formal charge of N: H
= 5 – 8/2 – 0 = +1 H NH
H
group number number of
number of shared unshared
of N electrons electrons

Charge on ion = 4 x 0 +1 = +1
 The arithmetic sum of all the formal
charges in a molecule or ion will equal
the overall charge on the molecule or ion
 -
(2) The Nitrate ion (NO3 )

O
N Recall: F = Z - S /2 - U
O O

Formal charge of O:
= 6 – 2/2 – 6 = -1
group number number of
number of shared unshared
of O electrons electrons
 Formal charge of O: O
= 6 – 4/2 – 4 = 0 N
O O
group number number of
number of shared unshared
of O electrons electrons

Formal charge of N:
= 5 – 8/2 – 0 = +1
group number number of
number of shared unshared
of N electrons electrons
Charge on ion = 2 x (-1) + 0 +1 = -1
(3) Water (H2O)
The sum of the formal charges on
each atom making up a molecule
must be zero

Formal charge of O = 6 – 4/2 – 4 = 0

Formal charge of H = 1 – 2/2 – 0 = 0

Charge on molecule = 0 + 2 x 0 = 0
 Resonance Theory
❖ We can write three different but
equivalent structures, 1–3
O O O
becomes becomes
C C C
O O O O O O
1 2 3

differ only in the positions of the electrons

 Structures 1–3, although not identical on paper, are
equivalent; all of its carbon–oxygen bonds are of equal
length
 O O O
becomes becomes
C C C
O O O O O O
1 2 3

❖ Resonance theory states that whenever a molecule or ion can be

represented by two or more Lewis structures that differ only in the
positions of the electrons, two things will be true:

● None of these structures, which we call resonance structures

or resonance contributors, will be a realistic representation for
the molecule or ion. None will be in complete accord with the
physical or chemical properties of the substance

● The actual molecule or ion will be better represented by a

hybrid (average) of these structures

© 2014 by John Wiley & Sons, Inc. All rights reserved.

 ● Resonance structures, then, are not
real structures for the actual
molecule or ion; they exist only on
paper
O O O
C C C
≡
O O O O O O

not an equilibrium!
The Use of Curved Arrows
❖ Curved arrows show the direction of electron flow in
a reaction mechanism

HO H NOT HO H

NOT
-O -O
N N
H H
H C H C
H + H +
❖ Examples
(1) Benzene

(2) Carboxylate ion (RCOO-)

O

R O
(3) Ozone (O3)
O
O O
How to Write Resonance Structures
❖ Resonance structures exist only on paper.
❖ We are only allowed to move electrons in
writing resonance structures

resonance structures

H2C CH2 CH CH2

not a proper resonance structure
❖ All of the structures must be proper
Lewis structures
H
H C O H
H

not a proper resonance structure

(hypervalent carbon having 5 bonds!!)
❖ The energy of the resonance hybrid is
lower than the energy of any resonance
contributing structure. stabilization
❖ The more stable a structure is, the greater is its contribution
to the hybrid.

❖ The more covalent bonds a structure has, the more stable it is.

❖ Charge separation decreases stability.

❖ Structures in which all the atoms have a complete valence
shell of electrons are more stable.
Example:

Write resonance structures for NCO- . Show the major

contributor.
 Isomers
❖ Isomers: different compounds that have the same
molecular formula
● Constitutional isomers: isomers that have the
same molecular formula but different connectivity

Molecular Formula Constitutional Isomers

and
C4H10 Butane 2-Methylpropane

Cl
Cl
and
C3H7Cl 1-Chloropropane 2-Chloropropane
How to Write and Interpret
Structural Formulas
Condensed Structural Formulas

1 2 3 4

1 2 3

Ball-and-Stick model
Bond-Line Formulas Ball-and-Stick model

H3
❖ Which of the following compounds are constitutional
isomers?
Three-Dimensional Formulas

❖ A dashed wedge ( ) represents a bond that projects

behind the plane of the paper
❖ A solid wedge ( ) represents a bond that projects out of
the plane of the paper
❖ An ordinary line ( ) represents a bond that lies in the
plane of the paper
Three-Dimensional Formulas
H
H H H
C H H
OR C C etc.
H C H
H H H
H
Ethane
Br
H

H OH Cl
H
Examples of bond-line formulas that include
three-dimensional representations