Chem All

Chemistry for Health Sciences
Four credits
Spring Semester 2021/2022
King Saud bin Abdulaziz University for Health Sciences
Textbook
General, Organic, and Biochemistry
9th Edition
Katherine J. Denniston
Joseph J. Topping
Danaè R. Quirk Dorr
Robert L. Caret
The Discovery Process
Role of Chemistry
public health pharmaceutical industry
CHEMISTRY food science
medical practitioners forensic sciences

Cosmology
Chemistry is the study of matter
• Study the chemical and physical properties of

matter.
• Study the chemical and physical changes that

matter undergoes.
• Study energy changes (gains or loses) as matter

changes.
Matter
• Matter - anything that has mass and occupies space

• Properties - characteristics of matter scientists can
use to categorize different types of matter, such as mp,
bp, density, reactivity,…etc.
• Ways to Categorize matter:
1. By State
2. By Composition
Three States of Matter
1.Gas - particles widely separated, no
definite shape or volume
2. Liquid - particles closer together,

definite volume but no definite shape
3. Solid - particles are very close together,

define shape and definite volume.
Particles are either random (amorphous)
or ordered (crystalline)
Composition of Matter
• Pure substance - a substance that has only one

component with specific chemical and physical
properties.
• Mixture - a combination of two or more pure
substances in which each substance retains its
own identity, not undergoing a chemical reaction.
• Element - a pure substance that cannot be
changed into a simpler form of matter by any
chemical reaction
• Compound - a pure substance resulting from
the combination of two or more elements in a
definite, reproducible way, in a fixed ratio
• Mixture - a combination of two or more pure
substances in which each substance retains its own
identity
• Homogeneous - uniform composition, particles well

mixed, thoroughly intermingled on the molecular or
atomic level
• Heterogeneous – nonuniform composition, random

placement
Summary: Classification of Matter
Physical Property vs. Physical Change
• Physical property - is observed without

changing the composition or identity of a
substance
• Physical change - produces a
recognizable difference in the appearance
of a substance without causing any
change in its composition or identity
- conversion from one physical state to
another. Example: melting an ice cube
Physical Properties and Physical Change
Copyright © 2017 McGraw-Hill Education. Permission required for reproduction or display
(a) Solid (b) Liquid (c) Gas

Separation by Physical Properties
Magnetic iron is separated from other nonmagnetic

substances, such as sand. This property is used as
a large-scale process in the recycling industry.
Chemical Property and Chemical Reaction
• Chemical property - results in a change in

composition and can be observed only
through a chemical reaction
• Chemical reaction (chemical change) - a
chemical substance is converted in to one or
more different substances by rearranging,
removing, replacing, or adding atoms
hydrogen + oxygen → water
reactants products
Classification of Properties
Classify the following as either a
chemical or physical property:
a. Color (Physical property)
b. Hardness (Physical property)
c. Flammability (Chemical property)
d. Odor (Physical property)
e. Taste (Physical property)
Classification of Changes
Classify the following as either a chemical or
physical change:
a. Boiling water becomes steam (Physical change)
b. Butter turns rancid (Chemical change)
c. Burning of wood (Chemical change)
d. Snow melting (Physical change)
e. Decay of leaves in winter (Chemical change)

Units of Measurement
A measurement is useless without its units
SI Units (International system of units).
– Fundamental units (basic units)
• There are 7 fundamental units in the SI system
Quantity Unit Symbol

▪ Length meter m
▪ Mass kilogram kg
▪ Time second s
▪ Temperature Kelvin K
▪ Amt. substance mole mol
▪ Current ampere A
▪ Luminous intensity candela cd
▪ Pressure Pascal Pa
-Derived units : All other units are derived from the

above basic units
Metric System Prefixes
• Basic units are the units of a quantity without any
metric prefix (Memorize)

Units of Measurement expressed
in Scientific Notation
• Used to express very large or very small
numbers easily and with the correct number
of value and accuracy.
• Represents a number as a power of ten:
N x 10-x where 1≤ N < 10
• Example:
4,300 = 4.3  1,000 = 4.3  103
Scientific Notation Rules
• To convert a number greater than 1 to
scientific notation, the original decimal
point is moved x places to the left, and the
resulting number is multiplied by 10x
• The exponent x is a positive number equal to
the number of places the decimal point moved
6200 = 6.20  103

Scientific Notation Rules
• To convert a number less than 1 to scientific
notation, the original decimal point is
moved x places to the right, and the
resulting number is multiplied by 10–x
• The exponent x is a negative number equal to

the number of places the decimal point moved
0.0062 = 6.2  10–3

Scientific Notation Example
• When a number is exceedingly large or small,
scientific notation must be used to input the
number into a calculator:
0.000000000000000000000006692 g
must be entered into calculator as:
6.692 x 10−24
Represent the following numbers in
scientific notation:
1. 0.00018
2. 3004
3. 305
4. 0.00304
Unit Conversions
• Factor-Label Method (Dimensional
Analysis)
–Uses Conversion Factors to:
- Convert from one unit to another within the
same system (Examples: mg in g, mm in
km,….etc)
- Convert units from one system to another
(Examples: ft in m, m in mile, gal in
L,….etc)
Unit Conversion - Example
• To convert from one unit to another
you must know the conversion factor,
which is the relationship between the
two units
– The Relationship:
1 m = 1000 mm
– The Conversion Factor:
1m or 1000 mm
1000 mm 1m
Using Conversion Factors
Convert 12 inch to cm
– The Relationship (English system):
1 inch = 2.54 cm (GIVEN)
– The Conversion Factor:
1 inch or 2.54 cm
2.54 cm 1 inch
Data Given: 12 inch
Use Conversion Factor with inch in denominator
12 inch x 2.54 cm/ 1 inch = 30.5 cm
Multistep Conversion - Example
Convert 0.0047 kilograms to milligrams
– The Relationships (metric system):
1 kg = 103 g and 103 mg = 1 g
– The Conversion Factors:
1 kg or 103 g and 1 g or 103 mg
103 g 1 kg 103 mg 1g
Data Given: 0.0047 kg
0.0047 kg x 103 g x 1 mg = 4.7 x 103 mg

1 kg 10−3 g
Practice Unit Conversions
1. Convert 5.5 inches to millimeters
Answer 1.4 x102 mm

2. Convert 50.0 mg to kg
Answer 5.00 x 10-5 kg

Additional Experimental Quantities
• Temperature - the degree of “hotness” of an object
• Heat – Form of energy that spontaneously flows
from a hot body to a cold one.
Temperature
MP water BP water
• Fahrenheit 32 oF 212 oF
• Celsius 0.0 oC 100 oC
• Kelvin 273 K 373 K
Daniel Gabriel Fahrenheit Anders Celsius Lord Kelvin

1686-1736 1701-1744 1824-1907
Germany Sweden England
Kelvin Temperature Scale
• The Kelvin (K) scale is another temperature
scale
• It is of particular importance because it is
directly related to molecular motion
• As molecular speed increases, the Kelvin
temperature proportionately increases
TK = ToC + 273
Conversions Between Fahrenheit
and Celsius
ToF = 1.8 x ToC + 32
ToC = ToF − 32
1.8
1. Convert 75oC to oF
2. Convert -10oF to oC
1. Ans. 167 oF 2. Ans. -23oC
Density
• Density
– the ratio of mass to volume
– use to characterize a substance as
each substance has a unique density
– Units for density include:
• g/mL
• g/cm3
• g/cc mass m
d= =
volume V
Volume =
Length x width x height
Volume =
1mx1mx1m=
1 m3
1 m3 = 1000 L
1 dm3 = 1 L
1 cm3 = 1 mL
Density
Examples
cork
water
brass nut
liquid mercury
Calculating Density
A 2.00 cm3 sample of aluminum is found to weigh
5.40 g. Calculate the density in g/cm3 and g/mL.
Use the expression:

• Density (d) = m/V
Substitute information given into the expression
d = 5.40 g = 2.70 g/cm3
2.00 cm3
• Since 1 cm3 = 1 mL,
= 2.70 g/mL
Use Density in Calculation
Calculate the volume, in mL, of a liquid that has
a density of 1.20 g/mL and a mass of 5.00 g.
• Density can be written as a Conversion Factor
1.20 g 1 mL
or
1 mL 1.20 g
• Multiply the Data Given (g) by the Conversion
Factor with the unit g in the denominator
5.00 g x 1 mL = 4.17 mL
1.20 g
Density Calculations
• Air has a density of 0.0013 g/mL. What is
the mass of 6.0-L sample of air?
(Ans. 7.8 g)
• Calculate the mass in grams of 10.0 mL if

mercury (Hg) if the density of Hg is 13.6
g/mL.
(Ans. 136 g)
Four credits
2.1 Composition of the Atom
• Atom - the basic structural unit of an element

• The smallest unit of an element that retains
the chemical properties of that element
• Atoms consist of three primary particles

• protons
• neutrons
• electrons
Electrons, Protons and Neutrons
• Nucleus - small, dense, positively
charged region in the center of the atom
containing:
- protons - positively charged particles
- neutrons - uncharged particles
Electrons: negatively charged particles located outside of
the nucleus of an atom
- Protons and electrons have charges that are equal in
magnitude but opposite in sign
- A neutral atom (no electrical charge) has the same
number of protons and electrons
Composition of the Atom
proton − positive charge

+ mass = 1.673 x 10-27 kg
neutron − no charge
mass = 1.675 x 10-27 kg
Atom
– electron − negative charge
mass = 9.109 x 10-31 kg
Selected Properties of the
Three Basic Subatomic Particles
Name Charge Mass(amu) Mass (kg)

Electrons (e-) −1 5.486  10-4 9.109  10-31
Protons (p+) +1 1.007 1.673  10-27
Neutrons (n) 0 1.009 1.675  10-27
Symbolic Representation of an Element
Mass
Number
A
Atomic Z X Symbol of
the atom
Number
• Atomic number (Z) - the number of

protons in the atom
• Mass number (A) - sum of the number of
protons and neutrons
• No. of neutrons =A-Z
Determining the Composition of an Atom
Calculate the number of protons, neutrons

and electrons in each of the following:
11
5 B
55
26 Fe
Isotopes
• Isotopes - atoms of the same element having
different masses
– contain same number of protons
– contain different numbers of neutrons
Isotopes of Hydrogen
Hydrogen Deuterium Tritium

Isotopes
• Isotopes of the same element have identical chemical
properties, however, some isotopes have different nuclear
reactivity such as radioactivity.
In the periodic table, the atomic mass is the weighted average
of the masses of all the isotopes that make up the element.
Example:-
Chlorine consists of chlorine-35 and chlorine-37 in a 3:1
ratio
What is the mass given? 35.5?!
(35x3/4 + 37 x1/4) = 35.5
Atomic Mass Determination
• Neon has three naturally occurring isotopes
Mass Abundance
20Ne 20.0 amu 90.48%
21Ne 21.0 amu 0.27%
22Ne 22.0 amu 9.25%
• What is the atomic mass of Neon?

90.48 0.27 9.25
= 20.0 × + 21.0 × + 22.0 × = 20.2 amu
100 100 100
2.2 The Periodic Table
• Dmitri Mendeleev and Lothar Meyer -

independently developed the precursor to
our modern Periodic Table
– They noticed that as you list elements in order of
atomic mass, there is a distinct regular variation
of their properties.
• Periodic Law - the physical and chemical
properties of the elements are periodic
functions of their atomic numbers
Classification of the Elements

The Periodic Table
• Period – a horizontal row of elements They
contain 2, 8, 8, 18, 18, 32, and 32 elements
• Group – (also called families) column of
elements
– Elements in a particular group or family share many
similarities, as in a human family
Category Classification of Elements
• Metals - elements that tend to lose electrons
during chemical change, forming positive ions
• Nonmetals – elements that tend to gain electrons
during chemical change, forming negative ions
• Metalloids - have properties intermediate
between metals and nonmetals
Metals
• Metals:
– A substance whose atoms tend to lose electrons
during chemical change
– Elements found primarily in the left 2/3 of the
periodic table
• Properties:
– High thermal and electrical conductivities
– High malleability and ductility
– Metallic luster
– Solid at room temperature
Nonmetals
• Nonmetals:
– A substance whose atoms may gain electrons,
forming negative ions
– Elements found in the right 1/3 of the periodic table
• Properties:
– Brittle
– Powdery solids or gases
– Opposite of metal properties
Using the Periodic Table
Most periodic tables give the element symbol,
atomic number and atomic mass.
• Identify the group and period to which each of
the following belongs:
a. P
b. Element 31
• Element “Cr” belongs to which class in the
periodic table?
2.3 Electron Arrangement and the
Periodic Table
• The electron arrangement is the primary
factor in understanding how atoms join
together to form compounds
• Electron configuration - describes the
arrangement of electrons in atoms
• Valence electrons - outermost electrons
– The electrons involved in chemical bonding
Energy Levels and Sublevels
PRINCIPAL ENERGY LEVELS
• n = 1, 2, 3, …
• The larger the value of n, the higher the energy level
and the farther away from the nucleus the electrons are
• The number of sublevels (or subshells) in a principal
energy level is equal to n
– in n = 1, there is one sublevel
– in n = 2, there are two sublevels
Principal Energy Levels
• The electron capacity of a principal energy
level (or total electrons it can hold) is
2(n)2
– n = 1 can hold 2(1)2 = 2 electrons
– n = 2 can hold 2(2)2 = 8 electrons
• How many electrons can be in the n = 3

level?
– 2(3)2 = 18
• Compare the formula with periodic table…..

Sublevels
• Sublevel (or subshell): a set of energy-equal
orbitals within a principal energy level
• Subshells increase in energy:
s<p<d<f
• Electrons in 3d subshell have more energy than
electrons in the 3p subshell
• Specify both the principal energy level and a subshell
when describing the location of an electron
Sublevels in Each Energy Level
Principle energy Possible
level (n) subshells
1 1s
2 2s, 2p
3 3s, 3p, 3d
4 4s, 4p, 4d, 4f

Orbitals
• Atomic Orbital - a specific region of a
sublevel containing a maximum of two
electrons
• Orbitals are named by their sublevel and
principal energy level
– 1s, 2s, 3s, 2p, etc.
• Each type of orbital has a characteristic shape
– s is spherically symmetrical
– p has a shape much like a dumbbell
Orbital Shapes
• s is spherical
symmetrical
• Each p has a dumbbell shape, differing

in the direction extending into space
Orbitals within Subshells
Subshell Number of orbitals Number of electrons
s 1 2
p 3 6
d 5 10
f 7 14
• How many electrons can be in the 4d

subshell?
Answer: 10
Electronic Structure: Summary
Shell number: 1 2 3 4
Electron capacity: 2 8 18 32
2.4 Electron Configuration Rules
• Electron Configuration - the arrangement
of electrons in atomic orbitals
• Aufbau Principle (building up principle) –

Electrons fill the lowest-energy orbital that is
available first
- helps determine the electron configuration
- Remember s<p<d<f in energy
Electron Configuration Rules
• Pauli Exclusion Principle – each orbital
can hold up to two electrons with their spins
in opposite directions (paired)
• Hund’s Rule – each orbital in a subshell is

half-filled (with one electron) before any
orbital becomes completely filled (with two
electrons)
Writing Electron Configurations
• Obtain the total number of electrons in the atom
from the atomic number
• Electrons in atoms occupy the lowest energy
orbitals that are available beginning with 1s
• Fill subshells according to the order depicted:
The exact arrangement of electrons in an atom’s shells and
subshells is the atom’s electron configuration.
• Electrons fill orbitals from the

lowest-energy orbitals upward.
• Above the 3p level, the energies
of the orbitals in different shells
begin to overlap.
• 4s fills before 3d and 5s fills
before 4d
• The energy level diagram can be
used to predict the order in
which orbitals are filled.
• Each orbital can hold only two electrons, which
must be of opposite spin.
• Two or more orbitals with the same energy are each
half-filled by one electron before any one orbital is
completely filled by the addition of the second
electron.
– The number of electrons in each subshell is indicated by
a superscript.
Rules for Writing Electron Configurations
• Remember:
– The s sublevel has one orbital and can hold two
electrons
– The p sublevel has three orbitals. The electrons

will half-fill before completely filling the orbitals
for a maximum of six electrons
– The d sublevel has five orbitals. The electrons will

half-fill before completely filling the orbitals for a
maximum of ten electrons
• H • Li
– Hydrogen has only 1 – Lithium has 3
electron electrons
– It is in the lowest – First two have
energy level & configuration of
lowest orbital Helium – 1s2
– Indicate number of – 3rd is in the orbital
electrons with a of lowest energy in
superscript n=2
– 1s1 – 1s2 2s1
Orbital diagrams show orbitals
as boxes and electrons as arrows
1s 1s 2s
Electron Configuration Examples
• Give the complete electron configuration
of each element
– Be (Z= 4)
– Na (Z= 11)
– P (Z= 15)
– Cl (Z= 17)
– Ag (Z= 47)
Shortened Electron Configurations
• The full electron configuration of a sodium
atom is:
1s22s22p63s1
• The Noble gas which comes before sodium
is neon. We can abbreviate sodium’s
electron configuration by using [Ne] to
represent the first 10 electrons:
[Ne] 3s1
These are the electron configurations for B – N in which
the 2p shell begins to fill.
These are the electron configurations for O – Ne in
which the 2p shell is completed.
Shortened Electron Configuration
Examples
• S (Z=16)
• Sr (Z= 38)
• Ti (Z =22)
• Sn (Z = 50)
• Mg (Z =12)
Electron Configuration Summary
Electron Configuration Summary
Representative
07_116 Noble
Elements d - Transition Elements Representative Elements gases
1A Group 8A
ns1 ns2np6
numbers
1 2
1 H 2A 3A 4A 5A 6A 7A He
1s1 ns2 ns2np1 ns2np2 ns2np3 ns2np4 ns2np5 1s2
Period number, highest occupied electron level
3 4 5 6 7 8 9 10
2 Li Be B C N O F Ne
2s1 2s2 2s22p1 2s22p2 2s22p3 2s22p4 2s22p5 2s22p6
11 12 13 14 15 16 17 18
3 Na Mg Al Si P S Cl Ar
3s1 3s2 3s23p1 3s23p2 3s23p3 3s23p4 3s23p5 3s23p6
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
4 K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
4s1 4s2 4s 3d 4s 3d 4s 3d 4s 3d 4s 3d 4s 3d 4s 3d 4s 3d 4s 3d 4s 3d 4s 4p 4s 4p 4s 4p 4s 4p 4s 4p 4s24p6
2 1 2 2 2 3 1 5 2 5 2 6 2 7 2 8 1 10 2 10 2 1 2 2 2 3 2 4 2 5
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
5 Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
5s25p1 5s25p2 5s25p3 5s25p4 5s25p5 5s25p6
5s1 5s2 5s 4d 5s 4d 5s 4d 5s 4d 5s 4d 5s 4d 5s14d8
2 1 2 2 1 4 1 5 1 6 1 7 4d10 1 10 2
5s 4d 5s 4d10
55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
6 Cs Ba La* Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
6s1 6s2 6s25d1 4f146s25d2 6s25d3 6s25d4 6s25d5 6s25d6 6s25d7 6s15d9 6s15d10 6s25d10 6s26p1 6s26p2 6s26p3 6s26p4 6s26p5 6s26p6
87 88 89 104 105 106 107 108 109 110 111
7 Fr Ra Ac** Unq Unp Unh Uns Uno Une Uun Uuu
7s1 7s2 7s26d1 7s26d2 7s26d3 7s26d4 7s26d5 7s26d7
f - Transition Elements
58 59 60 61 62 63 64 65 66 67 68 69 70 71
Lanthanides* Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
6s24f15d1 6s24f35d0 6s24f45d0 6s24f55d0 6s24f55d0 6s24f75d0 6s24f75d1 6s24f95d0 6s24f105d0 6s24f115d0 6s24f125d0 6s24f135d0 6s24f145d0 6s24f145d1
90 91 92 93 94 95 96 97 98 99 100 101 102 103

Actinides** Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
7s2f06d2 7s25f26d1 7s25f36d1 7s25f46d1 7s25f66d0 7s25f76d0 7s25f76d1 7s25f96d0 7s25f106d0 7s25f116d0 7s25f126d0 7s25f136d0 7s25f146d0 7s25f146d1
2.5 Valence Electrons and the Octet Rule
• Valence Electrons – outermost electrons in
an atom
– The electrons involved in bonding
• The noble gases are extremely stable
– Called inert as they don’t readily bond to other
elements
• The stability is due to a full complement of
valence electrons in the outermost s and p
sublevels.
The Octet Rule
• Octet Rule - elements usually react in such
a way as to attain the electron configuration
of the noble gas closest to them in the
periodic table
– Elements on the right side of the table move “forward”

to the next noble gas
– Elements on the left side move “backward” to the noble
gas of the previous row
• Atoms will gain, lose or share electrons in

chemical reactions to attain this more stable
energy state
Octet of Electrons
• Elements in families other than the noble
gases are more reactive
– Strive to achieve a more stable electron
configuration
– Change the number of electrons in the atom to
result in full s and p sublevels
• Stable electron configuration is called the
“noble gas” configuration
Ions
• Ions - electrically charged particles that result
from a gain or loss of one or more electrons by
the parent atom
• Cation - positively charged
– result from the loss of electrons
– Na → Na+ + 1e−
• Anion - negatively charged

– results from the gain of electrons
– F + 1 e− → F−
Ion Formation and the Octet Rule
• Metallic elements tend to form positively
charged ions called cations
• Metals tend to lose all their valence
electrons to obtain a configuration of the
noble gas
Na Na+ + e−
Sodium atom Sodium ion
[Ne]3s1 [Ne]
Anion Formation and the Octet Rule
• Nonmetallic elements tend to form
negatively charged ions called anions
• Nonmetals tend to gain all valence electrons
to obtain a configuration of the nearest
noble gas
O + 2e− O2−
Oxygen atom Oxygen ion
[He]2s22p4 [He] 2s22p6 or [Ne]
Cation Formation and the Octet Rule
• All atoms of a group lose the same number
of electrons
• Resulting ion has the same number of
electrons as the nearest (previous) noble gas
atom
Al Al3+ + 3e−
Aluminum atom Aluminum ion
[Ne]3s23p1 [Ne]
Using the Octet Rule
• The octet rule is very helpful in predicting
the charges of ions in the representative
elements
• Transition metals still tend to lose electrons
to become cations but predicting the charge
is not as easy
• Transition metals often form more than one
stable ion
– Iron forming Fe2+ and Fe3+ is a common example
Isoelectronic
Isoelectronic – have the same number of electrons
• Give the charge of the • Which of the

most probable ion following pairs of
resulting from these atoms and ions are
elements isoelectronic?
– Ca – Cl−, Ar
– Sr – Na+, Ne
– S – Mg2+, Na+
– P – O2-, F−
– N3-, Cl −
– K+ , S2-
2.6 Trends in the Periodic Table
• Many atomic properties correlate with

electronic structure and also with their
position in the periodic table
– atomic size
– ion size
Atomic Size
• The size of an element increases moving
down from top to bottom of a group
• The valence shell is higher in energy and
farther from the nucleus traveling down the
group
• The size of an element decreases from left

to right across a period
• The increase in magnitude of positive charge in
nucleus pulls the electrons closer to the nucleus
Variation in Size of Atoms
Cation Size
Cations are smaller than their parent atom
• More protons than electrons creates an increased
nuclear charge
• Extra protons pull the remaining electrons closer
to the nucleus
• When a cation is formed (isoelectronic with a
noble gas), the valence shell is lost which
decreases the diameter of the ion relative to the
parent atom
Anion Size
Anions are larger than their parent atom
• Anions have more electrons than protons
• Excess negative charge reduces the pull of
the nucleus on each individual electron
Relative Size of Select Ions and
Their Parent Atoms
Four credits
Outline
• Chemical Bonding
• Ionic and Covalent Compounds
• Naming Compounds and writing Formulas of
Compounds
• Drawing Lewis Structures
• Molecular Geometry VSEPR
• Molecular Polarity
• Properties Based on Molecular Geometry and
Intermolecular forces.
3.1 Chemical Bonding
Chemical bond - the force of attraction between any
two atoms in a compound. Chemical bond
𝐴−𝐵
This attractive force overcomes the repulsion of the

positively charged nuclei of the two atoms
participating in the bond.
Interactions involving valence electrons are

responsible for the chemical bond
Lewis Symbols
Lewis symbol - a way to represent atoms using the element
symbol and valence electrons as dots.
As only valence electrons participate in bonding, this makes it
much easier to work with the octet rule.
The number of dots used corresponds directly to the number of
valence electrons located in the outermost shell of the atoms of the
element.
Lewis Symbols
Figure 3.1 Lewis Symbols for Representative Elements

Lewis Symbols
Example 3.1
Draw the Lewis symbol of Carbon and
indicate the bonds that carbon will form
when chemically bonded to other atoms.
C
Carbon can form 4 bonds
Principal Types of Chemical Bonds
1- Ionic bond - attractive force due to the transfer
of one or more electrons from one atom to another.
The attraction is due to the opposite charges of the
ions
2- Covalent bond - attractive force due to the
sharing of electrons between atoms.
• Some bonds have characteristics of both types
and not easily identified as one or the other
Ionic Bonding: NaCl
Consider the formation of NaCl
Na + Cl → NaCl
Using Lewis symbols to show how electrons are lost and gained
when sodium and chlorine become ions.
Na → Na+ + e−
Ionic compounds do not actually exist as individual units. They are

arranged in regular three-dimensnional repeating array called crystal
lattice strucure.
Example 3.2.
Using Lewis symbols, write the reactions showing electrons are lost
or gained when calcium and oxygen become ions
Covalent Bonding
Consider the formation of H2:
H + H → H2
• Each hydrogen has one electron in its valance shell.
• If it were an ionic bond it would look like this:
• However, both hydrogen atoms have an equal tendency

to gain or lose electrons
• Electron transfer from one H to another usually will
not occur under normal conditions
Covalent Bonding
• Instead, each atom attains a noble gas configuration
by sharing electrons
H + H → H :H
Each hydrogen
atom now has two The shared
electrons around it electron
and attained a He pair is called a
configuration Covalent Bond
Covalent Bonding
Features of Covalent Bonds
• Covalent bonds form between atoms with similar
tendencies to gain or lose electrons
• Compounds containing covalent bonds are called
covalent compounds or molecules
• The diatomic elements have completely covalent
bonds (totally equal sharing)
– H2, N2, O2, F2, Cl2, Br2, I2
Each fluorine is
.. .. .. .. surrounded by 8
: F +  F : → : F : F : electrons – Ne
.. .. .. .. configuration
Examples of Covalent Bonding
.. ..
2H  +  O → H : O : H
.. ..
H 2 electron shared
. ..
4H  +  C → H : C : H
 
H
8 electrons, C
obeys the octet
rule
Polar Covalent Bonding and Electronegativity
Polar covalent bonding - bonds made up of unequally
shared electron pairs
somewhat positively charged somewhat negatively charged

.. ..
H + F:→ H : F:
 
• The electrons spend more
time with fluorine
• This sets up a polar covalent These two
bond electrons are
• A truly covalent bond can not shared equally
only occur when both atoms
are identical
Polar Covalent Bonding and Electronegativity
Polar Covalent Bonding in HF
Fluorine is electron rich = -

(partial negative charge)
Hydrogen is electron
deficient = + (partial
positive charge)
This results in unequal

sharing of electrons in the
pairs = polar covalent bonds
Electronegativity
Electronegativity
Electronegativity - a measure of the ability of an atom to attract
electrons in a chemical bond.
Elements with high electronegativity have a greater ability to attract

electrons than do elements with low electronegativity.
Electronegativity increases
most
electronegative
elements
Electronegativity increases
Least
electronegative
elements
Electronegativity
Electronegativity calculation
• The difference in electronegativity determines the extent
of bond polarity.
• The greater the difference in electronegativity (∆𝐸𝑁 )

between two atoms, the greater the polarity of their bond
• ∆𝐸𝑁 < 0.5 → nonpolar covalent bond

• 2.0 > ∆𝐸𝑁 > 0.5 → polar covalent bond
• ∆𝐸𝑁 > 2.0 → Ionic bond
Electronegativity
In the below examples, the electronegativity values will be given.
Example 3.3.
Use the electronegativity values to classify the bonds in SiO2 as
ionic, polar covalent, or nonpolar covalent.
∆𝐸𝑁= [EN of O]-[EN of Si] = 3.5-1.8=1.7
∆𝐸𝑁 falls in the range of polar covalent bond.
Example 3.4.
Which would be more polar, a H-F bond or H-Cl bond?
•H-F … ∆𝐸𝑁 = [EN of F]-[EN of H]= 4.0 - 2.1 = 1.9
•H-Cl … ∆𝐸𝑁= [EN of Cl]-[EN of H]= 3.0 - 2.1 = 0.9
The HF bond is more polar than the HCl bond

Example 3.5: Arrange these elements based
on their electronegativity.
Se, Ge, Br, As
Ge < As < Se < Br
Example 3.6: Arrange these elements based on

their electronegativity.
Be, Mg, Ca, Ba
Ba < Ca < Mg < Be
3.2 Naming Compounds and Writing
Formulas of Compounds
Nomenclature - the assignment of a correct and unambiguous

name to each and every chemical compound
Two naming systems:
1-Ionic compounds
2-Covalent compounds
Ionic Compounds
A formula of a compound is the representation of the fundamental
compound using chemical symbols and numerical subscripts
NaCl AlCl3 MgF2
• Metals and nonmetals usually react to form ionic compounds.
• The metals are cations and the nonmetals are anions.
• Formula of an ionic compound is the smallest whole-number
ratio of ions in the substance.
• Cations and anions must combine to give a formula with a net
charge of zero
• Metals have a charge equal to group number, nonmetals have a
charge equal to the group number minus eight
Example 3.5.
Predict the formula of the ionic compounds formed from combining
ions of the following pairs of elements:
1. sodium and oxygen → (Na+ and O2-) → 𝑁𝑎2 𝑂
2. lithium and bromine → (Li+ and Br-) → 𝐿𝑖𝐵𝑟
3. aluminum and oxygen → (Al3+ and O2-) → 𝐴𝑙2 𝑂3
4. barium and fluorine → (Ba2+ and F-) → 𝐵𝑎𝐹2
5. calcium and nitrogen → (Ca2+ and N3-) → 𝐶𝑎3 𝑁2
6. magnesium and bromine → (Mg2+ and Br-) → 𝑀𝑔𝐵𝑟2
7. aluminum and bromine → (Al3+ and Br-) → 𝐴𝑙𝐵𝑟3

Writing Names of Ionic Compounds from the Formula
of the Compound
• Name the cation followed by the name of the anion.
• A positive ion retains the name of the element; change the anion
suffix to -ide
• Metals that exist with only one possible cation charge are
group IA (1+), group IIA (2+), Ag+, Cd2+ , Zn2+ and Al3+
Formula cation and anion stem + ide = Compound name
NaCl sodium chlor + ide sodium chloride
Na2O sodium ox + ide sodium oxide
Li2S lithium sulf + ide lithium sulfide
AlBr3 aluminum brom + ide aluminum bromide
CaO calcium ox + ide Calcium oxide
of the Compound
• If the cation of an element has several ions of different
charges (as with transition metals) use
1- Stock system or systematic name which uses a Roman
numeral following the metal name
• Roman numerals give the charge of the metal
• Examples:
• FeCl3 is iron(III) chloride
• FeCl2 is iron(II) chloride
• Cu2O is copper(I) oxide
• CuO is copper(II) oxide
of the Compound
2-Common Nomenclature System
• Use -ic to indicate the higher of the charges that ion might
have
• Use -ous to indicate the lower of the charges that ion might
have
• Examples:
• FeCl2 is ferrous chloride
• FeCl3 is ferric chloride
• Cu2O is Cuprous oxide
• CuO is cupric oxide
Formulas
Monatomic of Compounds
ions
Monatomic ions: ions consisting of a single charged atom such as H+
and Cl-.
Table 3.2 Common Monatomic Cations and Anions
Cation Name Anion Name
H+ Hydrogen ion H- Hydride ion
Li+ Lithium ion F- Fluoride ion
Na+ Sodium ion Cl- Chloride ion
K+ Potassium ion Br- Bromide ion
Cs+ Cesium ion I- Iodide ion
Be2+ Beryllium ion O2- Oxide ion
Mg2+ Magnesium ion S2- Sulfide ion
Ca2+ Calcium ion N3- Nitride ion
Ba2+ Barium ion P3- Phosphide ion
Al3+ Aluminum ion
Ag+ Silver ion
Note: You should memorize the charges, formulas, and names of the ions
highlighted in red (important in biological system).
Polyatomic ions: ions composed of 2 or more atoms bonded
together with an overall positive or negative charge
– Within the ion itself, the atoms are bonded using covalent
bonds
– The positive and negative ions will be bonded to each other
with ionic bonds
• Examples:
• NH4+ ammonium ion
• SO42- sulfate ion
Table 3.3 Common Polyatomic Cations and Anions
Ion Name Ion Name
H3O+ Hydronium CO32– Carbonate
NH4+ Ammonium HCO3– Bicarbonate
NO2– Nitrite ClO– Hypochlorite
NO3– Nitrate ClO2– Chlorite
SO32– Sulfite ClO3– Chlorate
SO42– Sulfate ClO4– Perchlorate
HSO4– Hydrogen sulfate CH3COO– (or Acetate
C2H3O2–)
OH– Hydroxide MnO4– Permanganate
CN– Cyanide Cr2O72– Dichromate
PO43– Phosphate CrO42– Chromate
HPO42– Hydrogen phosphate O22– Peroxide
H2PO4– Dihydrogen phosphate
Note: You should memorize the charges, formulas, and names of the ions
highlighted in red (important in biological system).
Example 3.6 Name each of the following compounds
1. NH4Cl Ammonium chloride
2. BaSO4 Barium sulfate
3. Fe(NO3)3 Iron(III) nitrate
4. CuHCO3 Copper(I) bicarbonate
5. Ca(OH)2 Calcium hydroxide
6. Na2SO4 Sodium sulfate
Example 3.7 Write the formula of each compound
1. Sodium sulfate Na2SO4

2. Aluminum oxide Al2O3
3. Magnesium phosphate Mg3(PO4)2
4. Calcium carbonate CaCO3
5. Barium chloride BaCl2
7. Chromium(II) sulfate CrSO4
8. Ammonium sulfide (NH4)2S
Covalent Compounds
Covalent compounds are typically formed from nonmetals.
Molecules - compounds characterized by covalent bonding

•Not a part of a massive three-dimensional crystal structure
•Exist as discrete molecules in the solid, liquid, and gas states
Examples:
NO H2O ICl PCl5 P2O5 NH3
Naming Covalent Compounds
1. The names of the elements are written in the order in which
they appear in the formula
2. A prefix indicates the number of each kind of atom
Table 3.4 Prefixes Used to Denote Numbers of Atoms in a Compound
Prefix Number of Prefix Number of Atoms
Atoms
Mono- 1 Hexa- 6
Di- 2 Hepta- 7
Tri- 3 Octa- 8
Tetra- 4 Nona- 9
Penta- 5 Deca- 10
3. If only one atom of a particular element is present in the
molecule, the prefix mono- is usually omitted from the
first element
Example: CO is carbon monoxide
4. The name starts with the less electronegative element.
5. The stem of the name of the last element is used with the
suffix –ide
6. The final vowel in a prefix is often dropped before a
vowel in the stem name
Example 3.8 Name each of the following compounds
1. SiO2 Silicon dioxide

2. N2O 5 Dinitrogen pentoxide
3. CCl4 Carbon tetrachloride
4. IF7 Iodine heptaflouride
5. NO Nitrogen monoxide
6. PCl5 phosphorous pentacholride
7. ICl iodine monochloride
Use the prefixes in the names to determine the subscripts for the elements
• Some common names that are used:

– H2O water
– NH3 ammonia
– C2H5OH ethanol or ethyl alcohol
– C6H12O6 glucose
3.3 Properties of Ionic and Covalent
Compounds
1- Physical State
Ionic compounds are usually solids at room temperature
Covalent compounds can be solids, liquids, and gases
2- Melting and Boiling Points

Melting point - the temperature at which a solid is converted to a
liquid
Boiling point - the temperature at which a liquid is converted to a gas
Ionic compounds have much higher melting points and boiling points
than covalent compounds
A large amount of energy is required to break the electrostatic

attractions between ions
Ionic compounds typically melt at several hundred degrees Celsius
Compounds
3- Structure of Compounds in the Solid State
– Ionic compounds are crystalline
– Covalent compounds are crystalline or amorphous – having no
regular structure
4- Solutions of Ionic and Covalent Compounds

– Ionic compounds often dissolve in water, where they dissociate -
form positive and negative ions in solution
– Electrolytes - ions present in solution allowing the solution to
conduct electricity
– Covalent compounds usually do not dissociate and do not conduct
electricity - nonelectrolytes
Compounds
Comparison of Ionic vs. Covalent Compounds
Property Ionic Covalent

Often composed of Metal + nonmetal 2 nonmetals
Electrons are Transferred Shared
Physical state is Solid and crystalline Gas, liquid, solid;
crystal or amorphous
Dissociation Yes, they are No, they are
electrolytes nonelectrolytes
Boiling and Melting High Low
point
3.4 Drawing Lewis structures
Lewis Structure Guidelines
1. Use chemical symbols for the various elements to write the skeletal
structure of the compound
• The least electronegative atom will be placed in the central
position
• Hydrogen always occupies terminal positions
• Halogens occupy terminal positions, except when more
electronegative elements are present
• Carbon often forms chains of carbon-carbon covalent bonds
2. Determine the number of valence electrons associated with each
atom in the compound
• Use these valence electrons to determine the number of valence
electrons around each atom
• Polyatomic cations, subtract one electron for every positive
charge
• Polyatomic anions, add one electron for every negative charge
Lewis Structure Guidelines
3. Connect the central atom to each of the surrounding with single
bonds
4. Next, complete octets of all the atoms bonded to the central atom
• Hydrogen needs only two electrons
• Electrons not involved in bonding are represented as lone pairs
• After the terminal atoms have an octet, provide the central atom
with an octet if valence electrons are still available
5. If there are not enough valence electrons to give the central atom
an octet, move lone pair electrons from terminal atoms to form a
new bond with the central atom.
– Continue to shift the electrons until all atoms have an octet.
6. Recheck that all atoms have the octet rule satisfied and that the total
number of valance electrons are used
Example 3.8 Draw the Lewis structure of CO2
1. Draw a skeletal structure of the molecule
O C O
2. Draw valence electrons around each atom
3. Connect the central atom to each of the surrounding with bonds in a way
to complete octets around each atom
4. Recheck the electron distribution

• 8 electrons around each atom, octet rule satisfied
7. Drawing
3.4 DrawingLewis
LewisStructures
structures
Common bonding patterns for C, N, O, X (Halogen),
and H.
6. Molecular
3.4 Drawing Formulas and Lewis Structures
Lewis structures
• Lewis structure: A molecular representation that
shows both the connections among atoms and the
locations of lone-pair valence electrons
Computing Formal Charge
• The formal charge is the hypothetical charge on an

atom in a molecule or polyatomic ion.
• The best Lewis structures will have formal charges on
the atoms that are zero or nearly zero.
FC = (group number) – [(number of bonds) + (number of unshared e-)]
Consider nitrosyl chloride, NOCl Best
Cl N O Cl N O Lewis
structure
Cl 7 – [2+ 4] = +1 Cl 7 – [1 + 6] = 0
N 5 – [3 + 2] = 0
N 5 – [3 + 2] = 0
O 6 – [2 + 4] = 0
O 6 – [1 + 6] = -1
Formal charge = (# valence e-) – (# of bonds + # of unshared e-)
• In a neutral molecule, the sum of the formal

charges is zero. For an ion, the sum of the formal
charges is equal to the charge of the ion.
• An atom in a Lewis structure that has the number

of bonds expected on the basis of its group
number has no formal charge.
“Normal” covalent bonding patterns:

Carbon Nitrogen Oxygen Halogens
C N
O X
One bond
C N O Three lone pairs
C N Two bonds
Two lone pairs
C Three bonds
One lone pair
Four bonds
No lone pairs
Structures with formal charges:

Carbon Nitrogen Oxygen Halogens
C N O X
N
N O
C
N
N
O
N
Example 3.10 Draw the Lewis structure of CO32-
1. Draw a skeletal structure of the molecule
2. Draw valence electrons around each atom
3. Connect the central atom to each of the surrounding with bonds in a way to
complete octets around each atom
4. Recheck octet and formal charge

Resonance structures
• Experimental evidence shows all bonds are the

same length, meaning there is not really any
double bond.
• None of theses three Lewis structures exist, but
the actual structure is an average or hybrid of
these three Lewis structures
• Resonance - two or more Lewis structures that
contribute to the real structure
Example 3.11 write Lewis structures for the following:
1. H2O
2. NH3
3. CO2
4. NH4+
5. N2
6. CH3COO-
7. C2H4
8. SO2
9. NO3-
Lewis structures: Exceptions to the Octet Rule
Limitations of the Octet Rule
There are some molecules that violate the octet rule.
1. The covalent compounds of Be (e.g. BeH2, BeF2,

BeCl2).
2. The covalent compounds of the IIIA Group (e.g. BF3,
BCl3).
3. Elements in period 3 and beyond can exceed the
octet rule.
(PCl5, SF6, ClF3, XeCl4, XeF2, [BrF4]-, ..etc).
1. Incomplete octet - less then eight electrons around an

atom other than H
H – Be – H
Another examples: BF3 and BCl3

2. Expanded octet - an element in the 3rd period or below

may have 10 and 12 electrons around it
• Consider the Lewis structure of PF5
• Phosphorus is a third period element
1 P atom has 5 valence electrons

5 F atoms have 7 valence electrons each
Another examples: SF4, SeCl4, and SF6

• Example: Write Lewis dot and dash

formulas for the sulfur hexafluoride, SF6.
SF6
F
F F
S
F F
F
3.5 Molecular Geometry: VSEPR Theory
VSEPR theory - Valance Shell Electron Pair Repulsion theory is used

to predict the shape of the molecules
All electrons around the central atom arrange themselves so they can
be as far away from each other as possible – to minimize electronic
repulsion.
• In the covalent bond, bonding electrons are localized around the

nucleus.
• The covalent bond is directional, having a specific orientation in
space between the bonded atoms.
• Ionic bonds have electrostatic forces which have no specific
orientation in space.
Molecular Geometry: VSEPR Theory
A Stable Exception to the Octet Rule
• Consider BeH2
– Only 4 electrons surround the beryllium atom
– These electrons in the bonds to the two atoms have minimal
repulsion when located on opposite sides of the structure
– Linear structure having bond angles of 180°
3.4 Drawing
Molecular Geometry:
Lewis structures
VSEPR Theory
Another Stable Exception to the Octet Rule
• Consider BF3
– There are 3 bonded atoms around the central atom
– These bonded atoms have minimal repulsion when placed
in a plane, forming a triangle
• Trigonal planar structure with bond angles of 120°
3.4 Drawing
Molecular Geometry:
Lewis structures
VSEPR Theory
Basic Electron Pair Repulsion of a Full Octet
• Consider CH4
– There are 4 bonded atoms around the central carbon
– Minimal electron repulsion when electrons are placed at the
four corners of a tetrahedron
– Each H-C-H bond angle is 109.5°
• Tetrahedron is the primary structure of a full octet
3.4 Drawing
Molecular Geometry:
Lewis structures
VSEPR Theory
Basic Electron Pair Repulsion of a Full Octet with One Lone Pair
• Consider NH3
– There are three bonded atoms and one lone pair (four groups)
– A lone pair is more electronegative with a greater electron
repulsion
– The lone pair takes one of the corners of the tetrahedron without
being visible, distorting the arrangement of electron pairs
• Ammonia has a pyramidal structure with 107°bond angles
3.4 Drawing
Molecular Geometry:
Lewis structures
VSEPR Theory
Basic Electron Pair Repulsion of a Full Octet with Two Lone Pairs
• Consider H2O
– There are two bonded atoms and two lone pair (four groups)
– All 4 electron pairs are approximately tetrahedral to each other
– The lone pairs take two of the corners of the tetrahedron without
being visible, distorting the arrangement of electron pairs
• Water has a bent or angular structure with 104.5° bond angles
CH4 NH3 H2 O
Number of lone pairs 0 1 2
Angle 109.5° 107° 104.5°
VSEPR Model: Lone pairs require more room than bonding pairs
and tend to compress the angles between the bonding pairs.
3.4 Drawing
Molecular Geometry:
Lewis structures
VSEPR Theory
Table 3.5 Predicting Geometric Shape Using Electron Pairs
Bonded Nonbonding Bond Angle Molecular Exampl

Atoms Lone Electron Geometry e
Pairs
2 0 180° Linear CO2
3 0 120° Trigonal planar SO3
4 0 109.5° Tetrahedral CH4
3 1 ~107° Pyramidal NH3
2 2 ~104.5° Bent H2O
3.4 Molecular
3.6 Drawing Lewis
Polarity
structures
Molecular Polarity
Polar molecules when placed in an electric field will align
themselves in the field.
Molecules that are polar behave as a dipole (having two “poles” or

ends). One end is positively charged the other is negatively charged
Nonpolar molecules will not align themselves in an electric field
Use the following symbol to denote the polarity of each bond
Positive end of the Negative end of the bond,

bond, the less more electronegative atom
electronegative atom attracts the electrons more
strongly towards it
3.6 Molecular Polarity
Bond Polarity
Example 3.12
Predict which of the following bonds are polar and if
polar use a vector to indicate in which direction the
electrons are pilled.
Si – Cl S – Cl
H–C C≡ 𝑁
C–C O-S
Molecular Polarity
Guidelines for Determining Polarity
• Molecules that have no lone pair on the central atom, and all
terminal atoms are the same are nonpolar
• Molecules with one lone pair on the central atom are polar
• Molecules with more than one lone pair on the central atom are
usually polar
Polar Covalent Molecules
O
H Cl O
H H C
H3C CH3
NonPolar Covalent Molecules
O C O
Molecules that have no lone pair on the central atom, and all
terminal atoms are the same are nonpolar
Example 3.13
Predict whether each of the following molecules is polar.
NH3 PCl3 CO2 CCl4 H2O CH4 HF O2

3.5 Properties Based on Molecular
Geometry and Intermolecular Forces
Intramolecular forces – attractive forces within molecules

Example: Chemical bonds
Intermolecular forces – attractive forces between molecules
Intermolecular forces determine many physical properties such as

solubility of once substance in another and the freezing and boiling
points of liquids.
1-Solubility
Solubility - the maximum amount of solute that dissolves in a given
amount of solvent at a specific temperature
“Like dissolves like”

Polar molecules are most soluble in polar solvents
Nonpolar molecules are most soluble in nonpolar solvents
Does ammonia, NH3, dissolve in water?

Yes, both molecules are polar
Solubility
+ +
- -
Solubility
• What do you know about oil and
water?
– “They don’t mix”
• Why?
– Because water is polar and oil is
nonpolar
Oil remains insoluble and floats on the

surface of the water as it is less dense
2-Boiling Points (b.p.) of Liquids and Melting Points
(m.p.) of Solids
The greater the intermolecular force, the more energy is required
leading to higher m.p. of a solid and b.p. of a liquid
Factors Influencing Boiling and Melting Points

1-Molecular mass
Larger molecules have higher m.p. and b.p. than smaller molecules as
it is more difficult to convert a larger mass to another phase
2-Polarity
Polar molecules have higher m.p. and b.p. than nonpolar molecules of
similar molecular mass due to their stronger attractive force
Table 3.6 Melting and Boiling Points of Selected Compounds in
Relation to Their Bonding Type
Formula (Name) Bonding Type B.P. (℃)
N2 (nitrogen) Nonpolar covalent –196
O2 (oxygen) Nonpolar covalent –183
NH3 (ammonia) Polar covalent –33
H2O (water) Polar covalent 100
NaCl (sodium chloride) Ionic 1413
KBr (potassium bromide) Ionic 1435
Example 3.14
Predict which compound in each following pairs should
have the higher melting and boiling points.
H2O and C2H4 H2O because it is polar

CO and CH4 CO because it is polar
NH3 and N2 NH3 because it is polar
Cl2 and ICl ICl because it is polar
C2H6 and CH4 C2H6 because it has higher molar mass
F2 and Br2 Br2 because it has higher molar mass
CHCl3 and Cl2 CHCl3 because it is polar and has higher
molar mass
Four credits
Types of Chemical Reactions
• Chemical reactions generally follow one of a few

simple patterns such as :
– Combination
– Decomposition
– Single-replacement
– Double-replacement
Combination Reactions
• The joining of two or more elements or compounds,
producing a product of different composition
A + B → AB
• Examples:
2Na(s) + Cl2(g) → 2NaCl(s)
MgO(s) + CO2(g) → MgCO3(s)
2H2(g) + O2(g) → 2H2O (g)
Decomposition Reactions
• Produce two or more products from a single reactant
• Reverse of a combination reaction
AB → A + B
• Examples:
2HgO(s) → 2Hg(l) + O2(g)
CaCO3(s) → CaO(s) + CO2(g)
CuSO4.5H2O(s) → CuSO4 (s) + 5H2O (g)
Single - Replacement Reactions

• One atom replaces another in the compound
producing a new compound
A + BC → B + AC
• Examples:
Cu(s)+2AgNO3(aq) → 2Ag(s)+Cu(NO3)2(aq)
2Na(s) + 2H2O(l) → 2NaOH(aq) + H2(g)
Double- Replacement Reactions

• Two compounds undergo a “change of partners” by
exchanging atoms to produce two new compounds
AB + CD → AD + CB
• Examples:
HCl(aq)+NaOH(aq) →NaCl(aq)+H2O(l)
Pb(NO3)2(aq) + 2NaCl(aq) → PbCl2(s) + 2NaNO3(aq)
Practice Equation classification

Classify each of the following reactions as combination,
decomposition, single-replacement , or double replacement
a) HNO3 (aq)+KOH(aq) →KNO3 (aq)+H2O(l)

b) Al(s) + 3NiNO3(aq) → Al(NO3)3(aq) + 3Ni(s)
c) KCN(aq) + HCl(aq) → HCN(s) + KCl(aq)
d) MgCO3(s) → MgO(s) + CO2(g)
Oxidation-Reduction Reactions
(Redox Reactions)
• Oxidation-reduction processes are responsible for many
types of chemical change
• Oxidation - defined by one of the following

– loss of electrons
– gain of oxygen
• Example: Mg → Mg2+ + 2e-

– Oxidation half-reaction
• Reduction - defined by one of the following:

– gain of electrons
– gain of hydrogen
• Example: Cl2 + 2e- → 2Cl-

– Reduction half-reaction
• Cannot have oxidation without reduction

Oxidation and Reduction as Complementary Processes
Mg → Mg2+ + 2e- (oxidation half-reaction)

Cl2 + 2e- → 2Cl- (reduction half-reaction)
Mg + Cl2 → Mg2+ + 2Cl-
Oxidizing Agent Reducing Agent

• Is reduced • Is oxidized
• Gains electrons • Loses electrons
• Causes oxidation • Causes reduction
Voltaic Cells
• Voltaic cell – electrochemical cell that converts stored
chemical energy into electrical energy
• Consider the following reaction:
Zn(s) + Cu2+(aq) → Zn2+(aq) + Cu(s)
• Zn is being oxidized
• Cu2+ is reduced
Identify the oxidizing agent and reducing agent in the following
redox reaction?
Voltaic Cell as an Example
Oxidation States
Oxd. State = Oxid. # = the # of electron gained or lost by an atom of that element
when it forms the compound.
Guidelines for assigning oxidation numbers.

1. The oxidation number of any free, uncombined element is zero such as Na, Cu,
Ag, H2, O2, ..etc
2. The oxidation number of an element in a simple (monatomic) ion is the charge

on the ion such as Na+, Cl-
IA metals have oxidation numbers of +1.
IIA metals have oxidation numbers of +2.
IIIA metals have oxidation numbers of +3.
3. In the formula for any compound, the sum of the oxidation numbers of all
elements in the compound is zero (e.g. overall oxidation number = zero in H2SO4).
4.In a polyatomic ion, the sum of the oxidation numbers of the constituent
elements is equal to the charge on the ion (e.g. overall oxidation number = -2 in
SO42-).
Oxidation States
5. Fluorine, F, has an oxidation number of –1 in its compounds.
6. Hydrogen, H, has an oxidation number of +1 unless it is
combined with metals, where it has the oxidation number -1.
– Examples – LiH, BaH2
7. Oxygen, O, usually has the oxidation number -2.
– Exceptions:
In peroxides O has oxidation number of –1.
• Examples - H2O2, CaO2, Na2O2
Assigning Oxidation Numbers:

– An atom in its elemental state has an oxidation
number of 0.

– A monatomic ion has an oxidation number equal
to its charge.
– In a molecular compound, an atom usually has the
same oxidation number it would have if it were a
monatomic ion.
• Hydrogen is usually +1.
• Oxygen is usually –2.
• Halogens are usually –1.
Oxidation Numbers
Example: Assign oxidation numbers to each element in
the following compounds:
NaNO3
• Na = +1
• O = -2
• N = +5
Calculate
+1 + 3(-2) + x = 0
x = +5
General Chem. Chap. 5 18

Oxidation Numbers
HClO4
H = +1
O = -2
Cl = +7
HCO3−
O = -2
H = +1
C = +4
Calculate
+1 + 3(-2) + x = -1
x = +4
Oxidation Numbers
NO2-
• O = -2
• N = +3 Calculate
2(-2) + x = -1
x = +3
HNO3
H = +1
O = -2
N = +5
Applications of Oxidation and Reduction
A. Corrosion - the deterioration of metals caused by an

oxidation-reduction process
– Example: rust (oxidation of iron)
4Fe(s) + 3O2(g) → 2Fe2O3(s)
B. Combustion of Fossil Fuels

– Example: natural gas furnaces
CH4(g) + 2O2(g) → CO2(g) + 2H2O(g)
Applications of Oxidation and Reduction
C. Bleaching
• Most bleaching agents are oxidizing agents
• The oxidation of the stains produces compounds that
do not have color
– Example: Chlorine bleach - sodium hypochlorite (NaOCl)
D. Metabolism
• Break down of molecules into smaller pieces by
enzymes
-Ethanol is oxidized to acetaldehyde
-Acetaldehyde is oxidized to acetic acid
-Acetic acid is oxidized to carbon dioxide
Summary
Practice: Use oxidation numbers to show that the
production of iron metal from its ore (Fe2O3) by reaction
with charcoal (C) is a redox reaction. Which reactant has
been oxidized, and which has been reduced? Which
reactant is the oxidizing agent, and which is the reducing
agent?
2 Fe2O3 (s) + 3 C (s) → 4 Fe (s) + 3 CO2 (g)
Solution
• Practice: Assign oxidation states and identify the

oxidizing agent and reducing agent in the
following redox reaction
3MnO2(s) + 4Al(s) → 3Mn(s) + 2Al2O3(s)
-2 -2
0 0
+4 +3
You do it!
Four credits
Outline
4.1 The Mole Concept and Atoms
4.2 The Chemical Formula, Formula Mass, and Molar Mass
4.3 The Mole Concept and Molecules
4.4 The Chemical Equation and Balancing Chemical Equations
4.5 Calculations using the Chemical Equation (Stoichiometry)

• Atoms are exceedingly small, and their masses have been
experimentally determined for each element.
– Unit of measurement for mass of an atom is
atomic mass unit (amu = mass of a proton)
1 a.m.u. = 1.661  10-24 g
• Carbon-12 assigned the mass of exactly 12 amu, and has been chosen
to be the reference point. (Other elements have been measured in
relative to C-12 standard).
• Periodic table gives atomic masses in amu
Example 1
What is the atomic mass of one atom of fluorine?
Answer:
Mass of one atom = 19.00 amu X 1.661x10-24 /1 amu= 3.156 x 10-23 g
This is very very small
Chemists usually work with larger quantities and it is more convenient
to work with grams than amu when using larger quantities
• Practical unit for defining a collection of atoms is the mole
1 mole of atoms = 6.022  1023 atoms
• Avogadro’s number is basis for the concept of the mole
In general: I mole of anything = Avogadro’s number unit of that thing
e.g. 1 mole of Cu =6.022 x1023 atoms of Cu
1 mole of O2 = 6.022 x1023 O2 molecules
1 mole of chairs = 6.022 x1023 chairs
• We must define the mole as a counting unit

– The mole is abbreviated mol
• A mole is a number unit that defines an amount of something, such
as Dozen defines 12
• Atomic mass - one atom of an element corresponds

to average mass of a single atom in amu
• Molar mass – one mole of an element corresponds
to the mass of a mole of atoms in grams
– 1 atom of F is 19.00 amu
– 1 mole of F is 19.00 g
Calculating Atoms, Moles, and Mass
The relationship between moles and atoms is given by

Avogadro’s Number and between moles and grams is
given by molar mass
1 mol of X = 6.022 x 1023 atoms of X = Molar Mass in grams of X
X is any atom
Example 2
Calculate the number of mol of S represented by 1.81 x 1024 atoms of S.
Solution
Step 1- The relationship between moles and atoms is given by
Avogadro’s Number.
1 mol S = 6.022 x 1023 atoms S
Step 2-Write this as two possible fractions, and choose the one
appropriate to this problem
Cont. Example 2
Step 3-Set up the problem with the starting unit (atoms) in
the denominator of the conversion factor.
1 mol S
1.81 x 1024 atoms S x 6.022 x 1023 atoms S = 3.01 mol S
Data Given Conversion Factor =Desired Result

Example 3
What is the mass, in g, of 3.01 mol of S?
Solution
3.01 mol S x = 96.5 g S

Data Given Conversion Factor Desired Result
Example 4
Calculate the number of atoms of S in 1.00 g of S.
1 mol S 6.022 x 10 23 atoms S

1.00 g S x x
32.06 g S 1 mol S
Molar Mass Avogadro’s Number
= 1.88 x 1022 atoms S

Interconversion Between Moles, Particles, and Grams
or
mass (g) number of atoms
# moles (n) = # moles (n) =
MM (g/mole) NA
Mass (g) = # of moles x MM (g/mole) No. of atoms = n x NA

Practice Calculations
1. Calculate the number of atoms in 1.7 moles of
boron. (Answer 1.02×1024 B atoms)
2. Find the mass in grams of 2.5 mol Na (sodium).
(Answer 57.48g)
3. Calculate the number of atoms in 5.0 g aluminum.
(Answer 1.12×1023 Al atoms)
4. Calculate the mass of 5,000,000 atoms of Au
(gold) (Answer 1.64×10-15 g)
4.2 The Chemical Formula, Formula Mass,
and Molar Mass
• Chemical formula - a combination of symbols of
the various elements that make up the compound.
• Formula unit – usually used for ionic compounds

the smallest collection of atoms that represents
whole material composition
– The identity of the atoms or ions
– The relative number of each type of atom or ion
and Molar Mass
Consider the following formulas:
• H2 – 2 atoms of hydrogen are chemically bonded forming diatomic
hydrogen, subscript 2
• H2O – 2 atoms of hydrogen and 1 atom of oxygen, lack of subscript
means one atom
• NH3 – 1 N atom and 3 H atoms
• C3H8 – 3 C atoms and 8 H atoms
and Molar Mass
NaCl – 1 ion each of sodium and chlorine

Ca(OH)2 – 1 ion of calcium and 2 ions of the hydroxide
polyatomic ion, subscript outside parentheses applies to
all atoms inside
(NH4)2SO4 – 2 ammonium ions and 1 sulfate ion
Ammonium ion contains 1 nitrogen and 4 hydrogen
Sulfate ion contains 1 sulfur and 4 oxygen
Compound contains 2 atoms of N, 8 H, 1 S, and 4 O
and Molar Mass
Formula Mass and Molar Mass
• Formula mass - the sum of the atomic masses of all atoms
in the compound as represented by its formula
– expressed in amu
• What is the formula mass of H2O?
– 16.00 + 2(1.008) = 18.02 amu
• Molar mass – mass of a mole of compound in grams / mole
– Numerically equal to the formula mass in amu
• What is the molar mass of H2O?
– 18.02 g/mol H2O
and Molar Mass
Example 5: What is the formula mass and the molar mass
of C6H12O6?
Ans. 180.16 g/mol
Example 6: What is the molar mass of (NH4)3PO4?

3(N) + 12(H) + P + 4(O)=
3(14.01) + 12(1.008) + 30.97 + 4(16.00)= 149.10 g/mol
and Molar Mass
The formula mass of calcium nitrate, Ca(NO3)2, is:

1 Ca = 1 40.08 = 40.08 amu
2  N = 2  14.01 = 28.02 amu
6  O = 6  16.00 = 96.00 amu
Formula mass = 164.10 amu
Molar mass (MM) = 164.10 g or 164.10 g/mol
Example 7: How many moles are contained in 60.0 g of

ozone, O3?
Useful info. Molar mass O = 16.0 g
MM of O3 = 3 x 16.0 = 48.0 g
 1 mole 
? moles O 3 = 60.0 g O 3   = 1.25 moles
 48.0 g O 3 
or
mass (g) 60.0 g

# moles = MM (g/mole) = = 1.25 mole
48.0 g/mole
Example 8: How many molecules are contained in 60.0 g of

ozone, O3?
Remember
1 mole of O3= 6.022 x 1023 molecules of O3 = 48.0 g of O3
 6.022 1023 molecules 

? molecules O 3 = 1.25 moles  
 1 mole 
= 7.53 1023 molecules O3
Example 9: Calculate the number of C3H8 molecules in

74.6 g of propane.
Useful info. NA = 6.022 x 1023, MM of C3H8 = 44.11 g
? C3 H 8 molecules = 74.6 g C3 H 8 
 1 mole C3 H 8  6.022 10 23 C3 H 8 molecules 
   =
 44.11 g C3 H 8  1 mole C3 H 8 
1.02  10 24 molecules
4.4 The Chemical Equations
• Chemical equation - shorthand notation of a

chemical reaction
– Describes all of the substances that react and all the
products that form, physical states, and experimental
conditions
– Reactants – (starting materials) – the substances that
undergo change in the reaction
– Products – substances produced by the reaction
Chemical Equation Features

1. Identity of products and reactants must be specified
using chemical symbols
2. Reactants are written to the left of the reaction arrow
and products are written to the right
3. Physical states of reactants and products may be shown
in parentheses
4. Symbol  over the reaction arrow means that energy is
necessary for the reaction to occur
5. Equation must be balanced
Chemical Equation Features


2HgO( s ) ⎯
⎯→ 2Hg(l ) + O 2 ( g )
Reactants Products
 – energy is needed
Physical states are shown in parentheses
(s) = solid (l) = liquid (g) = gas

(aq) = dissolved in aqueous solution
The Experimental Basis of a Chemical Equation

The chemical equation must represent a chemical change
where one or more substances changed into new substances
with different chemical and physical properties.
Evidence of a Reaction Occurring can be
•Release of a gas
– CO2 is released when acid is placed in a solution containing CO32- ions
•Formation of a solid (precipitate)
– A solution containing Ag+ ions mixed with a solution containing Cl- ions
•Heat is produced or absorbed
– Acid and base are mixed together
•Color changes
4.4 Balancing Chemical Equations
D
2HgO( s) ¾
¾® 2Hg(l ) + O2 ( g )
• A chemical equation shows the molar quantity of
reactants needed to produce a particular molar
quantity of products.
• The relative number of moles of each product and
reactant is indicated by placing a whole-number
coefficient before the formula of each substance in the
chemical equation.
• Law of conservation of mass - matter cannot be either
gained or lost in the process of a chemical reaction.
The total mass of the products must equal the total
mass of the reactants.
Coefficient - how many of that substance

are in the reaction
D
2HgO( s) ¾
¾® 2Hg(l ) + O2 ( g )
• The equation must be balanced
– All the atoms of every reactant must also
appear in the products
• Number of Hg on left? 2
– on right 2
• Number of O on left? 2
– on right 2
• Meaning of a Chemical Equation:


Fe 2 O 3 + 3 CO ⎯⎯→ 2 Fe + 3 CO 2
Reactants Products
1 molecule 3 molecules 2 atoms 3 molecules
1 mole 3 moles 2 moles 3 moles

159.7 g 84.0 g 111.7 g 132 g
Total mass on both sides are: Mass is conserved
159.7 + 84 = 243.7 g 111.7 + 132 = 243.7 g

H2 + O2 → H2O
• Is the law of conservation of mass obeyed
as written? NO
• Balancing chemical equations uses
coefficients to ensure that the law of
conservation of mass is obeyed
Steps in Equation Balancing
H2 + O2 → H2O
The steps to balancing:

Step 1. Count the number of moles of atoms of
each element on both product and
reactant sides
Reactants Products
2 mol H 2 mol H
2 mol O 1 mol O
H2 + O2 → H2O
Step 2. Determine which elements are not
balanced – do not have same number on both
sides of the equation
– Oxygen is not balanced
Step 3. Balance one element at a time by
changing the coefficients
H2 + O2 → 2H2O
This balances oxygen, but is hydrogen still balanced?

H2 + O2 → 2H2O
How will we balance hydrogen?
2H2 + O2 → 2H2O
Step 4. Check! Make sure the law of conservation of mass

is obeyed
Reactants Products
4 mol H 4 mol H
2 mol O 2 mol O
Balance the below equations
NH3 burns in oxygen to form NO & water

2 NH 3 + 5
2 O2 ⎯
⎯→ 2 NO + 3 H 2 O
or correctly

4 NH 3 + 5 O 2 ⎯
⎯→ 4 NO + 6 H 2 O
C3H8 burns in oxygen to form CO2 and H2O


C3 H 8 + 5 O 2 ⎯
⎯→ 3 CO 2 + 4 H 2 O
Example:
Write balanced chemical equation for burning of C7H16 in oxygen to form
carbon dioxide and water.
35
Practice Equation Balancing
Balance the following equations:
1. C2H2 + O2 → CO2 + H2O
2. AgNO3 + FeCl3 → Fe(NO3)3 + AgCl
3. C2H6 + O2 → CO2 + H2O
4. S2Cl2 + NH3 → N2S4 + NH4Cl + S8
5. C2H5OH + O2 → CO2 + H2O

4.5 Calculations Using the Chemical Equation
(Reaction Stoichiometry)
• Calculating quantities of reactants and products in a

chemical reaction has many applications.
• Need a balanced chemical equation for the reaction of

interest.
• The coefficients represent the number of moles of

each substance in the equation.
• Examine the reaction:

2H2 + O2 → 2H2O
• Coefficients tell us?
– 2 mol H2 reacts with 1 mol O2 to produce 2 mol H2O
• What if 4 moles of H2 reacts with 2 moles of O2?
– It yields 4 moles of H2O
• How many moles of O2 are needed to react with 4.26
moles of H2?
2H2 + O2 → 2H2O
• Use the factor-label method to perform this calculation
__mol
1 O 2 2.13 mol O
4.26 mol H 2 ´ = 2
__
2 mol H 2
• Digits in the conversion factor come
from the balanced equation
Calculate the mass of O2 that will react with 1.00 mol of C3H8?
C3H8(g) + 5O2(g) → 3CO2(g) + 4H2O(g)

5 𝑚𝑜𝑙 𝑂2
𝑛𝑂2 = nC3H8×conversion factor = 1.00 mol C3H8 × = 5.00 mol O2
1𝑚𝑜𝑙 𝐶3𝐻8
Mass of O2 = Molar mass of O2 × 𝑛𝑂2 = 32.0 g/mol × 5.00 mol O2 = 160 g O2
It can be done in one step

Data given × conversion factor × conversion factor = desired results
5 𝑚𝑜𝑙 𝑂2 32 𝑔𝑂2
1.00 𝑚𝑜𝑙 𝐶3 𝐻8 × × = 160g 𝑂2
1 𝑚𝑜𝑙𝐶3 𝐻8 1 𝑚𝑜𝑙𝑂2
Calculate the mass of CO2 that will be produced from 1.00 mol
of C3H8?
C3H8(g) + 5O2(g) → 3CO2(g) + 4H2O(g)
3 𝑚𝑜𝑙 𝐶𝑂2
𝑛𝐶𝑂2 = nC3H8×conversion factor = 1.00 mol C3H8 × = 3.00 mol CO2
1𝑚𝑜𝑙 𝐶3𝐻8
Mass of CO2 = Molar mass of CO2 × 𝑛𝐶𝑂2 = 44.01g/mol CO2 × 3.00 mol CO2 = 132 g CO2

3 𝑚𝑜𝑙 𝐶𝑂2 44.01 𝑔𝐶𝑂2
1.00 𝑚𝑜𝑙 𝐶3 𝐻8 × × =132g 𝐶𝑂2
1 𝑚𝑜𝑙𝐶3 𝐻8 1 𝑚𝑜𝑙𝐶𝑂2
Calculate the mass of C3H8 required to produce 36.0 g of
H2O?
C3H8(g) + 5O2(g) → 3CO2(g) + 4H2O(g)
𝑚𝑎𝑠𝑠 𝑜𝑓 𝐻2𝑂 𝑖𝑛 𝑔 36.0 𝑔 𝐻2 𝑂
𝑛𝐻2 𝑂 = = 𝑔 = 2.0 mol H2O
𝑀𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 18.0𝑚𝑜𝑙
1 𝑚𝑜𝑙𝐶 𝐻
𝑛𝐶3 𝐻8 = 𝑛𝐻2𝑂 ×conversion factor = 2.00 mol H2O× 4𝑚𝑜𝑙 H3 O8= 0.50 mol 𝐶3 𝐻8
2
Mass of 𝐶3 𝐻8 = Molar mass of 𝐶3 𝐻8 × 𝑛𝐶3𝐻8 = 44.09g/mol ×0.5 mol O2 = 22.0 g 𝐶3 𝐻8

Data given × conversion factor × conversion factor × conversion factor = desired results
1 𝑚𝑜𝑙 𝐻2𝑂 1 𝑚𝑜𝑙 C3H8 44.09 𝑔 C3H8

36.0 𝑔 𝐻2𝑂 × × × = 22.0 g C3H8
18.0 𝑔𝐻2𝑂 4 𝑚𝑜𝑙𝐻2𝑂 1 𝑚𝑜𝑙C3H8
Calcium hydroxide may be used to neutralize aqueous

hydrochloric acid (HCl). Calculate the mass of hydrochloric
acid that would be neutralized by 0.500 mol of calcium
hydroxide.
Ca(OH)2(s) + 2HCl(g) → CaCl2(aq) + 2H2O(l)

2 𝑚𝑜𝑙 𝐻𝐶𝑙 2 𝑚𝑜𝑙 𝐻𝐶𝑙
𝑛𝐻𝐶𝑙 = 𝑛𝐶𝑎 𝑂𝐻 2
× 1 𝑚𝑜𝑙 𝐶𝑎(𝑂𝐻)2 = 0.500 𝑚𝑜𝑙 𝐶𝑎(𝑂𝐻)2 × 1 𝑚𝑜𝑙 𝐶𝑎(𝑂𝐻)2 = 1.00 mol HCl
36.46 𝑔 𝐻𝐶𝑙
𝑚𝐻𝐶𝑙 = molar mass of HCl x 𝑛𝐻𝐶𝑙 = x 1.00 mol HCl = 36.5 g HCl
1 𝑚𝑜𝑙 𝐻𝐶𝑙

2 𝑚𝑜𝑙 𝐻𝐶𝑙 36.46 𝑔 𝐻𝐶𝑙
0.500 𝑚𝑜𝑙 𝐶𝑎(𝑂𝐻)2 × × =36.5 g HCl
1 𝑚𝑜𝑙 𝐶𝑎(𝑂𝐻)2 1 𝑚𝑜𝑙 𝐻𝐶𝑙
Example
What mass of CO is required to react with 146 g of
iron(III) oxide?
Sequence:
Mass (g) Fe2O3 nFe2O3 nCO Mass (g) CO
Useful Info. MM CO = 28.0 g, Fe2O3 = 159.7 g


Fe 2 O 3 + 3 CO ⎯⎯→ 2 Fe + 3 CO 2
 1 mol Fe 2 O 3   3 mol CO 
? g CO = 146 g Fe 2 O 3   
 159.7 g Fe 2 O 3  1 mol Fe 2 O 3 
 28.0 g CO 
 
 1 mol CO 
= 76.8 g CO
44

Practice Example
Na + Cl2 → NaCl
1. Balance the equation

2. Calculate the grams NaCl produced when 5.00 mol Na
reacts with an excess of Cl2
(In other words, calculate the theoretical yield of NaCl)
Theoretical and Percent Yield
• Theoretical yield - the maximum amount of product
that can be produced (by calculation)
– Pencil and paper yield
• Actual yield - the amount produced when the reaction
is performed (in laboratory only will be given)
– Laboratory yield
actual yield
• Percent yield: % yield = ´100%
theoretical yield
= 125 g CO2 actual  100 % = 94.7 %

132 g CO2 theoretical
Example: If the theoretical yield of iron was 30.0 g and actual
yield was 25.0 g, calculate the percent yield:
2 Al(s) + Fe2O3(s) → Al2O3(aq) + 2Fe(aq)
actual yield
% yield = ´100%
theoretical yield
= 25.0 g  100 = 83.3%
30.0 g
Do it: Calculate the theoretical yield (in grams) of Fe
produced when 3.00 mol Fe2O3 reacts with Al. What is the
% yield of the reaction, if the actual yield was 300g?
[Ans. 89.5%]
Example:
Given the reaction represented by the balanced equation:
If 7.50 g of NaCl was actually produced when 5.00 g of Cl2

reacted with Na. Calculate the percent yield.
𝑎𝑐𝑡𝑢𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
𝑝𝑒𝑟𝑐𝑒𝑛𝑡 𝑦𝑖𝑒𝑙𝑑 = × 100%
𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
7.50𝑔
= × 100%
???
Theoretical yield of NaCl must be calculated

Example 15
Theoretical yield of NaCl
𝑚𝑎𝑠𝑠 𝑜𝑓 𝐶𝑙2 5.00𝑔

𝑛𝐶𝑙2 = = = 0.0705 𝑚𝑜𝑙
𝑚𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜𝑓 𝐶𝑙2 70.90𝑔/𝑚𝑜𝑙
2𝑚𝑜𝑙𝑁𝑎𝐶𝑙
𝑛𝑁𝑎𝐶𝑙 = 𝑛𝐶𝑙2 × 𝑐𝑜𝑛𝑣𝑒𝑟𝑠𝑖𝑜𝑛 𝑓𝑎𝑐𝑡𝑜𝑟 = 0.0705𝑚𝑜𝑙𝐶𝑙2 × = 0.141 𝑚𝑜𝑙 𝑁𝑎𝐶𝑙
1𝑚𝑜𝑙 𝐶𝑙2
58.44𝐻𝐶𝑙
𝑚𝑁𝑎𝐶𝑙 = molar mass of NaClx 𝑛𝑁𝑎𝑐𝑙 = x 0.141 mol NaCl= 8.24 g
1 𝑚𝑜𝑙 𝐻𝐶𝑙
𝑎𝑐𝑡𝑢𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
𝑝𝑒𝑟𝑐𝑒𝑛𝑡 𝑦𝑖𝑒𝑙𝑑 = × 100%
𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
7.50𝑔
= × 100%= 91.0%
8.24𝑔
Four credits
6.1 Properties of Solutions
• Solution - homogeneous mixture of two or
more substances
• Solute – the component of a solution that is
present in lesser quantity. [More than one
solute could be present in solution].
• Solvent – the solution component present in
the largest quantity
• Aqueous solution - solution where the
solvent is water
Examples of Solutions
• Although most common solutions are liquids,
solutions can be liquids, solids or gases
• Air (gas solution):- oxygen and several trace
gases are dissolved in the gaseous solvent,
nitrogen
• Alloys (solid solution):-brass and other
homogeneous metal mixtures in the solid state
• Focus on liquid solutions as many important
chemical reactions take place in liquid solutions
General Properties of Liquid Solutions
• Clear, transparent, no visible particles
• May be colored or colorless
• Nonelectrolytes solutions solutes do not dissociate
Example: C6H12O6 (glucose)
• Electrolytes solutions are formed from solutes that
are soluble ionic compounds
Example: Ionic Compounds
NaCl(s) ¾H¾®
¾
2O
Na + (aq) + Cl- (aq)
Aqueous Solutions
Electrolytes and Extent of Ionization
• Aqueous solutions consist of a solute dissolved in water.
Classification of solutes:
1- Nonelectrolytes: Solutes that do not conduct electricity in
water because they do not form ions in solution.
Examples: C2H5OH – ethanol

C6H12O6 - glucose (blood sugar)
C12H22O11 - sucrose (table sugar)
Aqueous Solutions: Nonelectrolytes
Glucose Sucrose
H2
H HO C
H C O H
H C OH H
C C
OH H
HO
H C O H C C O
H OH
C H H C HO H 2C O
OH
C H C
HO
HO C C OH H
C C CH 2 OH
H HO HO H
Nonelectrolytes do not conduct electricity because they do not form

ions in solution.
Aqueous Solutions: Strong Electrolytes
2- Strong electrolytes:
Conduct electricity extremely well in aqueous solutions
because they are completely ionized (100%) in water.
• Examples of strong electrolytes
1. HCl, HBr, HNO3, H2SO4 etc.

• strong soluble acids
2. NaOH, KOH, LiOH, Ca(OH)2 etc.
• strong soluble bases
3. NaCl, KBr, etc.
• soluble ionic salts
• ionize in water essentially 100%
Aqueous Solutions: Strong Electrolytes
Strong Acids and Bases
• Strong acids or bases ionize 100% in water.
• Acids generate H+ in aqueous solutions.
Note: HCl is an example of gas solute in solution because HCl is a

gas, which dissolved in water to provide aqueous HCl
+ -
H
N
O
+
3H
O
2 H
O
(
3a
q
)+N
O
(
a
q
3)
or
+ -
H
N
O
3 H
(
a
q
) +
N
O(
a
3q
)
• Bases generate OH- in aqueous solutions
Aqueous Solutions: Weak Electrolytes
3- Weak electrolytes:
Conduct electricity poorly in aqueous solutions
because they are partially ionized in water.
1. CH3COOH (acetic acid)
• weak acids
2. NH3 (ammonia)
• weak bases
Aqueous Solutions: Weak Electrolytes
• Weak acids ionize partially (less than 10%)
in water.
– Typically ionize 10% or less!
– Example: CH3COOH, acetic acid
Aqueous Solutions: Electrolytes
• Strong electrolytes are substances that ionize

completely when dissolved in water.
• Weak electrolytes are substances that are only partially
ionized in water.
• Nonelectrolytes are substances that do not produce ions
when dissolved in water.
Degree of Solubility
• Solubility - how much of a particular solute can
dissolve in a certain solvent at a specified
temperature
• Factors which affect solubility :
1- Polarity of solute and solvent
• The more different they are, the lower the solubility
2- Temperature
• Increase in temperature usually increases solubility
3- Pressure
• Usually has no effect
• If solubility is of gas in liquid, directly proportional
to applied pressure
The Effect of Temperature on Solubility:
Solids in Liquids
Most solids become more soluble as temperature rises.

Saturation
• Saturated solution - a solution that contains the
maximum amount of dissolved solute at a particular
temperature
• Supersaturated solution - contains more solute than

can be dissolved at the current temperature
• How is this done?
• Heat solvent, saturate it with solute then cool slowly
• Sometimes the excess will precipitate out
• If it doesn’t precipitate, the solution will be
supersaturated. [This type of solution is inherently unstable.
With time, excess solute will precipitate, and the solution will
revert to a saturated solution.
Solubility of Gases: Henry’s Law
• Henry’s law – the number of moles of a gas
dissolved in a liquid at a given temperature is
proportional to the partial pressure of the gas
above the liquid [e.g. n  P].
• Gas solubility in a liquid increases with the
pressure of the gas and decreases with
increasing the temperature.
S P
S 1∕T
Representation of Henry’s Law
• Gases are most soluble at low temperatures
• Solubility decreases significantly at higher
temperatures
– Carbonated beverages: CO2 solubility less when warm
– Respiration: facilitates O2 and CO2 exchange in lungs
6.2 Concentration Based on Mass
• Concentration - amount of solute dissolved
in a given amount of solution
• Concentration of a solution has an effect on:
– Physical properties
• Melting and boiling points
– Chemical properties
• Solution reactivity
1- Mass/Volume Percent (g/mL)
• Amount of solute = mass of solute in grams
• Amount of solution = volume in milliliters
amount of solute
concentration =
amount of solution
• Concentration is expressed as a percentage
by multiplying ratio by 100 = mass/volume
percent or % (m/V)
m g of solute
% =  100%
V mL of solution
Calculating Mass/Volume Percent
Calculate the % (m/V) of 2.00  102 mL solution
containing 20.0 g sodium chloride
20.0 g NaCl = mass of solute
2.00  102 mL = total volume of solution
% (m/V) = (20.0 g NaCl / 2.00  102 mL) x 100%
= 10.0% (m/V)
Calculate Mass of Solute from
Mass/Volume Percent
Calculate the number of grams of glucose in
7.50  102 mL of a 15.0% solution
m grams of solute
% =  100%
V milliliters of solution
15.0 (m/V) = [X g glucose/(7.50  102 mL)]  100

X g glucose  100 = (15.0 m/V)(7.50  102 mL)
X g glucose = 113 g glucose
Examples You do it
1) A solution of heparin sodium, an anticoagulant for blood,
contains 1.8 g of heparin sodium dissolved to make a
final volume of 15 mL of solution. What is the
mass/volume percent concentration of this solution?
Answer = 12%
2) How many grams of NaCl are needed to prepare 250 mL of

a 1.5% (m/v) saline solution?
Answer = 3.75 g
2- Mass/Mass Percent
m g solute
% =  100%
m g solution
• Mass/mass percent is most useful for
solutions of 2 solids whose masses are
easily obtained
• Calculate % (m/m) of platinum in gold
ring with 14.00 g Au and 4.500 g Pt
[4.500 g Pt / (4.500 g Pt + 14.00 g Au)]  100
= (4.500 g / 18.50 g)  100 = 24.32% Pt
3- Volume/Volume Percent
• Percent concentrations
– For liquid solutions, concentrations are expressed as
volume/volume percent concentration, (v/v)%.
Example: How many milliliters of methyl alcohol are needed

to prepare 75 mL of a 5.0% (v/v) solution?
Solution:
4- Parts per million (ppm) and parts per
billion (ppb)
Parts per million (ppm) or Parts per billion (ppb)
• When concentrations are very small, it is more convenient to
use parts per million (ppm) or parts per billion (ppb). The
“parts” can be in any unit of either mass or volume as long as
the units of both solute and solvent are the same:
Example
The maximum allowable concentration of chloroform, CHCl3, in
drinking water is 100 ppb. What is the maximum amount (in grams)
of chloroform allowed in a glass containing 400 g of water?
Solution:
6.3 Concentrations Based on Moles
• Chemical equations represent the relative

number of moles of reactants producing
products
• Many chemical reactions occur in solution

where it is most useful to represent
concentrations on a molar basis
Molarity and Molality
• The most common mole-based concentration unit is molarity
• Molarity (M)
– Defined as the number of moles of solute per liter of solution
mol solute
M=
L solution
• Molality (m)
– Defined as the number of moles of solute per kg of solvent
– The denominator is in kg solvent, not in kg solution
mol solute
m=
kg solvent
Calculating Molarity from Moles
• Calculate the molarity of 2.0 L of solution
containing 5.0 mol NaOH
• Use the equation
moles solute
M=
L solution
• Substitute into the equation:
M = 5.0 mol solute = 2.5 M
2.0 L solution
Calculating Molarity From Mass Example
• If 5.00 g glucose are dissolved in 1.00  102 mL of
solution, calculate molarity, M, of the glucose
solution
• Convert from grams glucose to moles glucose:
5.00 g x 1 mol = 2.78 x 10−2 mol

180 g
• Convert from mL to L of solution:
1.00 x 102 mL x 1 L = 1.00 x 10−1 L

103 mL
Calculating Molarity From Mass
Example - Continued
• If 5.00 g glucose are dissolved in 1.00  102 mL of
solution, calculate molarity, M, of the glucose
solution
• Substitute into the equation:
M = mol glucose
L solution
M = 2.78  10-2 mol glucose

1.00  10-1 L solution
M = 2.78  10-1 M
Calculating Molality
What is the molality of a solution made by
dissolving 200 g of sugar (C12H11O22) in 500 g
water?
Answer =0.789 mol/kg
Determine the mass of calcium nitrate required to

prepare 3.50 L of a 0.800 M Ca(NO3)2 ; (MM = 164.0
g/mole).
Answer = 459.2 g
Dilution of Solutions
Dilution is required to prepare a less
concentrated solution from a more
concentrated one
– M1 = molarity of solution before dilution
– M2 = molarity of solution after dilution
– V1 = volume of solution before dilution
– V2 = volume of solution after dilution
mol solute
M = moles solute = (M)(L solution)
L solution
Dilution Equation
• In a dilution, will the
number of moles of solute
change?
– No, only fewer per unit
volume
• So, M1V1 = M2V2

• Knowing any three terms
permits calculation of the
fourth
Calculating Molarity After Dilution
• Calculate the molarity of a solution made by

diluting 0.050 L of 0.10 M HCl solution to a
volume of 1.0 L
– M1 = 0.10 M molarity of solution before dilution

– M2 = Desired Result
– V1 = 0.050 L volume of solution before dilution
– V2 = 1.0 L volume of solution after dilution
Calculating Molarity After Dilution
• Calculate the molarity of a solution made by
diluting 0.050 L of 0.10 M HCl solution to a
volume of 1.0 L
• Solve the dilution expression for M2
M1V1 = M2 (0.10 M) (0.050 L) = M2
V2 (1.0 L)
M2 = 0.0050 M
Dilution of Solutions
Examples: You do it!

1. What volume of an 18.0 M sulfuric acid is required to make
2.50 L of a 2.40 M sulfuric acid solution?
Answer = 0.333L
1. Suppose we need to prepare 500 mL of 1.00 M acetic acid

(HC2H3O2) from a 17.5 M stock solution of acetic acid.
What volume of the stock solution is required?
Answer = 28.6 mL
1. If 10.0 mL of 12.0 M HCl is added to enough water to give

100.0 mL of solution, what is the concentration of the
solution?
36
Answer 1.20 mL
Four credits
1. Acids and Bases: Definitions
• Acids: Taste sour, dissolve some metals,
cause plant dye to change color
• Bases: Taste bitter, are slippery, are
corrosive
• Three theories that help us to understand
the chemistry of acids and bases
1. Arrhenius Theory
2. Brønsted-Lowry Theory
3. Lewis Theory
Arrhenius Theory
• Acid - a substance, when dissolved in
water, dissociates to produce hydrogen
ions:
– Hydrogen ion: H+ also called “proton”
HCl is an acid:
HCl(aq) → H+(aq) + Cl-(aq)
Arrhenius Theory
• Base - a substance, when dissolved in
water, dissociates to produce hydroxide
ions
NaOH is a base
NaOH(aq) → Na+(aq) + OH-(aq)
Brønsted-Lowry Theory
• Acid – proton (H+) donor

• Base - proton (H+) acceptor
– Notice that acids and bases are not defined
using water
– When writing the reactions, both accepting
and donating are evident
HCl(aq) + H2O(l) → Cl-(aq) + H3O+(aq)

acid base
What donated the proton? HCl

Is it an acid or base? Acid
What accepted the proton? H2O

Is it an acid or base? Base
NH3(aq) + H2O(l) NH4+(aq) + OH-(aq)

base acid
Now let us look at NH3 and see why it is a

base
Did NH3 donate or accept a proton? Accept
Is it an acid or base? Base
What is water in this reaction? Acid
Lewis Theory
• Developed in 1923 by G.N. Lewis.

– This is the most general and comprehensive definition of
acids and bases.
– Emphasis on what the electrons are doing rather than what
the protons are doing.
• Acids are defined as electron pair acceptors.
• Bases are defined as electron pair donors.
• Acid-base reactions are accompanied by coordinate
covalent bond formation.
Lewis Theory
Lewis Definition
• One Lewis acid-base example is the ionization of ammonia.
• Look at this reaction in more detail paying attention to the
electrons.
H +
H -
H H
N + N
H
O
H + O
H H
H H
Base - it donates Acid - it accepts

the electron pair the electron pair Notice that a coordinate
covalent bond is formed
on the ammonium ion.
Lewis Theory
• The reaction of lithium fluoride (LiF) and boron
trifluoride (BF3) provides an example of a reaction
that is only a Lewis acid-base reaction.
– It does not involve H+ at all, thus it cannot be an
Arrhenius nor a Brønsted-Lowry acid-base reaction.
+ BF3 → Li+ + BF4-
• You must draw the detailed picture of this reaction

to determine which is the acid and which is the
base.
Summary: Acid-Base Definitions
• A base must have a lone pair of electrons to accept H+
from an acid.
• A base can be either neutral (B:) or negatively charged
(B:–).
Summary: Acid-Base Definitions
• Arrhenius, Brønsted-Lowry, and Lewis Acid-Base
theories expand on one another.
Arrhenius
Brønsted-Lowry
Lewis
Example
• Look at the reaction of ammonia and hydrobromic
acid.
NH3 + HBr → NH4++ Br-
• Is this reaction an example of:
1. Arrhenius acid-base reaction
2. Brønsted-Lowry acid base reaction
3. Lewis acid-base reaction
4. or a combination of these?
You do it!
2. Conjugate Acids and Bases
• The acid base reaction can be written in
the general form:
HA + B A- + BH+
acid base
• Notice the reversible arrows

• The products are also an acid and base
called the conjugate acid and base
Conjugate Acids and Conjugate Bases
HA + B A- + BH+
acid base base acid
• Conjugate Acid – what the base becomes after it
accepts a proton
- BH+ is the conjugate acid of the base B
• Conjugate Base – what the acid becomes after it

donates its proton
- A- is the conjugate base of the acid HA
• Two species that differ by a proton are called acid-base
conjugate pairs.
Conjugate Acid- Base Pair
HA + B A- + BH+
acid base base acid
• Conjugate Acid-Base Pair – the acid and
base on the opposite sides of the equation
- BH+ / B constitute a conjugate acid-base
pair
- HA / A- constitute a conjugate acid-base
pair
Conjugate Acid- Base Pair
• An important part of BrØnsted-Lowry acid-base theory
is the idea of conjugate acid-base pairs.
• For example we can use this reaction:
• HNO3 + H2O → H3O+ + NO3-
1. Identify the reactant acid and base.

HNO3 is the acid, conjugate base is NO3-
2. Find the species that differs from the acid by a proton,
that is the conjugate base.
H2O is the base, conjugate acid is H3O+
Acid-Base Properties of Water
• Water possesses both acid and base properties
– Amphoteric – a substance possessing both acid
and base properties
– Water is the most commonly used solvent for both
acids and bases
– Solute-solvent interactions between water and both
acids and bases promote solubility and dissociation
Conjugate Acid-Base Practice
Write the chemical reaction for the following acids
or bases in water.
Identify the conjugate acid base pairs.
1. HF (a weak acid)
2. H2S (a weak acid)
3. HNO3 (a strong acid)
4. CH3NH2 (a weak base)
Note: The degree of dissociation also defines weak
and strong bases
3. Acid and Base Strength
• Acid and base strength – degree of
dissociation
– Not a measure of concentration
– Strong acids and bases – reaction with water is
virtually 100% (Strong electrolytes)
– Example:
HCl(aq) + H2O(l) H3O+(aq) + Cl-(aq)

strong acid
KOH(aq) K+(aq) + OH-(aq)

strong base
Strong Acids and Bases
• Strong Acids:
– HCl, HBr, HI Hydrochloric Acid, etc.
– HNO3 Nitric Acid
– H2SO4 Sulfuric Acid
– HClO4 Perchloric Acid
• Strong Bases:
– NaOH, KOH, Ba(OH)2
– All metal hydroxides
Memorize
Weak Acids
• Weak acids and bases – only a small
percent dissociates (Weak electrolytes)
• Weak acid examples:
– Acetic acid:
CH3COOH(aq) + H2O(l) CH3COO-(aq) + H3O+(aq)
– Carbonic Acid:
H2CO3(aq) + H2O(l) HCO3-(aq) + H3O+(aq)
Weak Bases
• Weak base examples:
– Ammonia:
NH3(aq) + H2O(l) NH4+(aq) + OH-(aq)
– Pyridine:
C5H5NH2(aq) + H2O(l) C5H5NH3+(aq) + OH-(aq)
– Aniline:
C6H5NH2(aq) + H2O(l) C6H5NH3+(aq) + OH-(aq)
Acid-Base Dissociation
HA + B A- + HB+
• The reversible arrow isn’t always written
– Some acids or bases essentially dissociate 100%
– One way arrow is used
• HCl + H2O → Cl- + H3O+

– All of the HCl is converted to Cl-
– HCl is called a strong acid – an acid that dissociates
100%
• Weak acid - one which does not dissociate 100%
Conjugate Acid-Base Strength
• The weaker the acid or base, the stronger the
conjugate partner.
• The relative strength of any acid depends on the

weakness (or stability) of its conjugate base:
Acid strength order HCN < CH3COOH < HF

Conjugate base order CN- > CH3COO- > F-
• An acid-base equilibrium always favors reaction
of the stronger acid with the stronger base, and
formation of the weaker acid and base.
Write a balanced equation for the reaction between a
phosphate ion (PO43–) and water, and determine in which
direction the equilibrium is favored.
Solution:
The phosphate ion is the conjugate base of a weak acid
(HPO42–) and is, therefore, a relatively strong base. HPO42– is
a stronger acid than H2O, and OH– is a stronger base than
PO43–, so the reaction is favored in the reverse direction.
HPO2−
4 (aq)
2-
4. Self-ionization of Water
• Pure water is virtually 100% molecular
• Very small number of molecules dissociate
– Dissociation of acids and bases is often called
ionization
H2O(l) + H2O(l) H3O+(aq) + OH-(aq)
• Dissociation of water is self-ionization
• Very weak electrolyte
Self-ionization of Water
• H3O+ is called the hydronium ion
• In pure water at room temperature:
– [H3O+] = 1  10-7 M
– [OH-] = 1  10-7 M
• What is the equilibrium expression for:
H2O(l) + H2O(l) H3O+(aq) + OH-(aq)
Keq = [H3O+][OH-]
Remember, liquids are not included in equilibrium
expressions
Ion Product Constant for Water
• The ion product constant for water as the
symbol Kw
Kw = [H3O+][OH-]
• In pure water, [H3O+] = [OH-] = 1.0  10-7
M, what is the value for Kw?
1.0  10-14 (unitless)
• Kw depends on Temperature only. It has constant
value in all aqueous solutions
• The values of [H3O+] and [OH-] varies based on
the solution acidity and basicity
pH: A Measurement Scale for Acids & Bases
• The common range for [H3O+] or [OH-] values is 1 to

1 x 10-14.
• In most solutions, [H3O+] is fraction (Ex: 1 x 10-7 =
0.0000001), therefore we express acidity using pH scale.
• pH scale – a scale that indicates the acidity or basicity of
a solution using this equation:-
pH = -log[H3O+]
• Common ranges from 0 (very acidic) to 14 (very basic)
• The pH scale is rather similar to the temperature scale
assigning relative values of hot and cold
Molarity and pH
For a strong acid For a strong base
[H3O+]molarity pH [OH-] molarity pH
pH
1.0 x 100 0.00 1.0 x 100 14.00
1.0 x 10-1 1.00 1.0 x 10-1 13.00
1.0 x 10-2 2.00 1.0 x 10-2 12.00
More Acidic
More basic
1.0 x 10-3 3.00 1.0 x 10-3 11.00
1.0 x 10-4 4.00 1.0 x 10-4 10.00
1.0 x 10-5 5.00 1.0 x 10-5 9.00
1.0 x 10-6 6.00 1.0 x 10-6 8.00
1.0 x 10-7 7.00 1.0 x 10-7 7.00
Each 10 fold change in concentration

changes the pH by one unit
A Definition of pH
• Use these observations to develop a concept of
pH
– Acidic solution, [H3O+]  and [OH-]  (pH < 7)
– Basic solution, [OH-]  and [H3O+]  (pH > 7)
– Neutral solution, [H3O+] = [OH-]. (pH = 7)
• In all of these cases:
1.0  10-14 = [H3O+][OH-]
(All above numbers are based on Kw = 1.0 x 10-14

and Kw changes only with temperature)
Measuring pH
• Approximated using indicator / pH paper that develops a color
related to the solution pH
• Measured using pH meter whose sensor measures an

electrical property of the solution that is proportional to pH
pH Scale
pH = -log [H+] same as -log [H3O+]
Thus, for a solution in which

[H+]= 1 x 10 -7
pH = - log(10 -7) = 7
pH and pOH Scales
• A convenient way to express the acidity and basicity
of a solution is the pH and pOH scales.
• The pH of an aqueous solution is defined as:

pH = -log H 3O +

• In general, a lower case p before a symbol is read as the
‘negative logarithm of’ the symbol.
• Thus we can write the following notations.
pOH = -log OH - 

 

pAg = -log  Ag + 

 

and so forth for other quantities
Calculating pH
• How do we calculate the pH of a solution when either
the H3O+ or OH- ion concentration is known?
• How do we calculate the H3O+ or OH- ion
concentration when the pH is known?
• Use the expressions:
pH + pOH = 14.00
[H3O+][OH-] = 1.0 x 10-14
pH = -log[H3O+]
Calculating pH from Acid Molarity
What is the pH of a 1.0  10-4 M HCl solution?
– HCl is a strong acid and dissociates in water
– 1 mol HCl produces 1 mol [H3O+] in solution
– Therefore, 1.0  10-4 M HCl solution has
[H3O+] = 1.0  10-4M
pH = -log [H3O+]
pH = -log [1.0  10-4]
pH = -[-4.00] = 4.00
Calculating [H3O+] from pH
What is the [H3O+] of a solution with pH = 6.00?
pH = -log[H3O+]
• An alternative mathematical form of this equation is:
[H3O+] = 10-pH
[H3O+] = 10-6.00
[H3O+] = 1.0 x 10-6 M
Calculating the pH of a Base
What is the pH of a 1.0  10-3 M KOH solution?
• KOH is a strong base, so it dissociates
completely
• 1 mol KOH produces 1 mol OH- ion in solution
• Therefore, 1.0 x 10-3 M KOH has
[OH-] = 1.0 x 10-3 M
• To use the pH formula, we need to know the
[H3O+] instead:
pH = -log[H3O+]
Calculating the pH of a Base
What is the pH of a 1.0  10-3 M KOH solution?
• Therefore the Kw equation is needed:
1.0 x 10-14 = [H3O+][OH-]
1.0 x 10-14 = [H3O+][1.0  10-3 ]

• Divide both sides by 1.0 x 10-3 :
1.0 x 10-11 = [H3O+]
• Now use the pH equation:
pH = -log[H3O+]
pH = -log (1.0 x 10-11)
pH = 11.00
Calculating [OH-] from pH
What is the [OH-] of a solution with pH = 5.00?
• First find [H3O+]
[H3O+] = 10-pH
[H3O+] = 10-5.00
[H3O+] = 1.0  10-5
• Next, use the Kw equation to find [OH-]
1.0 x 10-14 = [H3O+][OH-]
1.0 x 10-14 = 1.0  10-5 [OH-]
1.0 x 10-9 = [OH-]
5. Acid Ionization and the Acidity Constant Ka
➢The strength of an acid is represented by its

ionization constant (acidity constant), Ka
product of concentrations of ionized species

Ka= concentration of intact acid
HA + H2O A + H3O
A H3O
Ka =
HA
The Acidity Constant, Ka
The Ka implies the concentrations of the acid and the ions
Ka > 1 Ionized products greater than intact acid.
Ka < 1 Ionized products less than intact acid.
Ka >> 1 Ionization goes to completion (strong acid).

(e.g., > 103)
Ka << 1 Ionization occurs partially.

(e.g., < 10–3)
The Acidity Constant, Ka
➢Since the Ka values for various acids have
such a wide range, a more manageable way to
discuss this measure of acidity is to use
pKa = – log (Ka)

Compare pKa and Ka Values
strong acids weak acids

pKa
-2 0 2 4 6 8 10 12 14
102 10-2 10-6 10-10 10-14

Ka
The smaller the value of the pKa

the stronger the acid.
47 47
Ionization of Weak Monoprotic Acids
• Let’s look at the dissolution of acetic acid, a weak
acid, in water as an example.
• The equation for the ionization of acetic acid is:
→ +
CH 3COOH + H 2 O  H 3O + CH 3COO -
Ka =
H O CH COO 
3
+ -
= 1.8  10
3 -5
CH 3COOH 
for acetic acid
Weak Monoprotic Acids
Example 1: Write the equation for the ionization of the
weak acid HCN and the expression for its ionization
constant.
→ +
HCN  H + CN -
Ka =
H CN 
+ -
HCN 
Weak Monoprotic Acids
• The ionization constant values for several acids are given
below.
– Which acid is the strongest? (Values not to be memorized)
Acid Formula Ka value

Acetic CH3COOH 1.8 x 10-5
Nitrous HNO2 4.5 x 10-4
Hydrofluoric HF 7.2 x 10-4
Hypochlorous HClO 3.5 x 10-8
Hydrocyanic HCN 4.0 x 10-10
Weak Bases
B(aq) + H2O(l) BH+(aq) + OH–(aq)

base acid Conjugate Conjugate
acid base
Kb is the basicity constant

Kb = [BH+][OH–]/[B]
Kb always refers to the reaction of a base with water to

form the conjugate acid and the hydroxide ion.
Weak Monoprotic Bases
(Values not to be memorized)
52 52
Ammonia as a Weak Base
NH3 is a base Kb = 1.8 x 10-5
NH3 + H2O NH4+ + OH-
acid1 base2 acid2 base1
NH4+ is an acid Ka = 5.6 x 10-10
NH4+ NH3 + H+
acid1 base1
Ka Kb = Kw = (5.6 x 10-10) (1.8 x 10-5) = 10-14

pKa + pKb = pKw = (9.25) + (4.75) = 14
Summary: Acid & Base Strength
- Strong acids have weak
conjugate bases
- Weak acids have strong
conjugate bases
The strength of a base is

inversely related to the strength
of its conjugate acid; the weaker
the acid, the stronger its
conjugate base, and vice versa.
pKa + pKb = pKw

This equation applies to an acid and its conjugate base.
54 54
6. Reactions Between Acids and Bases
Neutralization Reaction
• Neutralization reaction – the reaction of an acid
with a base to produce a salt and water
HCl(aq) + NaOH(aq) → NaCl(aq) + H2O(l)
Acid Base Salt Water
• Break apart into ions:
H+(aq) + Cl-(aq) + Na+(aq) + OH-(aq) →
Na+(aq) + Cl-(aq) + H2O(l)
• Net ionic equation
– Show only the changed components
– Omit any ions appearing the same on both sides of
equation (Spectator Ions)
H+(aq) + OH-(aq) → H2O(l)
• The net ionic neutralization reaction is more
accurately written:
H3O+(aq) + OH-(aq) → 2H2O(l)
• This equation applies to any strong acid / strong
base neutralization reaction
• An analytical technique to determine the
concentration of an acid or base is titration
• Titration involves the addition of measured
amount of a standard solution to neutralize the
second, unknown solution
• Standard solution – solution of known
concentration
Acid – Base Titration
Buret – long glass
tube calibrated in mL
• Standard solution
which contains the
is slowly added
standard solution
until the color
changes Indicator – a
• The equivalence
substance which
point is when the changes color as
moles of H3O+ pH changes
and OH- are equal Flask contains a
solution of unknown
concentration plus
indicator
Titration Experiment
• Place a known volume of acid whose concentration
is not known into a flask
• Add an indicator
• Known concentration of base is placed in a buret
• Drip base into the flask until the indicator changes
color
• Indicator changes color
– equivalence point is reached
– mol OH- = mol H3O+ present in the unknown acid
• Volume dispensed from buret is determined
• Calculate acid concentration from the following
data:
– Volume of HCl: 25.00 mL
– Volume of NaOH added: 35.00 mL
– Concentration of NaOH: 0.1000 M
– Balanced reaction shows that 1 mol HCl reacts with
1 mol NaOH (a 1:1 ratio)
• At the equivalent point (endpoint):
moles OH- = moles H+
moles NaOH = moles of HCl
MNaOH x VNaOH = MHCl x VHCl
MHCl is unknown and can be calculated as follow:-

MHCl = (MNaOH x VNaOH) / VHCl
Polyprotic Substances
• The previous example have the acid and base at
a 1:1 combining ratio
– Not all acid-base pairs do this
• Polyprotic substance – donates or accepts more
than one proton per formula unit
– HCl is monoprotic, producing one H+ ion for each
unit of HCl
– Sulfuric acid is diprotic, each unit of H2SO4
produces 2 H+ ions
H2SO4(aq) + 2NaOH(aq) → Na2SO4(aq) + 2 H2O(l)

Titration of polyprotic acids
H2SO4(aq) + 2NaOH(aq) → Na2SO4(aq) + 2 H2O(l)
Example:- If 20.0 mL of H2SO4 is titrated with 36.5 mL of

0.10 M NaOH, what is the concentration of H2SO4.
Solution: According to the equation above, at the equivalent

point:
moles of NaOH = 2 moles of H2SO4
MNaOH.VNaOH = 2 MH2SO4.VH2SO4
7. Buffer Solutions
• Buffer solution - solution which resists large
changes in pH when either acids or bases are added
• These solutions are frequently prepared in

laboratories to maintain optimum conditions for
chemical reactions
• Blood is a complex natural buffer solution

maintaining a pH of ~7.4 using mainly carbonic
acid (H2CO3) and bicarbonate (HCO3-) ions
Buffer Solutions
• Buffers act to establish an equilibrium between a
conjugate acid/base pair
• Buffers consist of either
– a weak acid and its salt (conjugate base)
– a weak base and its salt (conjugate acid)
• An example is acetic acid, CH3COOH, and its
conjugate base CH3COO-
• An equilibrium is established in solution

between the acid and the salt anion
Buffer Solutions
Buffer: A combination of substances that act together
to prevent a drastic change in pH; Example: Weak acid
and its conjugate base
Buffer Solutions
• If OH– is added to a buffer solution, the pH increases
only slightly; the acid component of the buffer
neutralizes the added OH–.
• If H+ is added to a buffer solution, the pH decreases

only slightly; the base component of the buffer
neutralizes the added H+.
Determining Buffer Solution pH
• Buffering process is an equilibrium reaction
described by an equilibrium-constant
expression
– In acids, this constant is Ka
[H3O+][CH3COO-]
Ka = [CH3COOH]
• If you want to know the pH of the buffer,
solve for [H3O+], then calculate pH
Henderson-Hasselbalch Equation
• Equilibrium-constant expression and the pH
expression can be combined
– Henderson-Hasselbalch Equation is this combined
expression
• For the acetic acid/sodium acetate buffer system:
[H3O+][CH3COO-]
Ka = [CH3COOH]
• Taking the – log of both sides:
[CH COO-]
- log Ka = - log [H3O+] - log [CH 3COOH]
3
Henderson-Hasselbalch Equation
• The – log Ka is actually the pKa, much like
– log [H3O+] is actually the pH:
[CH3COO-]
pKa = pH - log
[CH3COOH]
• Solving for pH:
[CH3COO-]
pH = pKa + log
[CH3COOH]
• The generalized expression is:

[conjugate base]
pH = pKa + log
[weak acid]
Calculating the pH of a Buffer Solution
Example:
Calculate the pH of a buffer solution in which
– Both the acetic acid (acid) and sodium acetate (salt)
concentrations are 2.0  10-2 M
– The Ka for acetic acid is 1.75 x 10-5
Solution:
pH = pKa + log [base]
[acid]
pH = pKa = -log(1.75 x 10-5)
pH = 4.76
Example:
A buffered solution contains 0.25 M NH3
(Kb = 1.8 x 10-5 ) and 0.4 M NH4 Cl .
a. Calculate the pH of this solution.
Solution:
NH3 + H2 O ↔ NH4+ + OH-
Ka = Kw / Kb = 10-14 / 1.8 x 10-5 = 5.6 x 10-10
pH = pKa + log (base/acid)

= 9.25 + log ( 0.25/0.40)
= 9.25 - 0.20 = 9.05
Buffer Capacity
• Buffer Capacity – a measure of the ability
of a solution to resist large changes in pH
when a strong acid or strong base is added
• Also described as the amount of strong acid
or strong base that a buffer can neutralize
without significantly changing pH
• pH of a buffered solution is determined by
the ratio [A-]/[HA]. The capacity of a
buffered solution is determined by the
magnitudes of [HA] and [A-].
Buffer Capacity
- Optimum (most effective) buffering will occur when
[HA] = [A-]. It is under this condition that their ratio is
most resistant to H+ or OH- added.
- pKa of weak acid selected for buffer should be as

close as possible to desired pH (i.e. [HA] / [A-] = 1).
Example:
Which of the organic acids in the following table would be the most
appropriate for preparing a pH 4.15 buffer solution?
Solution:
Looking at the Ka and pKa values in the table, the ascorbic
acid (pKa = 4.10) will produce a buffer solution closest to
the desired pH of 4.15.
Example:
Which of the two solutions has higher buffer capacity?
(1) Solution A : 5.00 M HC2H3O2 and 5.00 M NaC2H3O2
(2) Solution B :0.05 M HC2H3O2 and 0.05 M NaC2H3O2
For acetic acid, Ka = 1.8 x 10-5
Solution A, with larger quantities of buffering components,

has a much higher buffering capacity than solution B.
Four credits
An Introduction to Organic Chemistry
The Saturated Hydrocarbons:

Alkanes and Cycloalkanes
(Lectures 22-24)
General, Organic, and Biochemistry ,
9th Edition, Katherine J. Denniston, Joseph J. Topping, Danaè R. Quirk Dorr, Robert L. Caret
Organic Chemistry A Brief Course

13th Edition, Hart Hadad and Craine Hart
Outlines
• 10.1 The Chemistry of Carbon
• 10.2 Alkanes
• 10.3 Cycloalkanes
• 10.4 Geometric Isomers of Cycloalkanes
• 10.5 Reactions of Alkanes and Cycloalkanes

10.1 The Chemistry of Carbon
Why are there so many organic compounds?
1. Carbon forms stable, covalent bonds with other
carbon atoms
• Carbon can form up to 4 covalent bonds with other
carbon atoms
2. Carbon atoms form stable bonds with other
elements, such as:
• Oxygen
• Nitrogen
• Sulfur
• Halogen
• The presence of these other elements confers many
new physical and chemical properties on an organic
compound
Reason 3
3. Carbon atoms form double or triple
bonds with other atoms to produce a
variety of structures with differing
properties:
Double Bonds: Triple Bonds:

H H
H C C H
H C C H
O
N C H
H C H
Reason 4
4. The number of ways to arrange carbon and
other atoms is nearly limitless:
– Branched chains
– Ring structures
– Linear chains CH2
CH2
CH2
CH3 CH2 CH2 CH2 CH3 CH2
CH2
CH3 CH CH3
CH3
Important Differences Between Organic
and Inorganic Compounds
Organics Inorganics
Bond type have covalent usually have ionic bonds (electron
bonds (electron transfer)
sharing)
Structure •Molecules • Three-dimensional crystal

•Nonelectrolytes structures
• Often water-soluble, dissociating
into ions -electrolytes
Important Differences Between Organic
and Inorganic Compounds
Organics Inorganics
Melting –have lower melting –usually have higher melting

Point & points points
Boiling •Intermolecular forces •Ionic bonds require more
Point broken fairly easily energy to break
Water Nonpolar, water insoluble Water-soluble, readily

Solubility dissociate
Families of Organic Compounds:
The most general classification of organic

compounds divides into hydrocarbons and
substituted hydrocarbons.
Hydrocarbons
• Contain only carbon and hydrogen
• They are nonpolar molecules
– Not soluble in water (water is polar)
– Are soluble in typical nonpolar organic solvents
• Toluene
• Pentane
• Hydrocarbons are constructed of chains or rings
of carbon atoms with sufficient hydrogen atoms
to fulfill carbon’s need for four bonds.
Substituted Hydrocarbons
• is one in which one or more hydrogen atoms is
replaced by another atom or group of atoms
(Functional group)
Division of the Family of Hydrocarbons
CnH2n+2 CnH2n CnH2n CnH2n-2

Learning Goal: Recognize structures that represent each of the families of
Hydrocarbons
Classes of Hydrocarbons
• Alkanes are compounds that contain only carbon-
carbon and carbon-hydrogen single bonds
(Saturated hydrocarbons)
– A saturated hydrocarbon has no double or triple
bonds
Classes of Hydrocarbons
• Alkenes and alkynes are unsaturated because they
contain at least one carbon to carbon double or
triple bond
Cyclic Structure of Hydrocarbons
• Some hydrocarbons are cyclic because they
form a closed ring.
– Cycloalkanes (Saturated hydrocarbons)
– Aromatic hydrocarbons contain a benzene ring
or related structure (Unsaturated hydrocarbons)
Summary:
Hydrocarbons can be divided into:
• Saturated hydrocarbons
– Alkanes
– Cycloalkanes
• Unsaturated hydrocarbons
– Alkenes and alkynes
– Aromatic
10.2 Alkanes
• The general formula for a chain alkane is CnH2n+2
– In this formula n = the number of carbon atoms in
the molecule
• Sources of alkanes: Petroleum and natural gas
• Alkanes are saturated hydrocarbons
– Contain only carbon and hydrogen
– Bonds are carbon-hydrogen and carbon-carbon single
bonds
10.2 Alkanes
Formulas Used in Organic Chemistry
• Molecular formula - lists kind and number of
each type of atom in a molecule, no bonding
pattern:
C2H6 C3H8
• Structural formula - shows each atom and
bond in a molecule
H H H H H
H C C H H C C C H
H H H H H
10.2 Alkanes
Formulas Used in Organic Chemistry
• Condensed formula - shows all the atoms in
a molecule in sequential order indicating
which atoms are bonded to which
CH3-CH3 CH3-CH2-CH3
• Line formula - assume a carbon atom at any
location where lines intersect
• Each carbon in the structure is bonded to the
correct number of hydrogen atoms
Condensed and line Formulas
10.2 Alkanes
Names of First Ten Continuous-Chain Alkanes
Worked Example 1: Which of the following are alkanes?

a) C7H18 b) C7H16 c) C8H16 d) C27H56
10.2 Alkanes
Formulas Used in Organic Chemistry - Example
Write the structural and condensed formulas for the
following line formula:
Next, add the correct

number of H atoms:
First, place the C skeleton:
10.2 Alkanes
The Tetrahedral Carbon Atom
(a) Lewis dot structure

(b) The tetrahedral shape around the carbon
atom
(c) The tetrahedral carbon drawn with dashes
and wedges
(d) The stick drawing of the tetrahedral carbon
atom
(e) Ball and stick model of methane
10.2 Alkanes
Comparison of Ethane and Butane Structures
10.2 Alkanes
Isomers
• Many carbon compounds exist in the form of
isomers
• Structural (or Constitutional) isomers are
compounds with the same molecular formula
but different structures
• An isomer example: both are C4H10 but have
different structures:
Butane Methylpropane
CH3 CH2 CH2 CH3 CH3 CH CH3
CH3
Physical Properties of Hydrocarbons
1. Nonpolar molecules
2. Not water soluble; soluble in nonpolar organic
solvents
3. Low melting points and low boiling points
4. Generally less dense (lighter) than water
5. As length (molecular weight) increases, melting
and boiling points increase as does the density
6. Van der Waals attraction (London Dispersion
Forces)
Physical Properties of Hydrocarbons
• Alkanes
– Melting and boiling points increase with increasing
molecular weight within a homologous series.
Compound Formula MW mp (ºC) bp (ºC)

(g/mol)
Methane CH4 16 –182 –164

Pentane CH3(CH2)3CH3 72 –130 36
Decane CH3(CH2)8CH3 142 –30 174
Pentadecane CH3(CH2)13CH3 212 10 271
Eicosane CH3(CH2)18CH3 282 37 343
26
Physical Properties of Isomers
• Isomers with the same molecular formula

and have different physical properties:
Physical Properties of Isomers
As branching increases, boiling point decreases
Carbon Classification
• Carbon atoms are classified according to the
number of other carbon atoms to which they
are attached:
H H H
Primary (1o) Secondary (2o) Tertiary (3o)

carbon carbon carbon
Classification of H atoms
The hydrogen is classified based on the type of
carbon. For example hydrogen that is attached to
secondary carbon is considered secondary hydrogen.
Worked Example-2
Classify each of the carbon atoms in the following
structures as primary, secondary, tertiary, or quaternary.
a. CH3CH2C(CH3)2CH2CH3
b. CH3CH2CH2CH2CH(CH3)CH(CH3)CH3
c.
d.
Ans.
Nomenclature
• The IUPAC (International Union of Pure and
Applied Chemistry) is responsible for
chemical names
• Before learning the IUPAC rules for naming
alkanes, the names and structures of eight
alkyl groups must be learned
• These alkyl groups are historical names
accepted by the IUPAC and integrated into
modern nomenclature
Alkyl Groups
• An alkyl group is an alkane with one hydrogen
atom removed
• It is named by replacing the -ane of the alkane
name with -yl
• Methane becomes a methyl group
H H
H C H H C
H H
methane methyl group
CH4 CH3-
Ethyl Groups
• For ethane, all 6 H’s are equivalent
• Removing one H generates the ethyl group
• All 3 structures shown at right are the
same: H H
H C C
H H
H H
H H
H C C H ethyl
C C H
H H groups =
H H
H H
ethane
H C C H
H
Names and Formulas of the First
Five Alkyl Groups
Structures and Names of Some
Branched-Chain Alkyl Groups
Main Carbon Chain Length and
Prefixes
IUPAC Names for Alkanes
1. Determine the parent name for an alkane

by selecting the longest continuous chain
of carbon atoms in the formula
– The longest chain may bend and twist, it is
seldom horizontal
– Any carbon groups not part of the base chain
are called branches or substituents
– These carbon groups are also called alkyl
groups
IUPAC Names for Alkanes – Rule 1
• Rule 1 applied
– Find the longest chain in each molecule
CH3 CH3
CH3 CH2 CH2 CH2 CH2 CH2 CH CH2 CH3
CH3 CH2 CH CH2 CH CH3 CH2
CH3
8 Carbon chain 7 Carbon chain

octane heptane
2. Number the carbon atoms in the chain starting
from the end with the first branch
1 CH3 CH3
8 7 6
CH3 CH2 CH2 2 CH2 5
CH2 CH
4 2 CH
3 CH
2 2 CH
1 3
6
CH3 CH2 CH CH2 CH CH3 CH2
5 4 3
7
CH3
– If both branches are equally from the ends, continue

until a point of difference occurs
3. Write each of the branches/substituents in
alphabetical order before the parent name
(e.g. name of the longest chain)
– Indicate the position of the branch on the main
chain by prefixing its name with the carbon
number to which it is attached
– Separate numbers and letters with a hyphen
– Separate two or more numbers with commas
– For halogens: (F-(fluoro); Cl-(chloro), Br-(Bromo);
I-(iodo).
Write IUPAC Name for Alkane Using Substituent
Prefix Rule
• When a branch/substituent occurs more than
once
– Prefix the name with
• di
• tri
• tetra
These prefixes are not considered in an alphabetizing
– Then list the number of the carbon branch for that
substituent to the name with a separate number
for each occurrence
• Separate numbers with commas
• e.g., 3,4-dimethyl or 4,4,6-triethyl
4- When two chains of equal length compete to be
parent, choose the chain with greatest number of
substituents
Examples
5 4 3 2 1
CH3 CH2 CH2 CH CH3 parent alkane
CH3
alkyl group
3-methylpentane
Examples
5 4 3 2 1
CH3 CH2 CH2 CH CH3 parent alkane
CH3
alkyl group
2-methylpentane
Examples
1 2 3 4
CH3 CH CH CH3
CH3 CH3
2,3-dimethylbutane
CH3
4 3 2 1
CH3 CH2 C CH3
CH3
2,2-dimethylbutane
Examples
1 2 3 4
CH3 CH CH CH3
CH3 CH3
2,3-dimethylbutane
CH3
4 3 2 1
CH3 CH2 C CH3
CH3
2,2-dimethylbutane
Examples
CH3 CH3
7 6 5 3 1
CH3 CH CH2 CH CH CH CH3
4 2
CH3 CH3
2,3,4,6-tetramethylheptane
Examples
CH3 CH3
7 6 5 3 1
CH3 CH CH2 CH CH CH CH3
4 2
CH3 CH3
2,3,4,6-tetramethylheptane
Note: Number the chain so that the substituents get

the lowest possible numbers.
Examples
2 1
CH2 CH3
CH3 CH CH2 CH2 CH3

3 4 5 6
3-methylhexane
Examples
2 1
CH2 CH3
CH3 CH CH2 CH2 CH3

3 4 5 6
3-methylhexane
Caution: Be careful to choose the longest chain as

the parent alkane.
Examples
CH3
CH2 CH3
CH3 CH2 CH CH2 CH CH3
4-ethyl-2-methylhexane
Examples
CH3 CH2 CH3
CH3 CH CH CH2 CH CH2 CH3
CH3
5-ethyl-2,3-dimethylheptane
for order: ethyl before dimethyl

Example: Draw from IUPAC Name
• Draw the structural formula for 1-bromo-4-
methylhexane.
• Add in H atoms to complete the structure
Br H H H H H
H C C C C C C H
H H H H H
H C H
H
• Draw the condensed formulas:
Br
CH2 CH2 CH2 CH CH2 CH23
CH32
Worked Example-3
Determine the IUPAC name for each of the following
molecules
a. 2,4-Dimethyloctane
b. Trichlorofluoromethane
c. 3-Chloro-4-fluoro-2-methylheptane
Worked Example-4
Draw the condensed formula of each of the following
compounds
a. 1-Bromo-2-chlorohexane
b. 2,3-Dimethylpentane
c. 1,3,5-Trichloroheptane
d. 3-Chloro-5-iodo-4-methyloctane
e. 1,2-Dibromo-3-chlorobutane
f. Chlorotrifluoromethane
Worked Example-5
Name the following using the IUPAC Nomenclature System:
a.
b.
c.
d.
Worked Example-6
Which of the following pairs of compounds are identical?
Which are constitutional isomers? Which are completely
unrelated?
a. Identical, both are 2,2,-Dibromobutane

b. Isomers of molecular formula C6H12Br2: same
molecular formula but different bond connectivity
10.3 Cycloalkanes
• Cycloalkanes have two less hydrogens than
the corresponding chain alkane
• The general formula of cycloalkane is CnH2n
– Hexane=C6H14 versus cyclohexane=C6H12
• To name cycloalkanes, prefix cyclo- to the
name of the corresponding alkane
– Place substituents in alphabetical order before
the base name as for alkanes
– For multiple substituents, use the lowest possible
set of numbers; a single substituent requires no
number
Cycloalkane Structures
Cyclopropane
Cyclobutane
Cyclohexane
Type of Formula: Structural Condensed Line

Naming a Substituted Cycloalkanes
Cl .
Cl
.
.
1,1-dichlorocyclopropane
62
Worked Example-7
Name each of the following cycloalkanes using
IUPAC nomenclature
Chlorocycloheptane Methylcyclopropane
Disubstituted Cycloalkanes
CH2 CH2 6
H2C CH CH3 1
5
H2C CH =
4
CH2 CH3 2
3
1-Ethyl-2-methylcyclohexane
???
64
Cis-trans Isomers in Cycloalkanes
• Atoms of an alkane can rotate freely around the
carbon-carbon single bond having an unlimited
number of arrangements
• Rotation around the bonds in a cyclic structure is
limited by the fact that all carbons in the ring are
interlocked
– Formation of cis-trans isomers, geometric isomers, is a
consequence of the lack of free rotation
• Stereoisomers are molecules that have the same
structural formulas and bonding patterns, but
different arrangements of atoms in space
– cis-trans isomers of cycloalkanes are stereoisomers
whose substituents differ in spatial arrangement
Cis-trans Isomers in Cycloalkanes
• Two groups may be on the same side (cis) of the imagined
plane of the cycloring or they may be on the opposite side
(trans)
• Geometric isomers do not readily interconvert, only by
breaking carbon-carbon bonds can they interconvert
Worked Example-8
Determine whether each of the following is a
cis- or trans-isomer
Worked Example-9
d.
10.5 Reactions of Alkanes
• Alkanes, cycloalkanes, and other hydrocarbons

can be:
– Oxidized (by burning) in the presence of excess
molecular oxygen, in a process called combustion
– Reacted with a halogen (usually chlorine or
bromine) in a halogenation reaction
Alkane Reactions
The majority of the reaction of alkanes are
combustion reactions
– Complete CH4 + 2O2 CO2 + 2H2O
Complete combustion produces
–Carbon dioxide and water
– Incomplete 2CH4 + 3O2 2CO + 4H2O

• Incomplete combustion produces
–Carbon monoxide and water
– Carbon monoxide is a poison that binds
irreversibly to red blood cells
Halogenation
Halogenation is a type of substitution
reaction, a reaction that results in a
replacement of one group for another
– Products of this reaction are:
• Alkyl halide or haloalkane
• Hydrogen halide
– This reaction is important in converting
unreactive alkanes into many starting materials
for other products
– Halogenation of alkanes ONLY occurs in the
presence of heat and/or light (UV)
Halogenation Reaction Equations
Halogenation Reaction Equations
In complex alkanes, including branched alkanes,

halogenation can occur at all positions to give a
mixture of monosubstituted products
Worked Example-10
Write a balanced equation for each of the
following reactions. Show all possible products
a. Bromination of propane
b. Chlorination of butane
c. Chlorination of cyclobutane
d. Bromination of pentane
Worked Example-10
Medical Prospective: Halogenated
Hydrocarbons used as Anesthetics
• Halogenated hydrocarbons are hydrocarbons containing
two or more halogen atoms.
• Some halogenated hydrocarbons are used in medicine as
anesthetics (pain relievers). For example, chloroethane
and chloromethane are known as local anesthetics.
• Some polyhalogenated compounds are notorious for

problems they have cause. For instance, some
insecticides such as DDT, chlordane, and lindane do not
break rapidly in the environment.
Four credits
(Lectures 25 – 27)
1
Outlines
• 11.1 Alkenes and Alkynes: Structure and physical
properties
• 11.2 Alkenes and Alkynes: Nomenclature
• 11.3 Geometric Isomers
• 11.4 Alkenes in Nature
• 11.5 Reactions involving Alkenes and Alkynes
2
11.1 Alkenes and Alkynes:
Structure and Physical Properties
Both alkenes and alkynes are unsaturated
hydrocarbons
Alkenes: The alkene functional group is carbon-carbon

double bond (C=C) with a general formula CnH2n
Alkynes: The alkyne functional group is carbon-carbon
triple bond (C≡C) with a general formula CnH2n-2
Simplest alkene: ethene (ethylene) C2H4
Simplest alkyne: ethyne (acetylene) C2H2

3
Conversion to Alkanes
Alkenes and alkynes can be converted to alkanes
4
Aliphatic Hydrocarbon Structure
Comparison
5
Bonding and Geometry
of Two-Carbon Molecules
6
Structural Comparison of Five
Carbon Molecules
Basic tetrahedral Planar around the Linear at the

zig-zag shape double bond triple bond
7
Physical Properties
• Physical properties of the alkenes and alkynes
are quite similar to those of alkanes
– Nonpolar
– Not soluble in water
– Highly soluble in nonpolar solvents
• Boiling points rise with molecular weight
8
11.2 Alkenes and Alkynes: Nomenclature
• Base name from longest chain containing the
multiple bond
• Change from -ane to -ene in the case of double bond
or –yne in the case of triple bond.
• Number from the end, that will give the first carbon
of the multiple bond the lower number
• Prefix the name with the number of the first multiple

bond carbon
• Prefix branch/substituent names as for alkanes
9
Alkenes and Alkynes: Nomenclature
• If the multiple bond is equidistant from both ends of

the chain, number from the end nearest the first
branch point.
10
Comparison of Names
11
Nomenclature of Alkenes and Alkynes
CH3
CH2 CH3
CH3 CH CH2 CH C
CH2 CH3
3-Ethyl-6-methyl-3-heptene
CH3 CH C C CH2 CH3
CH3
2-Methyl-3-hexyne
12
Nomenclature of Alkenes
5 3 1
CH 3
6 H3C 2
4 2-methyl-3-hexene
CH 3
7
H3C H
6
3 1
5 CH3
5-methyl-3-heptene
H3C 4 2
11
Nomenclature: IUPAC Rules
Write the IUPAC name for each of the following:
4-Methyl-2-hexyne 4-Bromo-2-ethyl-1-pentene
14
Molecules With More Than One
Double Bond
• Alkenes having more than one double bond:
– 2 double bonds = alkadiene
– 3 triple bonds = alkatriene
• Same rules for alkynes
15
Naming Cycloalkenes
• Cyclic alkenes are named like cyclic alkanes
– Prefix name with cyclo
• Numbering must start at one end of the double
bond and pass through the bond
• Substituents must have the lower possible
numbers
– Either number clockwise or counterclockwise
Cl CH2 CH3
CH CH
CH2 CH
CH
5-chloro-3-methylcyclohexene 16
Naming Haloalkenes
• Double or triple bonds take precedence over a halogen or
alkyl group
– 2-Chloro-2-butene
– If 2 or more halogens, indicate the position of each
• If halo and alkyl groups are present as substituent, and are

taking the same number from either end of the chain,
follow the alphabetical order.
17
Worked Example-1
Name each of the following using the IUPAC
Nomenclature
18
Sample Questions
a c
d 19
11.3 Geometric Isomers:
A Consequence of Unsaturation
• Carbon-carbon double bonds are rigid
– Orbital shape restricts the rotation around the
bond
– Results in cis-trans isomers
– Requires two different groups on each of the
carbon atoms attached by the double bond
20
Geometric Isomers
cis trans
H H R H
R R H R
All substituents are All substituents are
on one side on different sides
of  bond of  bond
19
Geometric Isomers
The example below shows two different structures
based on restricted rotation about the double bond
22
Identifying cis and trans Isomers
• If one end of the C=C has two groups the same,
cis-trans isomers are not possible
• Both carbons of the C=C must have two
different groups attached
• Find a the carbon atoms of the parent chain
relative to C=C
– If both groups or atoms of the same type are on the
same side of the double bond, the molecule is cis-
– If on the opposite side, the molecule is trans-
23
Distinguishing cis-trans Isomers
•Each carbon is attached to 2 different groups
–The parent chain atoms are attached on
opposites of the plane of the double bond =
trans
•trans-2,3-Dichloro-2-pentene
Cl CH2 CH3
C C
CH3 Cl
24
cis-trans Isomers
• Decide whether each compound is cis, trans, or neither
CH3
Cl CH CH3
C C
CH3 CH CH3
CH3
no cis/trans if same group on double bonded carbon

CH3
CH3 CH CH3 CH3 CH2 CH2 CH3
C C C C
H CH3 H H
Parent chain carbons are trans Parent chain carbons are cis
23
cis-Fatty Acids
• Fatty acids are long-chain carboxylic acids found
in vegetable oils (unsaturated fats) and animal
fate (saturated fats)
cis-Oleic acid
• The naturally occurring fatty acid in olive oil

(oleic acid) is a cis-fatty acid
26
trans-Fatty acids
• Its geometric isomer is a trans-fatty acid, with no
natural source:
• Trans-fatty acids have been reported

to lower levels of “good” HDL cholesterol in the
body (and elevate “bad” LDL cholesterol)
27
11.4 Alkenes in Nature
• Alkenes are abundant in nature
– Ethene ripens fruit and promotes plant growth
– Polyenes built from the isoprene skeleton are
called isoprenoids
• Polyenes are alkenes with multiple double bonds
• Isoprene:
CH3
CH2 C CH CH2
28
Isoprenoids – Geraniol and D-Limonene
29
Isoprenoids – Myrcene and Farnesol
30
11.5 Reactions Involving Alkenes and Alkynes
• The key reaction of alkenes:
1. Addition: two molecules combine to give one new
molecule
• Hydrogenation – the addition of hydrogen atoms
• Halogenation – the addition of halogen atoms
• Hydration – the addition of a water molecule
• Hydrohalogenation – the addition of a hydrogen halide
molecule
2. Oxidation: oxidation of alkenes using oxidizing agent
• Oxidation with permanganate-using potassium
permanganate
• Ozonolysis – using ozone
31
Addition: General Reaction
• A small molecule, AB, reacts with the double

bond
• The double bond breaks and its electrons are
used to bond to the A and B pieces
• Some additions require a catalyst
32
Types of Addition Reactions
1. Symmetrical: same atom added to each
carbon
• Hydrogenation - H2 (Pt, Pd, or Ni as catalyst)
• Halogenation - Br2, Cl2
2. Unsymmetrical: H and another atom are
added to the two carbons
• Hydrohalogenation - HCl, HBr
• Hydration - H2O (requires strong acid catalyst
e.g., H3O+, H2SO4, H3PO4)
3. Self-addition or polymerization
33
Hydrogenation: Addition of H2
Hydrogenation is the addition of a molecule of

hydrogen (H2) to a carbon-carbon double bond to
produce an alkane
•The double bond is broken
•Two new C-H bonds result
•Platinum, palladium, or nickel is required as a catalyst
•Heat and/or pressure may also be required
34
Hydrogenation
CH3 CH3
Pt/C
H
+ H2
H
• It is a reduction reaction
• With the help of metal catalysts, H2 adds to the
double bond.
• The catalyst is necessary, since the H-H bond is
too strong.
33
Hydrogenation
CH3 CH3
Pt/C
H
+ H2
H
H H
Hydrogenation occurs as follows:

1. Absorption of hydrogen on the metal surface
2. Alkene approaches surface
3. Addition of hydrogen is strictly syn;
both H atoms come from one side.
34
35
Halogenation: Addition of X2
Halogenation is the addition of a molecule of

halogen (X2) to a carbon-carbon double bond to
produce an alkane
•Two new C-X bonds result
•Reaction occurs quite readily without a catalyst
•Cl and Br are most often the halogen added 38
Bromination of an Alkene
• Left beaker contains bromine, but no

unsaturated hydrocarbon
• Right beaker contains bromine, but reaction
with an unsaturated hydrocarbon results in a
colorless solution 39
Halogenation: Addition of X2
Example
38
Hydrohalogenation: Addition of HX
Hydrohalogenation is the addition of a hydrogen halide

molecule(HX; HBr, HCl, HI) to a carbon-carbon double bond
to produce an alkyl halide.
• C-X and C-H chemical bonds result
•Reaction occurs quite readily without a catalyst 41
Hydrohalogenation: Unsymmetrical Alkenes
• An alkene can be combined with a hydrogen

halide such as HBr or HCl
• The reaction product is an alkyl halide
• Markovnikov’s Rule is followed in this reaction
42
Markovnikov’s Rule
• Dimitri Markovnikov (Russian) observed
many additions to C=C systems
• He noticed that the majority of the
hydrogen went to a specific end of the
double bond
• He formulated an explanation
• When HX adds to a double bond, the Hydrogen
most often goes to the carbon of the double
bond, which had more hydrogens attached.
43
Addition of HX to Unsymmetrical Alkenes
CH2 CH3 CH2 CH3

H2C C + HBr(aq) H2C Br
CH3 H CH3
Markovnikov’s Rule
When hydrogen halide (HX) is added to an unsymmetrical alkene, the
hydrogen goes to the carbon with more hydrogen and the halogen adds
to the carbon with fewer hydrogen.
42
Hydrohalogenation
43
Hydrohalogenation
Example 4
H
HCl
Cl
cyclopentene chloro-cyclopentane
44
Hydration: Addition of water
• A water molecule can be added to an alkene

– The addition of a water molecule to an alkene is
called hydration
• Presence of strong acid is required as a catalyst
• Product resulting is an alcohol
47
Addition of Water: Hydration
CH 2 CH 2
H 3C CH
1-butene
+ H 2O
X
When only water is added to alkenes,
NO reaction takes place.
46
acid catalysis
H
CH2 CH2 H+, trace CH2 CH2
H3C CH + H2O H 3C CH
1-butene 2-butanol OH
When small amounts of acid are present,

hydration of the double bond takes place.
47
H2O/ H+
OH
H H
Markovnikov’s Rule also is applied here, H goes to the

carbon with more hydrogens
48
Alkene Reactions: Examples
• Predict the major product in each of the
following reactions
• Name the alkene reactant and the product
using IUPAC nomenclature
51
Oxidation of Alkenes
a) Oxidation with Permanganate; a Chemical Test
Potassium
permanganate
Purple
Brown black
If KMnO4 reacts with alkene, its color will change from

purple to brown black.
KMnO 4, Cold
OH , H2O
Ref. Hart et. al. Organic Chemistry A Brief Course, 13th ed., page 97-98 52
Oxidation of Alkenes
b) Ozonolysis of Alkenes
Ref. Hart et. al. Organic Chemistry A Brief Course, 13th ed., page 97-98 53
Polymers of Alkenes
• Polymers are macromolecules composed of
repeating units called monomers
– Polymers can be made up of thousands of monomers
linked together
• Many commercially important materials are
addition polymers made from alkenes and
substituted alkenes
– Addition polymers are named for the fact that they
are made by the sequential addition of the repeating
alkene monomer
General Knowledge 54
Polymers of Alkenes
General Knowledge 55
Alkyne Reactions
1. Hydration of Alkynes
• Hydration of an alkyne is a more complex process

– The initial product is not stable
• Enol produced – both an alkene and an alcohol
• Product is rapidly isomerized
– Final product is either
• Aldehyde
• Ketone
56
Hydration of Alkynes
O H
HO H
C C H
H3C CH2 H
H3C CH2 H
KETONE
ENOL
Stable
Less Stable
The less stable ENOL readily tautomerizes into ketone.
53
Hydration of Terminal Alkynes
58
2.
54
55
Hydrogenation of Alkynes
H 3C H
H 3C H 2C
H
H 2C C C CH 3 H 2 / Lindlar
cis-2-pentene
2-pentyne CH 3
• Lindlar’s catalyst: H2 /Pd / CaCO3

• The resulting alkene is a cis-alkene
56
HBr
57
4.
58
Four credits
(Lectures 28-30)
Aromatic Hydrocarbons
Benzene’s structure was first proposed 150 years ago
– A cyclic structure for benzene, C6H6
– Something special about benzene
• Although his structures showed double bonds, the
molecule did not react as if it had any unsaturation
– Originally named aromatic compounds for the

pleasant smell of resins from tropical trees (early
source)
2
Representative Aromatic
Compounds
O
OH
O
Aspirin
3
Aromatic Hydrocarbon: Benzene
• Now aromatic hydrocarbons are characterized by a
much higher degree of chemical stability than
predicted by their chemical composition
• Most common group of aromatic compounds is

based on the 6-member aromatic ring, benzene
• The benzene ring consists of:

– Six carbon atoms
– Joined in a planar hexagonal arrangement
– Each carbon is bonded to one hydrogen atom
4
Aromatic Hydrocarbon: Benzene
• Aromatic compounds do not undergo the kinds of
Addition reactions like the alkenes and alkynes.
➢ For instance, aromatic compound do not delocalize
bromine solutions the way alkenes and alkynes do
5
Benzene Resonance Structure
• Two equivalent structures proposed by Kekulé
are recognized today as resonance structures
• The real benzene molecule is a hybrid with each
resonance structure contributing to the true
structure
6
Benzene Structure – Modern
Modern concept of benzene structure is based
on overlapping orbitals
– Each carbon is bonded to two others by sharing
a pair of electrons
– Each carbon atom also shares a pair of electrons
with a hydrogen atom.
Two commonly symbols are

used to describe the benzene
ring; b was proposed by
Kekulé, and d represents the
electron cloud.
7
Model of Bonding in Benzene
– Remaining 6 electrons are located in p orbitals
that are perpendicular to the plane of the
carbon ring
• These p orbitals overlap laterally
• Form a cloud of electrons above and below the ring
8
Aromaticity
• Uninterrupted arrangement of p double
bonds
• Cyclic molecule
• Total number of p-electron pairs is odd
(1,3,5…)
• Molecule has to be planar
• Exceptionally stable molecules
9
Aromaticity
cyclooctatetraene
cyclobutadiene
Cyclobutadiene: planar, cyclic, all atoms have p orbitals,

2 pairs of p electrons
Cyclooctatetraene: nonplanar, cyclic, all atoms have p

orbitals, 4 pairs of p electrons
10
Aromaticity
cyclopentadienyl cation cyclopentadienyl anion
cyclopentadiene ..
2 p electron pairs 3 p electron pairs
2 p electron pairs
aromatic
Polycyclic Aromatic Rings
naphthalene, planar, 5 pairs azulene, planar, 5 pairs

11
Polynuclear Aromatic Hydrocarbons
Polynuclear aromatic hydrocarbons (PAH) are

composed of two or more aromatic rings joined
together
• Many have been shown to cause cancer
12
Heterocyclic Aromatic Compounds
• Rings with at least one atom other than carbon
as part of the structure of the aromatic ring
– This hetero atom is typically O, N, S
– The ring also has delocalized electrons
13
Heterocyclic Aromatics
• Heterocyclic aromatics are similar to benzene
in stability and chemical behavior
• Many are significant biologically
– Purines and pyrimidines are components of DNA
and RNA
– Pyridine is found in nicotine
– Pyrrole is a component of hemoglobin and
chlorophyll
14
IUPAC Names: Benzenes
• Most simple aromatic compounds are
named as derivatives of benzene
• For monosubstituted benzenes, name
the group and add “benzene”
15
Historical Nomenclature
Some members of the benzene family have unique names before the
IUPAC system, and was adopted that are still frequently used today
O
OH OCH3 NH2 CH
phenol anisole aniline benzaldehyde
O
O
CCH3 COH CH3
CH CH2
acetophenone styrene benzoic acid toluene

16
Nomenclature: Rules
1) Choose the parent name: Benzene
2) Number the ring to provide the substituents the lower numbers,
and according to the priority.
3) Write the substituents prefixes in and alphabetically order
Cl
Br
F
2-bromo-1-chloro-4-fluorobenzene
17
Disubstituted Benzene
• For disubstituted benzenes, name the
groups in alphabetical order
– The first named group is at position 1
– If a “special group” is present, it must be
number 1 on the ring
• An older system of naming indicates groups
using
– ortho (o) = 1,2 on the ring
– meta (m) = 1,3 on the ring
– para (p) = 1,4 on the ring
18
Disubstituted Benzene Derivatives
CH2 CH3
CH3
Br
1-bromo-2-ethylbenzene
NO2
o-bromoethylbenzene
Cl 3-nitrotoluene
m-nitrotoluene
Cl
1,4-dichlorobenzene
p-dichlorobenzene 19
Examples
CH CH2
OCH3 CH3
NO2
Cl
NO2 m-Nitrotoluene
p-Chlorostyrene
p-Nitroanisole
or OH
4-Nitroanisole CH2CH3
o-Ethylphenol
20
Benzene As a Substituent
When the benzene ring is a substituent on
a chain (C6H5), it is called a phenyl group
– Note the difference between
• Phenyl
• Phenol (a functional group)
21
Example:
Draw each of the following compounds
1. 1,3,5-Trichlorobenzene
2. 2,5-Dibromophenol
3. para-Dinitrobenzene
4. 2-Nitroaniline
5. meta-Nitrotoluene
22
Reactions of Benzene
• Benzene does not readily undergo addition
reactions
• Benzene typically undergoes electrophilic
aromatic substitution reactions:
– An atom or group substitutes for an H on the
ring
– All benzene reactions we consider require a
catalyst
– The reactions are:
1. Halogenation
2. Nitration
3. Sulfonation
4. Alkylation
23
Electrophilic Aromatic Substitutions
• Electrophilic aromatic substitutions include:
E
 + –
H
+E Y +H Y
X+
NO2+
+ SO
3H
R+
+
RC=O
24
Benzene Halogenation
Halogenation places a Br or Cl on the ring
– The reagent used is typically Br2 or Cl2
– Iron or iron halide are used as catalysts
Benzene Nitration
•Nitration places the nitro group on the ring
•Sulfuric acid is needed as a catalyst
Benzene Sulfonation
Sulfonation places an SO3H group on the ring
– Concentrated sulfuric acid is required as a catalyst
– This is also a substitution reaction
Benzene Friedel-Craft Alkylation
Friedel-Craft alkylation places an alkyl group on
the ring
– Lewis acid is required as a catalyst
C(CH3)3
H
AlCl3
+ (CH3)3CCl + HCl
H3C
Electrophile is +
tert-butyl cation C CH3
H3C
Benzene Friedel-Craft Acylation
Friedel-Craft aacylation places an acyl group on
the ring
– Lewis acid is required as a catalyst
O
H
O
AlCl3 C CH2CH3
+ CH3CH2CCl
+ HCl
Electrophile is an acyl cation

+ •• +
CH3CH2C O •• CH3CH2C O ••
Oxidation of Alkylbenzenes
CH3
Na2Cr2O7 O
H2SO4
or CH2R COH
H2O, heat
or CHR2
Na2Cr2O7
H2SO4
CR3 No Reaction
H2O, heat
3o carbon, no C-H bond 30

Example
O
CH3
COH
Na2Cr2O7
H2SO4
H2O
heat
NO2 NO2
p-Nitrotoluene p-Nitrobenzoic acid
31
Example
O
CH(CH3)2
COH
Na2Cr2O7
H2SO4
H2O
CH3 COH
heat
O
32
Oxidation of the Side Chain Using Hot KMnO4
• Alkyl side chains of aromatic rings can be oxidized to the

carboxylic acid using hot KMnO4
33
Oxidation of the Side Chain Using Hot KMnO4
• Unsaturated side chains of aromatic rings can also be oxidized to
the carboxylic acid using hot KMnO4
34
Reduction of Carbonyl group:
Clemmensen Reduction
O
R Z n (H g ) R
HCl
Zn(Hg): Zinc Amalgam
Example
35
Four credits
Stereoisomerism
Reference Book: ORGANIC CHEMISTRY - A BREIF COURSE by D. Hart, C. Hadad, L.
Craine and H. Hart, 13th ed., Brooks/Cole, Cengage Learning, 2012.
1
Isomerism: Constitutional Isomers and Stereoisomers
Recall Isomers: are different compounds that have the same molecular
formula (Same number and types of atoms).
2
Stereoisomerism
• Stereoisomers are compounds that have the

same molecular formula and the same
connectivity of atoms but differ in their
arrangement in space.
• Stereoisomerism has a huge influence on the

chemical properties of the molecules.
3
Chirality and Enantiomers
• The mirror images of your hand cannot be superimposed
on each other; one does not completely fit on top of the
other.
• Objects that have handedness in this manner are said to

be chiral (pronounced ky-ral, from the Greek cheir,
meaning “hand”).
Stereochemistry and Chirality
Chiral: When two mirror images of a molecule are not
superimposable upon one another. It is called chiral
molecule.
- Asymmetric: a molecule that does not have any plane

of symmetry.
- Plane of symmetry: a plane that passes through a

molecule and can divide it into two identical halves.
5
AChiral: When two mirror images of a molecule are
superimposable upon one another. It is called achiral
molecule.
Achiral examples
Tennis ball
Their mirror images are superimposable because they have a plane

of symmetry (SYMMETRIC). Objects lack handedness.
• All that is required for a molecule to be achiral is one

plane of symmetry.
Is it Chiral or Achiral glass?
achiral
achiral
8
Is it Chiral or Achiral School desk?
chiral
9
Chirality: Stereogenic Centers
A carbon atom that is both tetrahedral geometry (four single

bonds) and has four different groups attached to it is
called :
• A chiral carbon atom

• A chiral center
• An asymmetric center
• A stereoegnic center
• A stereocenter
10
A molecule with a single chirality center is chiral.

Examples
H H
* *
CH3 C CH2CH3 CH3 C CH2CH3
OH Cl
2-butanol 2-chlorobutane
11
CH3
Limonene
H
* CH2CH2CH3
CH3CH2 C
*
CH3
H C CH2
3-methylhexane
CH3
—H
a chirality center can be part of a ring
—CH2CH2
attached to the chirality center are: —CH2CH=C
—C=C
12
Enantiomers
• A chiral compound and its mirror image are

called Enantiomers.
Enantiomers are type of configurational isomers ; they
are said to have opposite configurations.
Enantiomers 13
Enantiomers
14
Enantiomers
• Asparagine: mirror plane
O OH HO O
C C
H2N C H H C NH2
CH2 CH2
C C
H2N O O NH2
L-asparagine D-asparagine
(from asparagus) (from vetch)
bitter taste sweet taste
Enantiomers 15
Enantiomers
• Most importantly, pairs of enantiomers often

differ in their activity as drugs.
Enantiomers Configuration/ Designation
• R (clockwise) and S (counterclockwise)
3 3
4 4
2
2
1
1
17
Configuration and the R-S Convention
The priority order of the four groups is set in the following way:
Rule 1.
The atoms directly attached to the stereogenic center are ranked according to
atomic number: the higher the atomic number, the higher the priority.
Cl > O > C > H
high priority Low priority
Rule 2.
If a decision can not be reached with rule 1, work outward from the
stereogenic center until a decision is reached. For example, C2H5- has higher
priority than CH3-
18
Rule 3.
Multiple bonds are treated as if they were an equal number of
single bonds. For example, the vinyl group –CH=CH2 is counted
H
as C CH2
This carbon is treated C C This carbon is treated

as if it were singly bonded as if it were singly bonded
to two carbons to two carbons
Similarly C C
C CH is treated as C C H
C C
and
H
C O is treated as C O
H
O C
19
Example 1
Assign a priority order to each of the following sets of groups:
a. –CH3, -CH(CH3)2, -H, -NH2
-NH2 > -CH(CH3)2 > -CH3 > -H,
b. –OCH3, -NHCH3, -CH2NH2, -OH
–OCH3 > -OH > -NHCH3 > -CH2NH2
c. –OH, -F, -CH3, -CH2OH
-F > –OH > -CH2OH > -CH3

20
Example 2
Assign a priority order to

–CH=O, -CH=CH2, -CH2CH3 and -CH2OH
–CH=O > -CH2OH > -CH=CH2 > -CH2CH3
The aldehyde carbon is treated as though it is bonded to two oxygens
21
(in plane of the page
(dash)Away from us, out of the plane of the page
(Wedge)Towards us, out of the plane of the page
22
Assign the configuration (R or S) to the following enantiomer of

3-methylhexane CH3
H
C
CH3CH2
CH2CH2CH3
The priority order of the four different groups attached to stereogenic center
–CH2CH2CH3 > -CH2CH3 > -CH3 > -H
We write the name :

(R)-3-methylhexane
23
Eye image repeated
24
Example 3
Determine the configuration (R or S) at the stereogenic center in
CH3
CH O
A. H
HO
C B. C
CH2CH2CH3 H2N H
Ph
3
2 CH3
CH O
C
1 H 4
C 1 H2N H 4
HO Ph
CH2CH2CH3 2
3
clockwise or counterclockwise or
R- S- 25
Example 4
- Draw the structure of (R)-2-bromobutane.
*
Solution CH3CHCH2CH3
-Br > –CH2CH3 > -CH3 > -H
Br 1
3
Br 2
CH3
4 C2H5
C H
C H or
C H 4 or
CH3 C H 4
3 CH2CH3 C2H5
Br
Br
2 2 1 CH3
1 3
- Draw the structure of (S)-2-phenylbutane.

C 6H 5 > CH2CH3 > CH3 > H
3
CH3 1 C6H5
2 CH CH
4 2 3
C H C H or C H 4
C6H5 or 3 C H 4
CH3CH2
1 CH2CH3 CH3 CH3
2
3 C6H5 26
2 1
Properties of Enantiomers
1. They have same physical properties such as

melting point, boiling point, density, spectroscopy.
They differ in optical activity or optical rotation.
mirror
CO2H CO2H
C C
OH HO
CH3 CH3
H H
(R)-(-)-lactic acid (S)-(+)-lactic acid

mp = 53 oC mp = 53 oC
[] (H2O) = + 2.6 [] (H2O) = - 2.6
27
Properties of Enantiomers
2. They have different biological-physiological

properties.
CO2H
CO2H CO2H
lactic acid lactic acid C
C C H
CH3
HO dehydrogenese dehydrogenese
CH3 O CH3 HO
H
(S)-(+)-lactic acid pyruvic acid (R)-(-)-lactic acid
The enzyme lactic acid dehydrogenase oxidizes (+)-lactic acid to

pyruvic acid, but it does not oxidize (-)-lactic acid
28
Properties of Enantiomers: Optical activity
3. Optical activity: Each enantiomer rotates the
plane of polarized light by the angle of rotation ()
called optical rotation. Both enantiomers would
have the same specific rotation (number of degrees)
but in the opposite directions (opposite signs ).
A polarimeter is used to make such measurements.

29
• The enantiomer that rotates the plane of polarized

light in a clockwise direction is called dextrorotatory
(D) and is called the (+) enantiomer.
• The other enantiomer (counterclockwise rotation) is

levorotatory (L), the (-) enantiomer.
• Racemic Mixture: A 50:50 mixture of two

enantiomers: no optical rotation!
30
𝑡 𝛼
Specific rotation = 𝛼 𝜆 =
𝑐.𝑙
Specific rotation, 𝛼 𝑡𝜆 , is an intrinsic property of chiral molecule

at specific temperature of the solution (t) , nature of the solvent,
and wavelength of the light (𝝀).
Observed rotation, 𝛼 , is function of concentration of the chiral

molecules (c, in unit of g/mL) and length of the sample tube (𝒍 , in
unit of decimeter (1 dm =10 cm))
Compound Rotation Compound Rotation
azidothymidine +99 Na glutamate +25.5
Cefotaxine +55 Morphine -132
Cholesterol +31.5 Progesterone +172
Codeine -136 Sucrose +66.5
epinephrine -5.0 testosterone +109
Example 5
Camphor is optically active molecule. A camphor sample (1.5g) dissolved in ethanol
(optically inactive) to a total volume of 50 mL, placed in a 5-cm polarimeter sample
tube, gives an observed rotation of +0.66⁰ at 20 ⁰C (using the sodium D-line).
Calculate and express the specific rotation of camphor.
𝛼 =+0.66
𝒍 = 5 cm = 0.5 dm
𝑚𝑎𝑠𝑠 𝑔 1.5𝑔
𝑐= =
𝑣𝑜𝑙𝑢𝑚𝑒 𝑚𝐿 50 𝑚𝐿
𝑡 𝛼
Specific rotation = 𝛼 𝜆 =
𝑐.𝑙
Fisher Projection Formulas
A Fisher Projection is a type of two-dimensional

formula of a molecule used to represent the three-
dimensional configurations of stereogenic centers.
Fisher Projections are used extensively in biochemistry and in
carbohydrate chemistry.
Rules for Fischer projections H

Arrange the molecule so that
horizontal bonds at chirality Br Cl
center point toward you and F
vertical bonds point away
from you.
(R)-configuration
33
Rules for Fischer projections 4
H
1 2
Br Cl
F
3
Clockwise = (R)-configuration
Projection of molecule on page is a cross.

When represented this way it is understood that
horizontal bonds project outward, vertical bonds
are back. 34
Example 6
Determine the absolute configuration of the following enantiomers:
1 4
Cl H
3 3 2
2
CH3 CH2CH3
CH3 CH2CH3
OH
H 1
4
clockwise = (R)-configuration counterclockwise = (S)-configuration
3 3
CH3 CH3
1 enantiomers 1 4
4H OH HO H
CH2CH3 CH2CH3
2 2
(S)-configuration (R)-configuration
Note:- lowest priority group is on the horizontal; R is changed to S
35
Compounds with More Than One Stereogenic Center
• How many stereoisomers when a particular molecule

contains two chiral centers?
Stereoisomers = 2n where n is the number of chiral centers
H H
1 2 * 3 * 4
CH3 C C CH3
Br Cl
2-bromo-3-chlorobutane
What are all the possible R and S combinations of the two
chirality centers in this molecule?
Carbon-2 R R S S
Carbon-3 R S R S 36
2-bromo-3-chlorobutane
H H
1 2 * 3 4
CH3 C C* CH3
Br Cl
4 Combinations = 4 Stereoisomers
What is the relationship between these stereoisomers?
enantiomers: 2R,3R and 2S,3S

2R,3S and 2S,3R
37
mirror
mirror
1 CH3 1 CH3 1 CH3 1 CH3
2 2 2 2
Br C H H C Br Br C H H C Br
3 3 3 3
H C Cl Cl C H Cl C H H C Cl
4 CH3 4 CH3 4 CH3 4 CH3

enantiomers enantiomers
(2R,3R) (2S,3S) (2R,3S) (2S,3R)
but not all relationships are enantiomeric
Stereoisomers that are not enantiomers are diastereomers.

similar but not identical chemical and physical properties
38
The (2R,3R) and (2R,3S) forms of the isomers are not mirror
images because they have same configuration at C-2, though
they have opposite configuration at C-3, they are
stereoisomers but not enantiomers. They are diastereomers.
1 CH3 1 CH3
2 2
Br C H Br C H
3 3
H C Cl Cl C H
4 CH3 4 CH3
(2R,3R) (2R,3S)
Diastereomers stereoisomers that are not mirror

images of each others.
39
Meso Compounds
• Consider the stereoisomers of 2,3-dichlorobutane.
40
Meso Compounds
this structure and its

mirror image are the
same
it is called a meso form
a meso form is an achiral molecule that has chirality centers
41
Meso Compounds
O H H O
HOC C
* C* COH
OH OH
tartaric acid
CO2H CO2H CO2H
H OH HO H H OH
HO H H OH H OH
CO2H CO2H CO2H

Configuration : (R,R) (S,S) meso (R,S) achiral
[] (H2O) +12 -12 0
M.P, oC 170 170 140
42
Summary of Meso Compounds
Any meso compound should have the following:

❑ Has more than one stereogenic center
❑ Achiral molecule
➢ Plane of symmetry
➢ The molecule and its mirror image are superimposable (e.g. same compound)
43
Four credits
(Lectures 34-36)
Alcohols: Structure and Physical
Properties
• An organic compound containing a hydroxyl group
attached to an alkyl group
• Alcohols have the general formula R-OH
H H OH
H H H
Physical Properties of Alcohols
• R-O-H has a structure similar to that of water
• Hydroxyl group is very polar
• Hydrogen Bonds can form readily
– High boiling points relative to their molar masses
due to ability to hydrogen bond
CH3CH2CH2CH3 CH3CH2CH2OH
b.p. = -0.5oC b.p. = 97.2oC
Alcohols have higher

boiling points than Alcohols are soluble in
hydrocarbons of water because of
comparable M.W. Hydrogen Bonding
because of Hydrogen between alcohol and
Bonding between water
different alcohol
molecules
Physical Properties of Alcohols
In homologous series, as MW increases b.p. increases, but solubility
in water decreases.
Alcohol Classification
Alcohols: Nomenclature
• IUPAC: based on the longest chain containing the
OH carbon
• The -e of the alkane name is replaced with -ol
• The chain is numbered from the end giving the -OH
carbon the lower number
• The name is prefixed with the number indicating
the position of the OH group
• Alcohol has priority over multiple bonds, halogens,
and alkyl groups.
• For cyclic alcohols, the OH is at C-1
IUPAC Name of Alcohols
CH3
CH3 CH CH CH3
OH
1. Name the parent compound – 4 carbons = butane
2. Replace the –e with –ol = butanol
3. Number the parent chain to minimize number of
carbon with the –OH group = number from right to
left
4. Identify, name, and number all substituents =
methyl on C-3
3-methyl-2-butanol
CH3
CH3CH2OH
CH3CCH2CH2CH3
Ethanol
(Ethyl alcohol) OH
2-Methyl-2-pentanol
CH3CHCH2CH2CH2CH3 HO Br
2 3
1 5
OH CH3
H3C 4
2-Hexanol
3-bromo-2-pentanol
1. Determine longest chain with OH
Blue chain is longer; however,
Red chain contains OH
6 5 4 3 2 1
CH3CH2CH2CH2CHCH2OH
C
C CH2CH2CH3
1 2 3
2-propyl-1-hexanol
Write IUPAC Name of Cyclic Alcohol
CH3
OH
1. Name the parent compound – 6 carbon ring = cyclohexane

2. Replace the –e with –ol = cyclohexanol
3. Number the ring to minimize number of carbon with the
–OH group = number counterclockwise
4. Identify, name, and number all substituents = methyl on C-3
3-Methylcyclohexanol
OH must be at C-1
Common Names of Alcohols
CH3
CH3 CH CH3
CH3 C CH3
OH
OH
t-butyl alcohol isopropyl alcohol
The common names for alcohols consist of the alkyl

cycloalkyl group name or , a space, and the word
alcohol
Examples
OH
2 OH
3 1
4 6
5
2,3-dimethyl-1-cyclohexanol Cyclohexanol Phenol

2,3-dimethylcyclohexanol
2 OH
H3C 3 1
4 6
5
CH3
3-ethyl-5-methyl-1-cyclohexanol
3-ethyl-5-methylcyclohexanol
More Examples
H
CH2 CHCH2OH
CH2OH
2-propen-1-ol
OH (allyl alcohol)
phenylmethanol cyclohexanol
(benzyl alcohol) (cyclohexyl alcohol)
Name the following alcohols by the IUPAC system: You do it

H OH
OH
ClCH2CH2OH
Organic Chem. Hart-Chap. 7 13

Examples
Write a structural formula for the following: You do it
3-penten-2-ol
cyclobutanol
3-bromopropanol
The hydroxyl group is named as a substituent when it
occurs in the same molecule with carboxylic acid,
aldehyde, or ketone functionalities, which have
priority in naming. Examples are:
CHO OH
CO2H
But
OH
OH NO2
m-hydroxybenzoic acid p-hydroxybenzaldehyde
p-nitrophenol
(not p-hydroxynitrobenzene)

Medically Important Alcohols
• Methanol
– Colorless and odorless liquid
– Used as a solvent
– Toxic, can cause blindness and death if ingested
– Can be used as a fuel
CH3 OH
Ethanol
• An odorless and colorless liquid
• Widely used as a solvent
• The alcohol in alcoholic beverages
– Derived from fermentation of carbohydrates
– Beverage produced varies with the starting
material and the fermentation process
2-Propanol (Isopropyl alcohol)
• Colorless, but has a slight odor
• Commonly called rubbing alcohol
• Toxic when ingested
• Used as a:
– Disinfectant
– Astringent
– Industrial solvent
CH3 CH CH3
OH
1,2-Ethanediol (Ethylene glycol)
• Used as automobile antifreeze
• Has a sweet taste, but is extremely
poisonous
• Added to water
– Lowers the freezing point
– Raises the boiling point
CH2 CH2
OH OH
Reactions Involving Alcohols
Preparation of Alcohols
• Hydration
– Addition of water to the carbon-carbon double bond of
an alkene produces an alcohol
– Requires a trace of acid as a catalyst
Preparation of Alcohols
• Hydrogenation
– Addition of hydrogen to the carbon-oxygen double
bond of an aldehyde or ketone produces an alcohol
– A type of addition reaction
– Also considered a reduction reaction
– Requires Pt, Pd, or Ni as a catalyst
Dehydration of Alcohols
• Alcohols dehydrate with heat in the presence of strong
acid to produce alkenes
• Dehydration is a type of elimination reaction
– A molecule loses atoms or ions from its structure
– Here –OH and –H are removed / eliminate from
adjacent carbon atoms to produce an alkene and water
– A reversal of the hydration reaction that forms alcohols

Dehydration of Alcohols to Alkenes
• Alcohols can be dehydrated by heating them with a

strong acid.
H2SO4
CH3CH2OH H2C CH2 + H2O
160°C
H2SO4
OH + H2O
140°C
(79-87%)
23
Dehydration of Alcohols to Alkenes
CH3
H3C
H3C C OH H2SO4
C CH2 + H2O
heat
CH3
H3C
(82%)
24
Zaitsev’s Rule
• Some alcohol dehydration reactions produce a
mixture of products
• Zaitsev’s rule states that in an elimination
reaction the alkene with the greatest number of
alkyl groups on the double bonded carbon is the
major product of the reaction
Predict the Product of Dehydration
• What are the major and minor products when 3-
methyl-2-butanol is dehydrated?
– Zaitsev’s rule states that in an elimination reaction
the alkene with the greatest number of alkyl groups
on the double bonded carbon is the major product of
the reaction
Examples: Zaitsev’s Rule
27
Oxidation of Alcohols
➢ Remember, we distinguish three types of alcohols:
R
R
R CH2 OH CH OH R C OH
R'
R
10 20 30
➢Dehydrogenation (oxidation) is possible for
10 and 20 only leading to aldehydes and ketones,
respectively.
O O
R R
H R'
aldehyde ketone 28
29
Strong Oxidizing Agents:
CrO3/H2SO4 (Jone’s reagent)
O
-
Mild Oxidizing Agent: O H O Cr Cl
Pyridinium chlorochromate O
HO Cr OH N
(PCC)
O PCC
30
• Primary alcohols usually oxidize to carboxylic
acids
– The symbol [O] represents an oxidizing agent
(KMnO4 or H2CrO4) which is used to oxidize a
1o alcohol to carboxylic acid
H O
R C OH [O]
R C OH
H
• The oxidizing agent (pyridinum chlorochromate; PCC)
which is used to oxidize a 1o alcohol to an aldehyde
H O
R C OH PCC
R C H
H
PCC is a more selective oxidizing agent.
Oxidation can be stopped at the aldehyde level.
O
CH3(CH2)6CH2OH PCC CH3(CH2)6C H

CH2Cl2, 25 oC
1-octanol octanal
PCC is prepared by dissolving CrO3 in hydrochloric acid

and then adding pyridine, shown below:
CrO3 + HCl + N N+ H CrO3Cl-
pyridine pyridinium chlorochromate (PCC)
33
• Using any of the Oxidizing agents (KMnO4,
H2CrO4 or PCC), Secondary alcohols oxidize to
ketones
– This reaction is also an elimination of 2H
Tertiary Alcohols Do Not Undergo
Oxidation Reactions
• Tertiary alcohols do not oxidize as there is no
H on the carbonyl carbon to remove
Organic Oxidation and Reduction
• In organic systems changes may be tracked:
Oxidation: Reduction:
– gain of oxygen – loss of oxygen
– loss of hydrogen – gain of hydrogen
Examples: Oxidation Reactions
H
CrO3
O
H+, acetone
OH
(Jones' reagent)
cyclohexanol cyclohexanone
Jones' reagent
CH3(CH2)6CH2OH CH3(CH2)6CO2H
1-octanol octanoic acid
37
Phenol
• Phenols are compounds in which the hydroxyl group is
attached to a benzene ring
– Polar compounds due to the hydroxyl group
– Simpler phenols are somewhat water soluble
– Components of flavorings and fragrances
• Phenols have the formula Ar-OH
– Ar must be an aromatic ring (e.g., Benzene)
Because they have same functional group, alcohols and phenols
have many similar properties. But whereas it is relatively easy,
with acid catalysis to break the C-OH bond, this bond is difficult
to break in phenols.
CH3 CH3
H3C C O+ H H3C C+ + H2O
CH3
CH3 H t-butyl cation
O+ H + + H2O
H
a phenyl cation
• Alkoxides (RO−), the conjugate bases of alcohols, are
strong bases just like hydroxide ion.
-
2 RO K+
RO H + 2K + H2
alcohol potassium
alkoxide
-
RO H + NaH RO Na+ + H2
sodium sodium
hydride alkoxide
Write the equation for the reaction of t-butyl alcohol with potassium metal.
CH3 CH3
-
2 H3C C OH + 2K 2 H3C C O K+ + H2
CH3 CH3
t-butyl alcohol potassium t-butoxide

• Treatment of Alcohols with sodium hydroxide does
not covert them to their alkoxides. This is because
alkoxides are stronger bases than hydroxide. Phenols,
however, can be converted to phenoxide ions.
-
RO H + NaOH // RO Na+ + H2O
alcohol
-
OH + NaOH O Na+ + H2O
phenol sodium phenoxide

Write an equation for the reaction, if any, between.
• p-Nitrophenol and aqueous potassium hydroxide.

• Cyclohexanol and aqueous potassium hydroxide .
-
O2N OH + KOH O2N O K+ + H2O
p-nitrophenol potassium p-nitrophenoxide
OH + KOH No Rxn
cyclohexanol

Ethers
• Ethers have the formula R-O-R
– R can be aliphatic or aromatic
• Ethers are slightly polar due to the polar C-O-C
chemical bonds
• Do not hydrogen bond to one another as there
are no –OH groups
Ether Physical Properties
• Ethers have much lower boiling points than
alcohols due to the lack of hydrogen bonding
Nomenclature of Ethers
• Common names for ethers consist of the names
of the two groups attached to the O listed in
alphabetical order (or size) and followed by
‘ether’
What is the name of the following compounds?
CH3CH2CH2CH2CH2-O-CH3
O
diphenyl ether

• In the IUPAC system, the smaller alkoxy group (–OR) is
named as substituent.

Reactivity of Ethers
• Chemically, ethers are moderately inert
– Do not normally react with reducing agents or bases
– Extremely volatile
– Highly flammable = easily oxidized in air
Preparation of Ethers
• Symmetrical ethers may be prepared by dehydrating

two alcohol molecules and this reaction requires heat
and acid catalyst (Acid-catalyzed condensation of
alcohols)
Diethyl ether
49
Preparation of Ethers
• Addition of Alcohol to Alkenes
tert-Butyl methyl ether
tert-Butyl ethyl ether

50
The Williamson Ether Synthesis
Most important for laboratory synthesis of unsymmetric

ethers is Williamson synthesis, which involve the
reaction of alkoxide with alkyl halide.
(71%)
Another Example: Alkoxide ion can be derived from primary,
Alkyl halide must be primary secondary, or tertiary alcohol
51
Write equations for the synthesis of the following
ethers by the Williamson method:
A. OCH3 B. (CH3)3COCH3
OH + NaH
A. O- Na+ + H2
O- Na+ + CH3Br OCH3 + NaBr
(CH3)3COH + 2 K (CH3)3CO- K+ + H2
B.
(CH3)3CO- K+ + CH3Br (CH3)3COCH3 + NaBr

Medical Uses of Ethers
• Ethers are often used as anesthetics
• Accumulate in the lipid material of nerve cells
interfering with nerve impulse transmission
• Today halogenated ethers are used routinely as
general anesthetics
– Less flammable
– Safer to store and to work with
Thiols
• Thiols have the formula R-SH
• Similar in structure to alcohols with S replacing O
• Name is based on longest alkane chain with the
suffix –thiol position indicated by number
Naming Thiols
• Write the IUPAC name for the thiols shown
Thiols and Scent
• Thiols, as many other sulfur-containing
compounds can have nauseating aromas
– Defensive spray of North American striped skunk
– Onions and garlic
• Compare with pleasant scents below
Disulfide Formation
The thiol-disulfide
redox pair controls a
critical factor in
protein structure
called a disulfide
bridge
– Two cysteine
molecules (amino
acids) can undergo
oxidation to form
cystine
– Forms a new bond
called a disulfide Copyright © 2017 McGraw-Hill Education. Permission required for reproduction or display
bond
Summary of Reactions
Four credits
Lectures 37 – 39
Structures and Physical Properties
Structure and Physical Properties
• Aldehydes and ketones are polar compounds
• The carbonyl group is polar
– The oxygen end is electronegative
Aldehydes and ketones do not form Hydrogen bonding with each other.
They have weak intermolecular dipole-dipole forces working between molecules.
Hydrogen Bonding in Carbonyls
• Aldehydes and ketones cannot form
intermolecular hydrogen bonds
• However, water can form hydrogen bonds to
them
Physical Properties
Carbonyls boil at
• Higher temperatures than:
– Hydrocarbons
– Ethers
• Lower temperatures than:
– Alcohols
Nomenclature and Common Names
Naming Aldehydes
• Locate the parent compound
– Longest continuous carbon chain
– Must contain the carbonyl group
• Replace the final –e of the parent with –al
• Number the chain with the carbonyl carbon as 1
• Number and name all substituents
Naming Aldehydes
For substituted aldehydes, we number the chain
starting with the aldehyde carbon.
What is the name of this molecule?
1. Parent chain – 5 carbons = pentane
2. Change suffix – pentanal
3. Number from carbonyl end – L to R
4. Number / name substituents – 2-methyl
5 4 3 2 1
2-methylpentanal
Nomenclature of Aldehydes
• Aldehyde group has priority over the multiple
bond hydroxyl, alkyl, and halogens group.
For cyclic aldehydes, the suffix –carbaldehye is used.

Aromatic aldehydes often have common names:
IUPAC and Common Names With
Formulas for Several Aldehydes
Ketones
Simplest ketone MUST have 3 carbon atoms so that
the carbonyl group is interior
• Base name: longest chain with the C=O
• Replace the –e of alkane name with –one
• Indicate position of C=O by number on chain so
that C=O has lowest possible number
• Ketone group has priority over the multiple bond,
hydroxyl, alkyl, and halogens group.
4-methyl-2-heptanone
Nomenclature of Cycloketones
Common names of ketones are formed by adding the

word ketone to the names of the alkyl or aryl groups
11
Problems
12
Examples:
Write the correct names for the following:
a. 3-Methylbutanal (no number is necessary for the

aldehyde function)
b. 2-Butenal (the number locates the double bond
between C-2 and C-3)
c. Cyclobutanone
d. 3-Heptanone
13
Important Aldehydes and Ketones
• Methanal (formaldehyde) - gas used in aqueous
solutions as formalin to preserve tissue
• Ethanal (acetaldehyde) - produced from ethanol
in the liver causing hangover symptoms
• Propanone (Acetone) - simplest possible ketone
– Miscible with water
– Flammable
– Both acetone and methyl ethyl ketone (butanone) are
very versatile solvents
Important Uses of Carbonyl Compounds
• Used in many industries

– Food chemicals
• Natural food additives
• Artificial additives
– Fragrance chemicals
– Medicines
– Agricultural chemicals
Vanillin and 2-Octanone
Benzaldehyde and Cinnamaldehyde
Citral and α-Demascone
Preparation of Aldehydes and Ketones
Preparation of aldehydes and ketones
• Principal means of preparation is oxidation of the
corresponding alcohol
– Primary alcohol produces an aldehyde
– Secondary alcohol produces a ketone
– Tertiary alcohol does not oxidize
• This oxidation process removes two hydrogens
1° Alcohol Oxidation
• An aldehyde is formed
2° Alcohol Oxidation
• A ketone is formed
The oxidizing agents: (KMnO4/OH- or H2CrO4 or

PCC or CrO3 /H2SO4 {Jone’s reagent})
3° Alcohol: No oxidation
• 3o alcohols cannot undergo
oxidation:
Examples
OH CrO3
O
H+, acetone
(Jones' reagent)
cyclopentanol cyclopentanone
CH3
CH3 O
PCC
CH3 OH
{C5H5NH+ ClCrO3–} CH3 H
5-methyl-1-hexanol
5-methylhexanal
Reactions of Aldehydes and Ketones
1. Oxidation and Reduction
a. Aldehydes: oxidized to carboxylic acids
b. Ketones: no further oxidation
c. Aldehydes and ketones are reduced to
alcohols: aldehydes to primary alcohols and
ketones to secondary alcohols
2. Addition
a. Alcohols to give hemiacetals and acetals
b. Reaction with nitrogen compounds
Oxidation of Aldehydes
• Aldehydes are easily oxidized to carboxylic
acids by almost any oxidizing agent
– So easily oxidized that it is often difficult to prepare
them as they continue on to carboxylic acids
Visually Distinguishing Aldehydes
From Ketones
Visual tests for the aldehyde functional group
based on its easy oxidation are:
• Tollen’s Test
– Silver ion is reduced to silver metal
– Use a basic solution of Ag(NH3)2+
– The silver metal precipitates and coats the container
producing a smooth silver mirror
Tollen’s Test
Benedict’s Test
• Benedict’s Test
– Reagent is a buffered aqueous solution of Cu(OH)2 and sodium
citrate
– Reacts with aldehydes, but not with ketones
– Cu2+ is reduced to Cu+
• Solution of Cu2+ is a distinctive blue color
• Color fades during the reaction as Cu+ precipitates as the
red solid, copper(I) oxide, Cu2O
- No reaction with ketone
Cu2+
solution Cu2O precipitate
𝐶𝑢2+ (aq) + Aldehyde ՜ 𝐶𝑢2 𝑂 𝑠 + 𝐶𝑎𝑟𝑏𝑜𝑥𝑦𝑙𝑎𝑡𝑒 𝑎𝑛𝑖𝑜𝑛(aq)

Benedict’s Test on Glucose
• Benedict’s Test
Reduction of Aldehydes & Ketones
• Both aldehydes and ketones are readily
reduced to alcohols
– Reduction occurs with hydrogen as the reducing agent
• Classical reaction is hydrogenation
– React with hydrogen gas
– Requires a catalyst – Ni, Pt, Pd
Reduction of Aldehydes and Ketones
➢ Aldehydes and ketones are reduced to
alcohols.
➢ The most commonly used reducing
reagents are sodium borohydride (NaBH4),
lithium aluminum hydride (LiAlH4)., and
their derivatives.
H H
Na H B H Li H Al H
H H
Sodium borohydride Lithium aluminum hydride
➢Examples:
Aqueous acid (H+, H2O) is added afterwards to protonate the alkoxide ion.
33
Addition Reactions
• Principal reaction is the addition reaction

across the polar C=O double bond
– Very similar to the addition hydrogenation of
alkenes
– Requires catalytic acid in the solution
• Product of the reaction is a hemiacetal
– Hemiacetals are quite reactive
– Undergo a substitution reaction with the –OH
group of the hemiacetal is exchanged for another
–OR group from the alcohol
– Reaction product is an acetal
– This reaction is reversible
Hemiacetal and Acetal Formation
or or
HemiKetal Ketal
Generalized structure Generalized structure

of a hemiacetal/ketal of an acetal/ketal
Hemiacetal and Acetal Formation
• Product of the addition reaction is a

hemiacetal followed by formation of an acetal
HemiKetal and Ketal Formation
HemiKetal
HemiKetal Ketal
Reaction of Aldehydes or Ketones with Nitrogen
Compound: Formation of Imine Schiff base
These reactions leads to loss of water molecule
38
Keto-Enol Tautomerism
• Aldehydes and ketones may exist as an equilibrium
mixture of 2 forms (known as tautomers), called Keto
form and the enol form.
• These two forms are isomers and differ in the location
of:
– A hydrogen atom
– A double bond
– This type of isomerism is called Tautomerism.
– The keto form has a C=O while the less stable enol form has a
C=C.
• The keto form is usually the most stable
Examples
Write formulas for the keto and enol forms of acetone.
H
O O
H C H
H H C
H C C C C H
H
H H H H
enol form
keto form
Problem. Draw the structural formulas for the

enol form of
A. Acetaldehyde B. Cyclohexanone
A. O H
 -H
H C
H
O
C C
H C H
-C H
H H
Acetaldehyde enol form
H
O O
H H
B.
H
Cyclohexanone enol form
* Most simple aldehydes and ketones exist mainly in the keto form.
** Resonance stabilization of the aromatic ring is greater than the

usual energy difference that favors the keto over the enol form.
H
O O
H
enol form keto form

of phenol of phenol
Carbonyl compounds that do not have an -H
cannot form enols and exist only in the keto form.
O
H
C O
C
O
C
H H
benzaldehyde benzophenone formaldehyde

Summary of Reaction Equations
or or
HemiKetal Ketal
Four credits
Functional Group Formulas
Ar= Aromatic hydrocarbon R = Aliphatic hydrocarbon
Carboxylic Acids
Structure
• Carboxylic acid groups consist of two
very polar functional groups
– Carbonyl group
– Hydroxyl group
• Carboxylic acid groups are very polar
Carboxylic acid Ester – Carboxylic Acid Derivative

Physical Properties
• Low molar mass carboxylic acids
– Sharp, sour taste
– Unpleasant aromas
• High molar mass carboxylic acids
– Fatty acids important in biochemistry
• Low molar mass carboxylic acids are water soluble
due to hydrogen bonding with:
– Water
– Each other

Boiling Points
Due to carboxylic acids forming intermolecular
hydrogen bonds, boiling points are at higher
temperatures than those of any other functional group
studied
Nomenclature of Carboxylic Acids
• Determine the parent compound by selecting the
longest continuous chain as usual.
• Number the chain so that the carboxyl carbon is
carbon 1.
• Replace the –e ending with –oic acid
• If two carboxyl groups are present use –dioic acid
• Complete the name of the compound by Naming
the substituents, if any, as usual.
Carboxylic Acid
Naming Examples
2 1 4 3 2 1
2CH2 CO2H HO2C C C CO2H
Butynedioic acid
Nomenclature of Carboxylic Acids
The carboxyl group has priority over alcohol, aldehyde,
and ketone. The prefix oxo- is used to locate the carbonyl
group of aldehyde and ketone as a substituent.

Names and Structures of Some
Common Carboxylic Acids
Benzoic Acid Derivatives
Carboxylic Acids with a Phenyl
Substituent
• The phenyl group is benzene with one hydrogen
removed:
Some Important Carboxylic Acids
• More complex carboxylic acids are found
in a variety of foods
• Citric Acid is found in citrus fruits
• Bacteria in mild produce lactic acid as a product
of fermentation of sugars
• Tartaric acid is used in baking powder because

it will react with carbonates in the dough
• Malic acid gives the sour taste to green apples
• Fatty acids are long chain carboxylic acids
found in plant and animal sources
Preparation of Carboxylic Acids
Oxidation of primary alcohols and aldehydes
Reactions Involving Carboxylic Acids:
Carboxylate Anion Formation
• Carboxylic acids behave as acids because when

they are dissolved in water they will deprotonate
to form a carboxylate ion and the hydronium ion
• Carboxylic acids are weak acids with dissociations
of less than 5%

Neutralization Reactions
• to form carboxylate salts
– A process of neutralization
– Acid protons are removed by the –OH- to form
H2O and carboxylate ion
– Equilibrium shifts to the right with removal of H+
Acid-Base Reactions

Salts of Carboxylic Acids
• Nomenclature
– First add the cation’s name
• Sodium
– Then drop the –oic acid and add –ate
• Sodium benzoate
• Uses of carboxylic acids
• Soaps like sodium stearate
• Preservatives
• Anti-fungal medicines
• Used to control food pH
14.2 Esters
Structure and physical properties
• Esters are mildly polar, somewhat water soluble
• Frequently found in natural foodstuffs
• Many have pleasant aromas
– Isoamyl acetate = banana oil
3-methylbutyl ethanoate
– Ethyl butanoate = pineapple aroma
Ethyl butanoate
– Isobutyl formate = raspberry aroma
Isobutyl methanoate
• Boil at approximately the same temperature as
carbonyls with comparable molecular weight
Ester IUPAC Nomenclature
Form from the reaction of a carboxylic acid with an
alcohol, which is reflected in the naming
1. Use the alkyl group as the first name
(Alcohol part of the ester)
2. Base the name for the acid part of the structure
from the longest chain ending in the C=O
(Carboxylic acid part of the ester)
3. Change the –oic acid of the acid name to –oate

Example: Naming Esters
Name the following esters:
• Alkyl portion = first name ethyl

• Parent carboxylic acid = butanoic acid
• Change suffix to reflect ester = Ethyl butanoate
• Alkyl portion = first name propyl

• Parent carboxylic acid = ethanoic acid
• Change suffix to reflect ester = Propyl
ethanoate
Naming Esters
Naming esters is much like naming the salts
of carboxylic acids:
• Alkyl portion = first name ethyl

• Parent carboxylic acid = ethanoic acid
• Change suffix to reflect ester =
Ethyl ethanoate
Ester Formation:
Fischer Esterification
Carboxylic acids react with alcohols to produce esters and
water
• The reaction is catalyzed by strong acid

Hydrolysis of Esters
• The main reaction of esters is hydrolysis,
reaction with water
– This reaction is also called hydration = cleavage of
any bond by the addition of a water molecule
• However, the uncatalyzed reaction is slow and
requires heat
• The reaction can be either acid or base
catalyzed
Acid hydrolysis of Esters
Acid hydrolysis products are:
• Acid
• Alcohol
Base Hydrolysis of Esters
The base catalyzed hydrolysis of an ester:
• Saponification or soap-making
• Products are:
– Acid salt
– Alcohol
• Acid can’t exist in basic conditions, so the
product is the salt of the carboxylic acid using
the cation of the base catalyst

Saponification
• Saponification (soap-making) is:
– Base-catalyzed hydrolysis of fats (glycerol triesters)
Saponification
➢This reaction is used to make soap
O
H2O
C CH2CH3 + NaOH
CH3 O
O
C + HOCH2CH3
CH3 O Na
27
Soap
• Sodium stearate:
ionic
(hydrophilic)
hydrocarbon
(hydrophobic)
28
Simplified Action of Soap
• The wiggly lines
represent the long
carbon chains of each
soap molecule
• Particles of oil and

grease are surrounded
by soap molecules to
form a micelle
Sample Problem
➢Complete the following reaction:
O hydrolysis in
C aqueous acid
CH3 O
O
H3O
C + HO
CH3 OH
30
Reduction of Esters
• Esters can be reduced to 1o - alcohols by lithium
aluminum hydride.
O
LiAlH4, ether
R C R CH2OH + R'OH
OR'
ester primary alcohol
• Example
O
LiAlH4, H3O+
C
CH2OH + CH3CH2OH
OCH2CH3

Acid Chlorides and
Acid Anhydrides
• Acid chlorides are derivatives of carboxylic
acids having the general formula:
• Are named:
– by replacing the –ic acid ending of the
common or IUPAC name with –yl chloride
Acid Chlorides, preparation
• Reaction of carboxylic acids with thionyl chloride
O
C
OH reflux
+ SOCl2
thionyl
chloride
benzoic acid
O
C
Cl
+ SO2 + HCl
sulfur hydrogen
O O
dioxide chloride
benzoyl chloride
R C + SOCl2 R C Cl + HCl + SO2
• Reaction ofOHcarboxylic acids with phosphorus pentachloride
(PCl5)
O O
R C + PCl5 R C Cl + HCl + POCl3

OH
33
Reactions of Acid Chlorides
34
Reactions of Acid Chlorides
O
CH3 C
Cl
+ 2 HN(CH2CH3)
diethylamine 2 Et2O
m-toluoyl chloride
O
CH3 C
N(CH2CH 3)
2 + (CH3CH2)NH2 Cl
N,N-diethyl-m-toluamide
(DEET)
35
Acid Anhydrides
• Acid anhydrides have the formula:
• The molecule is 2 carboxylic acid molecules with

a water molecule removed
– Anhydride means without water
• Symmetrical anhydrides are those with both acyl
groups the same
• Symmetrical anhydrides are named by replacing
the -acid ending of the acid with –anhydride
Formation of Acid Anhydrides
• Acid anhydrides can be formed in a reaction
between two carboxylic acids
Reactions of Anhydrides
38
Acid Anhydride Reactions
With Alcohols
• Acid anhydride reacts with alcohol to
produce:
– Ester
– Carboxylic acid
O O
CH3CH2OH + H3C O CH3 ????

Amides
• Amides are formed in a reaction between a
carboxylic acid derivative and an amine or
ammonia
• The amide bond is the bond formed between:
– Carbonyl group from the carboxylic acid
– Amino group from the amine or ammonia
Physical Properties of Amides
• Most amides are solids at
room temperature due to
internal hydrogen bonding
• They are not bases
• Strong intermolecular
hydrogen bonding between
the N-H bond of one amide
and the C=O bond of
another
• Very high boiling points
• Simple amides are quite
soluble in water
Amide Nomenclature
• Names are derived from the carboxylic acid
• Remove –oic acid and replace with –amide
• Nitrogen substituents are prefixed to the
name and indicated by N-
42
Preparation of Amides
• 1o and 2o amines react with acid chlorides and
acid anhydrides to produce amides
• Two molar equivalents of the nitrogen source are
required in these reactions
• These reactions are acyl group transfers
A Preview of Amino Acids, Proteins,
and Protein Synthesis
 A protein is a polymer of amino acids linked by the
amide bonds
 As the amino group and the carboxyl group link,
water is lost
Summary of Reactions
Learning check
Give the IUPAC names of the following compounds
Learning check
An ester is formed by reacting an alcohol with a carboxylic acid.
Draw the structural formula of the following ester molecule and
give the name of the alcohol and the carboxylic acid that form the
ester.
a) Methyl ethanoate
a) Ethyl methanoate
Four credits
(Lectures 43-45)
Amines
• Amines are derivatives of ammonia
• Most important type of organic base found in
nature
• Consider as if substituted ammonia:
– R can be either aliphatic or aromatic
Comparison of NH3 to Amines
• Amines have a trigonal pyramidal structure
Classification of Amines
Physical Properties
• Amines form hydrogen bonds but not as strongly
as alcohols
– Nitrogen is less electronegative than oxygen
• Tertiary amines cannot hydrogen bond to each
other
Amine Boiling Points
• Amines have boiling points between alkanes and alcohols
• Tertiary amines boil lower than 1o or 2o of similar MW

Boiling Point Example
Which molecule in each pair will have
the higher boiling point?
• Methanol or Methylamine
• Dimethylamine or Water
• Methylamine or Ethylamine
• Propylamine or Butane
Solubility
• All amines can form
hydrogen bonds with
water
• Amines up to 6 carbons
long are water soluble
due to this hydrogen
bonding
• Water solubility
decreases as the length
of the hydrocarbon
portion of the molecule
increases
Nomenclature of Amines
Amines can be named in different ways:
a) Primary amines are named as alkanamine as follow:
1. Find the parent compound - Longest continuous
carbon chain containing the amine group
2. Dropping the final –e of the parent name and
adding the suffix –amine
3. Number the parent chain to give the amine carbon
the lowest possible number
4. Name and number all substituents as usual
b) Common name of amines
• Name the alkyl groups attached to the N in
alphabetical order
• Add –amine
• The name is continuous, no spaces between
groups
C) In the IUPAC system, the amino group, -NH2, is named as a
substituent, as in the following examples:

Amino groups as substituents
Amino groups rank below OH groups and higher oxidation states

of carbon, in such cases name the amino group as a substituent.
12
Aromatic & Heterocyclic Amines
• Heterocyclic amines are:
– Cyclic compounds
– Have at least one N in the ring
– MANY are physiologically active and many are critical in
biochemistry
Medically Important Amines:
Decongestants and Sulfa Drugs
• Decongestants
shrink the
membranes lining
the nasal passages
• Sulfa drugs (first

chemicals used to
fight infections) are
also made from
amines
General Knowledge
Amines as Bases
• Amines are weak bases
• They accept H+ when dissolved in water
– Lone pair electrons of nitrogen can be shared with a
proton from water
– An alkylammonium ion is produced
– Hydroxide ions are also formed, making solutions basic

An Example of an Amine in Water
• Example of the basicity of amines:

• Amines form salts by accepting a proton from
strong mineral acids
Alkylammonium Salts
• Name amine salts by replacing the suffix –
amine with ammonium
• Add the name of the anion
• Converting amines to salts often makes
insoluble amines soluble as the salts are
ionic
Preparation of Amines
1) Reduction of nitro compounds:
Aromatic nitro compounds, i.e.
N O2 NH2
3 H 2, N i
+ 2 H 2O
or
1 ) S n C l2 , H C l
2 ) N a O H , H 2O
2) Reduction of amides:
O
1 ) L iA lH 4 , e th e r
N H2
2 ) H 3O + N H2
Works for 2° and 3 amides as well.

3) Reduction of nitriles:
1 ) L iA lH 4 , e t h e r
N
2 ) H 3O + N H2
or
H 2, N i
N
N H2
Reactions: Addition of Amines
➢ Amines react with the carbonyl group of
aldehydes and ketones in the presence of an acid
catalyst to give products that contain a carbon–
nitrogen double bond:
O H2N
H N
C + + H2O
CH3 H C
CH3 H
an Imine
(a Schiff base)
Summary of Functional Groups
Summary of Functional Groups
Name the functional group in each of the following
molecules.
NH2 O O
What are the functional groups found
+ in Cthese
C
CH3 O CH3
molecules? HO
p-hydroxyaniline
acetic anhydride
O
NHCCH 3
HO
acetaminophen
Artificial Sweetener (TYLENOL®)
Atorvastatin
(Lipitor)

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Chemistry for Health Sciences

CHEMISTRY food science

medical practitioners forensic sciences

• Study the chemical and physical properties of

• Study the chemical and physical changes that

• Study energy changes (gains or loses) as matter

• Matter - anything that has mass and occupies space

2. Liquid - particles closer together,

3. Solid - particles are very close together,

• Pure substance - a substance that has only one

• Homogeneous - uniform composition, particles well

• Heterogeneous – nonuniform composition, random

• Physical property - is observed without

Copyright © 2017 McGraw-Hill Education. Permission required for reproduction or display

(a) Solid (b) Liquid (c) Gas

Magnetic iron is separated from other nonmagnetic

• Chemical property - results in a change in

hydrogen + oxygen → water

a. Boiling water becomes steam (Physical change)

b. Butter turns rancid (Chemical change)

c. Burning of wood (Chemical change)

d. Snow melting (Physical change)

e. Decay of leaves in winter (Chemical change)

Quantity Unit Symbol

-Derived units : All other units are derived from the

Copyright © 2017 McGraw-Hill Education. Permission required for reproduction or display

6200 = 6.20  103

• The exponent x is a negative number equal to

0.0062 = 6.2  10–3

0.0047 kg x 103 g x 1 mg = 4.7 x 103 mg

Answer 1.4 x102 mm

Answer 5.00 x 10-5 kg

Daniel Gabriel Fahrenheit Anders Celsius Lord Kelvin

Use the expression:

• Calculate the mass in grams of 10.0 mL if

• Atom - the basic structural unit of an element

• Atoms consist of three primary particles

proton − positive charge

Name Charge Mass(amu) Mass (kg)

• Atomic number (Z) - the number of

Calculate the number of protons, neutrons

Hydrogen Deuterium Tritium

• What is the atomic mass of Neon?

• Dmitri Mendeleev and Lothar Meyer -

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• How many electrons can be in the n = 3

• Compare the formula with periodic table…..

4 4s, 4p, 4d, 4f

• Each p has a dumbbell shape, differing

• How many electrons can be in the 4d

• Aufbau Principle (building up principle) –

• Hund’s Rule – each orbital in a subshell is

• Electrons fill orbitals from the

– The p sublevel has three orbitals. The electrons

– The d sublevel has five orbitals. The electrons will

90 91 92 93 94 95 96 97 98 99 100 101 102 103

– Elements on the right side of the table move “forward”

• Atoms will gain, lose or share electrons in

• Anion - negatively charged

• Give the charge of the • Which of the

• Many atomic properties correlate with

• The size of an element decreases from left

This attractive force overcomes the repulsion of the