CHEM1100 - Module 1 - SEM2 - 2019 - Combined Student Notes 1pp - 2.pd PDF

Welcome!
CHEM1100 Chemistry 1 - Module 1

Your CHEM1100 Lecturers
Module 1 Module 2 Module 3
A/Prof. Jack Clegg A/Prof. Idriss Blakey Prof. Gary Schenk

(Course Coordinator)
Email: CHEM1100@scmb.uq.edu.au
Course Activities

UQ2U Blended Structure
Each lecture (L) session will be delivered with embedded links to online learning
resources – use these to be successful in learning!
Lecturer Explanation In-class discussion Thinking/Problem- Self-study

solving
Lecture notes are incomplete – you need to take notes and supplement the information
using the online content and your textbook.
Laboratory Practicals
You must attend your safety induction in Week 1 (this week) before you can begin experiments.
For Experiment 1 in week 3 you will need:
Your own Your own lab

safety glasses coat
You will also need to come to lab with your hair tied up and wearing closed in shoes.
CHEM1100 Course Assessment

Course Assessment Hurdles
Read the Electronic Course Profile

(ECP) …
In order to pass this course, you must meet ALL of the following requirements:
1. You must achieve an overall course mark of 50% or higher; and
2. You must obtain a weighted average mark of 40% or more across the two examination components; and
3. You must obtain a weighted average mark of 40% or more across all other non-examination course assessment items
and learning tasks; and
4. You must complete 100% of the laboratory component of the course (both the Experiments and the Report).
You cannot obtain a grade of more than 2:
1. If you obtain a weighted average mark of 30% or less across the two examination components.
2. If you obtain a weighted average mark of 30% or less on the non-examination course assessment items and learning
tasks

Sapling Account
Sapling is the online quiz system that you will use to complete Step 3 in each Online
Chemistry Learning Module (OCL) … it will help you master concepts in chemistry!
IMPORTANT: You must register for your account using the link
provided in the CHEM1100 Bb Assessment Folder.
Your UQ Student email address only should be used
Enter your student ID number as your ID (4xxxxxxx i.e. not s4xxxxxx).
If you enter an incorrect ID, you can edit your profile once registered.
If this UQ information is not provided you will receive zero for this
assessment item.
Your lab team will assist you to
register in the lab induction!
Textbook
Chemistry 4e
Blackman, Bottle, Schmid,
Mocerino and Wille.
John Wiley. 2018
4th Edition
It will be assumed in every lecture that you
have pre-read relevant sections in the
textbook in preparation
Yes, you can use the 1st – 3rd Editions

But you will need to work out relevant
page numbers
If SchoolLocker does not stock the digital

edition you can buy it online ($75)
https://www.wileydirect.com.au/buy/chemistry-4th-edition/

Blackboard (Bb) is the centre of our CHEM1100 universe!
Every Monday a course Bb
announcement will summarise
the weeks activities/deadlines
An email will not be sent every

time new information is
added.
LET’S TAKE A LOOK!!
You must check Bb regularly.

Chemistry PASS
(Peer Assisted Study Sessions)
f2f PASS
Bb-PASS iPASS
f2f PASS (face-to-face PASS) is a one
Chemistry Bb-PASS is the Bb iPASS are interactive online
hour session of mentored group
presence of PASS to support support sessions.
study led by 2nd and 3rd year
you as you work
independently on chemistry
students, where you are able to: Using Adobe Connect, an
practice problems. This is • Work on PASS practice problems. iPASS leader can guide you
where you can find: • Clarify concepts not fully through collaborative study
• PASS practice problem understood. exercises with the use of a
worksheets. • Revise your own learning. document camera, “share
• Answers (pdf & videos) to • Identify gaps in your own document options” in Adobe
PASS practice problems. knowledge. connect, as well as web
• f2f PASS and iPASS • Practice learning in the language cameras and microphones.
timetable. of chemistry. iPASS is scheduled in the
• Blackboard groups to sign • Be part of an interactive learning evenings to serve students
on. community! who cannot attend f2f PASS.
• Study resources and links.
scmb
School of Chemistry and Molecular Biosciences
Podium Consultation sessions
• Chemistry Podium = veranda area on 3rd floor of the Chemistry building
(Bld 68). It is open to all students as a study/lunch space.
• Lecturers from each module will be available to answer any questions
about CHEM1100 on the Chemistry Podium.
• Days & times will be advertised in the weekly Bb email announcement
each Monday.

UQ Student Services – Non-Academic Help
There are many services for helping students on campus with non-
academic problems
• UQ Union: SHOC (student help on campus): part-time jobs, tax, disputing

grades, gender/sexuality, harassment/discrimination, legal issues, …
• UQ student services: financial, international students, disability, scholarships,
careers, …
• Ally program
• and more !
http://www.uq.edu.au/student-services/
Clubs and societies: connect with other students

Student Services help videos.
Student Services produce a weekly video to help you navigate the first semester. You
can find these at:
• Cloudstor:
You can find shorter grabs for social media as well as the digital screen versions (no
sound, same as above).
• YouTube:
• O-Week: Getting Started
• Week 1: Get Set
• Week 2: Go
• Week 3: Assignment Tips
• Week 4: Census Date

Preparing for CHEM1100
 Complete the UQ online module ’Successful (Blended) Learning’
 Watch our chemistry orientation video on Edge or Bb
 Check the list of prior chemistry knowledge that we assume you have (Bb)
 Check that you have the required maths skills
If you are not confident, we provide “Maths in Chemistry” resources
on Bb, you can also find help in Maths ‘Drop In’ Centre.
 Read the ECP and note assessment hurdles
 Register for Edge and Sapling

Chemistry preliminaries
We assume that you know what an atom is …
• A discrete chemical species comprising a positively charged nucleus surrounded
by one or more negatively charged electrons. A nucleus typically consists of
neutral neutrons and positively charged protons. An atom is always charge
neutral.
• A molecule is a chemical species in which a group of atoms possess definite
structure held together by bonds.
• An ion is a chemical species with a positive or negative charge.
• A particle can be any of: subatomic particle, a single atom, a cluster of atoms, a
molecule, or a cluster of molecules.

Subatomic particles
Particle Symbol Charge (C) Mass (kg)
electron e- -1.6022 x 10-19 9.1094 x 10-31
proton p +1.6022 x 10-19 1.6726 x 10-27
neutron n 0 1.6749 x 10-27
1 amu = atomic mass unit

= exactly 1/12 the mass of 1 atom of carbon 12 (12C)
= 1.660 538 ⨉ 10-27 kg

Atomic symbols
• Z is the atomic number (the number of protons in the nucleus) – this defines the
element. Z is also equal to the number of electrons in a neutral atom.
• A is the mass number (the sum of the protons and neutrons) – atoms of a given element
with different mass numbers are called isotopes. The masses given in the periodic table
are averages from natural isotopic abundances.
• X is the atomic symbol of the element (i.e. from the periodic table, H for Hydrogen etc.
• n is the charge on the atom (i.e. the difference between the number of electrons and the
number of protons in an atom) – a neutral atom has no charge.
From memory … write down the atomic symbol for the element sodium

Atomic mass

Which element has 16 neutrons?
A. Oxygen
B. Sulfur
C. Titanium
D. Cadmium

Calculate the molar mass of CaCO3

Why we really do chemistry
• https://www.youtube.com/watch?v=2pXyJ7P0B0k
• https://www.youtube.com/watch?v=9k_NmB3_pMg

L2
Atomic Structure
Learning Checklist:
 Understand the relationship between Schrodingers wave functions and orbitals
 Define and describe Quantum numbers n, l and m
 Describe general features of atomic orbitals and recognise and draw different representations (including graphical)
 Recognise shapes and orientations of s, p and d orbitals

What did the ancient Greeks know?
Leucippus and Democritus (about 490 BC) introduced the idea that matter is made up of
atoms, which are indivisible - the joint founders of atomic theory. Leucippus stated that
atoms are:- imperceptible, individual particles that differ only in shape and position.

What do we know? ….. matter is made of atoms and/or ions
https://www.youtube.com/watch?v=Ftw7a5ccubs
We can visualise atoms and groups of atoms experimentally!
The surface of a single grain of An oxygen atom on a
table salt gallium arsenide surface
Scanning tunnelling microscope (STM)

image showing an array of ring-shaped
benzene molecules
How do we describe atoms?
Max Planck Niels Bohr Albert Einstein Lise Meitner
Werner Heisenberg Louis De Broglie Erwin Schrödinger Marie Curie

Energy
E = hν frequency
Planck’s constant
high energy low energy
CHEM1100 Chemistry 1 - Module 1 Blackman p168

Light as waves
c=νλ
E = hν
CHEM1100 Chemistry 1 - Module 1 Blackman p166-7

Light as a Particle – The photoelectric effect
E = hν

Electromagnetic radiation (light) exhibits wave properties and particulate properties
How can the same thing be described two different ways?

How can the same thing be described two different ways?
Reality depends on how you look at (measure) it.

Light has wave like properties
c c = velocity of light (3 x 108 m s-1)

v= ν = frequency (s-1)
λ λ = wavelength (m)
Light has particle like properties – “quanta”

E = hν
h = Planck’s constant = 6.626 x 10-34 Js
A quantum of energy = hν;

in atoms and molecules, Energy is given out (or accepted) in whole number
packets

Calculate the energy of a photon of red light with a wavelength
of 655 nm?

The energy levels of atoms and molecules are quantised. Light is
absorbed or emitted when the energy of the light (hν) exactly
matches the difference in an atom or molecule’s energy levels (∆E).
∆E =hv
Energy is quantised

The energy levels of the H atom are given by the Rydberg
formula
−R
En = 2
n
R is called the Rydberg
constant
= 2.179 872 171 x 10-18 J
n is the “principal” quantum

number
R is the most accurately determined

physical constant that exists.
http://physics.nist.gov/
The difference between two energy levels n1 and n2 is
1 1
∆En →n = − R(
En − En = 2
− 2
)
1 2 1 2
n1 n2
emission spectrum of the H atom

What is the energy of the n=3 → n=2 transition in H?
What wavelength of light does this correspond to?

What is the wavelength of light that is emitted when an excited
electron in the hydrogen atom falls from the n = 5 level to the
n = 2 level?
A. 5.12 × 10-7 m
B. 4.34 × 10-7 m
C. 6.50 × 10-7 m
D. 5.82 × 10-7 m
E. 3.04 × 10-7 m

If an excited electron in the hydrogen atom falls from the n = 5 level to the n =
3 level, which statement regarding the emitted photon is CORRECT?
A. The photon will be the same wavelength as the previous question because the starting n level
determines the wavelength of the emitted photon.
B. The photon would be a longer wavelength photon than the previous question because it will
be a higher energy photon.
C. The photon would be a longer wavelength photon than the previous question because it will
be a lower energy photon.
D. The photon would be a shorter wavelength photon than the previous question because it will
be a higher energy photon.
E. The photon would be a shorter wavelength photon than the previous question because it will
be a lower energy photon.

Dual nature of Light
The de Broglie equation
ℎ
𝜆𝜆 = λ = Wavelength
𝑚𝑚𝑢𝑢 m = Mass
u = velocity
h = Planck’s constant
It is possible to calculate the wavelength of a particle!

Calculate the wavelengths of:
a) an electron travelling at 1.00 x 105 ms-1
b) a table tennis ball with a mass of 11 g travelling at 2.5 ms-1

Heisenberg: we can never know both the momentum and position of an
electron in an atom - a fundamental limitation to just how precisely we can
know both the position and momentum of a particle at a given time
What does this mean?
It means we cannot be precise about position, momentum, energy, time.

We need to speak (mathematically) in terms of PROBABILITY.

WERNER HEISENBERG (1901 - 1976)
h
∆x ⋅ ∆p ≥
4π

For a summary of the really important concepts this week you need to
understand about waves and particles see WYKTK sheet:-
What you need to understand: waves and particles
on the CHEM1100 Blackboard page (learn.uq.edu.au)

L3
Quantum Numbers
Learning Checklist:
 Explain fundamental ideas of matter, energy and light (wave and particle)
 Understand that energy is quantised and its relationship to the atom/molecule (n -principal quantum number)
 Apply formulas to interconvert between energy, wavelength and frequency and determine the difference between
two energy levels.
 Apply the de Broglie equation solve numeric problems
 Explain the Heisenberg principle and its implications (probability)

Schrödinger derived a set of equations or wave functions for electrons:
1. Electrons confined in their orbits would set up standing waves.
2. The square of the wavefunctions gives the orbitals, which can be thought
of as probability clouds.
3. The densest area of the cloud is where there is the greatest probability of
finding the electron.
4. The least dense area is where you have the lowest probability of finding
the electron.
the wavefunction
The “Schrödinger Equation”

or “wave equation”

Only certain solutions to the wave equation exist (watch video )
Classically you can think about it in terms of “boundary conditions” or fitting

a de Broglie wave in an atomic orbit – only certain orbits are possible.
Destructive interference would result in cancellation of the wave.
For the H atom, the solutions to the wave equation are of the form:
Ψn, l, m l
An atom requires three integral numbers to fix the energy levels and probabilities.
n, l and m are the QUANTUM NUMBERS

The wave function ψ of each electron can be described as a set of three
quantum numbers:
1. Principal number (n) describes the energy level or distance from the
nucleus.
2. Angular momentum quantum number (l) indicates how fast the electron
moves in its orbit (angular momentum called “azimuthal” in Textbook)
• related to the shape of the orbital.
3. Magnetic (ml) describes its orientation in space.
Ψn, l, m l

Principal quantum number (n)
• n has integral values:
1, 2, 3, 4, 5, 6, ……….∞
• The principal quantum number is related to the size and energy of the
orbital
• As n increases, the orbital becomes larger and the electron spends
more time farther from the nucleus
• An increase in n also means higher energy, because the electron is less
tightly bound to the nucleus

Angular momentum quantum number (l)
• Has integral values from
0, 1, 2, 3, 4, ………… (n-1) for each value of n
• Related to the shape of atomic orbitals
Angular (azimuthal) momentum quantum numbers and corresponding letters used to
designate ATOMIC ORBITALS
l 0 1 2 3 4
Letter s p d f g
used
s (sharp) - spherical
p (principal) - dumb-bell shaped
d (diffuse) - clover-leaf shapes
f (fundamental) - more complicated shapes
Magnetic quantum number (ml)
• Has integral values between
-l and +l including 0
e.g. for l = 3, ml = -3, -2, -1, 0, 1, 2, 3
• The value of ml is related to the orientation of the orbital in space relative to

the other orbitals.

n l Orbital ml No. of
designation orbitals
1 0 1s 0 1
2 0 2s 0 1
1 2p -1,0,+1 3
3 0 3s 0 1
1 3p -1,0,+1 3
2 3d -2,-1,0,+1,+2 5
4 0 4s 0 1
1 4p -1,0,+1 3
2 4d -2,-1,0,+1,+2 5
3 4f -3,-2,-1,0,+1,+2,+3 7
Which set of quantum numbers could correctly
describe a 3d electron in scandium?
A. n = 2, l = 1, ml = 1
B. n = 3, l = 2, ml = -2
C. n = 3, l = 3, ml = 2
D. n = 3, l = 3, ml = 3
E. n = 3, l = 2, ml = 4

How many valid sets of quantum numbers exist for 4d orbitals?
Give two examples.

For a summary of the really important concepts you need to understand about
quantum numbers see the sheet:
What you need to understand: quantum numbers
On the CHEM1100 Blackboard page (learn.uq.edu.au)

Atomic Orbitals
• derived using the mathematical tools of quantum mechanics,
• representation of the three-dimensional volume (i.e., the region in space) in which an
electron is most likely to be found
• CANNOT be observed experimentally (electron density can, however, be observed
experimentally)
• not possible to determine the exact location of an electron in an atom, but
• the probability of finding an electron at a given position can be calculated
• the higher the probability of finding an electron at a given position, the larger the electron
density at that position
probability is
represented by

Representations of orbitals
a) the electron density plot
b) electron density picture
c) electron contour diagram

(a boundary surface encompassing 90% of the
probability of finding the electron)

Consider the hydrogen atomic orbitals – the s, p and d hydrogen atomic
orbitals
Hydrogen s orbitals

90% boundary surfaces of the 1s, 2s and 3s orbitals

Hydrogen 2p orbitals
• 3 degenerate (of equal energy) orbitals
• designated px, py, pz
blue +
pink -

Hydrogen 3d orbitals
• 5 degenerate (of equal energy) orbitals
• designated dxy, dxz, dyz, dz2, dx2-y2
blue +
pink -

Hydrogen 4f orbitals
7 degenerate (of equal energy) orbitals. (signs not shown)

L4
Atomic orbital electron distributions
and energies
Learning Checklist:
 Explain the relationship between shielding and penetration and how this changes the energy relationships between
orbitals (non-degenerate)
 Understand the effects of electrons on one another
 Define electron spin quantum number (ms)
 Define the Pauli Exclusion Principle
 Represent elements using Orbital Diagrams and Electron Configurations and understand the information they contain
 Define Hund’s Rule
 Apply the Aufbau principle when writing electron configurations

Hydrogen atomic orbitals
• the energy of a particular orbital is determined by its
value of n
• Thus, for hydrogen, all orbitals with the same value of n
have the same energy - they are degenerate

What about Non-Hydrogen atomic orbitals?
C atom: 6 electrons
a many electron atom:
1s2 2s2 2p2
• What do the 2p2 electrons “feel”?

OR
• What happens as we add more electrons to the orbitals and more protons
to the nucleus?

Many electron occupancy of Atomic Orbitals
H HC
Not the full story, we also have to take “shielding” into account.
Shielding and penetration
• In atoms with >1 electron, shielding and penetration have an effect on the overall energy
relationships between the orbitals
• For atoms other than hydrogen (>1 electron), the orbital energy relationship is different

What effects do electrons have on one another?
• Electrostatic attraction between the nucleus and an electron
• Electrostatic repulsion between electrons
As a free electron approaches the He+ cation,

it is attracted to the +2 charge on the nucleus
but repelled by the -1 charge from the 1s
electron

Shielding
• The partial cancellation of the electrostatic attraction between the
nucleus and an electron within an atom, caused by one or more
electrons of lower principal quantum number
The outer electrons

feel a reduced nuclear
charge (called Zeff)

Shielding
• Consider now an atom containing two electrons, with one in the 2s orbital
and one in the 2p orbital.
• We can rationalise the regions of space occupied by these two electrons if we look at
the electron densities.
Consider the hydrogen atomic orbitals – the s, p and d hydrogen atomic
orbitals
Hydrogen s orbitals

Penetration
• The presence of the radial node in the 2s orbital means that there is a
region of space relatively close to the nucleus in which the 2s electron is
likely to be found.
• An electron in a 2s orbital will spend more time nearer to the nucleus

than an electron in a 2p orbital.
• This is described as penetration.
• The 2s orbital penetrates more than the 2p orbital.

Shielding
• In the hydrogen atom (one electron) the energy is identical whether the
electron is in the 2s or 2p orbital.
• An e- in the 2s orbital penetrates more than the 2p orbital.
• The 2s orbital has some probability that is closer to the nucleus than the 2p
orbital.
An e- experiences a greater
nuclear charge in the
2s orbital.
• The 2s orbital also sheilds the
2p e- from the nuclear charge.

Orbital penetration
Electron density
3s orbitals are more penetrating and they shield the 3p orbitals

3p orbitals are more penetrating and they shield the 3d orbitals
Very important consequence of the effects of shielding and
penetration
For one electron systems For atoms other than one

e.g. hydrogen electron systems

Electron Spin quantum number (ms)
• S.A. Goudsmit and George Uhlenbeck

discovered that electrons have “spin”
• A fourth quantum number was required to
account for details of the spectra of atoms

A beam of neutral Ag atoms deflected in an inhomogeneous

magnetic field: The Stern – Gerlach experiment

• Electron spin quantum number (ms)
has a value of +½ or -½
• So...
ms = +½ or ms = -½
spin up spin down

Using all these thoughts we can now put electrons and orbitals together:
Why not:

Quantum numbers
An electron in an atom is described by 4 quantum numbers
Ψ𝑛𝑛,𝑙𝑙,𝑚𝑚 𝑙𝑙 ,𝑚𝑚 𝑠𝑠
The Pauli Exclusion Principle
In any given atom no two electrons can have
the same set of four quantum numbers

Quantum numbers
So, the correct electron configuration for Helium is:
1s 2s 2p 3s
The next element is lithium

1s 2s 2p 3s
Writing this:
Includes all this 2s1

Information:
1s2

Writing this:
1s 2s 2p 3s
2s2
Includes all this
Information:
1s2

In a single atom, what is the maximum number of electrons that
can be described by the quantum numbers: n = 3, l = 3, ml = 1 ?
A. 0
B. 2
C. 6
D. 10
E. 14

Lecture 3 practice problem REVISITED …
How many valid sets of quantum numbers

exist for 4d orbitals? Give two examples.

Why is C:
And not?:
Hund’s Rule
The lowest energy configuration for an atom is the one having the maximum number of
unpaired electrons allowed by the Pauli principle in a particular set of degenerate orbitals.
CHEM1100 Chemistry 1 - Module 1 Blackman p149 - 152
The Aufbau Principle
The Aufbau Principle allows us to write

electron configurations.
“The most stable arrangement of

electrons in an atom results from
placing each successive electron in the
most stable (lowest energy) available
atomic orbital”

The Aufbau Principle
e.g. element As (Z = 33)
1s2 2s2 2p6 3s2 3p6 4s2 3d10 4p3

H 1s1
He 1s2
Li 1s22s1 or [He]2s1 Notice the short-hand abbreviation
Be 1s22s2 or [He]2s2 using noble gas configurations
B 1s22s22p1 or [He]2s22p1
C 1s22s22p2 or [He]2s22p2
N 1s22s22p3 or [He]2s22p3
O 1s22s22p4 or [He]2s22p4
F 1s22s22p5 or [He]2s22p5
Ne 1s22s22p6 or [He]2s22p6
Na 1s22s22p63s1 or [Ne]3s1
Mg 1s22s22p63s2 or [Ne]3s2
Al 1s22s22p63s23p1 or [Ne]3s23p1
Si 1s22s22p63s23p2 or [Ne]3s23p2
P 1s22s22p63s23p3 or [Ne]3s23p3
S 1s22s22p63s23p4 or [Ne]3s23p4
Cl 1s22s22p63s23p5 or [Ne]3s23p5
Ar 1s22s22p63s23p6 or [Ne]3s23p6
What is the electronic configuration of Scandium (21)?
1s2 2s2 2p6 3s2 3p6 3d1 4s2
[Ar] 3d1 4s2

Which of the following statements about quantum
theory is incorrect?
(A) The exact energy and exact position of an electron cannot be determined
simultaneously.
(B) In the Aufbau process, lower energy orbitals are filled before higher energy orbitals.
(C) When filling orbitals of equal energy in the Aufbau process, two electrons will occupy
the same orbital before electrons are placed in a new orbital.
(D) No two electrons can have the same four quantum numbers.
(E) Electrons have both wave- and particle-like properties.

S2 MidSemester Exam 2015

For a summary of the really important concepts you need to understand about shielding,
penetration, the Aufbau principle, electronic configurations, and valence electrons see
the sheet:
What you need to understand: orbital shielding and penetration

L5
Lewis Structures & Bonding
Learning Checklist:
 Identify valence electrons for each atom
 Explain the difference between covalent, polar covalent and ionic bonding
 Understand how electronegativity effects bond polarity and determines the type of bond formed
 Draw Lewis dot structures using the modelled method
 Understand and explain the octet rule, know the exceptions for sulfur and phosphorus

Consider the element fluorine
• When two F atoms form an F2 molecule, the outermost VALENCE ELECTRONS

form the chemical bond
• 2s2 2p5 electrons (7 valence electrons)
• The VALENCE ELECTRONS are those in the outermost shell (the highest
principal quantum number level)
For more information see: http://www.cem.msu.edu/~reusch/VirtualText/intro2.htm

Valence electrons
1s2 2s2 2p5
Fluorine (F) valence electrons 2s2 2p5
1s2 2s2 2p6 3s2 3p6 4s2 3d10 4p3
Arsenic (As) valence electrons 4s2 4p3

Chemical bonding
Covalent bonding
• Occurs when electrons are shared by nuclei – “an overlap of atomic
orbitals”
Polar covalent bonds

• Intermediate cases
• A type of covalent bond where electrons are shared unequally between
atoms
Ionic bonding
• Occurs when an atom that loses electrons relatively easily reacts with an
atom that has a high affinity for electrons – “an electrostatic attraction”

Interactions between 2 atoms: a chemical bond
• Consider two H atoms that approach each other – a balance of attractive
and repulsive forces are experienced by the electrons positioned between
the two atoms
• There is a particular separation distance at which the balance of forces is

minimised – this is the bond length (74 pm for two H atoms)

Electronegativity and bond polarity
• the tendency of an atom in a molecule to attract electrons towards itself is
called electronegativity
• if atom a has a significantly greater electronegativity than atom b the

shared electrons will tend to be closer to a than b
• A diatomic molecule will be polar
δ- δ+

Electronegativity MOST
LEAST

Electronegativity – Pauling Scale
Why are hydrocarbons (compounds containing only C and H) non-polar?

Electronegativity and bond polarity

Electronegativity
The difference in the electronegativity of two atoms that are interacting
determines what type of bond will be formed.
ELECTRONEGATIVITY BOND TYPE EXAMPLE
DIFFERENCE
ZERO COVALENT F2 (4.0 - 4.0 = 0)
INTERMEDIATE POLAR δ+ δ- HF (4.0 - 2.1 = 1.9)

COVALENT
LARGE IONIC LiF (4.0 - 1.0 = 3.0)
+ -
The covalent chemical bond
Chemical Bonds
• forces that cause a group of atoms to behave as a unit
• result from a tendency of a system to seek its lowest possible energy
Covalent Bonds
• the localised electron bonding model
• description of the valence electron arrangement
• prediction of geometry
• description of the type of atomic orbitals used by the atoms to share
electrons or accomodate lone pairs

Applying what we have thought about so far, you should be able to ...
1. Write an electron configuration for an element
2. Assign electrons to orbitals and identify valence electrons
3. Predict the electronegativity of an atom in a bond
Write the lowest (ground) energy electron configuration for:
• Oxygen
• Sulfur
• Calcium

Lewis structures – dot formulae
You should have prepared for this activity!
G. N. LEWIS

Draw Lewis structures for a N2 & a CO2 molecule

Lewis structures – the octet rule
• The second row elements (C, N, O and F) should always be
assumed to obey the octet rule.
• The second row elements B and Be often have fewer than eight
electrons around them in their compounds.
• The second row elements never exceed the octet rule, since their
valence orbitals (2s & 2p) can accommodate only 8 electrons.
• Third row and heavier elements often satisfy the octet rule but
can exceed the octet by using their vacant d orbitals.
• When writing a Lewis structure satisfy the octet rule for the atoms
first. If electrons remain after the octet rule has been satisfied,
then place these electrons on the elements having available d
orbitals (elements in period 3 or beyond).
CHEM1100 Chemistry 1 - Module 1 Blackman p 178-180

Lewis Structure of PCl5

Lewis structures – e.g. PCl5
• Count the number of valence electrons
• P = 5, Cl = 7, so total valence
electrons = 5 + (5x7) = 40
• Two electrons in each P-Cl bond

• 5 x 2 = 10 electrons used
• Complete the octets on the Cl atoms

• 30 electrons used to complete the octets.
• 40 electrons used; no electrons remain

Draw the Lewis Structure for SO2

Draw all the possible Lewis structures for SO42- ion

L6
Formal Charge, Resonance
Structures
Learning Checklist:
 Explain and determine the formal charge of a molecule
 Explain the origin of a bond and apply the conventions of how to represent it
 Draw resonance structures by representing these as Lewis dot structures and the relationships between these
model structures the actual structure

Bond representation
Single bonds:
(Hashed) (Wedge)
Bond in plane of page Bond going INTO the page Bond coming OUT OF the page
(away from you) (towards you)
Double bonds: 1 σ and 1 π bond - more about that later
and 2 π bond - more about that later

Triple bonds: 1 σ
Each bond = 2 electrons

Formal charge
• Individual atoms (within a molecule) may possess positive, negative or no

charge.
• The estimate of individual charges of atoms is called FORMAL CHARGE.
e.g. +1, -2, 0 etc
• Formal charge can be used to distinguish between several possible Lewis

structures.
• Generally, the Lewis structure with the smallest formal charges on individual atoms
will be the correct one.
• The concept assumes equal sharing of electrons in each bond.

Formal charge
number of number of e-s

Formal number of e-s
= valence e-s in - - ½ in covalent
charge in lone pairs
neutral atom bonds
Formal charge (P) = 5 – 0 – 10/2 = 0
Formal charge (Cl) = 7 – 6 – 2/2 = 0

Now, this time considering formal charges, draw all the possible
Lewis structures for SO42- ion again.
-1 O
2- 2-
O 0 0 O O 0
S +1 S 0
O O O
-1 -1 O
-1 -1
This isn’t the best This one minimizes the
Lewis structure. Formal Charges further.
Remember: (1) S can break the octet rule, and (2) There will be 6 equivalent resonance
structures.
All six resonance structures

Total valence Draw single No. electrons Complete No. of
electrons bonds remaining octets electrons
HF 1+7=8 H-F 6 H=2

H F
F=8
N2 5+5=10 N-N 8 N N
N=8
NH3 5+3(1)=8 H N H 2 H N H H=2

H H
N=8
H H
CH4 4+4(1)=8 0 H=2
H C H H C H
C=8
H H
F
CF4 4+7(4)=32 24 F F=8
F C F F C F
C=8
F
F

Delocalisation and resonance structures
• Molecules may sometimes be represented by more than one LEWIS

STRUCTURE
• Each structure is called a RESONANCE STRUCTURE
• RESONANCE STRUCTURES are common when multiple bonds are

present

Lewis Structure for the Nitrate (NO3-) ion
O
1. Draw the atoms N
O O
2. Count up the valence electrons

Nitrogen (5) + Oxygen (3 x 6) + 1(anion) = 24 valence electrons
O
3. Draw the bond connectivities
N
O O
4. Count the remaining electrons
(24 – (3 x 2) = 18).
Complete the octets of the atoms
bonded to the centre atom.
5. Place any leftover electrons

(24-24 = 0) on the centre atom
6. The central atom does NOT have an octet

• it has 6 electrons
• Add a multiple bond (first try a double bond) to see if the
central atom can achieve an octet

7. The central atom now has an octet but there are a
number of possible LEWIS structures
• These are RESONANCE STRUCTURES
[Check the formal charges!!]

• The N-O bonds in NO3- are all exactly the same and
shorter than a single bond but longer than a double bond
Important points about resonance
• The actual structure in the NO3- ion is an average of the three resonance
structures (none of which exist in isolation), and the nitrate ion is more
stable than any of the three structures.
• Resonance structures do not imply an interconversion between structures.
• Don’t confuse the resonance arrow ↔ with an equilibrium arrow ⇌
• One resonance structure in isolation is meaningless.
• The weighted average of all resonance structures gives an accurate
representation.

Benzene (C6H6)
• Two (Lewis) resonance structures

• We know that all C-C bond lengths in benzene are equivalent (1.40 Å).
• but typically C-C ≈ 1.55 Å and C=C ≈ 1.33 Å

Benzene (C6H6)
• Neither of the representations of benzene is accurate. The electron
density is delocalised over all C-C bonds (not localised between alternate
pairs of C atoms)
• STAY TUNED: You will learn much more about benzene and related compounds in the
organic chemistry lectures.
Friedrich August Kekulé (1829-1896): German organic chemist
who first describes the correct structure of benzene in 1872.

Resonance
• NOTE: Resonance doesn’t ALWAYS mean that all resonance
hybrids contribute equally ….
Contributes the least: Less contribution from Contributes the most:

more negative charge this resonance hybrid: negative charge on the
on a less negative formal charge most electronegative
electronegative atom, carried by the less atom.
positive formal electronegative atom (N).
charge on the more
electronegative atom,
r(N-N) = 0.145 nm, r(N=N) = 0.125 nm, r(N≡N) 0.110 nm
total formal charge is
the greatest. Average = 0.127 nm
N-N bond distance in N2O is 0.1128 nm

Assuming each resonance form contributes equally, which is
the shortest bond in anthracene?
1. a
b
2. b c e
a d
3. c
4. d
5. e
Resonance forms for anthracene

For a summary of the really important concepts you need to understand about Lewis
structures, formal charge and resonance structures see the sheet:
What you need to understand: Lewis structures

L7
Valence Shell Electron Pair Repulsion
Theory (VSEPR)
Learning Checklist:
 Explain the difference between a bonding electron pair and a lone electron pair
 Explain the difference in the magnitude of repulsion between two lone electron pairs, between a lone electron pair
and a bonding electron pair, and between two bonding electron pairs
 Use VSEPR theory to determine the geometry and shape of a molecule

Molecular Geometry
What dictates the shapes of molecules?
• non-bonded atoms avoid each other through mutual repulsion of their

bonding electrons
• bonding electrons are repelled by lone pair electrons
Valence Shell Electron Pair Repulsion Theory

(VSEPR)

Consider CH4 (Methane) H
The two dimensional Lewis structure H C H

• but the molecule is not planar
H
The three dimensional structure

• The molecules adopts a three dimensional tetrahedral
geometry
• typical tetrahedral bond angle 109.5o
CHEM1100 Chemistry 1 - Module 1 Blackman p. 254-5

Valence Shell Electron Pair Repulsion Theory
Bonding pair of electrons
• the electrons are shared by two nuclei
Lone pairs of electrons

• the electrons must be close to a single nucleus
• they tend to take up more of the space around that
atom

VSEPR: Ammonia (NH3)
• the lone pair is repelled by the bonding

electrons
• distorted tetrahedral geometry
• ∠HNH 107.3o

VSEPR: Water (H2O)
• 2 lone pairs repel the bonding electrons
• bent geometry
• ∠HOH ANGLE 104.5 o

VSEPR: Degrees of repulsion
• For CH4, NH3 and H2O the bond angles follow the series
• HCH > HNH > HOH
The magnitudes of repulsion:

(LONE PAIR/LONE PAIR) > (BONDING PAIR/LONE PAIR) > (BONDING PAIR/BONDING PAIR)
LP-LP > BP-LP > BP-BP
CHEM1100 Chemistry 1 - Module 1 Blackman p. 253

VSEPR: Magnitude of repulsion
CHEM1100 Chemistry 1 - Module 1 Blackman, p255

NUMBER OF MOLECULAR GEOMETRY EXAMPLE
ELECTRON PAIRS
2 LINEAR BeCl2
3 TRIGONAL BF3
PLANAR
4 TETRAHEDRAL CH4
5 TRIGONAL PCl5
BIPYRAMIDAL
6 OCTAHEDRAL SF6

TOTAL No. BONDING ARRANGEMENT MOLECULAR e.g.
ELECTRON ELECTRON OF ELECTRON GEOMETRY
PAIRS PAIRS PAIRS
3 2 BENT O3
4 3 TRIGONAL NH3
PYRAMIDAL
4 2 BENT H2O
5 4 DISTORTED SF4
TETRAHEDRON
("sawhorse")

Taking into account any lone pairs on the central
atom, what is the molecular geometry of chloroform,
CHCl3?
A. Square planar
B. Octahedral
C. Tetrahedral
D. Trigonal Pyramidal
E. Linear

The shape of the molecule NCl3 can be described
as:
(A) Trigonal planar
(B) Tetrahedral
(C) Trigonal pyramidal
(D) Bent
(E) Linear

VSEPR: Multiple lone pairs around a central atom
Where do lone pairs go when there are several possible locations?
• e.g. SF4
• A sulfur atom has 6 valence electrons F
• Fluorine atoms have 7 each F
• Total = 34 electrons S F
F
• Bind the atoms together
• Now each F atom has 8 electrons; S has 10
• All formal charges are zero
• What is the geometry?
• Overall electron geometry for this molecule (including the lone pair) is
trigonal bipyramidal
CHEM1100 Chemistry 1 - Module 1 Blackman, p 256-9
Trigonal bipyramidal geometry
a
Two different types of sites
• "axial" and "equatorial“ e
e
e
• an axial site has three 90° interactions a
• an equatorial site has two 90° interactions and two 120°

interactions
• equatorial sites are thus better for larger groups
• lone pairs occupy equatorial sites

Trigonal bipyramidal electron geometry
• Five sets of electron pairs
 different molecular geometry depending on the number of bonding pairs vs
lone pairs

PhET Molecular Shape Simulation
What shape did you predict the molecules would have in the activity in the Padlet?
Now go to the 3D visualisation of the molecule and check whether you were right!

Trigonal bipyramidal electron geometry
• Five sets of electron pairs
 different molecular geometry depending on the number of bonding pairs vs
lone pairs

Trigonal bipyramidal electron
geometry
Geometry of SF4
• 5 electron pairs
• lone pair on S atom will occupy an equatorial site
• molecular geometry (NOT including lone pairs) is a distorted tetrahedron

or "sawhorse“ (note do not mix up geometries e.g. ‘Seahorse’!)
• In 5-coordinate systems, lone pairs occupy the equatorial positions
preferentially over the axial positions.
Octahedral electron geometry
• Six sets of electron pairs
→ different molecular geometry depending on the number of bonding pairs vs.
lone pairs

F F
Octahedral electron geometry Xe
e.g. XeF4 F F
• Xe has a filled noble gas configuration, 8 valence electrons
• F has 7 valence electrons
• Total = 36 electrons
Bind atoms together
• Xe has 12 electrons
What is the geometry?
• 2 possibilities: lone pairs adjacent or opposite each other
• Lone pair / lone pair repulsion is largest , therefore opposite
 Square planar molecular geometry
CHEM1100 Chemistry 1 - Module 1 Blackman p 260

TOTAL BONDING ARRANGEMENT OF MOLECULAR e.g.
NUMBER OF ELECTRON ELECTRON PAIRS GEOMETRY
ELECTRON PAIRS
PAIRS
5 3 T-SHAPED IF3
5 2 LINEAR I3-
6 5 SQUARE BrF5
PYRAMIDAL
6 4 SQUARE XeF4
PLANAR

Taking into account any lone pairs on the central
atom, what is the molecular geometry of thionyl
chloride, SOCl2?
A. Square planar
B. Octahedral
C. Tetrahedral
D. Trigonal Pyramidal But distorted!
E. Linear

Sulfur Lewis Structures
Sulfur does not appear to obey the octet rule because it can accommodate 10 valence
electrons. e.g. SOCl2
As a third row element, it has d orbitals and can accommodate electrons in these orbitals
at the same energy level as 3s and 3p.

For VSEPR problems see worked example
5.4 on page 184
For a summary of the really important concepts you need to understand

about VSEPR see the sheet:
“What you need to understand: Valence Shell Electron Pair Repulsion

Theory”

How many lone pairs of electrons are there in the anti-ulcer
compound cimetidine?
1. 4
2. 5
3. 6
4. 7
5. 8

The H-Y-H bond angle in the compound depicted above is most likely to
be:
a) Exactly 109.5° X Y X
b) Exactly 120°
c) Approximately 104.5°
d) Approximately 117°
e) Approximately 180°

L8
Hybridisation
Learning Checklist:
 Understand that hybridisation is a bonding theory used to explain the shapes of molecules predicted by VSEPR
 Understand how sp3 hybridisation is used to explain the tetrahedral shape and sp2 hybridisation is used to explain
trigonal planar shape of molecules.
 Analyse bonding in molecules using hybridisation.

In the molecule XeF4, how many pairs of electrons
(bond pairs plus lone pairs) surround Xe, and what is
the molecular geometry?

Hybridisation
A theory to explain how we can get the shapes VSEPR predict from the atomic
orbitals that house our valence electrons. (Blackman p. 196-205)
Experimentally, we know CH4 is

tetrahedral in shape with all C-H
bond lengths equal and HCH angle
of 109.5°
Lewis structure for

methane (CH4)
CHEM1100 Chemistry 1 - Module 1 Blackman Section 5.6 p270-1

Methane (CH4): Hybridisation
• Consider the electron configurations for C & H
Orbital diagram for C
1s 2s 2p
Orbital diagram for H
1s
TWO ISSUES
1. Using the 2s and 2p orbitals on C we will get two types of C-H
bonds
a. those from overlap of a 2p orbital of carbon and a 1s orbital of H, and
b. those from overlap of a 2s orbital of C and a 1s orbital of H
2. The carbon 2p orbitals are mutually perpendicular so we would

expect all bond angles to be 90°
• But this is not the case
• CH4 is tetrahedral!

Either:
• the models we have been using are wrong
or
• carbon adopts a set of atomic orbitals other than
the “native” 2s & 2p orbitals to bond to the H
atoms
• To account for the known structure of CH4 we
assume that the carbon atom has four equivalent
atomic orbitals, arranged tetrahedrally.
• How do we achieve this?

“mixing” atomic orbitals in this way is called “hybridisation”

http://intro.chem.okstate.edu/1515SP01/Lecture/Chapter10/Lec11601.html
CHEM1100 Chemistry 1 - Module 1 Blackman p.271-4

Methane (CH4): sp3 hybridisation
Hybridise (mix): 2s + 2px + 2py + 2pz → 4 new sp3 hybrid orbitals

Hybridisation
Orbitals on the same atom which lie close to one another in energy have
the ability to combine with one another in an additive way forming
what are called HYBRID ORBITALS
http://www.uwosh.edu/faculty_staff/gutow/Orbitals/N/ethylene_VB.shtml

CH4 – a tetrahedral molecule

but
how do the C-H bonds form?

Methane (CH4): The sigma bonds
SIGMA (σ) bond

Sigma bonds
SIGMA (σ) bond - the electron pair is shared in a region in space centered on
a line running between the atoms

Sigma bonds
σ bond formation from two sp3 hybrid orbitals
σ bond formation from two p orbitals

C-H σ BOND
There are 4 C-H σ bonds in CH4

sp2 Hybridisation – explaining planar structures
Hybridise (mix): 2s + 2px + 2py  3 new sp2 hybrid orbitals (sp2 hybridisation)
One p orbital remains unhybridised

sp2 Hybridisation
One p atomic
orbital remains
unhybridised

sp2 Hybridisation

Linking to molecular geometry
What molecular geometry will be observed in a molecule with sp2

hybridisation and bonds around a central atom?
Take a moment to talk to a

neighbour and avoid brain
freeze before we extend ideas!

Ethene (ethylene): sp2 hybridisation
Consider ethene (ethylene; CH2=CH2)
• the structure suggests sp2 hybridisation at each carbon atom

Hybridise (mix):
2s + 2px + 2py
 3 new sp2 hybrid orbitals
4 C-H σ bonds &1 C-C σ bond
One p orbital (2pz) remains

unchanged and is perpendicular to
the plane of the hybrid orbitals
CHEM1100 Chemistry 1 - Module 1 Blackman, p. 280

Ethene (ethylene): the pi (π) bond
pi (π) bond
• results from sharing an electron pair in the space above and below the σ
bond
• the π bond occupies the space above and below a line joining the atoms

Ethene (ethylene): the pi (π) bond
pi (π) bond formation from two p orbitals
Remember σ bond formation from two p orbitals?

H H
C C
H H

How to recognise how an atom is hybridised
Lewis Structure VSEPR Hybridisation
Tetrahedral
Atom must
accommodate Geometry sp 3
4 “things” (either
lone pairs or atoms)
Atom must
accommodate
Trigonal Planar
Geometry
sp2
3 “things” (either
lone pairs or atoms)

sp3 or sp2?
H
H C H O
C C
C
C C H3 C CH3
H
H C
H Acetone
Benzene
H H CH3
H3 C N N N
CH2 C C C C N
Note: Lone pairs not
N N CH3 always drawn in!
C
Cyanazine
Examples of sigma bonds formed without hybrid orbitals

L9
More Hybridisation …
Learning Checklist:
 Understand how sp hybridisation is used to explain the linear shape of molecules.
 Analyse bonding in molecules using hybridisation.

Ethyne (acetylene): sp hybridisation
H C C H
Lewis Structure
Apply what you learnt in the last lectorial and have a

go at explaining the structure of ethyne using hybrid
orbitals …
sp Hybridisation
Hybridise (mix): 2s + 2px  2 new sp hybrid orbitals (sp hybridisation)
Two p orbitals remain unhybridised

sp Hybridisation
Two p atomic
orbitals remain
unhybridised

Ethyne (acetylene): sp hybridisation
Hybridise (mix): 2s + 2px  2 new sp hybrid orbitals (sp hybridisation)
Two p orbitals remain unhybridised (2py & 2pz)

Ethyne (acetylene): the triple bond
H C C H
C-H σ Bond C-C σ Bond C-H σ Bond

sp3 hybridisation (methane) sp2 hybridisation (ethene) sp hybridisation (ethyne)
SIGMA (σ) bond
H H
C C
H C C H
H H

Molecular nitrogen (N2): hybridisation
Hybrid picture of N2
• 1 σ and 2 π bonds = a triple bond
2pz 2pz
2py 2py

Hybridisation
1. Hybridise the central atom only
2. Only use valence shell electrons
3. The number of hybrids formed equals the number of atomic orbitals
used
4. Hybrid orbitals get 1 electron for a σ bond, 2 electrons for a lone pair
5. Any electrons remaining go into unhybridised orbitals (which can form π
bonds)
6. C-C 1 σ bond
C=C 1 σ bond; 1 π bond
C≡C 1 σ bond; 2 π bonds

Hybridisation summary
Hybridisation No. of shape angle Types of Bonding
hybrids bonds
sp3 4 tetrahedral 109.5° 4σ 4 single bonds/lone

pairs (e.g. methane)
sp2 3 trigonal 120° 3 σ + 1π 2 single bonds / lone

planar pairs plus 1 double
bond (consisting of 1σ
and 1π between the
same 2 atoms) (e.g.
ethene)
sp 2 linear 180° 2σ+2π 1 single bond/lone pair plus
1 triple bond (consisting of
1σ and 2π between the
same 2 atoms e.g. ethyne)
OR 2 double bonds (e.g. -
C=C=C-)

sp3 or sp2 or sp
H H CH3
H3 C N N N
CH2 C C C C N O C O
N N CH3
C
Carbon dioxide
H
Cyanazine

Consider the following structure:
H O
H
C C C C C H
H
The number of σ and π bonds found in this molecule are:

a) 9 σ bonds and 4 π bonds
b) 9 σ bonds and 3 π bonds
c) 6 σ bonds and 4 π bonds
d) 6 σ bonds and 3 π bonds
e) 7 σ bonds and 4 π bonds
Past exam question

What have we learned so far?
• Understanding ATOMIC ORBITALS allows us to write the electron
configuration of any atom or ion in its ground state.
• This electron configuration allows us to identify the number of VALENCE
ELECTRONS in an atom.
• Knowing the number of valence electrons and following a few rules allows us
to draw a chemically sensible LEWIS STRUCTURE for a molecule which
accounts for all valence electrons
• VSEPR allows us to predict the SHAPE of this molecule based on the Lewis
Structure.
• The “shape” that a central atom is required to adopt allows us to identify the
HYBRID MOLECULAR ORBITALS that the atom may need to generate to
achieve this shape.

Atomic Electron Valence LEWIS
VSEPR = SHAPE
Configuration Electrons Structure
SHAPE =
HYBRIDISATION
These are great theoretical models that allow us to

make meaning of a lot of what we observe in
chemistry, BUT NOT EVERYTHING so they are not
perfect!

Some practice questions…

CHEM1100 Midsemester exam 2018
Questions A11 and A12 concern the analgesic paracetamol, the structure of which is shown below:
A11. How many lone pairs of electrons are there in the structure of paracetamol?
(A) 1
(B) 2
(C) 3
(D) 4
(E) 5

Questions A11 and A12 concern the analgesic paracetamol, the structure of which is shown below:
A12. What hybridisation would be adopted by each of the oxygen and carbon atoms labelled i, ii
and iii in the structure of paracetamol shown?
(A) i = sp, ii = sp2, iii = sp3
(B) i = sp3, ii = sp2, iii = sp
(C) i = sp3, ii = sp2, iii = sp2
(D) i = sp2, ii = sp3, iii = sp3
(E) i = sp2, ii = sp, iii = sp2

This question concerns the molecule, ethene C2H4.
a) Draw the Lewis structure for ethene.
b) Identify the geometry adopted by both of the carbon atoms in ethene AND the hybridisation
each carbon would adopt to achieve this geometry.

This question concerns the molecule, ethene C2H4.
c) Draw a diagram representing the bonding present in a molecule of ethene, clearly identifying the
sigma (σ) bonds present, any pi (π) bonds present and the positions of the electrons in the molecule.
Label the hybrid and atomic orbitals in your diagram.

Blackman 4th Ed. – Review problem 5.53
Capsaicin is the molecule responsible for the spiciness of chillies.
a) How many π bonds does capsaicin have?
b) Which orbitals are used for bonding by each of the labelled atoms?

Blackman 4th Ed. – Review problem 5.53
Capsaicin is the molecule responsible for the spiciness of chillies.
c) What are the bond angles around each of the labelled atoms?
d) Redraw the structure of capsaicin adding the lone pairs.

L10
Molecular Orbital (MO) Theory
(A new and different theory of bonding)
Learning Checklist:
 Understand that molecular orbitals arise from the combination of atomic orbitals.
 Understand that the in-phase combination of atomic orbitals gives bonding molecular orbitals and that the out-of-
phase combination atomic orbitals gives antibonding molecular orbitals.
 Draw molecular orbital electron diagrams.
 Analyse bonding in molecules using molecular orbital theory.
Blackman Section 5.7 p. 83
OK – Let’s revise the whole thing!!
• Draw the Lewis Structure of:

O2 and N2
Atomic electronic conformation of oxygen:
6 Valence electrons
1s 2s 2px 2py 2pz
Atomic electronic conformation of nitrogen:

5 Valence electrons
1s 2s 2px 2py 2pz

Lewis structure of O2 & N2
Both structures predict that all electrons are paired. This can be
tested experimentally:
• http://www.youtube.com/watch?v=yJs5ENtilIo

diamagnetic paramagnetic

But it isn’t quite that simple…
Lewis structures and VSEPR can’t be used to explain all of the properties of
molecules and so we need a new, more powerful model to explain bonding.
This is known as the “molecular orbital model”.
In this model we consider solutions for the wave equation for the entire
molecule. In other words, electrons are not considered to be localised on their
individual atoms in “atomic orbitals”, but are instead in new “molecular
orbitals” which arise from the overlap of atomic orbitals.

Solutions to the wave equation for the single atom case provide
Atomic Orbitals
Solutions to the wave equation for the molecular case provide

Molecular Orbitals
Molecular orbitals - have similar characteristics to atomic orbitals:-
• maximum of 2 electrons allowed per orbital

• square of the wave function gives the
probability of finding the electron
• Hund’s rule is obeyed

Atomic orbitals display a property called phase.
When orbitals overlap they can do so “in phase” OR “out of phase”.
http://hyperphysics.phy-astr.gsu.edu/hbase/sound/interf.html
The Molecular Orbital Model
Consider the bonding between two H atoms
(HA AND HB)
ATOMIC WAVEFUNCTIONS ΨA AND Ψ B
Wavefunctions can interfere constructively (Ψ HH) – leading to

BONDING MOLECULAR ORBITALS
Ψ HH = Ψ A + Ψ B
OR
destructively (Ψ *HH) – leading to
ANTIBONDING MOLECULAR ORBITALS
Ψ *HH = Ψ A - Ψ B

How do s orbitals form molecular orbitals?
Wavefunctions interfere
destructively σ∗-ANTIBONDING ORBITAL
(Ψ* HH )
Ψ* HH = Ψ A - ΨB
out of phase
Wavefunctions interfere σ-BONDING ORBITAL

constructively
(Ψ HH)
Ψ HH = ΨA + ΨB
in phase

H2 antibonding
HA HB (designated *)
MOs
molecular orbital
higher in energy
than the atomic
orbitals of which it
is composed
bonding
molecular orbital
lower in energy
than the atomic
orbitals of which it
is composed
sigma (σ) molecular orbital: σ bonding, σ* antibonding
CHEM1100 Chemistry 1 - Module 1 Blackman p.284
BOND ORDER
the difference between the number of bonding electrons

and the number of antibonding electrons
number of bonding electrons - number of antibonding electrons

BOND ORDER =
2
BOND ORDER - an indication of bond strength

- the higher the bond order the
stronger the bond

HYDROGEN MOLECULE, H2
Bond order = 2/2 = 1

What if we add an electron? The H2- ion

What about another electron? H22- ion
Can we get
students to
generate this
one by
H1s H1s applying ideas?
bond order = (2-2)/2 = 0

molecule is not stable with respect to the two separate H atoms

What about He2?
bond order = 0
molecule is not stable with respect to the two separate He
atoms
Li2 MOLECULE

σ1s2 < σ 1s*2 < σ 2s
2 < σ 2s*
What Molecular Orbitals do p-orbitals form??
IN PHASE OUT OF PHASE
leads to leads to
bonding orbitals antibonding orbitals

How do p orbitals form molecular orbitals?
“end-on” overlap
“side-on” overlap

- + - +
+ -
- +
+
-
- + -
So what does O2 look like using MO
OA O2 OB
NOTE: Hund's Rule leads

to 2 unpaired electrons =
PARAMAGNETIC
E
N
E
R
G
Y
8−4
Bond order = =2
2

Draw the MO diagram for F2

What about heteronuclear molecules?
NO molecule
• If the atoms involved are N atom σ

σ 2p
2p
**
O atom
close together on the
π𝜋𝜋x** *
𝜋𝜋πyy*
periodic table and so the 2p
x
2p
orbitals are of similar energy
πx π
then the process is similar 𝜋𝜋x 𝜋𝜋yy
to the homonuclear σ
σ2p
2p
Energy
examples: σσ2s**
2s
2s 2s
BOND ORDER =
8 - 3 = 2.5
2 σ
σ2s2s
CHEM1100 Chemistry 1 - Module 1 Blackman 291

Hydrogen Fluoride, HF
• So what if the two atoms are very different?
• Then the energy of the various orbitals are going to be very different. We
need some rules to guide us:
• Orbitals are lower in energy in more electronegative atoms.
• Orbitals with the same designation but in different atoms are lower in
energy if the nuclear charge is larger i.e. the 1s orbital in F is MUCH lower
in energy that the 1s orbital in H.
• MOs can only form between atomic orbitals that are relatively close
together in energy.

Hydrogen Fluoride, HF
HF molecule F atom
H atom
4σ**
4σ
H 1s can interact “end on”

with 2pz (for example) and
1s
form the two MOs. 22ppx 2py
2py
2pz 2px 2py
x
2px and 2py cannot
σ
form π-bonds with
33σ
H1s (wrong
Energy
symmetry) so they
remain “non-
H 1s orbital is not bonding” orbitals
close enough in
energy to interact 2s
2σ
2σ
with the F 2s orbital.

Draw the MO diagram for OH-
Is it paramagnetic or diamagnetic?

S1 Mid Semester MCQ
The bond order of the O2 diatomic molecule in its lowest energy state is:
A. 0
B. 2
C. 4
D. 6
E. 8

WARNING
The text book discusses (at some length) the MO diagrams for B2, C2
and N2.
These examples are complicated by a variation in the order of MOs

that is unique to these examples and not relevant to any other
cases you will come across in the future so we are not going to
cover them!!

The end of Intro to MO Theory
• Now, that was not so bad – was it???
• MO theory is a much more sophisticated approach to explaining the
interaction of orbitals that lead to bond formation in molecules.
• It is a DIFFERENT theory to the VSEPR-Hybridisation theory we learned
previous.
• DO NOT TRY TO MIX THE TWO THEORIES
• They are two theories to explain the phenomenon of chemical bonding
which we do not fully understand.

L11
Alkanes, alkenes, alkynes
Learning Checklist:
 Use different representations for drawing organic molecules.
 Apply naming rules to name simple organic molecules.
 Explain and apply valence and bonding requirements in organic molecules.
 Define, identify, and draw structural isomers.

Organic compounds
• Compounds of carbon
• Carbon can form covalent bonds
with itself and many other
elements, leading to an
enormous variety of molecules
• Central to life (e.g. DNA, proteins)
• Central to our society – food,
fuels, medicines, polymers, dyes,
fibres, wood, paper, modern
materials and coatings
CHEM1100 Chemistry 1 - Module 1 Blackman Chapter 16

Organic chemistry
• Organic chemistry is the basis of molecular biology and biochemistry
• Biological processes all involve reactions of organic compounds
All aspects of life are engineered at the molecular level and

without an understanding of molecules we can only have a
sketchy understanding of life itself. All approaches at the higher
level are suspect until confirmed at the molecular level.
https://www.youtube.com/watch?v=FzcTgrxMzZk

Most organic compounds are complex
NAMES, such as cholesterol or erythromycin, don’t tell us very much. To understand organic
chemistry, we need to understand STRUCTURES – the ways atoms connect to make
molecules. This allows us to predict physical and chemical properties of organic compounds,
and to understand their reactions.

Representing simple molecules

Portraying simple hydrocarbon molecules
Note ‘zig-zag’ representation!

http://preparatorychemistry.com/Bishop_Jmol_alkanes.htm
Naming compounds
• Naming organic compounds (or organic nomenclature) is complicated
and governed by a lot of rules.
THESE ARE COVERED IN THE ON-LINE LEARNING MODULE AVAILABLE ON

THE CHEM1100 BLACKBOARD SITE. YOU MUST COMPLETE THIS MODULE
THIS WEEK!

Valence in organic chemistry
To draw correct structural formulas, we need to know how many bonds each
type of atom can form.
• "Valence" - number of bonds to an atom in a stable, (uncharged) molecule (= “combining
power”).
• The elements relevant to organic chemistry each have one common valence.
• In stable uncharged molecules, the following valences apply for each atom:
C 4 H 1
O 2 N 3
F 1 Cl 1
Br 1 I 1

Valence and bonding requirements
To draw correct structural formulas for neutral molecules, need to know how many bonds
each type of atom can form:
Every C has four bonds
Every N has three bonds

Note: 3D shape of
central atom not
Every O has two bonds shown here
Every H or halogen (Cl, Br

etc ) has one bond
REPRESENTING STRUCTURES
Molecular (= chemical) formulae:
• shows actual numbers of each type of atom per molecule
• e.g. for butane C4H10
• Structural formulae:
• shows how atoms are joined together
• most useful way of representing organic compounds
consider CH3CH2CH2CH3 also represented as CH3(CH2)2CH3
3D structure Line structure

LINE STRUCTURES
Interpretation:
• A carbon at each end and each corner
• Each C has enough hydrogens to give it a total of FOUR bonds
• H’s attached to C not shown explicitly
• H’s attached to other atoms (usually N,O) always shown
• Single bonds are shown as one line; double bonds as two lines; triple
bonds as three lines
• Does not always show actual shape.
• 3D shape important. (more on this later!)

Draw the line structure for the molecule below:

Examples of structural formulae
H3C CH3
C CH Note DOUBLE BOND
H3C 2-methyl-but-2-ene
Cyclic structures (ring of C atoms)

OH
Note OH group attached to C on the
cyclohexane ring
cyclohexanol

Isomers
Isomers are compounds which have:
• same molecular formula, but atoms arranged in different ways (different structures)
(eg: C2H6O, C4H10)
• they are different compounds with different properties

Homework- draw examples of structural formulae
Draw as many possible structures as you can for the molecular formula
C4H10O
Which ones look sensible?

Hydrocarbon family tree

Hydrocarbons: alkanes
• Contain only C & H atoms
• Hydrocarbons with single bonds only:
• ALKANES are “saturated”
• Maximum H’s for the number of carbons
• General formula CnH2n+2
• Homologous series CH4, C2H6, C3H8 etc
Alkanes: sp3 hybridised carbon

Hydrocarbons: alkenes
• Contain one or more C=C double bonds

• General formula CnH2n for a single double bond
• e.g.. CH3-CH=CH2
• Homologous series C2H4, C3H6 etc
• The C=C double bond is planar
Alkenes: sp2 hybridised carbon

Hydrocarbons: alkynes
• Contain one or more C≡C triple bonds

• General formula CnH2n-2 for a single triple bond
• e.g. CH3-C≡CH
• Homologous series C2H2, C3H4 etc
Alkynes: sp hybridised carbon

Hydrocarbons: arenes
ARENES
• Contain one or more benzene-like rings
Alternating
• Also called AROMATIC hydrocarbons double bonds
• Alkenes, alkynes and arenes are all UNSATURATED hydrocarbons
• Benzene reacts differently to alkenes and alkynes

• can be explained by differences in their bonding picture

Hydrocarbons: useful tips
• Helpful to remember how many σ and 𝜋𝜋 electrons
are present in each type of C-C bond or structure:
Alkane ; C-C; 2 σ electrons, 0 𝜋𝜋 electrons

Alkene ; C=C; 2 σ electrons, 2 𝜋𝜋 electrons
Alkyne; C≡C; 2 σ electrons, 4 𝜋𝜋 electrons
Arene; benzene has 6 𝜋𝜋 electrons
Benzene:
sp2 hybridisation for each carbon
& delocalisation of 6 𝜋𝜋 electrons
http://www.chemeddl.org/resources/models360/models.php?pubchem=241
L12
Hybridization and
functional groups & Revision
Learning Checklist:
 Identify and draw different representations of functional groups in organic molecules.
 Explain the hybridisation in different functional groups.
 Explain and apply how we classify carbon atoms and functional groups in organic molecules.

Organic molecules and functional groups
• CARBON SKELETON
• C & H framework with single and/or multiple C-C bonds.
• C-C single bonds relatively unreactive
• FUNCTIONAL GROUPS
• Attached to carbon skeleton are groups of atoms, which determine reactivity
• Reactivity due to
• double/triple bonds
• functional groups (with other types of atoms)
• COMPOUNDS with the same functional groups undergo similar reactions!

Important functional groups containing oxygen atoms

Functional groups priorities when there are more than one
If there are two functional groups in a single molecule (eg alcohol and carboxylic acid) does one have priority?
Functional Group Structure Suffix Prefix

Carboxylic acid -COOH -oic acid carboxy
Carboxylic esters -COOR -oate alkoxycarbonyl
Decreasing Priority
Amides -CONH2 amide amido

Aldehydes -CHO -al formyl
Ketones -CO- -one oxo
Alcohols -OH -ol hydroxy
Amines -NH2 amine amino
Halides* -F, -Cl, -Br, -I fluoro, chloro, -
bromo, iodo
Nitro* -NO2 nitro -
* These functional groups always appear as prefixes

Structural isomers
Draw as many possible KETONE structures as you can for the molecular formula
C5H10O?

Classifying carbon atoms
It is often useful to classify carbon atoms in an organic molecule according to the number of
other carbon atoms that they are bonded to.
• Carbon atoms that are bonded to:
• One other carbon atom are described as primary (1°)
• Two other carbon atoms are described as secondary (2°)
• Three other carbon atoms are described as tertiary (3°)
• Four other carbon atoms are described as quaternary (4°)
C C
C C C C C C C C C C C
C
primary secondary tertiary quaternary
Classifying functional groups
Functional groups can also be classified according to the substitution of the carbon atom to
which they are attached.
• The degree of substitution can affect the chemistry of the functional group.
H 1° C H 2° C CH3 3° C
H3C C OH H3C C OH H3C C Br
H CH3 CH3
primary secondary tertiary

alcohol alcohol alkyl halide
Why don’t we see quaternary alcohols or quartenary alkyl halides?

Amines
• Amines are classified slightly differently to alcohols and alkyl halides. Primary,
secondary, tertiary for amines refers to the number of carbon atoms attached
to the nitrogen.
• If there are four carbon atoms attached to the nitrogen, it must be a
quartenary alkylammonium cation.
primary secondary tertiary quartenary

amine amine amine alkylammonium
cation
Which of the molecules below contain an aldehyde functional
group?
OH
H OH
O
(1) (2) (3)
OH
HO
O (4)
(5)
O
A. Both 2 and 5
B. Only 2
C. Only 5
D. Only 4
E. All of 2,4 and 5

Bonding in organic molecules
Now .... Let’s bring it all together! Od
ACETONE – An Organic Ketone

(you will learn more about these in the organic lectures.) C
a
H3C CH3
b c
a) What is the geometry of the central carbon atom labelled a and the oxygen
atom labelled d?
b) What hybridisation are these atoms likely to adopt to achieve this
geometry?
c) Is the C=O bond a polar bond?
• IF NO – why not? What is your reasoning for this answer?
• IF YES – which atom will have the higher electron density?

Bonding in acetone
- trigonal
sp2
-
δ
δ- O
+
C δδ+
H3C CH
- trigonal
3
sp2

Blackboard activity – Functional groups

DON’T FORGET
IUPAC Nomenclature
• Naming organic compounds (or organic nomenclature) is complicated
and governed by a lot of rules.
THESE ARE COVERED IN THE ON-LINE LEARNING MODULE AVAILABLE ON

THE CHEM1100 BLACKBOARD SITE. YOU MUST COMPLETE THIS MODULE
THIS WEEK!

Chemists entertaining themselves with common names
Putrescine
Traumatic Acid
Nanokid
Penguinone
L12
Module 1 Revision Session

Mid-Semester Exam
20 MCQ – only module 1 content
2 SAQ (Short Answer Questions)
10 minutes perusal
• WHAT TO BRING:
• *** Student card ***
• At least 3 HB or 2B pencils
• A soft, clean eraser
• At least 3 black or blue pens
• A UQ approved calculator (see advice on Bb)
• A watch (not an Apple watch, you will NOT be permitted to use your phone to track time).
Midsemester exam
• WHAT NOT TO BRING
• Notes, books or clean paper of any kind (working
paper will be supplied).
• A mobile phone or any form of electronic device
other than an approved calculator.
• Any sort of alarm or other device that makes noise.

Bringing it all together
In this module we have looked at atomic structure:

• models describing the behaviour of electrons in an atom
• How these electrons are involved in bonding between atoms
We’ve studied different models of bonding between atoms

• Lewis structures
• Valence Shell Electron Pair Repulsion (VSEPR) theory Increasing model
• Valence Bond Theory (hybridisation) complexity
• Molecular Orbital Theory

How many unpaired electrons does a Si atom (atomic number 14)
have in its lowest energy electron configuration?

Which answer correctly corresponds to these orbitals placed in
ascending order of energy in a multi-electron system:
4s, 3p, 2s, 3d, 3s, 2p, 5p
A. 2s, 2p, 3s, 3p, 4s, 3d, 5p

B. 2s, 2p, 3s, 3p, 3d, 4s, 5p
C. 2s, 2p, 3s, 3p, 3d, 5p, 4s
D. 2p, 2s, 3p, 3s, 4s, 3d, 5p
E. 2s=2p, 3s=3p=3d, 4s, 5p

On the basis of Lewis structures for N2O, which of the following
statements is FALSE?
A. The N-N bond length will be shorter than the N-O bond length.
B. The molecule is linear.
C. The molecule will have a dipole moment of zero
D. There is more than one possible Lewis structure for this molecule.

The best two Lewis structures in which the formal charges are minimised are:
Formal -1 +1 0 0 +1 -1
charges
Of these – the right hand structure is more stable because the more electronegative
oxygen carries the negative formal charge

What shape is the XeF4 molecule?

Diatomic oxygen (O2): Lewis Structure
1. O O 4. Distribute remaining e- s
• options:
2. Valence electrons
O O O O
O 1s22s22p4 = 6 valence electrons
total for O2 = 2 x 6 • Can’t complete both octets
= 12 valence electrons and atoms are charged
• Must use multiple bond
3. O O
O O
4. Used 2 electrons
• 10 remaining • Best option as all atoms have
a completed octet and no
charge

Diatomic oxygen (O2): Lewis Structure
O O
BUT
• What is happening at the level of the atomic orbitals?
• GSEC: O 1s22s22p4
2s 2p
• Can the double bond arise from direct overlap of the singly occupied p
orbitals?
• NO, because the p orbitals are orthogonal to each other.
• Where do the lone pairs reside? Is one pair in a spherical 2s orbital and
the other in a 2p-orbital?
We need a more sophisticated model!
Diatomic oxygen (O2): VSEPR
Start with the Lewis structure: O O

• The molecule geometry must be linear, but where are the lone pairs?
• In VSEPR multiple bonds are treated as one set of electrons.
• Each oxygen has 3 electron sets (2 lone pairs + bonding set)
• Electron geometry must be trigonal planar around each oxygen atom.
• BUT how can we justify this if one lone pair is in a spherical 2s orbital and
the other in a 2p-orbital?

Diatomic oxygen (O2): Valence Bond Theory
We need a model that can explain the double bond and provide a good explanation of the
lone pairs.
Ground State
hybridise
Electron Configuration 2p sp2 2p
sp2
GSEC: O 1s22s22p4 2s
p overlap
 π orbital
O O
sp2 overlap
 σ orbital
Diatomic oxygen (O2): Valence Bond Theory
Hybridisation tells us that :
• O2 has a double bond
• the electron geometry around each atom is trigonal planar
• the lone pairs are in equivalent (and degenerate) orbitals
BUT (and it’s a big but)

• It doesn’t explain experimentally observed physical properties of O2
• O2 is paramagnetic so must have a net electron spin
• (1 or more unpaired electrons)

O2: Molecular Orbital
Theory
• Bond order = 2
• 2 unpaired electrons in π*orbitals!
• Explains paramagnetism
• Best model so far!

Interpreting
molecular orbital
diagrams:
They show the origin of
electrons from each
atom participating in
the bond and the
resulting molecular
orbital.

Organic Structures and Names
Recognise and interpret:
• Molecular formulae
• Condensed structures
• Expanded structures
• Line structures
• Ball and stick structures
• Space filling structures

Draw the expanded structure for the following molecule:
3-methylcyclopentene

Which one of the following structures is correct for 1,3-
dichlorobutane?
CHEM1100 2014, Semester 2 MSE

Applying steps for naming a molecule
2. Identify any
1. Count the functional groups =
longest carbon alcohol (family)
chain = 7 (hept) 6
4 2
5 3
7 1
3. Look for 4. Look for branched

double or triple substituents = methyl
bonds = double
6-methyl-5-hepten-2-ol
(common name = sulcatol)
• Principal functional group is a carboxylic acid therefore name as an –oic
acid;
• Also has an –OH
• use as a prefix, here “hydroxy”
• Principal chain length is 6C
• 3-hydroxyhex-4-enoic acid

What is the correct name of this molecule?

Draw the structure of the following molecule:
4-ethyl-2-hexene

Several MCQs may be based on a single structure
H-O-C bond
angle at c? Hybridisation of
atoms a and c?
Which of the following statements about the C=O double bond (a) in paracetamol is
CORRECT?
A. The C=O bond is a non-polar bond

B. The C=O bond is a polar bond with a higher electron density around the carbon nucleus.
C. The C=O bond is a polar bond with a higher electron density around the oxygen nucleus.
D. The oxygen atom must be sp3 hybridised in order to form the double bond.
E. The carbon atom must be sp hybridised in order to form the double bond.
Need help?
• PASS
• Podium consultations
• OCL activities

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Welcome!

CHEM1100 Chemistry 1 - Module 1

Module 1 Module 2 Module 3

A/Prof. Jack Clegg A/Prof. Idriss Blakey Prof. Gary Schenk

CHEM1100 Chemistry 1 - Module 1

Lecturer Explanation In-class discussion Thinking/Problem- Self-study

For Experiment 1 in week 3 you will need:

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Enter your student ID number as your ID (4xxxxxxx i.e. not s4xxxxxx).

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You must check Bb regularly.

CHEM1100 Chemistry 1 - Module 1

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Clubs and societies: connect with other students

CHEM1100 Chemistry 1 - Module 1

CHEM1100 Chemistry 1 - Module 1

CHEM1100 Chemistry 1 - Module 1

electron e- -1.6022 x 10-19 9.1094 x 10-31

proton p +1.6022 x 10-19 1.6726 x 10-27

neutron n 0 1.6749 x 10-27

1 amu = atomic mass unit

CHEM1100 Chemistry 1 - Module 1

CHEM1100 Chemistry 1 - Module 1

CHEM1100 Chemistry 1 - Module 1

CHEM1100 Chemistry 1 - Module 1

CHEM1100 Chemistry 1 - Module 1

CHEM1100 Chemistry 1 - Module 1

CHEM1100 Chemistry 1 - Module 1

CHEM1100 Chemistry 1 - Module 1

Scanning tunnelling microscope (STM)

Max Planck Niels Bohr Albert Einstein Lise Meitner

Werner Heisenberg Louis De Broglie Erwin Schrödinger Marie Curie

CHEM1100 Chemistry 1 - Module 1

high energy low energy

CHEM1100 Chemistry 1 - Module 1 Blackman p168

CHEM1100 Chemistry 1 - Module 1 Blackman p166-7

CHEM1100 Chemistry 1 - Module 1 Blackman p169

How can the same thing be described two different ways?

Reality depends on how you look at (measure) it.

CHEM1100 Chemistry 1 - Module 1

c c = velocity of light (3 x 108 m s-1)

Light has particle like properties – “quanta”

A quantum of energy = hν;

CHEM1100 Chemistry 1 - Module 1 Blackman p169

CHEM1100 Chemistry 1 - Module 1

CHEM1100 Chemistry 1 - Module 1 Blackman p179

n is the “principal” quantum

R is the most accurately determined

emission spectrum of the H atom

CHEM1100 Chemistry 1 - Module 1 Blackman p176-77

CHEM1100 Chemistry 1 - Module 1

CHEM1100 Chemistry 1 - Module 1

It is possible to calculate the wavelength of a particle!