OCR A
Analytical techniques
(IR and MS)
Module 4 – Core organic chemistry
brought to you by:
Information for the
teacher:
• Mastery learning – builds on the concept of developing automatic fluency in your
learners. We drive cars on auto-pilot so lets aim to for our students to work in
chemistry with the same level of autonomy. New material is present in smaller
chunks than we are used to with frequent practice and mastery of small sections
before we move on.
• There are other suggestions on the website of how to use these presentations but
there should be lots of practice as you go so please include and stop this
presentation and get your students to do your own worksheets and homeworks as
well as the problems included in the slides as you progress – have extra sheets or
extension activities available for those who work more quickly and try to only move
on once everyone in the class is getting over 80% of the problems correct – if not
return and reteach – it will save you time in the long run!
• Each lesson or at the end of a new section develop a habit of reviewing previous
learning and linking new ideas back to previous content.
• These PowerPoints follow the suggested structure for covering the content of the
latest OCR A Syllabus.
• The notes section of each slide provides links back to mastery learning ideas to
provide the teacher with an rationale of what this slide is aiming to achieve or test
and provide ideas for the teacher as to what content they might want to augment
that slide with.
• The notes section also includes explanation of problems where appropriate and
questions for the teacher to consider as their students progress.
• Please visit ChemCatalyst.co.uk for more information
Module 4 – Core organic
chemistry
Analytical techniques
(IR and MS)
Subject
Content
Expected learning
gains
• Understand and interpret IR spectra
to help identify unknown substances
• How society uses IR Spectroscopy to
fight air pollution
• Develop a mastery of mass
spectrometry so that you interpret
mass spectra and identify unknown
substances
• Combine these two techniques to
identify unknown samples
Just a minute starter
You have 1 minute to speak about
organic chemistry.
At the first repetition, pause or mistake
somebody else will take over
This will continue until the minute is up!
Starter 2:
Identification
• Substance X
decolourises
bromine water and
reacts with PCl5
producing steamy
white acidic fumes
• If the molecular
formula of X is C4H8O
suggest two possible
structural isomers
IR Spectroscopy
• 4.2.4 Analytical Techniques
Moving bonds
• The bonds which hold atoms in molecules
together are not static they vibrate
• These vibrations could be in the form of
stretching (symmetrical and asymmetrical),
bending, rocking, twisting or even wagging!
Absorption
• The bond absorbs electromagnetic
radiation of a certain frequency and the
vibrations are stimulated
• The EM radiation is in the infra red (IR)
region of the spectrum and corresponds
to a particular vibration
• RSC Infrared spectroscopy (IR)
In general, compounds that are symmetrical AND cannot
form a polar shape (namely, all homonuclear diatomics), like
N2 and O2 , cannot be detected in IR spectroscopy
How it works:
summary
The machine fires IR
radiation at the
sample
The frequency of IR
radiation is gradually
increased
The sample absorbs
the energy at
different levels
depending on the
bonds which are
present
The machine converts
the frequency into a
wavenumber and a
spectra of the sample
is produced
Data Sheet
• The data sheet shows you some common frequencies
• This is a handful of the more simple frequencies which are
used at AS level
C=O from carboxylic acids 1630 -
Here is the spectra for 1820
butanoic acid
100
Transmittance
50
%
O-H from carboxylic acids 2500 - 3300
0
4000 3000 2000 1500
1000 500
Wavenumber -1
Data Sheet
• You use the IR spectra to help you
identify a compound it won’t be the
only piece of information you know
• e.g. C3H6O could be propanal or 3-
propenol
• IR spectroscopy can help you work out
which is which
Here is the spectra
for propanal The peaks in the exam are
often simplified and
smoothed out to make it
more obvious and easier
to read
100
Transmittance
50
%
C=O from aldehydes 1630 -1820
0
4000 3000 2000 1500
1000 500
Wavenumber -1
Here is the spectra C=C from alkenes 1620-1680
for 3-propenol
100
It is
difficult
here to see
the
difference
Transmittance
between 50
the C-H
%
bonds and
the O-H
bonds
0
4000 3000 2000 1500
1000 500
Wavenumber -1
It can be hard to read but usually there will be
one peak you are sure about and will help you
answer the question
What substance?
100
Transmittance
50
%
0
4000 3000 2000 1500
1000 500
Wavenumber -1
1. Propanone 3. Propanoic acid
2. Propan-1-ol 4. Propanal
Check for
understanding
100
Transmittance %
50
0
4000 3000 2000 1500
1000 500
Wavenumber -1
Which spectra RED or BLACK shows the
presence of a nitrile group?
1. Complete table
2. Answer past paper questions
3. challenge: MCQ question above
Why do fluroalkanes have a higher
absorption than the other haloalkanes
• The intensity of a absorption band
depends on the polarity of the bond, the
bond with higher polarity will show more
intense absorption band.
Air pollution
You can use IR
spectroscopy to
monitor levels of air
pollution such as CO2,
CH4, NO and H2O which
are all susceptible to IR
radiation
Infrared gas sensors
bombard samples of air
with IR radiation and
can detect the
concentrations of
greenhouse gases
The drunkometer
• Infrared spectroscopy can be used to
measure alcohol levels using roadside
breathalysers
• A ray of infrared radiation is passed
through the breath that is exhaled into the
breathalyser chamber
• The characteristic bonds of ethanol are
detected and measured - the higher the
absorbance of infrared radiation, the more
ethanol in the person's breath
PPQs
• Paper F322, June 2009, Q5b
• Paper F322/01, June 2013, Q6cd
4.2.4 Analytical Techniques
Mass
Spectrometry
Mass Spectrometry
Mass Spectrometry
• The sample is vaporised, ionised, accelerated
and then deflected
• The peaks occur at different mass:charge ratios
(m/z)
• The charge is often +1 but the x-axis really only
measures the mass of the different fragment
• eg a fragment of 28 with a +1 charge is 28/1 = 28
• A fragment of 56 with a 2+ charge would also show up at 28
on the m/z scale
• It is used to find different isotopes and therefore
the relative atomic mass of an element
• It can also be used to identify the relative
molecular mass of compounds
Analysis using Mass
spectra
• The mass spectrometer is normally
used with infrared spectroscopy to
identify an unknown substance
• This is because you don’t always get all
the pieces of the puzzle you need from
just a mass spectrum
Example:butane
Butane C4H10 Mr = 58
Relative intensity (%)
Base
Peak
(most
abundant
) Butane loses one
electron and
forms a positive
ion
The peak with
the highest m/z
value shows the
relative
molecular mass
of the compound
This is called the
molecular ion
peak
m/z
Other peaks are caused by fragmentation
Only positive ions (cation fragments) are detected by the
machine anions and free radicals are not
A free radical?
How would I get one of those?
A free radical? How would I get one of
those?
High
energy
electron
A free radical? How would I get one of
those?
Radical fragment -
UNDETECTED
Cation fragment -
DETECTED
58 = CH3CH2CH2CH3+
Relative intensity (%)
43 = CH3CH2CH2+ (base peak)
29 = CH3CH2+
15 = CH3+
m/z
If only it were that
simple…
• Some times other small peaks exist
next to larger peaks
• Eg a small peak at 59 on butane
• How could it be 59?
• Remember there is an isotope of carbon 13
C
• This is called the M+1 peak – it is often
ignored!
Propanal vs. Propanone
Mr = Mr =
58 58
• Things to notice:
• The top diagram
• The peak at 58: the molecular ion peak.
• The peak at 57 could indicate the hydrogen has been
lost in fragmentation CH3CH2CO+.
• A strong peak at 29 shows either lose of CHO or
CH3CH2.
• These structures could only exist in propanal.
• The bottom diagram
• Also has a peak at 58: the molecular ion peak.
• There is a base peak at 43 and another strong peak
at 15.
• 43 corresponds to CH3CO+ and 15 is the rest of the
molecule ie CH3+
back and label the previous page correct
What do you know?
1. How are the mass spectra of
propanone and propanal similar?
2. How are the mass spectra of
propanone and propanal different?
3. What major peak would you find in the
mass spectrum for propanal but not
propanone?
4. What major peak would you find in the
mass spectrum for butna-1-ol but not
butan-2-ol?
PPQs – combining IR and
MS
• Paper F322, June 2010, Q4
• Paper F322, June 2011, Q6
• Paper F322/01, June 2013, Q6ab
• Paper F322/01, June 2013, Q8
Which of these ideas has been difficult?
• IR spectroscopy
• Identifying bonds using the data
booklet
• Mass spectrometry
• Combining techniques
Teacher self-
evaluation
• Changes to be made to PowerPoint,
teaching, resources?
• Ask the students for feedback
• Where are they now? Adjust
accordingly.
