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OCR A Level Chemistry Your notes

4.7 Analytical Techniques

Contents
4.7.1 Infrared Spectroscopy
4.7.2 Mass Spectrometry
4.7.3 Combined Techniques

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4.7.1 Infrared Spectroscopy

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Introduction to Infrared Spectroscopy
All covalent bonds act rather like springs, as opposed to rigid bars
Like springs, the bonds can vibrate in a number of different ways
The frequency of vibration occurs in the infra-red region of the electromagnetic spectrum
If an organic molecule is irradiated with infra-red energy that matches the natural vibration frequency
of its bonds, it absorbs some of that energy and the amplitude of vibration increases
This is known as resonance

Different modes of vibration in molecules. Each mode has a characteristic frequency of vibration

Infrared (IR) spectroscopy

Infrared (IR) spectroscopy is a technique used to identify compounds based on changes in vibrations
of atoms when they absorb IR of certain frequencies
A spectrophotometer irradiates the sample with IR radiation and then detects the intensity of IR
radiation absorbed by the molecule
IR energy is absorbed only if a molecule has a permanent dipole that changes as it vibrates

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Symmetrical molecules such as O2 or H2, are therefore IR inactive

The resonance frequency is the specific frequency at which the bonds will vibrate
Rather than displaying frequency, an IR spectrum shows a unit called wavenumber Your notes
Wavenumber is the reciprocal of the wavelength and has units of cm-1
Characteristic absorptions can be matched to specific bonds in molecules
This enables chemists to determine the functional groups present

Absorption values for infrared spectroscopy analysis table

Bond Location Wavenumber / cm−1

C–C Alkanes, alkyl chains 750 – 1100

C–X Haloalkanes (X = Cl, Br, I) 500 – 800

C–F Fluoroalkanes 1000 – 1350

C–O Alcohols, esters, carboxylic acids 1000 – 1300

C=C Alkenes 1620 – 1680

Aldehydes, ketones, carboxylic acids, esters,

C=O 1630 – 1820
amides, acyl chlorides and acid anhydrides
aromatic Several peaks in the range
Arenes
C=C 1450 – 1650

C=N Nitriles 2220 – 2260

C–H Alkyl groups, alkenes, arenes 2850 – 3100

O–H Carboxylic acids 2500 – 3300 (broad)

N–H Amines, amides 3300 – 3500

O–H Alcohols, phenols 3200 – 3600

Due to some absorption bands overlapping each other, other analytical techniques such as mass
spectroscopy should be used alongside IR spectroscopy to identify an unknown compound
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Interpreting & Predicting Infrared Spectra

Your notes
The best way to understand how to interpret an IR spectrum is by looking at examples and becoming
familiar with the characteristic features of an IR spectrum

Worked example
Examine the two spectra shown and determine which one belongs to propan-2-ol and which one
belongs to propanone

Answer:
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IR spectrum A is propanone
In IR spectrum A the presence of a strong, sharp absorption around 1710 cm-1 corresponds to
the characteristic C=O, carbonyl, group in a ketone. Your notes
IR spectrum B is propan-2-ol.
In spectrum B the presence of a strong, broad absorption around 3200-3600 cm-1 suggests
that there is an alcohol group present, which corresponds to the -OH group in propan-2-ol.

Examiner Tip
You can be asked to interpret or predict infrared spectra of both familiar and unfamiliar substances

Three of the key peaks to be aware of are:

1. The narrow scoop caused by the O-H bond of an alcohol at between 3200 and 3600 cm-1
2. The sharp spike caused by the carbonyl C=O bond that belongs to many compounds as listed in
the data booklet and table above
3. The broad scoop caused by the O-H bond of a carboxylic acid between 2500 and 3300 cm-1, this
right hand side of this peak is often distorted by the peaks from C-H bonds

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Uses of Infrared Spectroscopy

Infrared spectroscopy is used to identify pollutants in vehicle emissions in the air Your notes
Sensors detect and measure the amount of pollutants such as carbon monoxide, carbon dioxide
and unburnt hydrocarbons
This commonly occurs on motorways and in busy town centres to monitor localised pollution

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

Fingerprint Region
The region below about 1500 cm-1 is called the fingerprint region and is unique to every molecule
It has many peaks that can be difficult to assign
These peaks represent the complex vibrational interactions that occur between different bonds within
a molecule
The value of the fingerprint region is in being able to compare the IR spectrum to a known compound
from a database and coming up with an exact match
This is particularly useful, for example, in identifying a specific member of a homologous series
All members of the series will show the same type of bonds present, but no two molecules will have
the same fingerprint region
Infrared spectroscopy is one of a number of techniques used to determine the structure of organic
molecules
It is most commonly used in combination with other analytical techniques such as:
Elemental analysis - to determine the empirical formula
Mass spectrometry - to determine the molecular mass and fragment ions from the whole
molecule
(NMR spectroscopy is also included in the techniques but this is not covered as part of the AS
course)

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4.7.2 Mass Spectrometry

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Interpreting Mass Spectra
When a compound is analysed in a mass spectrometer, vaporised molecules are bombarded with a
beam of high-speed electrons
These knock off an electron from some of the molecules, creating molecular ions:

The relative abundances of the detected ions form a mass spectrum: a kind of molecular fingerprint
that can be identified by computer using a spectral database
The peak with the highest m/z value is the molecular ion (M+) peak which gives information about
the molecular mass of the compound
This value of m/z is equal to the relative molecular mass of the compound

The M+1 peak

The [M+1] peak is a smaller peak which is due to the natural abundance of the isotope carbon-13
The height of the [M+1] peak for a particular ion depends on how many carbon atoms are present in
that molecule; The more carbon atoms, the larger the [M+1] peak is
For example, the height of the [M+1] peak for an hexane (containing six carbon atoms) ion will be
greater than the height of the [M+1] peak of an ethane (containing two carbon atoms) ion

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Worked example
Your notes
Determine whether the following mass spectrum belongs to propanal or butanal

Answer:
The mass spectrum corresponds to propanal as the molecular ion peak is at m/z = 58
Propanal arises from the CH3CH2CHO+ ion which has a molecular mass of 58
Butanal arises from the CH3CH2CH2CHO+ ion which has a molecular mass of 72

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Fragmentation Peaks in Mass Spectra

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The molecular ion peak can be used to identify the molecular mass of a compound
However, different compounds may have the same molecular mass
To further determine the structure of the unknown compound, fragmentation analysis is used
Fragments may appear due to the formation of characteristic fragments or the loss of small
molecules
For example, a peak at 29 is due to the characteristic fragment C2H5+
Loss of small molecules gives rise to differences between peaks of, for example, 18 (H2O), 28 (CO),
and 44 (CO2)
An alcohol can typically dehydrate in a MS, so one peak to look for is M-18

Alkanes
Simple alkanes are fragmented in mass spectroscopy by breaking the C-C bonds
M/z values of some of the common alkane fragments are given in the table below
m/z values of Fragments Table

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Your notes

Mass spectrum showing fragmentation of alkanes

Alcohols
Alcohols often tend to lose a water molecule giving rise to a peak at 18 below the molecular ion
Another common peak is found at m/e value 31 which corresponds to the CH2OH+­fragment
For example, the mass spectrum of propan-1-ol shows that the compound has fragmented in four
different ways:
Loss of H• to form a C3H7O+ fragment with m/e = 59
Loss of a water molecule to form a C3H6+ fragment with m/e = 42
Loss of a •C2H5 to form a CH2OH+ fragment with m/e = 31
And the loss of •CH2OH to form a C2H5+ fragment with m/e = 29

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Your notes

Mass spectrum showing the fragmentation patterns in propan-1-ol (alcohol)

Worked example
Alcohol fragmentation

Which alcohol is not likely to have a fragment ion at m/z at 43 in its mass spectrum?
A. (CH3)2CHCH2OH
B. CH3CH(OH)CH2CH2CH3
C. CH3CH2CH2CH2OH
D. CH3CH2CH(OH)CH3

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Answer
The correct answer is option D
Your notes

Because a line at m/z = 43 corresponds to an ion with a mass of 43 for example:

[CH3CH2CH2]+
[(CH3)2CH]+
2-butanol is not likely to have a fragment at m/z = 43 as it does not have either of these fragments
in its structure.

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4.7.3 Combined Techniques

Your notes
Deducing Organic Structures
Organic chemists often use a number of techniques in combination to determine the structure of a
compound

Worked example
10.00 g of an organic compound, A, was analysed and found to contain 6.21 g of carbon, 1.03 g of
hydrogen and 2.76 g of oxygen. The relative molecular mass of the compound was 58.0
Determine the molecular formula of compound A.

Answer:

Therefore, the empirical formula of compound A is C3H6O

The empirical mass is (12.0 x 3) + (1.0 x 6) + 16.0 = 58.0
Therefore, the molecular formula of compound A is also C3H6O

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Worked example
Your notes
The infrared spectrum of compound A is shown below:

Identify the peaks on the infrared spectrum

Use your molecular formula and the infrared data to suggest two possible structures for compound A

Answer
The peaks at around 2850 cm-1 correspond to C-H bonds
This matches with the idea that compound A is a hydrocarbon derivative
The peak at around 1750 cm-1 corresponds to a carbonyl / C=O group
Couple with a molecular formula of C5H10O, this suggests that compound A could be an
aldehyde or a ketone
As you are told that compound A has a straight chain structure, you can deduce that the possible
structures are:
1. Propanal
2. Propanone

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Worked example
Your notes
The mass spectrum of compound A is shown below:

Use the data from the mass spectrum to deduce the structure for compound A from your suggestions

Answer
There are characteristic m/z peaks for a carbon chain:
m/z = 29 could represent C2H5+ or CHO+
Therefore, compound A is propanal
Also, propanone would give a clear signal at m/z = 15 as it could fragment on either side of the
carbonyl group

Examiner Tip
You can be expected to work with any empirical and molecular formula combined with infrared and
mass spectral data to identify unknown compounds

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