Use your notes from the functional group tests we looked

at last lesson to answer the 6 mark exam question below:

Test-tube reactions can be used to identify the functional groups in
organic molecules.
You are provided with samples of each of the four compounds.

Describe how you could distinguish between all four compounds

using the minimum number of tests on each compound.
You should describe what would be observed in each test.
 09/05/2022

Mass spectrometry

Do now:
BRAIN DUMP everything you can remember about mass spectrometry from
atomic structure topic

MASS SPEC
What is Mass Spectrometry?
• Mass spectrometry is used to determine the mass of a molecule/atom.
• When a compound is placed in a mass spectrometer, it loses an electron
and forms a positive ion called the molecular ion (M+).
• The molecular ion peak (M+ peak) is a clear peak with the largest m/z
ratio.
• A small peak at M+1 will also been seen. It exists because 1.1% of carbon
is present as the carbon-13 isotope.
Ethanol = C2H5OH
RFM = 46
M+ peak at 46 = A small proportion of
molar mass of ethanol molecules contain
molecule a C with a mass of 13
instead of 12 and will have
an RFM of 47

small
M+1 peak
Fragmentation Peaks
• There are many peaks in the mass spectrum because the molecular ion breaks
down into other ions when hit by the beam of high energy electrons during the
ionisation stage.
• This process is called fragmentation and involves the ion breaking down into a
cation and a radical.
• Only the cation will be detected by the spectrometer as it is positively charged.

You don’t need to learn these fragmentation patterns – you just need to be able to
problem solve and think logically to predict what fragment may have caused what
peak.
Exam Question – Identify an Alkane
Two students were provided with the mass spectrum of an alkane, shown below.

One student analysed peaks I and II and concluded that the alkane was one of two structures.

The other student analysed peaks I, II and III and was able to identify the alkane.

Analyse the peaks and explain why the two students obtained different conclusions.

• I = M+ peak = 58 = C4H10+ (butane)

• There are two possible isomers
• II = m/z peak = 43 = CH3CH2CH2+ or CH3CHCH3+
• Either isomer would produce peak II
• III = m/z peak = 29 = CH3CH2+ = only butane would produce this
Exam Question – Identify an Alcohol
The mass spectrum of alcohol A is shown below.

STEP 1:
M/Z peak = 60
OH = 17 m/z molecular ion peak = 60 ✓

60-17 = 43 Alcohol A identified as CH3 CH2CH2OH

C3H7 = 43 OR CH3CHOHCH3 ✓
A is a propanol
Peak X identified as [CH2OH]+
AND
Alcohol A identified as CH3CH2CH2OH ✓

Determine the structure of alcohol A and fragment ion X.

STEP 2: Possible Fragments
Methyl: CH3+ = 15
Ethyl: CH3CH2+ =29 STEP 3: A must be propan-1-ol because you would
Propyl: CH3CH2CH2+ = 43 not get a CH2OH+ peak with propan-2-ol
1C with OH: [CH2OH]+ =31
1. Compounds C and F can be analysed to obtain infrared and mass spectra.

i. Suggest the molecular formulae of two ions responsible for peaks in the mass spectrum
of C that are not in the mass spectrum of F.
CCl3+
2 The structure of an ester is shown below.
CF2Cl+
[2]
[C(=O)CH3] = 43
+
[CH3CH2O]+ = 45
• Molar Mass = 88
Which statement is most likely to be true about the mass spectrum of the ester?
• C is wrong; 88 = M+ peak
A. The peak at m/z = 45 is due to the fragment [C2H5O]+. • B is wrong – no chain of 3 carbons
B. The peak at m/z = 44 is due to the fragment [C3H8]+.
C. The peak at m/z = 88 is the M+1 peak. • A [C2H5O]+ equals 45 and that
D. There is no peak at m/z = 43.
fragment could be formed
A • D m/z = 43 could be formed from
Your answer
C2H3O+ [1]
High resolution MS
• Like normal MS, but to a higher degree of precision
• Allows compounds with the same molecular
formula to be distinguished