DP Chemistry: Drug detection & analysis
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Drug detection & analysis

D.9 Drug detection & analysis (4 hours)

Pause for thought

One of the quirks of the current syllabus is that sometimes it is not exactly clear what should be covered when teaching a topic. Much of this sub-topic is self-evident but one problem occurs in the ‘Applications and skills’ where it states:

“Description of the process of extraction and purification of an organic product”

It then goes on to state:

“Consider the use of fractional distillation, Raoult’s law, the properties on which extractions are based and explaining the relationship between organic structure and solubility.”

The use of solvent extraction relies on the relative solubility of the compound between two immiscible liquids, such as water and an organic solvent. The substance is extracted into the layer in which it is most soluble and the layers can then be separated using a separating funnel.

This describes the process but it is not clear from the guide whether students are also expected to understand and solve problems using the partition coefficient. Since ‘partition coefficient’ is not specifically mentioned and there is also no mention of ‘calculate’ or determine’ in the ‘Application and skills’ statement and no further reference under ‘Guidance’ one can only assume that it is not required, but at least one of the text books for the course does include it.

It may be worth explaining it and giving your students an example such as:

A chemist wishes to extract a drug X from an aqueous solution that contains 1 g of drug X in 100 cm3 of solution. The partition coefficient for drug X between ether and water is 40. Calculate how much of the drug would be extracted if:

(a) 100 cm3 of the aqueous solution is shaken with 10 cm3 of ether.

(b) 100 cm3 of the aqueous solution is shaken first with 5 cm3 of ether then the remaining aqueous layer is shaken with a further 5 cm3 of ether.

(a) Let mass of X extracted in ether be m, so [X(ether)] = 100m g dm-3

Partition coefficient, Kpc = [X(ether)] ÷ [X(aq)]

[X(aq)] = (1 –m) g in 100 cm3 = (10 – 10m) g dm-3

[X(ether)] = 40 x (10 – 10m) g dm-3 = 100m g dm-3

400 – 400m = 100m

so mass extracted using 10 cm3 of ether = 0.80 g

(b) First 5 cm3

Let mass of X extracted in 5 cm3 of ether be m1 ,so [X(ether)] = 200m1 g dm-3

[X(ether)] = 40 x (10 – 10m1) g dm-3 = 200m1 g dm-3

400 – 400m1 = 200m1

Mass of ether extracted, m1 = 0.667 g

Second 5 cm3

Let mass of X extracted in 5 cm3 of ether be m2 ,so [X(ether)] = 200m2 g dm-3

Now only 0.333 g of X remains in the 100 cm3 aqueous layer

[X(aq)] = (0.333 –m2) g in 100 cm3 = (3.33 – 10m2) g dm-3

[X(ether)] = 40 x (3.33–10m2) g dm-3 = 200m2 g dm-3

133.2 – 400m2 = 200m2 so m2 = 0.22 g

So total amount extracted using two lots of 5 cm3 of ether = m1 + m2 = 0.67 + 0.22 = 0.89 g

Students can understand from this that it is better to carry out several extractions with smaller quantities than to use all the extracting solvent at once.

Nature of Science

Advances in technology (IR, NMR and MS) which enable very small amounts of substances to be analysed comprehensively have assisted in drug detection, identification, isolation and purification.

Learning outcomes

After studying this topic students should be able to:

Understand:

  • Infrared spectroscopy, mass spectroscopy and proton NMR can all be used to analyse and identify organic structures.
  • The presence of alcohol in a breath sample can be detected either by using a a redox reaction or by a breathalyser that uses a fuel cell.

Apply their knowledge to:

  • Determine an organic structure by interpreting a variety of analytical spectra (IR, mass spectroscopy and 1H NMR).
  • Describe the process of extraction and purification of an organic product. This should cover fractional distillation, Raoult’s law, and the properties on which extractions are based.
  • Explain the relationship between organic structure and solubility.
  • Describe how chromatography and mass spectroscopy can be used to detect the presence of steroids in sport.
  • Explain how alcohol can be detected by using a breathalyzer.

Clarification notes

Students should be able to identify common organic functional groups in a given compound by recognition of common drug structures and from Sections 26, 27 and 28 of the data booklet which give data on IR, 1H NMR and mass spectral fragments respectively.

A common steroid structure is given in Section 34 of the data booklet.

International-mindedness

Cheating by taking illegal or banned drugs in sport is an international problem.

Teaching tips

If you have given your students the ten questions on spectroscopic analysis attached to Topics 11 and 21 and also used the 1H NMR of ibuprofen then they should have little difficulty in applying spectroscopic techniques to the analysis and structure of drugs. However what is new are the techniques required to extract and separate the drug in question.

Chromatography does not appear on the core/AHL so you will need to explain the principles underlying it before covering the specifics of gas-liquid chromatography. This is used to separate a mixture into its constituent components before each component can then be passed through a mass spectrometer in GC/MS. This technique is highly sensitive with a limit of detection in the low femtogram range (1 femtogram = 1 x 10-15 g), which makes it so powerful in the detection of drug abuse in athletes.

You will also need to cover how fractional distillation is an example of Raoult’s law and how the partition between two immiscible liquids can be used in solvent extraction (see Pause for thought above). If you have not already covered it when teaching sub-topic D.6, then it may also be worth mentioning the use of supercritical carbon dioxide as an extraction solvent.

The old-fashioned ‘blow in the bag’ breathalyser involves the redox reaction between ethanol and acidified dichromate ions and students should experience this reaction practically as there are often questions on it (including the half-equations) in the exam. The syllabus specifically states that fuel cells are used in modern breathalyzers but some work by measuring the amount of infrared absorbed by specific bonds in ethanol.

Study guide

Pages 164 & 165

Questions

For ten 'quiz' questions (for quick testing of knowledge and understanding with the answers explained) see MC test: Drug detection & analysis.

For short-answer questions see Drug detection & analysis questions together with the worked answers on a separate page Drug detection & analysis answers.

Vocabulary list

Raoult's law
partition
gas-liquid chromatography
GC/MS
breathalyzer

Teaching slides

Teachers may wish to share these slides with students for learning or for reviewing key concepts.

  

Other resources

1. How to identify the drugs present in a pill using gas chromatography and mass spectrometry by GlobalDrugSurvey.

  Using GC/MS to analyse a pill

2. A good animated explanation of fractional distillation by ChemSurvival.

  Fractional distillation

3. A rather simple video by the American Chemical Society which has a policeman 'explaining' how a breathalyzer works.

  Fuel cell breathalyzer

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