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Organic Analysis

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Organic Analysis

Organic analysis allows us to understand the structure and properties of unknown substances. It is especially useful outside of science and used at crime scenes, in forensic analysis, drug production, and therapeutics. Here you will learn how to analyse a completely unknown substance or powder, which might look like any other powder you find, to identify its functional groups and structure.

  • In this article, we will go through the definition of organic analysis and delve deeper into the topic.
  • We shall first go over elemental organic analysis.
  • We shall then go over qualitative tests to detect the presence of the alcohol, aldehyde, ketone, alkene and carboxylic acid functional groups.
  • Finally, we shall look briefly at quantitative organic analysis, delving into infrared spectroscopy and mass spectrometry.

Definition of Organic Analysis

Organic analysis allows us to understand the structures and molecular formulae of unknown compounds.

Organic analysis is a branch of chemistry which focuses on revealing the structure and formula of compounds through quantitative and qualitative methods of analysis.

Organic analysis can reveal the true structure of any compound you are trying to analyse. Solutions are often analysed to discover the organic compound present. Organic analysis can also identify the functional groups that are present in a molecule being tested, as well as what homologous series that compound belongs to.

Homologous series are groups of compounds with the same functional group which only differ in the amount of carbon atoms present in the chain. Adding a single carbon to the end of a compound changes the molecule, but does not alter the homologous series it belongs to.

This is important as compounds in the same homologous series behave similarly, which allows identification through simple tests. Doing a test for a single functional group will give the same outcome for compounds in the same homologous series. Additional tests (such as mass spectrometry) are required to distinguish compounds within the same homologous series, as the compounds react similarly in many chemical contexts.

Organic analysis is used in many different disciplines of chemistry but also goes beyond just science, with real-life applications such as in forensic laboratories for the detection of compounds. Organic analysis can also help us uncover new medicines and drugs to fight global diseases.

Organic Elemental Analysis

Organic elemental analysis refers to the quantification of "organic" elements from natural sources, usually bodies of water.

So what are the organic elements? Remember that no elements are organic or synthetic in their nature, but here the term organic elements refers to the elements that are crucial to life. There are 4 organic elements. These are carbon, oxygen, sulphur, and nitrogen. Hydrogen is often added to the list, yet it is not a key element. Here we will go on to describe how each one is analysed to determine its concentration or presence in water and soil samples.

Below we describe the qualitative tests you can perform on samples to determine the presence of each element.

Test for Nitrogen

This test, along with the test for sulfur, relies on Lassaigne’s Test, which can be applied in many different chemical contexts.

Lassaigne’s Test relies on preparing an extract of sodium fusion extract (SFE). This is an alkaline solution that can be later used for the detection of a wide range of elements in solution. This is dependent on the reactivity of the sample with the sodium metal ions in solution, which are very reactive.

  1. Boil sample with FeSO4

  2. Add concentrated sulfuric acid (H2SO4).

  3. If a dark blue (Prussian blue) colour appears, then nitrogen is present in the sample.

Test for Sulfur

This test also revolves around Lassaigne’s Test method.

If you add some freshly made sodium nitroprusside into your sample, and the solution turns a violet, or deep violet, then there is sulphur present in the sample.

Test for Oxygen

Oxygen is always dissolved in water. We quantify it to determine the amount of oxygen present in a water sample. For this, you would typically use a digital oxygen meter to determine the precise concentration of dissolved oxygen per volume of water collected. This would tell you how much oxygen is dissolved in the water source from which you collected it.

This type of analysis is useful to compare different fractions of water, especially from different conditions or from different sources, in order to compare how the environment or other chemical factors affect the water quality.

Qualitative Organic Analysis

Qualitative organic analysis refers to the analysis of compounds to identify the presence of functional groups.

Here, the analysis will give a yes or no answer, based on the presence of the functional group you are looking for. Qualitative analysis is usually determined by a certain colour change or reaction outcome. This is why these reactions are only qualitative, as they cannot give an absolute value or quantify the amount of product measured.

Nonetheless, qualitative analysis is very useful for the determination of functional groups present, which allows us to classify compounds into a homologous series. Here we will explore different types of functional groups, and how to test for them. These include: alcohols, aldehydes, ketones, alkenes and carboxylic acids.

Test for Alcohols

Some general tests for alcohols include their reactivity with phosphorus chloride or sodium metal, in which they effervesce. Another general test would involve putting some of the alcohol into a concentrated sodium hydroxide solution or sodium carbonate solution, in which alcohols should not dissolve.

A true test would require determining what type of alcohol is present, be it primary, secondary or tertiary. This depends on the level the alcohol can be oxidised to. You can perform a series of reactions to monitor the colour change to know what type of alcohol is present.

Alcohol Type. Organic Analysis. StudySmarterAlcohol Type Flowchart. Source: Lawrie Ryan, Cambridge International AS and A Level Chemistry Coursebook, 2014

In the flowchart, you can see a number of reactions occurring. Tertiary alcohols cannot be oxidised, this is why this is the first distinction we make. Secondly, the difference between primary and secondary alcohols is that primary alcohols can be fully oxidised into a carboxylic acid, while secondary alcohols can only be partially oxidised into a ketone. Taking this into account, we can perform experiments to test what type of alcohol is present.

Test for Carboxylic Acids

Similar to alcohols, carboxylic acids effervesce when in contact with sodium metal or phosphorus chloride.

Yet what differentiates carboxylic acids from alcohols, is that acids will react with solutions of sodium hydroxide or sodium carbonate. This is due to their acid-base neturalisation properties.

Most importantly, you can tell that an acid is acidic by performing a litmus test. Any acidic compound turns litmus red, thus carboxylic acids will turn blue litmus paper red. Additionally, you can use other acid-base indicators or even a digital pH meter to determine if the pH of the solution is below 7.

Test for Aldehydes and Ketones

There are two solutions with are commonly used to test for aldehydes. One is Tollen's reagent (ammoniacal silver nitrate solution). The other is Fehling's solution (alkaline copper solution). Aldehydes will always react with these solutions and form distinct products.

In the case of Tollen's reagent, aldehydes will produce a silver mirror, while with Fehling's solution, aldehydes will produce a red/orange precipitate of copper oxide. This is due to the reducing nature of aldehydes.

These tests can be also used to distinguish between aldehydes and ketones in a simple manner since ketones do not react with these solutions. So, no colour change is observed for either test with ketones. The reason behind this is that ketones cannot be oxidised and therefore cannot be involved in these redox reactions.

Alkenes

One important test you can perform to test for alkenes is to add it to bromine water. If in the process of the reaction, the colour of the solution decolourises (from brown to colourless), then the organic compound is an alkene. This is due to the fact that the double bond in alkenes is able to react with bromine water and break the bromine-bromine bonds through an addition reaction.

Flow Chart of Organic Qualitative Analysis

Here you will find a helpful flow chart of some qualitative organic analysis experiments you can perform to detect which functional groups are present in a compound you are analysing.

Flowchart. Organic Analysis. StudySmarterQualitative analysis flowchart. Source: Klimczyk, StudySmarter Original.

Quantitative Organic Analysis

Quantitative organic analysis determines an absolute value or measurement of a compound based on certain criteria being measured.

Quantitative analysis involves precise determination of physical or chemical properties of a compound. This can rely on determining the atoms present in the molecule, such as through combustion tests to see percentage composition, or functional groups, such as with techniques such as mass spectrometry or infrared spectroscopy.

Mass spectrometry

Mass spectrometry is a technique that is widely used throughout all disciplines of chemistry to identify organic compounds. It is a quantitative technique which relies on the production of spectra based on mass/charge ratio. But how do we get there?

So, if we take any substance, we can ionise it. This can be done for example by simply adding a proton (H+) to the compound. After this, since the molecule has a charge, we can detect it using a mass spectrometer and produce a plot. In mass spectrometry, various peaks will be formed which can be used to determine the molecular composition of the substance. The most important is the M+1 peak which when compared to the M peak will determine the amount of carbons present in the molecule. These will be the two highest peaks. This is due to the property of carbon having multiple isotopes, and in fact all elements which have naturally occurring and abundant varieties of isotopes will have multiple peaks.

What mass spectrometry can also do is fractionate compounds. This creates smaller fragments of the larger molecule. These will also be charged (ionised) and will create smaller peaks along the spectrum, which can be used to identify various functional groups. Even if you know the overall mass and number of carbons present in the molecule, you can use the smaller peaks to find out which functional groups are present, and overall how these carbons are arranged together1.

Infrared Spectroscopy

Infrared (IR) spectroscopy exploits some physical properties of bonds and molecules to determine what type of bonds are present in the molecule based on the chemical environment. You can model all bonds as a spring that can stretch, and if you apply a certain wavelength of radiation to it, the spring will behave in a very precise coordinated manner and absorb a specific wavelength.

IR spectroscopy allows us to detect which bonds are present (due to their chemical environment within the molecule), and thus to know what types of functional groups are present in compounds you are analysing. Hence, you can determine what is present within your molecule and how your atoms are arranged within the compound, provided you know which atoms are present or what the mass of your molecule is1.

You can read more about Infrared Spectroscopy here.

At the back of your textbook, you will find a table of IR absorbances for different types of bonds.

Organic Analysis - Key takeaways

  • Organic analysis is the study of unknown compounds to determine their structure and the functional groups present.
  • Organic analysis often relies on both qualitative and quantitative techniques complementing each other to get a broader overview of the compound analysed.
  • Elemental analysis can be performed through qualitative experiments.
  • Qualitative test-tube tests for functional groups can be used to determine the presence of alcohol, aldehyde, ketone, alkene and carboxylic acid functional groups.
  • Quantitative analysis includes infrared spectroscopy and mass spectrometry.

References

  1. - Lawrie Ryan, Cambridge International AS and A Level Chemistry Coursebook, 2014

Frequently Asked Questions about Organic Analysis

Organic analysis helps us to uncover the structure and properties of unknown substances. This can be through qualitative and quantitative methods which uncover the functional groups present. 

Qualitative analysis relies on different chemical tests that indicate the presence or absence of a  specific functional group in a given compound, yet provide no quantitative data. 

You can analyse organic compounds through quantitative or qualitative methods, both of which will step-by-step uncover the present structure and functional groups of a given unknown compound. 

Quantitative organic analysis relies on empirical methods, which mathematically determine the presence of ratios of elements in a compound. Some examples include titration or mass spectrometry.

Final Organic Analysis Quiz

Question

What are the two main methodologies of organic analysis?

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Answer

Qualitative and quantitative analysis

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Qualitative analysis can provide the empirical formula of a substance. 

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Answer

False

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What are the two main ways of quantitative analysis used in organic chemistry?

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Answer

Combustion with oxygen and titration. 

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Does quantitative analysis provide information about the presence of functional groups in a compound?

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Answer

No, qualitative analysis is used for that.

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Question

What will happen to a solution of bromine water if an alkane is introduced to the system?

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Answer

No change

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Question

How do alcohols react under a litmus test?

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Answer

An alcohol solution will be neutral in a litmus test. 

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How do you distinguish an alcohol from a carboxylic acid?

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Answer

Litmus test, as the acid will test positive for acidity while alcohol will be neutral. 

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Question

Does mass spectroscopy rely on ionised particles or ones with neutral charge?

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Answer

Charged particles, since only these are detectable. 

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Question

In infrared spectroscopy which component of the molecule absorbs the energy? 

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Answer

Atoms

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What ratio does mass spectrometry use to determine the amount of carbon present in a molecule?

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Answer

M and M+1 peaks

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Question

Which type of organic analysis fractionates a molecule? 

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Answer

Infrared spectroscopy

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Question

How do you determine the difference between a primary and secondary alcohol?

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Answer

React the alcohol with UI solution. If it turns red, this means there is a carboxylic acid from a primary alcohol. If the solution remains green, then there is a ketone from a secondary alcohol. 

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Question

Which solutions can you use to determine the presence of an aldehyde functional group?

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Answer

Fehling's solution and Tollens' reagent. 

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Question

How do you determine the difference between a tertiary alcohol from a secondary or primary one?

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Answer

React the alcohol with acidified dichromate. If the solution does not change colour (i.e remains orange), then it is a tertiary alcohol. 

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Question

What is infrared spectroscopy?

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Answer

An analytical technique used to identify the functional groups within organic molecules.  

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Question

What are two types of spectrometers used in infrared spectroscopy?

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Answer

- A dispersive infrared radiation spectrometer

- A Fourier transform infrared radiation spectrometer. 

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What is an absorption spectrum?

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Answer

 A plot that shows chemicals absorbing radiation over a range of frequencies.

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Question

What steps take place in the process of infrared spectroscopy?


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- A beam of radiation is passed through a sample.

 

- The sample, which is in a spectrometer, absorbs the infrared radiation. 

 

- Once the absorptions are detected and analysed, the absorption spectrum is printed or displayed on a computer. 

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Question

Which two columns do an infrared spectroscopy table have?


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Answer

- Bond

- Wavenumber

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Which three factors affect how much vibration is caused between the bonds?


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Answer

- Bond strength 

- Mass of the atom 

- Bond length

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Question

How is vibration caused?

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Answer

When the organic molecules absorb infrared radiation, the bonds between the different atoms are caused to vibrate. 

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What are the different types of vibrations?

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Answer

Stretch vibration and bending vibration 

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What is an infrared spectrum?

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Answer

An infrared spectrum of a molecule is a plot that is produced once the process of infrared spectroscopy has been performed. In the infrared spectrum, the transmittance is plotted along the y-axis, whilst the wavenumber is plotted on the x-axis.

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What are the peaks in an infrared spectrum?


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The peaks are a series of dips that represent the vibrations caused when infrared radiation is absorbed.

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What is transmittance?

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Transmittance measures the percentage of radiation that passes through a sample.

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What is wavenumber?

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The wavenumber is the number of waves in a given distance. This distance is known as 'wavelength'. Wavenumber is 1/wavelength, so they are inversely proportional.

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Question

Describe the fingerprint region.


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The fingerprint region is the area of the spectrum that is below 1500 cm-1. This region contains absorptions for some complicated vibrations which are usually caused by the bending or stretching of single bonds.

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What is an advantage of infrared radiation?

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It has a high scan speed so all the information needed for the whole frequency range can be obtained within seconds.

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What is a disadvantage of infrared radiation?

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If a sample contains water, then infrared spectroscopy is not applicable to it as a solvent like this would absorb infrared radiation.

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Question

What are the two main ways of quantitative analysis used in organic chemistry?

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Answer

Quantitative analysis relies on mass spectrometry and infrared spectroscopy.

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Question

What is the test for nitrogen called?

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Answer

Lassaigne's test

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