Sulfuric Acid and Sugar

November 28, 2014, The Canberra Times reported that, "Students were looking on as a teacher conducted an experiment involving sugar and sulfuric acid inside a cabinet when the glass container holding the acid exploded."
The experiment referred to is probably similar to the one shown in the YouTube video below in which concentrated sulfuric acid from a container is poured over sugar in a beaker.

Safety Notes

Sulfuric acid will cause permanent damage if it comes into contact with the eyes or skin. Concentrated solutions of sulfuric acid are extremely corrosive. When sulfuric acid is dissolved in water enough heat is released to make water boil! Carbon monoxide and carbon dioxide are both toxic gases. Sulfur dioxide gas is toxic in high concentration and is a severe respiratory irritant at lower concentration.Some people, especially those prone to asthma, may be especially sensitive to sulfur dioxide. In the presence of moisture, sulfur dioxide forms an acidic, corrosive solution, which in contact with the skin or eyes may lead to burns.

You will notice that the reaction seems to proceed slowly at first. The reaction mixture turns yellow as the reaction begins. This reaction releases heat, it is said to be an exothermic reaction. The heat produced by the reaction then speeds up the rate of further reactions, and, in the video, this is also accelerated by stirring the mixture.

Table sugar is made up sucrose, molecular formula C₁₂H₂₂O₁₁ and structural formula as shown below:

The reaction between sucrose and sulfuric acid in which solid carbon, water vapour and heat are produced is known as a dehydration reaction  :
C₁₂H₂₂O₁₁(s) → 12C(s) + 11H₂O(g)     ΔH = -918.9 kJ mol^-1 Since the enthalpy change for this reaction is negative, the reaction is exothermic, the reaction gives off heat.
Sulfuric acid molecules have a great affinity for water, that is, sulfuric acid will readily and spontaneously dissolve in water. The water produced by the dehydration of sucrose will then be used to dilute the sulfuric acid that is present. This reaction is also exothermic.
H₂SO₄(l) → H₂SO₄(aq)     ΔH = - kJ mol^-1 The heat produced by this reaction also speeds up the rate of the dehydration reaction and subsequent dilution reactions.
Solid carbon is black, so the "black snake" is just carbon.
But what causes the carbon to "rise up" out of the beaker? This must be the result of evolving gases forcing their way through the mixture as the reaction proceeds. The gases that have been identified as products of this reaction  are:

• carbon monoxide (CO) 66% of the dry gas volume (ie, water has been condensed out)
• carbon dioxide (CO₂) 17% of the dry gas volume
• sulfur dioxide (SO₂) 17% of the dry gas volume

Since sulfuric acid does not oxidize carbon, it is most unlikely that the carbon monoxide and carbon dioxide gases are the result of a reaction between the black snake carbon and sulfuric acid. It is much more reasonable to assume that some of the sucrose undergoes dehydration by the sulfuric acid while some this sucrose (and/or some of the resulting intermediate organic products) is oxidized by the sulfuric acid to produce carbon monoxide gas and carbon dioxide gas. During this process, the sulfuric acid will itself be reduced, resulting in the formation of sulfur dioxide gas.

Reference:
http://www.canberratimes.com.au/act-news/students-treated-after-spill-in-burgmann-anglican-school-sciencbe-laboratory-20141128-11vzad.html

Further Reading:
http://ausetute.com.au/safety.html
http://www.ausetute.com.au/mmcalcul.html  
http://www.ausetute.com.au/moledefs.html
http://www.ausetute.com.au/massmole.html
http://www.ausetute.com.au/concsols.html 
http://www.ausetute.com.au/molarvol.html
http://www.ausetute.com.au/molreact.html

Suggested Study Questions:

1.  Describe two hazards in the YouTube Video.
2.  Describe the safety precautions you would take to minimize the risk of the hazards identified in question 1 above.  
3.  Why do you think the concentrated sulfuric acid is added to the sugar rather than adding the sugar to the container of sulfuric acid?
4.  In a typical experiment, 25 mL of 18 mol L^-1 sulfuric acid is added to 50 g of granulated sugar (sucrose). Calculate the amount in moles of :
   • sucrose used
   • sulfuric acid used
5. Calculate the mass of carbon that could be produced in the typical experiment given in question 4.
6. What assumptions have you made in order to calculate the mass of carbon in question 5?
7. Assume that all 50 g of the sucrose is now oxidized at 25^oC to produce carbon dioxide gas and liquid water. What is the maximum volume of carbon dioxide gas, in litres, that could be produced?
8.  Predict what you think might happen if a 50 g of granulated sugar were quickly added to 25 mL of concentrated sulfuric acid in a 100 mL conical flask that was being swirled continuously.
9. Sucrose is a disaccharide, made up of the monosaccharide glucose and the monosaccharide fructose. Starch and cellulose are both polysaccharides, that is, they are made of repeating glucose monomer units. Predict what would happen if you spilled concentrated sulfuric acid on:
   • a paper cup (cellulose)
   • a piece of raw potato (starch)
   • a cotton shirt (cellulose)
10. Design an experiment that could safely be performed in the laboratory to test your predictions in question 9.
11. Do you think that concentrated sulfuric acid will react with the monosaccharide glucose? Explain your answer using a chemical equation.
12.  Design an experiment that could safely be performed in the laboratory to test your prediction in question 11.

Joules, Kilojoules and Calories

What units are used to measure energy?
Well, that depends on who you are and what you are doing!
If you are a chemistry student, your preferred unit should be joules, but it is likely that you will have to convert between joules and kilojoules quite often.
You might also come across calories and kilocalories as a unit of measurement of energy, and you will then need to convert between these units, and between these and joules and kilojoules.

AUS-e-TUTE has set of resources to help you learn how do these conversions, and to practice your conversion skills.

There is currently a free-to-view tutorial available for evaluation purposes at:

http://www.ausetute.com.au/energyconv.html

The Smell of Freshness

Organic compounds are added to cleaning products and air fresheners to make the air smell fresh and clean. Scientists are taking a closer look at the chemistry behind the use of these compounds to determine whether they are hazardous to human health.

One of the organic compounds that is widely used to provide the "smell of freshness" is a molecule known as limonene (1-methyl-4-(1-methylethenyl)-cyclohexene). The 2-dimensional structural formula of limonene is shown on the right.

Limonene is a colourless liquid at room temperature and pressure and is found naturally in the rind of citrus fruits such as lemons. It is one of the compounds that contributes to the typical odour of citrus fruit.
Commercial quantities of limonene are produced from citrus fruits using centrifugal separation or steam distillation.

Scientists are studying the reactions of limonene closely because the chemical reactions of this molecule with the ozone in the air in your home are the same as the chemical reactions that occur in the atmosphere that produce secondary organic aerosols (SOAs), microscopic particles suspended in the air, which contribute to the visible haze known as smog in densely populated areas.

The researchers tested various different scenarios for the production of SOAs in the home from limonene and found that the concentration of SOAs produced was between 5μg/cm³ and 100μg/cm³. The acceptable level of aerosols in breathable air is about 12μg/cm³.

The researchers suggest that the best way to reduce SOAs in your home is to either use unscented cleaners or to keep windows open while cleaning. 

Reference:
Somayeh Youssefi, Michael S. Waring. Transient Secondary Organic Aerosol Formation from Limonene Ozonolysis in Indoor Environments: Impacts of Air Exchange Rates and Initial Concentration Ratios. Environmental Science & Technology, 2014; 48 (14): 7899 DOI: 10.1021/es5009906

Further Reading:
Empirical Formula
Molecular Formula
2-Dimensional Structural Formula
Condensed Structural Formula
Skeletal Structural Formula
Percentage Composition
Parts Per Million (ppm) Concentration
Molar Mass

Suggested Study Questions:

1. Write the molecular formula for limonene.
2. Give the empirical formula for limonene.
3. Calculate the percentage of
   • carbon in a molecule of limonene
   • hydrogen in limonene
4. Draw a skeletal structural formula for limonene.
5. Limonene has the IUPAC name 1-methyl-4-(1-methylethenyl)-cyclohexene. Draw the 2-dimensional structural formula for limonene and circle each of the following groups:
   • cyclohexene parent hydrocarbon in red
   • methylethenyl branch in blue
   • methyl branch in black
6. Would you classify limonene as a saturated or unsaturated hydrocarbon? Explain your answer.
7. Convert these concentrations in μg/cm³ to concentrations in parts per million (ppm)
• 5μg/cm³
• 12μg/cm³
• 100μg/cm³
8. Calculate the molar mass of limonene.
9. Calculate the mass of limonene in 100 L of air at 25^oC and 100 kPa for each of the following concentrations:
   • 5μg/cm³
   • 12μg/cm³
   • 100μg/cm³

IUPAC Nomenclature and Organic Compounds

Imagine you are sitting a Chemistry exam.
The first question on the exam paper reads,

"Name the molecule shown below:"

How would you answer this question?

My first response is to name it Molly, short for molecule ofcourse. Not a very useful name, especially if I'm asked to name another molecule later on. It might get a bit confusing if I name every molecule Molly, even when the molecules are very different from each other.

So, the International Union of Pure and Applied Chemistry (IUPAC) has developed systems for naming compounds.
For this reason, you probably won't be asked to "name" the molecule, but you might be asked to "systematically name" the molecule, or to give the "systematic IUPAC name" for the molecule.

Even for the relatively simple molecule shown above, there is more than one way to systematically name the molecule using IUPAC nomenclature rules!

You could give a systematic IUPAC name based on the functional class of the compound. This molecule belongs to the functional class known as ketones (non-terminal C=O), two methyl (CH₃) groups are attached to the carbonyl carbon atom, so, according to the IUPAC rules for functional class nomenclature, I could systematically name it as dimethyl ketone.

I could give the same molecule a different systematic IUPAC name by applying the rules of substitutive nomenclature. In this case I name the parent hydride, propane, drop the final "e" and add a suffix denoting the non-terminal C=O functional group so that I get propanone, then I add in an infix which locates the functional group along the carbon chain, with the final name propan-2-one.

Because this is a simple molecule with just one functional group, I could use the infix as a prefix, so that the systematic IUPAC name would become 2-propanone. Or, because there is only one position for the C=O functional group to be in if this molecule is to be a ketone, I could drop the infix altogether and just systematically name the molecule as propanone.

So, some of the possible systematic IUPAC names for this molecule are:

• dimethyl ketone
• propan-2-one
• 2-propanone
• propanone

Because molecules can be named systematically in more than one way, there is a recommendation to adopt "preferred IUPAC names", or PINs. Usually the Preferred IUPAC Name is arrived at by using one of the recognized IUPAC systems for nomenclature, but not always.

If you were asked to give the Preferred IUPAC Name for the molecule shown above, the correct answer would be acetone ("Preferred names in the nomenclature of organic compounds" (Draft 7 October 2004) page 9), or, possibly propan-2-one ("Preferred names in the nomenclature of organic compounds" (Draft 7 October 2004) page 374). Acetone is the traditional name for this compound, literally meaning 'derived from acetic acid', and has been in use for more than 200 years, which is probably why the IUPAC would consider retaining the name "acetone" as the Preferred IUPAC Name for this compound.

Further Reading:
Introduction to Naming Organic Compounds

Nanoscopy

The Nobel Prize in Chemistry for 2014 has been awarded to Eric Betzig, Stefan W. Hell and William E. Moerner for the development of super-resolved fluorescence microscopy. This technique allows scientists to view objects at the nanometre scale and is therefore referred to as nanoscopy.

Since the 17^th century, we have been able to peer into the world of very small things using optical microscopes. In 1873, microscopist Ernst Abbe published an equation to show that optical microscopes could not be used to investigate things that were less than half the wavelength of light, that is, to be seen in an optical microscope the object must be greater than 0.2µm. An optical microscope can therefore be used to see some surface structure of a human hair, but you couldn't use it to see the actual protein building blocks making up the hair.

Stefan Hell was working on fluorescence microscopy, using fluorescent molecules to image parts of a cell. A brief pulse of light makes the fluorescent molecules glow temporarily, following the glow allows scientists to map where the molecules are in the cell. The technique can be used to tell where DNA is located for instance, but it could not be used to determined its structure. Stefan Hall proposed a new method, Stimulated Emission Depletion (STED) in which one pulse of light excites all the fluorescent molecules while another pulse quenches the fluorescence from all the molecules except those in a nanometre-sized volume in the middle. Only this volume is registered. An image is built up be sweeping along the sample and continually measuring light levels. In 2000 Stefan Hall was able to demonstrate the effectiveness of the STED microscope by imaging an E.coli bacterium at a resolution that could never be achieved using an optical microscope.

The nanoscopy method proposed independently by Eric Betzig and W E. Moerner, Single-Molecule Microscopy differs in that it relies on the the superposition of several images.

In 1989, W E. Moerner measured the light absorption of a single molecule for the first time.
W E. Moerner had found that one variant of green fluorescent protein (extracted from fluorescent jellyfish) could be made to fluoresce with light of 488nm wavelength, but that after awhile, the fluorescence faded and would not fluoresce again using 488nm light. The same protein, when hit by light of wavelength 405nm could be brought back to life, and then would fluoresce again when hit with light of 488nm.

In 2006 Eric Betzig demonstrated the usefulness of Single-Molecule Microscopy using a glowing protein coupled to a cell's lysosome. Using a weak light pulse, only some of the molecules were caused to fluoresce, and these were at distances greater than 0.2µm. This image was registered. When the fluorescence of these molecules died out, a new weak light pulse was used to initiate the fluorescence of a few more molecules.This new image was registered. This process was continued many times. When Betzig superimposed all the images, a super-resolution image of the cell's lysosome membrane was the result.

Methyl Orange

In March 2014, the Australian Competition and Consumer Commission (ACCC) prompted the recall of some clothing for having unacceptable concentrations of particular azo dyes.

Azo dyes are organic (carbon) compounds with the general formula R-N=N-R' and are named after their unusual N=N, azo, functional group.

They are synthetic dyes used to colour foods, cosmetics, carpets, clothes, leather and textiles.

The azo dye that most Chemistry students will be familiar with is methyl orange, an acid-base.

Read more in the September 2014 issue of AUS-e-NEWS for the chemistry of Methyl Orange

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Ammonium Nitrate Explodes

On Friday 6^th September 2014, a truck carrying 56 tonnes of ammonium nitrate exploded after rolling over near a bridge on the Mitchell Highway between Cunnamulla and Charleville in the Australian State of Queensland. Eight people were injured, and the Mitchell Highway has been closed "indefinitely".

The most important use for ammonium nitrate is as a fertilizer, but it can also be used as an explosive. An explosion results when ammonium nitrate is brought into contact with heat, a source of ignition such as a spark, or, with reducing agents. Unfortunately, explosions of ammonium nitrate are not rare. A massive explosion of ammonium nitrate on 17^th April 2013 resulted in the death of 15 people, and the destruction of the West Fertilizer Company storage and distribution facility in Texas, USA.

Ammonium nitrate can be produced in commercial quantities by reacting ammonia gas with  nitric acid.

Reference: 
http://www.brisbanetimes.com.au/queensland/truck-explosion-injures-eight-closes-mitchell-highway-20140906-10dam3.html

Further Reading
Naming Ionic Compounds 
Writing Ionic Formula 
Mole Definitions 
Molar Gas Volumes

Suggested Study Questions:

1. Write the chemical formula for ammonium nitrate 
2. Explain why this compound is considered to be an ionic compound.
3. Write a word equation for the reaction between ammonia gas and nitric acid to produce ammonium nitrate
4. Write a balanced chemical equation for the reaction in question 3.
5. Ammonium nitrate decomposes in to N₂O and H₂O when heated. Write a balanced chemical equation for this reaction.
6. Calculate the molar mass of ammonium nitrate.
7. Calculate the moles of ammonium nitrate present in the truck.
8. Assuming that the decomposition of ammonium nitrate results only in gaseous products, what volume of gas at 25^oC and 100 kPa would be released by ammonium nitrate in the truck?
9. Assume the truck could carry a load with a volume of 30,000 L. Can you suggest a reason why rapidly decomposing ammonium nitrate could explode, destroying the truck, the bridge and the road?