Explosive Medicine

You’ve probably heard of Alfred Nobel, the inventor of dynamite and gelignite. The commercialisation of these explosives enabled him to accumulate great wealth during his lifetime which, by the terms of his will signed in 1895, was used to establish the Nobel Prize. In later life he was prescribed Trinitrin, a medication used to relieve a heart condition known as angina.

What do dynamite, gelignite and Trinitrin all have in common?

They all contain nitroglycerin!

This is not a story about the life of Alfred Nobel.

It is a story about the fascinating chemistry of nitroglycerin…

Read more in the June 2018 issue of AUS-e-NEWS, AUS-e-TUTE's free quarterly newsletter for chemistry students and teachers.

Subscribe to AUS-e-NEWS at https://www.ausetute.com.au/ausenews.html

Cholera Vaccine

The holiday season is here, and some friends have decided to visit Panama (where else would an Engineer want to go for a holiday but to the Panama Canal?). One of the diseases they want protection against before traveling there is cholera which is caused by a water-born bacteria. The product they are taking is called DUKORAL® which comes in two parts. The first part part is a glass vial containing a whitish fluid which is the oral vaccine made up of inactivated cholera bacteria, which is probably of interest to the biology students reading this. Chemistry students, however, will be much more excited by the second part; a sachet containing a dry granular powder which is labelled as buffer.
The ingredients listed on the buffer sachet are:

• sodium bicarbonate
• citric acid, anhydrous
• raspberry flavour
• sodium carbonate, anhydrous
• sodium citrate
• saccharin sodium

The instructions for use by adults are:

1. Dissolve the effervescent granules from the buffer sachet in a glass of cool water (approximately 150 mL)
2.  Shake the vaccine vial
3. Add the vaccine to the effervescent (bubbly) solution. Mix well and drink mixture.

And, you have to take two of these doses 1 to 6 weeks apart, and 2 weeks before arrival at your destination.
The good news is that most people should be protected cholera for up to two years, so I guess my friends will make their way back to the tropics next year.

Suggested Reading
 http://www.ausetute.com.au/namiform.html
 http://www.ausetute.com.au/wriiform.html
http://www.ausetute.com.au/acidbase.html
 http://www.ausetute.com.au/buffers.html
http://www.ausetute.com.au/esters.html

Suggested Study Questions

1.  What is another, systematic name for sodium bicarbonate?
2. Give the molecular formula for each of the following:
   • sodium bicarbonate
   • citric acid, anhydrous
   • sodium carbonate, anhydrous
   • sodium citrate
3. Draw a structural formula for each of the following:
   • sodium bicarbonate
   • citric acid, anhydrous
   • sodium carbonate, anhydrous
   • sodium citrate
4. Use chemical terms to explain the relationship between:
   • sodium bicarbonate and sodium carbonate
   • citric acid and sodium citrate
5. Explain what a buffer is.
6. Explain why the dry, granular powder in the sachet was labelled "buffer".
7. Why do you think a buffer is needed for this vaccine to be effective?
8. What type of chemical compound is the "raspberry flavour" likely to be?
9. One molecule responsible for raspberry flavour is shown below:
   
   What 2 reactants would you need to produce to this molecule in the school laboratory?
10. What does the term effervescent mean?
11. Write a balanced chemical equation to show why effervescence is observed when the buffer in the sachet is added to water. 
12. What does the term "anhydrous" mean?
13. Why are some of the buffer sachet's ingredients listed as "anhydrous"?
14. What is the purpose of the saccharin in the buffer sachet?

Biodiesel

What's the difference between diesel and biodiesel?
I'm glad you asked!
AUS-e-TUTE has just added new resources (tutorial, game, test, exam) to help you learn how to synthesize and characterize biodiesel, as well as to distinguish between diesel and biodiesel.
AUS-e-TUTE Members should log-in to access these new resources: http://www.ausetute.com.au

If you are not an AUS-e-TUTE Member, there is a "free-to-view" biodiesel temporarily available at http://www.ausetute.com.au/biodiesel.html for evaluation purposes.

Want more information about AUS-e-TUTE Membership?
Go to http://www.ausetute.com.au/membership.html

Want to join AUS-e-TUTE?
Go to http://www.ausetute.com.au/register.html

Just want to check out what you can get for free?
Go to http://www.ausetute.com.au

Naming Esters the IUPAC Way

IUPAC naming of esters is not a bit hard, it's just a bit different to the way you name other organic molecules.

Follow AUS-e-TUTE's step-by-step guide to :

• naming esters
• drawing the structure of ester molecules
• writing the molecular formula for ester molecules

and you'll be amazed at how easily you can name, and draw the structure of, esters.

Then, when you think you've got the hang of that, why not try our ester naming game?
Or, test your skill with our ester test.
Preparing for an exam? We've got you covered! You can use our ester exam to practice your exam technique before you sit your exam.
And remember, AUS-e-TUTE's test and exam questions come with immediate feedback to help you understand where you go wrong and help you get the next question right.

AUS-e-TUTE Members should log-in to use these new resources. 

Not an AUS-e-TUTE Member?
There is currently a "free-to-view" tutorial available at http://www.ausetute.com.au/namester.html

Find out more about AUS-e-TUTE membership at : http://www.ausetute.com.au/membership.html
and you can join AUS-e-TUTE at http://www.ausetute.com.au/register.html

Pthalate in Plastics

Researchers in the USA have found a link between premature births and the exposure of  pregnant women to a group of organic (carbon based) chemicals known as phthalates.

Phthalates have been used for more than 50 years as plasticizers, substances which are added to plastics to increase their flexibility, transparency, durability and longevity. For example, adding phthalates to polyvinyl chloride (PVC) makes the PVC soft and flexible, ideal for flexible plastic tubing. You will find phthalates in many products you come into contact with every day, from vinyl upholstery and floor tiles, to plastic food containers and wrappers, to personal care products like perfumes, moisturizer, and liquid soap.

Phthalates have the general structural formula shown below:

R and R' represent alkyl groups.
If R and R' are both CH₃ (methyl) groups, the molecule is known as dimethyl phthalate (abbreviated as DMP).
If R and R' are both C₂H₅ (ethyl) groups, the molecule is known as diethyl phthalate (abbreviated DEP).
When R and R' are very small alkyl groups, like methyl or ethyl groups, the phthalates are colourless, odourless liquids at room temperature and pressure.
The phthalates are added to molten plastic, allowing the phthalates to mix with with the polymer. The polar C=O groups in the phthalate molecules interact with partial positive charges on atoms in the polymer chain, for example, the C^δ+ of the C-Cl covalent bond in a polyvinyl chloride polymer.
When the plastic is cooled, the interactions between the phthalate and the polymer chains remain, and the alkyl groups of the phthalate screen the polymer chains from interacting with each other so that the polymer chains can slide over each other. This results in a more flexible plastic.


Reference:
http://www.abc.net.au/news/2013-11-19/common-plastics-chemical-linked-to-pre-term-births/5101828

Further reading:
Esters and Esterification
Bond Polarity
Intermolecular Forces


Suggested Study Questions:

1. Draw the structural formula for
   • dimethyl phthalate
   • diethyl phthalate
2. Give the molecular formula for
   • dimethyl phthalate
   • diethyl phthalate
3. On the structural formula for dimethyl phthalate, circle a benzene ring.
4. On the structural formala for diethyl phthalate, circle an ester functional group.
5. Dimethyl phthalate can be prepared in an esterification reaction using phthalic acid and methanol. Draw the most likely structural formula for phthalic acid. 
6. In chemistry, what is meant by a polar bond?
7. On the structural formula of diethyl phthalate,  show the partial charges of the atoms in the polar areas of the molecule.
8. Draw a diagram to show the interaction between dimethyl phthalate and a section of the polyvinyl chloride polymer.

Methanol and the Home-Brewer

In June 2013, a young man in Queensland died as a result of drinking homemade liquor. It is believed that the liquor contained a toxic level of methanol (also known as wood alcohol). Drinking 10 mL of pure methanol can cause permanent blindness, drinking 30 mL of methanol can kill you.

The first step in the production of homemade liquors, is the fermentation of sugar.
Methanol, CH₃OH,is formed during fermentation.
When fermenting 6 kg of sugar dissolved in water for the production of distilled spirits such as whiskey or vodka, the home-brewer (and home-distiller) will typically find that the concentration of methanol in their brew is about 3 parts per million.

Many fruits are used by the home-brewer as the source of sugar to be fermented. Each fruit will lend a distinctive flavour to the final product. But fruits that are high in pectin will produce greater concentrations of methanol. Apples, apricots, guavas, quinces, plums, gooseberries, and citrus fruits like oranges, all contain high levels of pectin, typically more than 1% by mass pectin. Grapes, cherries and strawberries contain low levels of pectin, less than 1% by mass pectin.

Pectin contains  galacturonic acid which has the structural formula shown below:

In pectin, about 80% of the carboxyl groups in galacturonic acid are esterified with methanol. The remaining non-esterified carboxyl groups exist as the acid, or as salts with sodium, potassium or calcium. When pectin is broken down by enzymes during the brewing process, the methyl esters react with water to produce methanol.

The second step in the production of homemade liquor is the distillation step.
This is the crucial step in removing as much of the toxic methanol as possible.
The boiling point of methanol is about 65^oC, but the boiling point of ethanol (the desired product) is about 78^oC. During the distillation process, the first fraction collected should contain the methanol. This fraction should be collected and discarded. The next fraction should contain the desired liquor. It is highly recommended that any distillate collected after about 96^oC also be discarded.


Reference:
http://www.couriermail.com.au/news/queensland/ballandean-man-bill-lynam-who-lost-his-son-joel-to-homemade-liquor-poisoning-is-thankful-that-other-son-joshua-survived/story-fnihsrf2-1226664893229

Further Reading
http://ausetute.com.au/members/alkanolp.html (members only tutorial on alkanols)
http://ausetute.com.au/members/carboxyl.html (members only tutorial on alkanoic acids) 
http://ausetute.com.au/partspm.html 
http://ausetute.com.au/density.html 

Suggested Study Questions:

1. Draw the structural formula for methanol.
2. Locate the functional group present in methanol on the structural formula above. Name the functional group. 
3. At 25^oC methanol has a density of  0.79 g mL^-3. Calculate the mass of methanol present in a lethal dose of pure methanol .
4.  Convert the concentration of methanol given for homemade whiskey into a concentration in g mL^-1.
5. Assume the young man who died drank homemade whiskey. What minimum volume of homemade whiskey did he drink?
6. For galacturonic acid given the:
   • molecular formula
   • molar mass
7.  On the structural formula for galacturonic acid identify and name the functional groups present.
8. Draw the structure for the sodium salt of galacturonic acid.
9. Draw the structure for galacturonic acid esterified with methanol.
10. Give the molecular formula and molar mass for the structure above.
11. Apples contain about 1% by mass pectin. 10 kg of apples are to be used in the production of a homemade liquor. What mass of pectin will be present?
12. Assume exactly 100% of the carboxyl groups in galacturonic acid are esterified with methanol. How many moles of the ester are present in 10 kg of apples?
13. Write an equation representing the reaction between this ester and water to form methanol  and galacturonic acid.
14. How many moles of methanol could be produced by the break down of pectin in 10 kg of apples?
15. Assuming the young man who died had drunk this apple concoction without distilling and removing the methanol, what minimum volume of fermented apple-drink would he have had to have drunk?
16. Why do you think most countries have outlawed home-distilling?