Q. Just what exactly is organic chemistry?

A. In the early days of chemistry, scientists found they could extract interesting compounds from substances sourced from living systems, such as butter, animal fat and so on. For this reason, these isolated chemicals generally became known as “organic.”. Today, organic chemistry is more generally considered to be the study of chemicals which are primarily based on carbon (although there are a few exceptions, such as carbon dioxide, which is not considered organic). The vast majority of chemicals are organic by this definition, including vitamins, proteins, pesticides, plastics and many others.

Organic chemistry involves understanding the structures and names of these compounds as well as how they react and how they are synthesized.

Cadbury’s creme eggs. How do they get that yolk such a bright yellow?

Q. Why do we study organic chemistry?

A. In many ways, organic chemistry is the gateway to the study of many other sciences, including biochemistry and biology. A good knowledge of the basics of organic chemistry lets you understand how living systems function, since biological systems are mostly made of organic compounds.

In addition, many industrial processes are essentially organic chemistry. The paint and coating, nutraceutical and pharmaceutical industries all involve organic reactions, for example.

As well, some knowledge of organic chemistry is also useful in just about any field of science for practical reasons. A lot of organic compounds are used as solvents, for example, so its helpful to know the difference between ethanol, methanol and isopropanol.

Q. What do we learn in the lectures?

A. All kinds of things! We begin with a brief study of how organic molecules are put together, by talking about bonding and electron structures. We then learn how to name organic compounds using the formal naming system devised by IUPAC.

As well, we learn about the most common reactions of organic chemicals. We’ll discuss how some everyday organic compounds are made, such as polyethylene, aspirin and 2,4-D.

The fascinating effects of isomerism are also considered. Isomers are chemicals which have the same atoms but different properties depending on how the atoms are put together. For a good intro to isomerism, check out this video.

Finally, the course also teaches the theory and practice of some common lab techniques, such as distillation.

Q. What about labs?

A. There are five to six lab sessions in each of the two organic chemistry courses. In these labs, you will apply the theory and see the results in action. Experiments include synthesizing interesting chemicals, such as a bright red dye (an azo dye: see the photo above and the note below!). You will also learn many standard organic lab techniques, such as distillation, recrystallization and melting point analysis. If you ever wanted to start making moonshine whiskey in your backyard shed, this is your starting point! (just kidding, please don’t start making moonshine in your shed.)

Q. Is it tough?

A. Organic chemistry can be challenging, but it’s doable! The subject matter is not extremely difficult, but it requires dedication and good study habits since there is a bit of memorization required in some places to be able to use the nomenclature system and also to recall the various reactions. However, if you can remember that positive and negative charges attract each other, you have just conquered about half of organic chemistry.

Note: the image shows Cadbury’s Easter Creme Eggs, which were recently involved in a scandal when the treat was found to contain an azo dye after the company had promised to remove it.

The active ingredient in Tylenol and many other painkillers is a drug known as acetaminophen (or sometimes paracetamol). Acetaminophen has been around for a long time and works pretty well, but it’s well known that this particular drug is highly toxic to the liver when taken in overdose or when the patient’s liver function is already compromised (this is why you do NOT take Tylenol for a hangover!). In the U.S., for example, acetaminophen is believed to be responsible for about half of all cases of acute liver failure.

Acetaminophen (top) and new potential replacements (bottom).

The liver toxicity occurs because liver enzymes metabolize the drug into a harmful compound known as an iminoquinone. This metabolization has nothing to do with the pain killing function of acetaminophen and so a drug which is not metabolized in this way but still works to reduce pain would be beneficial.

A recent publication in ACS Medicinal Chemistry Letters details preliminary attempts to synthesize analogues of acetaminophen which still work like acetaminophen but don’t generate toxic metabolites. These are based on tweaking the acetaminophen structure to add two heterocycles in place of the single benzene ring in the original structure.

The new drugs are still in the preliminary stages and it’s not yet known if they will work. There is a precedent, however, the even more popular painkiller ASA (i.e. Aspirin) is based on tweaking the structure of an older drug.

2,4-dichlorophenoxyacetic acid (2,4-D) is a widely used synthetic herbicide. It affects only “broadleaf” plants (typically the plants we consider weeds) and not grasses or most crops, hence it can be widely applied without harming desirable vegetation. This chemical mimics natural plant hormones and causes rapid, uncontrolled growth of broadleaves, leading to death of the plant. Pure 2,4-D is actually relatively insoluble in water and so other forms, such as esters and salts, are now more widely used.

The 2,4-D structure.

2,4-D is applied so commonly that a 2003 study found that 63% of homes contained traces of this chemical in household dust! It was also a component of the infamous Agent Orange herbicide used during the Vietnam War. Exposure of military personnel to Agent Orange was subsequently connected to a wide variety of health problems. Currently, it is believed that these health issues were actually more likely due to the presence of other chemicals present in Agent Orange, such as traces of dioxin.

Who says data has to be dull? During the Fall 2012 session of the Chemical and Biosciences Data Analysis course, students had the opportunity to satisfy their curiosity concerning whatever subject they were interested in by using a statistical technique known as Analysis of Variance or ANOVA. Simply put, ANOVA compares two or more groups of numbers to see if there is a difference between them. Often, each of the groups is associated with a variable and so the test really tells you if one or more variables has some kind of effect. You can use ANOVA to test for the effect of just about any variable on just about anything you choose.

A generic cup of coffee (just in case there are any copyright issues!)

OK, so maybe that doesn’t sound all that interesting, but the fun part is choosing your variables!

Second year students were given the task of asking any question they wanted to and using ANOVA to find out the answer. They came up with some very creative questions, including …

• which weapon in a video game gives the best score on a tough level?
• do I answer math questions better after I run up a flight of stairs?
• does my cat prefer to play with string, bottle caps or twist ties?
• which brand of juice does my son prefer?
• which artificial sweetener tastes best?

Perhaps the most vital question of all, though, was “Which Tim Horton’s on campus has the shortest line up and when?” Students clocked wait times at our two locations at both 9 a.m. and 1 p.m. Surprisingly, the ANOVA test showed there were no statistically significant differences in wait times based on either the location or the time. Actually, this result is not surprising because most people will tell you that no matter which grocery line up you’re in, it’s the slowest. Now at least we know the best location to go to; whichever one is closer, since it doesn’t really make a difference.

Androstenedione (or “andro”) is a naturally occurring human hormone which is produced in the body as a precursor to other hormones such as testosterone and estradiol. Andro does not appear to be anabolic (does not promote muscle growth) but it can possibly enhance sports performance by temporarily raising testosterone levels in the body (meaning it falls into the category of compounds known as “androgenic”).

The structure of androstenedione.

Andro was legal in North America up until the end of the 1990’s and was used by popular sports figures such as Mark McGwire who, in 1998, broke the record for most home runs hit in a season. So perhaps it does help! It’s not recommended as  a sport supplement, however; as with other androgenic compounds, it carries the risk of side effects ranging from liver problems to cancer.

My name is Rachel Molloy and I was lucky enough to get a Summer Student Co-Op position at the Public Health Agency of Canada’s National Microbiology Laboratory.
The main objective for this position is to perform biological inventories of enteric bacterial pathogens that are considered level two pathogens. The lab I work in is accredited to ISO 17025. While performing my everyday duties I have been able to exercise and refine my skills in the areas of laboratory notebook keeping, standard operating procedures, GLP’s, MSDS’s, PSDS’s, Microsoft Office and general organization.

Rachel at work (photo property of the Public Health Agency of Canada’s National Microbiology Laboratory)

I am also receiving training in a variety of laboratory techniques that are used to do basic surveillance and for outbreak investigations, including molecular and genetic methods plus classical microbiology and tissue culture.

There are also many other services available at the National Microbiology Laboratory that I have taken full advantage of when I am not hard at work. There is a library on site with tons of science related literature and lots of seminars available on the science of infectious diseases (I attended one recently about the role of proteomics in HIV research).

The staff here are friendly and educated. I participate in my unit’s weekly meetings and have found the whole experience to be very welcoming.

I am grateful for those at the National Microbiology Laboratory for the wonderful experiences that I continue to have, and for Red River College for providing me the chance to have those experiences.

Theobromine is an alkaloid chemical produced by the cacao plant and thus is found in chocolate. Its molecular structure is very closely related to that of caffeine and it has some of the same properties – such as acting as a stimulant – albeit to a lesser extent.

The theobromine molecule.

Although one might expect to find bromine in this chemical, its name is actually derived from the Greek phrase “food of the gods” which is a pretty good description of chocolate!
In addition to being a weak stimulant, theobromine also has some other physiological effects. It can act as a diuretic and has been found to be better than codeine at stopping persistent coughs, due to its effect on the vagus nerve. Theobromine is also responsible for the fact that chocolate is toxic to dogs and some other animals.

Did you know that more than half of a dose of the common antibiotic amoxicillin moves right through the body and is excreted unchanged? That drug ends up in the sewer system and eventually at the local wastewater treatment plant, along with hundreds of other pharmaceutical compounds, antibacterials and related chemicals. Most municipal wastewater plants receive a constant stream of so-called micropollutants such as amoxicillin, present at levels in the part per billion or part per trillion range. Since these plants aren’t built to remove micropollutants, they pass right through and end up in our rivers and lakes. This is a growing concern, since many of these pollutants can eventually affect aquatic life and may also appear in drinking water supplies.

Michael Judge and Karanveer Singh of the Chemical and Biosciences program are currently working on a project, funded by the college Applied Research Department and the National Research Council of Canada, which is examining possible methods of removing micropollutants from wastewater. The project involves an extensive literature review of the existing methods, as a first step towards formulating a more ambitious research endeavor to investigate optimized removal processes. In addition, Karanveer is carrying out preliminary research into the optimization of high pressure liquid chromatography (HPLC) as a means of following the removal of selected micropollutants.

The tubocurarine molecule.

Tubocurarine is an alkaloid found in the bark of a South American vine. It is one of a number of toxic compounds known under the general name of “curare.” Tubocurarine is capable of paralyzing muscle tissue by interfering with the transmission of the nerve impulses which normally control muscle movement. For this reason, it only affects voluntary muscles (not the heart muscle, for example). However, since the diaphragm is a voluntary muscle, it can be fatal by inducing asphyxiation.
Traditionally, curare poisons have been used by South American hunters to coat arrows and darts in order to kill prey. Interestingly, curare does not pass through the digestive tract and so poisoned prey can be eaten without harm! Tubocurarine has also been used as a muscle relaxant during surgery to prevent unwanted movement of the patient, although it has now largely been replaced by synthetic drugs which provide the same effect but more safely.

Q. What does the Chemical and Biosciences Co-op Diploma program prepare students to do?

A. Our program trains students to work as technicians or technologists in a wide variety of corporate or government testing and research laboratory settings, as well as in other science-based environments, such as in the chemical, pharmaceutical or food processing industries. Students learn a range of skills, incorporating both chemistry and biology and, as a result, they may find work in many different fields and organizations, carrying out many different duties.

The following job descriptions are taken from the Canadian Council of Technicians and Technologists:

Things that Chemical technicians and technologists do at work are:

• Set up and conduct chemical experiments, tests and analyses using techniques such as chromatography, spectroscopy, physical and chemical separation techniques and microscopy.
• Operate and maintain laboratory equipment and apparatus and prepare solutions of gas or liquid, reagents, and sample formulations.
• Compile records and interpret experimental or analytical results.
• Develop and conduct programs of sampling and analysis to maintain quality standards of raw materials, chemical intermediates and products.
• Assist in the development of chemical engineering processes, studies of chemical engineering procurement, construction, inspection and maintenance and the development of standards, procedures and health and safety measures
• Operate experimental chemical or petrochemical pilot plants.
• Conduct or assist in air and water quality testing and assessments, environmental monitoring and protection activities and in the development of and compliance with standards.
• Assist in the design and fabrication of experimental apparatus.

Things that biological technicians and technologists do at work are:

• Conduct or assist in biological, microbiological and biochemical tests and laboratory analyses in support of quality control in food production, sanitation, pharmaceutical production and other fields.
• Perform or assist in experimental procedures in agriculture, plant breeding, animal husbandry, biology and biomedical research.
• Conduct field research and surveys to collect data and samples of water, soil, plant and animal populations.
• Conduct or assist in environmental monitoring and compliance activities for the protection of fisheries stock, wildlife and other natural resources.
• Conduct or supervise operational programs such as fish hatchery, greenhouse and livestock production programs.
• Analyze data and prepare reports.

Q. How does your program differ from a university BSc program?

A. Our program differs in a few important ways. For one thing, our program is compressed to two years, whereas a BSc is typically three or four years in length. This allows students to get out into the workforce as soon as possible and also reduces the overall cost of the educational process.

As well, although we teach a significant amount of theory, our main focus is on providing students with the applied skills that they need to make an immediate contribution to their employer. Our instructors typically have worked for years in industry or government before joining the college, and so we have a good understanding of the skills that are necessary for a successful career.

Q. How does the co-op portion of the program work?

A. During the first eight months of each year, students attend classes. During the last four months of each year, students typically work for an employer, which not only provides valuable  experience and contacts, as well as income, but also counts towards the credits necessary for graduation. For obvious reasons, we can’t force employers to hire students, and so we can’t guarantee that every student will receive a co-op placement, but our program does have a dedicated co-op coordinator whose job involves identifying suitable employers and communicating job opportunities to students. Our instructors also work closely with students to provide the skills and coaching necessary to write great resumes and to interview well. It is rare for a student who puts a reasonable amount of effort into their job search not to find co-op employment.

Q. Where do your students end up working?

A. All over the place! Our students have been hired by the City of Winnipeg, as well as by Health Canada. Many students find work at one of the numerous pharmaceutical organizations in Winnipeg. We also have students working in research labs, such as the St. Boniface Research Center. Others find employment in the painting and coatings, plastics or aerospace industries while still others are hired by food or agriculture businesses.

Q. What can I expect to earn as a graduate?

Over the last few years, students have earned an average annual starting salary of about $37,000 immediately after graduation. Some students have reported starting salaries as high as $50,000, but those students may already have had other degrees or experience.

A 2013 survey by the Manitoba chapter of CCTT found that the average salary of someone working in Manitoba as a technologist with a college diploma was about $75,000. This higher salary reflects the compensation that technologists typically receive later in their careers.

Q. What are my chances of finding employment coming out of the program?

Pretty good! On average, about 80% of students find employment in their field of study immediately following the program. Approximately another 10% go on to further educational studies.

Q. What do your students say about the program?

Each year, the college surveys graduating students and asks for their opinion of the program. For the last four years, 100% of students who responded to the survey said that they were satisfied or very satisfied! Over the last 15 years, the average satisfaction rate has been 95%!