Organic and Biochem , Part 1

1. Organic and Biochem, Part 1 SOL Objective CH. 6

2. SOL CH. 6 • Not really a separate objective. CH = chemistry, not chapter. • This year, we will have an Organic Chemistry and Biochemistry “flavor” from time to time. • Organic = any compound which contains carbon. Organic compounds usually also contain H and some combination of O, N, S, P, Cl and other elements. • Biochem = study of organic compounds which appear in living things.

3. Organic Products • Many of you probably buy organic products from grocery stores (I do too sometimes). • This means something different from Organic Chemistry. • Organic products do not use chemical fertilizers or pesticides or irradiation (used to prevent onions and potatoes from sprouting) or chemical additives (to enhance taste or appearance).

4. Organic Products ≠ Organic Chemistry • Many people prefer organic products for lots of reasons. People think they are eating healthier and not putting “chemicals” into their body by using organic products. • However, scientific evidence (so far) proves that there is little difference in organic produce in terms of taste, safety and nutritional value compared to “non-organic produced” food.

5. Organic Chemistry • All produce (organic or not) are composed of organic chemicals. This includes most foods and drinks you consume. • So are all pharmaceuticals (medicines and drugs), plastics, and many products you use and wear everyday. • Some organic chemicals are poisonous (toxic) or carcinogenic (cause cancer potentially), but many are tasty and even vital for life.

6. Organic Compounds • All organic compounds contain C. • However, not all organic compounds come from nature or living things. • But some do. • For example, some medicines come from natural products. Some medicines were created by scientists in a lab.

7. Natural vs Synthetic • Penicillin was originally isolated from a fungus and found to have antibiotic (kills bacteria) properties. However, the demand for penicillin soon outgrew the ability to get it from fungi and organic chemists figured out how to synthesize penicillin in the lab. • Regardless of whether it is found in nature or synthesized in a lab, all penicillin must have the same properties and be exactly the same in every way.

8. Important Pharmaceuticals • Think medicine. Pharmaceuticals are any chemical substances used for the diagnosis, cure, treatment or prevention of disease. • Common pharmaceuticals you should know • Aspirin • Vitamins • Insulin • All of the above are organic chemicals. • All of the above can occur naturally or can be synthesized in the lab.

9. Aspirin • Aspirin occurs naturally in willow tree bark. • Hippocrates (father of modern medicine) was known to make a powder of willow bark and leaves to cure headaches and fevers as early as 400 BC. • Aspirin was first isolated chemically in Germany in 1897 at Bayer, a chemical company. • Aspirin is quite easy to make in the lab. Many pharmaceutical products are very difficult to make.

10. Inorganic Chemistry • All chemicals which do not contain carbon are inorganic. • Additionally, some compounds which do contain carbon are NOT organic. Examples include: • Carbides (metals bonded to carbon) • Carbonates • Carbon dioxide (CO2) • Note that although water is VITAL to human life, water (H2O) is an inorganic compound, because it doesn’t contain any carbon.

11. 5 Branches of Chemistry • Inorganic Chemistry is the study of compounds which do not contain C. • Organic Chemistry is the study of compounds which DO contain C. • Biochemistry is the study of chemical processes which exist in living organisms. • Analytical Chemistry is the study of the separation of mixtures of compounds and identifying and quantifying those compounds. • Physical Chemistry is the study of physics as it applies to chemical systems at the atomic and molecular level.

12. -C-C-C-C-C-C-C-C- • Carbon has some unique properties which organic chemistry is based upon. • It can form long chains (or rings) by bonding to other carbons. • Each C forms 4 bonds. In addition to bonding to other carbons, carbon’s unique size as a Period 2 element allows it to form strong bonds with H and O and N and many other elements.

13. -C-C-C-C-C-C-C-C- • This ability to form long chains allows carbon to bond with itself to produce literally millions of unique compounds. • C can also form double and triple bonds with other C atoms. • Additionally, C can form double bonds with O. • C can form triple bonds with N.

14. Hydrocarbons • The simplest organic compounds are called hydrocarbons. • These compounds ONLY contain C and H. • Hydrocarbons are also called “fossil fuels” (because they come from decomposed living things) and “petrochemicals” (because they are found in petroleum). • Petroleum is a mixture of hydrocarbons found in geologic formations beneath the Earth’s surface.

15. HC = Hydrocarbons • Petroleum (also known as crude oil) is separated through a physical process called distillation. • In distillation, you boil a mixture of hydrocarbons. Since each hydrocarbon has a unique boiling point, they can be separated from each other in this way. • The simplest HC is methane. Methane’s formula is CH4. Learn this!

16. Methane • Methane boils at 90K. Since room temp = 298K, it is obviously a gas at room temp. • It is also called “natural gas.” • It comes out of the gas jets when we do labs which require a Bunsen burner. • The temp of a Bunsen burner flame is about 1,500 - 2,000°C.

17. Other Distillation Products • Gases from Petroleum • Ethane, C2H6, used primarily to produce ethene (also known as ethylene) which is used to produce plastics, such as polyethylene, and is also used force the ripening of fruit. • Propane, C3H8, also known as LP gas (liquified petroleum), can be stored as a liquid at low pressures. Used as fuel for gas grills. • Butane, C4H10, can also be liquified easily at low pressures. Used as fuel in cigarette lighters.

18. Other Distillation Products • Liquids from Petroleum • Gasoline (primarily octane, C8H18, but contains HC with 5-12 carbons). • Kerosene (contains HC with 12-16 carbons). Used for lamps, stoves and portable heaters. • Fuel Oil (contains HC with 15-18 carbons). Used for heating houses. Also used in diesel engines. • Lubricating Oil (contains HC with 16-20 carbons). Use as motor oil in car engines.

19. Other Distillation Products • Solids from Petroleum • Residue (solids remaining with > 20 carbons after distillation); used to make asphalt. • Paraffin wax (20-40 carbons). Has a variety of uses, but used to make candles which burn at a very low temp (40-50°C). It is white and odorless and tasteless. James Chadwick used it in experiments to identify the neutron. • Liquid paraffin is called mineral oil.

20. Wait! What? Wax was used to discover the neutron? • Chadwick in 1932 usedαparticles (emitted from radioactive Po) and bombarded Be. • Beryllium emitted neutrons during this experiment, but they were hard to detect, because they have no charge. • He put some paraffin in the path of these new particles. They hit the paraffin and knocked out some protons (hydrogen ions).

21. Wax. Seriously. • Protons have a positive charge and were much easier to detect. Obviously something had to hit it which had enough mass and force to knock the protons loose. • He figured out that the neutron had a little more mass than the proton. • Since it had no charge, the particles didn’t repel when it got close to the positively charged nucleus, and therefore, nothing slowed it down until it collided with the H which it then knocked out of the wax. • We will talk about this more in Unit 2 also (and it might make more sense then too).

22. Types of HC • Alkanes: only contain C-C single bonds. Known as saturated HC. It is saturated because it has the maximum number of hydrogens bonded to the carbons. • Alkenes: contains at least 1 C=C double bond. • Alkynes: contains at least 1 CΞC triple bond. • Alkenes and alkynes are unsaturatedHC, because more H could be bonded to the C atoms.

23. Reactivity of HC • The structure of the molecule helps determine the properties of the compound. All alkanes react the same, but they react differently compared to alkenes or alkynes. • Alkynes are MOST reactive. • Alkanes are least reactive. • That means alkenes are somewhere in the middle.

24. Reactivity of HC • From this you can extend your knowledge and predict • that triple bonds are more reactive than double bonds • and double bonds are more reactive than single bonds. • We will talk about WHY this is the case in later units.

25. Polymers • Large molecule composed of repeating units of simple molecules (called monomers). • Think about Legos. Each block is a monomer. When you hook a bunch of blocks together, you get a large chain (the polymer). • There are two types of polymers (more on this in a later unit). • Addition • Condensation

26. Polymers • Natural Polymers • Proteins (monomer = amino acids) • Starch and Cellulose (monomer = sugar molecules) • DNA and RNA (monomer = purine and pyrimidine bases) • Synthetic Polymers • Plastics • polyethylene (PE) also known as polythene • polyvinylchloride (PVC) • polystyrene also known as Styrofoam • Sodium polyacrylate (the absorbent polymer in Huggies diapers) • Fibers (nylon, rayon, polyester) • Kevlar • Teflon (polytetrafluoroethylene)

27. The End What Did you Learn?