1. Topic 3: Organic Chemistry

2. Organic Chemistry
Organic chemistry is the study of carbon and carbon containing molecular compounds
Organic compounds often also contain contain hydrogen and oxygen.
Carbon containing compounds are sometimes called hydrocarbons
Examples include Methane, Propane, Ethanol, Methanol, Ethanoic acid (acetic acid) vinegar

3. Petrochemical Industry Crude oil is an example of an organic fuel
Petrochemical Industry Crude oil is an example of an organic fuel. Thus it is also called hydrocarbon fuels

4. Crude Oil petroleum gases(l) gasoline jet fuel kerosene diesel oil
lubricating oils
wax
fuel oil
asphalt
Fractionating tower
separates crude oil
into different
materials

5. Page 9 of your data booklet has everything organic you need to know
Alkanes
Hydrocarbons/carbon chains with only single bonds between them
Said to be saturated
General Formula is CnH2n+2
Examples include
methane (CH4)
ethane (C2H6)
propane (C3H8)
Page 9 of your data booklet has everything organic you need to know

6. Diagrams like this maybe seen on the diploma as well…
Ethane
C2H6
Methane
CH4
Hexane
C6H14

7. Naming Alkenes and Alkynes
Alkenes are hydrocarbons that contain a double bond (unsaturated)
Alkynes are hydrocarbons that contain a triple bond (unsaturated)
Unsaturated fatty acids are more reactive than saturated fatty acids
To name these, you use same prefixes as alkanes
Suffix changed:
Alkenes – ene suffix
Alkynes – yne suffix

8. Alkenes & Alkynes
CnH2n-2
CnH2n

9. Example 1 and 2 : Name these molecules
2,4 dimethylhexane C
4-methylpent-2-ene

10. Example 3 and 4 : Name these molecules
hex-2-ene C
3,5-dimethylhex-2-ene

11. Example 5 and 6 : Name these molecules
hex-3-yne C
hexyne

12. Example 7 : Name this molecule
4,5-dimethylhex-2-yne

13. Benzene Rings
Hydrocarbons are often seen in a linear shape (in a line).
But sometimes, they are in a ring shape

14. Benzene Shapes
Benzene are compounds that have a hexagonal shape and have the general formula C6H6
A benzene ring can also be called a phenyl ring or aromatic ring

15. Benzene Uses
Benzene is a stable component of:
Gasoline and plastic
rubber cement
bug repellant, fungicides.
Because benzene is stable and not easily broken down by chemical or biological means, it is classified as a persistent organic pollutant (POP’s)

16. Dangers of Benzene
Burning steak on bar-b-que forms Benzopyrene, a multiple benzene ring “polycyclic aromatic hydrocarbon (PAH)”. Bezopyrene is found in the blackened parts on the meat and can causes DNA mutations.
What are some of the dangers of benzene containing compounds?
Carcinogenic when leaked into soil and water (also present in tobacco smoke and vehicle exhaust)
Carcinogenic substances interfere with DNA base pairing
Very stable
Found in the incomplete combustion of oils, gas, diesel, wood,
Cool Trivia

17. Benzene and DNA Mutations
PAH mimics compounds naturally found in DNA
PAH is not only found on charred food but in tobacco smoke and engine exhaust

18. 1. Halogenated Hydrocarbons also called alkyl halides
Halogenated hydrocarbons are hydrocarbon molecules that has one or more hydrogen atoms replaced by a halogen (chlorine, flourine, bromine, iodine)
Examples: CFC (Freons) (Chlorofluorocarbons)
Used in refrigerators and air conditioners
Linked to stratospheric ozone depletion
PVC (polyvinyl chloride)
Carbon tetrachloride, used as cleaning solvent, now known to be carcinogenic!

19. Naming Halogenated Hydrocarbons
Naming halogenated hydrocarbons is similar to naming regular hydrocarbons
Step 1: Name the parent chain
Step 2: Find all the halogen atoms
Step 3: Determine the prefix if necessary (di-, tri-)
Step 4: Communicate where each halogen atom appears F Cl C
Example 1: CH Cl
Example 2:
Trichloromethane
Trichlorofluoromethane

20. Naming Halogenated Hydrocarbons
Example 3:
Example 4: C Cl F Cl C
1,1,2- trichloro-1,2,2-trifluoroethane
Tetrachloromethane

21. Ozone and Concerns Regarding CFC’s
There are 2 types of ozone that exists in our atmosphere:
1. tropospheric (low level) ozone …the bad stuff
2. high altitude ...in the stratosphere…good stuff!!
Absorbs and protects us from excess UV radiation
Chlorofluorocarbons (CFC’s) cause stratospheric ozone to become thin = extra UV radiation

22. Harmful Halogenated Compounds
Many compounds contain halogenated compounds
Examples:
DDT (dichlorodiphenyltrichloroethane) – used in pesticides
Dioxins and furans (contains Cl2)- by product of pulp & paper industry
PCB’s (Polychlorinated biphenyls) – used in older electric transformers
agent orange (herbicide)
burning garbage that contains chlorine
DDT, dioxins and furans and PCB’s can bioaccumulate in the food chain
Many alkyl halides and benzene compounds cause birth defects and are known as teratogens

23. Abnormal bill: cannot eat!!
DDT
Synthetic organic pesticide
Initially mixed with talcum powder
Put into soldiers clothing
Helped prevent spread of typhus, malaria, yellow fever
Eventually used as pesticide to kill insects
Affects calcium metabolism in organisms hence
joint problems occurred in soldiers
deformities seen in fish
abnormally thin egg shells in birds
Double crested Cormorant
From Great Lakes
Crossed bill
caused by DDT
Abnormal bill: cannot eat!!

24. Agent Orange Herbicide used during Vietnam war
Defoliated jungles
Caused birth defects
Contains 2 main ingredients:
2,4,5-T and 2,4-D
2,4,5-trichlorophenoxyacetic acid
2,4-dichlorophenoxyacetic acid
Dioxins are a by-product of the manufacture of these

25. 2. Alcohols All alcohols contain a hydroxyl functional group Examples:
--OH (not hydroxide)
Examples:
CH3CH2OH (ethanol)
CH3OH (methanol)

26. Naming Alcohols Name is the same as with alkanes, EXCEPT:
Step 1: Drop the e from ane
Step 2: Add -ol
CH3OH (methanol)
C2H5OH (ethanol)
C3H7OH (propanol)
C4H9OH (butanol)
Step 3: Position of the OH group should be indicated if necessary
(2-ol means the hydroxyl is on carbon 2)

27. Name these molecules C OH
Pentan-3-ol C OH
Pentan-2-ol

28. Name this molecule C C C C C C OH
Hexan-3-ol

29. Carboxylic Acids
All carboxylic acids contain the carboxyl functional group – COOH
Common carboxylic acids include:
Vinegar
Citric acid
Lactic acid (build up in muscles causes cramping)
Asprin (acetylsalicylic acid)
Organic acids have similar properties as acids studies earlier.
Carbonyl group
hydroxyl group

30. Propanoic acid prevents mold growth in bread
Carboxylic Acids
Naming carboxylic acids
Step 1: alkane base, drop “e”
Step 2: add “-oic acid” C H OH O C H OH O
Methanoic acid found in bee stings
Propanoic acid prevents mold growth in bread

31. Esters
Esters are formed from a carboxylic acid and alcohol joined together
All esters contain the –COO- functional group
This is found in the middle joining the carboxylic acid and alcohol
Esters are commonly found in fats, polyester, plastic (bioplastics), soap and used as flavour and aroma

32. A
Membrane
Lipids B
Storage
Fats C
True
Waxes
Esters

33. Synthesis of Polyesters
Identify the
functional groups!!
It’s important to know that polyesters are made of an acid and an alcohol joined together.

34. Naming Esters C O H Methyl methanoate
Naming esters: (Esters always end in …oate)
Step 1: Find the ester functional group and circle it.
Step 2: Name the alcohol chain (single bonded oxygen) attached to the carbon
(ex. Methyl-)
Step 3: Name the carboxylic acid (double bonded oxygen) attached to the carbon (ex. Methan-)
Step 4: Combine the 2 names followed by the suffix -oate C O H
Example 1
Methyl methanoate

35. Naming Esters C O H C O H Ethyl ethanoate Ethyl methanoate Example 2

36. Pesticides and persistent organic pollutant (POP’s)
Identify the functional groups
A pesticide is a substance used to kill unwanted fungi, insects, animals and plants
Recall: Many pesticides contain halogenated hydrocarbons, especially Cl and benzene !!!!

37. Identify the functional groups in the following POP’s
Carboxylic acid, benzene, halogenated hydrocarbon
2,4-D
Carboxylic acid, benzene, halogenated hydrocarbon
dioxin
benzene, halogenated hydrocarbon

38. Effects of Insecticides
Most affect the nervous system
Some inactivate cholinesterase (an enzyme in the synapse)
Without cholinesterase, acetylcholine continuously stimulates post synaptic fiber causing convulsions & death!
Can mix with water and affect soil and aquatic organisms
Can drift to areas where insecticides are not used
Can lead to pesticide resistant organisms
Target Specific: so that it minimizes effects on other organisms and the environment

39. Fertilizer and Organic Matter
Excess use of fertilizers rich in nitrogen and phosphorous can leach from fields into our water system.
This results in what is known as an algal bloom (increase in algae)
Is this bad?
Yes, it uses up all the oxygen available in the water.

40. Biological Oxygen Demand (BOD)
BOD is the measure of the amount of oxygen used by microorganisms (such as algae) as they decompose waste
High BOD indicates that there is a high amount of organic waste or sewage in our water systems
Things that increase BOD:
Large amounts of organic waste
Nitrates and phosphates from run off and fertilizers (= high algae growth)
Warm temperatures
Answer to the table is ACB and BAC
Is high BOD a good thing?

41. Biomagnification
Biomagnification, aka bioamplification, or biological magnification
the increase in concentration of pesticides, dioxins and furans and heavy metals as we move up the food chain or very slow
breakdown of the substance (accumulate in water).
Toxins accumulate in fatty tissues and are not released in wastes

42. Alternatives to Chemical Insecticides
Genetically engineering plants to produce own pesticides, or are resistant to pests
Biological control / Natural Predators …ladybugs in Muttart
Sterilizing males …by radiation or chemicals
Juvenile hormone …prevent adulthood & breeding
Pheromones …baits males into traps & disorients males so they can’t find a mate