Download Science 30 Section 1 - Organic Chemistry and Pollution

Science 30
Section 1 - Organic Chemistry and Pollution
Name________________________________________________
Section 1




Section 1.1 - Basic Chem Review and Naming Hydrocarbons (Sci 20 Review)
Section 1.2– Function Groups: Halogenated Hydrocarbons
Section 1.3 – Functional Groups: Alcohols, Carboxylic Acids, and Esters
Section 1.4 – Exposure of Organic Chemicals in the Environment
Science 30 –Section 1 Organic Chem
Page 1
Section 1.1 – Basic Chemistry Review
The Periodic Table Review
•
•
•
•
•
•
•
•
Work on atomic theory led to advances in designing the periodic table.
The periodic table – The known chemical elements organized by their atomic structure.
(Currently 118)
Can be organized in different ways.
Individual boxes on the periodic table represent elements. When they combine in definite
proportions (ex. H2O, CO2, NaCl) they are called compounds.
Metals / Non-Metals
– The staircase separates the metals
and non-metals.
– Left = Metals
– Right = Non-metals
Groups / Periods
– Horizontal Rows = Periods
– Vertical Columns = Groups / Families
Atomic Mass
Solid / Liquid / Gas (at room temperature)
Science 30 –Section 1 Organic Chem
Page 2
Chemical Bonding and Naming Review
Ionic Bonds
Properties





Form between metals and nonmetals forming a crystal lattice.
Electrons are transferred (or
stolen)
Form solids
Very strong bonds / high melting
points
Ex. NaCl, LiF, MgBr2
Molecular (Covalent) Bonds







Form between two or more nonmetals
Electrons are shared.
Form solids, liquids and gasses
Weaker bonds / lower melting
points
Names often have prefixes (di, tri,
tetra, etc…) or common names
Ex. H2O, CO2, NO.
Some molecular compounds are
diatomic (they are on the
periodic table) and exist in
nature as pairs. Ex. O2, N2, H2
Organic Chemistry
Organic chemistry – the study of compounds composed of _____________________________
Hydrocarbons
– Simplest type of organic molecules
– Contains ________________________________________________________
– Can have ________________________________________________________
– Hydrocarbons play an important role in the petroleum industry.
Science 30 –Section 1 Organic Chem
Page 3
Naming Rules for Hydrocarbons (Nomenclature)




Single Bonds use –ane ending. (Double bond use –ene ending. Triple bond use the –yne
ending. Won’t be using them in this course…)
Start by finding the longest /parent chain.
Second, name all the branches. Number the chain so the first branch has the lowest
number possible.
If there is more than one branch of a certain length, use the prefixes (di, tri, tetra).
Branches are listed in alphabetical order without the prefix (i.e. ignore the di, tri, etc. when
ordering)
Science 30 –Section 1 Organic Chem
Page 4
Science 30 –Section 1 Organic Chem
Page 5
Examples: Make each compound using the kits then name it.
a)
b)
c)
d)
Science 30 –Section 1 Organic Chem
Page 6
e)
f)
Science 30 –Section 1 Organic Chem
Page 7
Hydrocarbons – Hexagonal Rings
•
Most of the hydrocarbons we looked at were in chains but they also exist in _________________
– Use different names for the same rings _______________________________________
•
Examples: benzene, tolulene, xylene,
naphthalene
Benzene Rings
• Years ago, naturally present in gasoline
• Found to be a __________________________________________________________________
• Levels in gasoline are now legislated
• If a spill occurs  leaching into ground water
• Contaminated soil must undergo______________________________________
– ______________________________________________________________________
•
•
Rings (such as benzene) are much harder to break down as they are _______________________
Known as _____________________________________________________________________
•
•
In linear hydrocarbons double bonds cause reactivity
In rings they are actually more stable because of Resonance
– Electrons shared by ALL carbons
Represented by new symbol
HIGHLY stable
•
•
Science 30 –Section 1 Organic Chem
Page 8
Section 1.1 Homework
1. Name the following:
a)
b)
c)
Science 30 –Section 1 Organic Chem
Page 9
2. Draw the following using a complete structural diagram and a line structural diagram
(Remember, each Carbon will have a maximum four bonds coming off of it. Each hydrogen will
have only one bond. Bond = Line)
a) Methane
b) 3-ethylhexane
c) Propane
d) 2,3-dimethylbutane
e) Octane
f) 5-ethyl-2,3-dimethylheptane
Science 30 –Section 1 Organic Chem
Page 10
Section 1.2 – Function Groups: Halogenated Hydrocarbons
(textbook reference – section 2.2 of Chem)
Objectives:
- identify and name carbon compounds, using IUPAC nomenclature that contain up to three
carbon atoms in the parent chain.
- list the sources of, and analyze the hazards posed by, halogenated hydrocarbons and benzene
derivatives
Functional Groups
See P. 249 for more examples.
Halogenated Hydrocarbons
Science 30 –Section 1 Organic Chem
Page 11
Naming Halogenated Hydrocarbons
1. Name parent chain (Ex. METHANE)
2. Locate all halogens (Ex, 4 fluorine)
3. Use halogen names
– Fluorine  fluoro
– Chlorine  chloro
– Iodine  iodo
– Bromine  bromo
4. Use prefixes for halogens (tetraflouro)
– Mono, di, tri, tetra, penta, hexa
5. NAME: tetrafluoromethane
Example 1:
Example 2:
Example 3:
Science 30 –Section 1 Organic Chem
Page 12
Halogenated Hydrocarbons
•
•
•
•
Most famous  ____________________________________________________________
Invented in the 1920s as a replacement for gases used in air-conditioning and refrigerants
Scientists discovered __________________________________________________________
____________________________________________________________________________
______________________________________________________________releasing a chlorine atom which interacts with
ozone and breaks it down
(Write the reactions below)
Protecting the Ozone Layer
• Montreal Protocol (p. 258)
• ______________________________________________________________________________
– HCFC (hydrochloroflurocarbons) are a better idea because they contain fewer chlorine
atoms
– HFC (hydrofluorocarbons) contain NO chlorine
– Halon (possibly worse for ozone than chlorine containing compounds not under
Montreal Protocol)
Science 30 – Section 1 Organic Chemistry
Page 13
Other Halogenated Compounds
• Many types of ________________________________________________________________
_____________________________________________________________________. (p. 259)
• Have a tendency
______________________________________________________________________________________________________________
______________________________________________
Science 30 – Section 1 Organic Chemistry
Page 14
Section 1.2 Homework
Read p.253-259 and answer the following in your workbook.
1.
2. Draw 1,1,2,2-tetrafluropropane.
3. Draw 1,1,2,2,3,3-hexachlorobutane.
Science 30 – Section 1 Organic Chemistry
Page 15
4. Suppose you are helping to dispose of an old non-working refrigerator or air-conditioning unit
found in the home of an elderly relative. Explain why it is important to ensure the refrigerant in
the appliance is properly disposed.
5. Read p.253 – Explain how CFC’s damage the ozone.
6. Read p.256 – Determine the locations on the Earth where the ozone layer is the lowest.
7. Read p.258 – What were some of the actions taken to protect the ozone and what effect did they
have?
Science 30 – Section 1 Organic Chemistry
Page 16
Section 1.3 – Functional Groups : Alcohols, Carboxylic Acids, and Esters
Objectives:
• Use IUPAC naming to identify and name alcohols, carboxylic acids, and esters.
• Identify some of the uses in daily life of functional groups.
Alcohols
•
•
•
Contain hydroxyl function group (R-OH)
Suffix “ol” on their names
– E.g. methanol, ethanol, propanol.
Common uses include use as a antifreeze, fuel, beverage,
solvents, hand sanitizers, and preservative.
Example Problem 2.6
• Draw the structure and name CH3CH2OH. Identify the location of the functional group.
Carboxylic Acids
•
•
•
Contain TWO function groups
– Hydroxyl group (C bonded to OH)
– Carbonyl function group (C double bonded to O)
– Combined forms Carboxylic group
– Represented as R-COOH
– Suffix “-ic acid”
Ex: formic acid, acetic acid (vinegar)
Found in many soaps and oils.
Identify the functional groups
Science 30 – Section 1 Organic Chemistry
Page 17
Esters
• Formed by reaction between a carboxylic acid and an alcohol
• During reaction water is produced
• Fats, fatty acids in the body are esters
• Can be used to enhance odours
Use a two name system made up of the acid and the alcohol (ending in –ate)
Identify the functional groups
Example #1
Example #2
Science 30 – Section 1 Organic Chemistry
Page 18
Polyesters
• Reaction of many alcohols and carboxylic acids
• Forms long chains
– Towropes, t-shirts, personal flotation devices
• Both the carboxylic acid and the alcohols must have two functional groups so it can grow on
both sides (p.276)
• Other key words: polymer, plastics (p.275)
Summary
Know the Following Applications
Methane: Natural gas. Not toxic, but combustible. Alkane
Ethanol: Used as a fuel in combustion engines, alcoholic beverages, hand sanitizers.
Ethanoic Acid (Acetic Acid): Vinegar – weak acid, used in cooking, cleaning products, industrial use for
paints, solvents, and ester production.
Benzene: Industrial intermediate used in production of rubber, lubricants, drugs, explosives, and
pesticides. Found naturally in crude oil.
Science 30 – Section 1 Organic Chemistry
Page 19
1.3 Homework
1. Fill in the table below for alcohol:
Alochol
with….
1 carbon
Drawing
Systematic Name
methanol
2 carbon
3 carbons
4 carbons
5 carbons
Science 30 – Section 1 Organic Chemistry
Page 20
2. Fill in the table below for carboxylic acids:
Carboxylic
acid with….
1 carbon
Drawing
Systematic Name
methanoic acid
2 carbon
3 carbons
4 carbons
5 carbons
Science 30 – Section 1 Organic Chemistry
Page 21
3. The molecule for cholesterol is shown below:
a) Based on the name (Cholesterol) which functional group would it best belong to? ___________________
b) Circle the functional group on the diagram above.
4. Ethan-1,2-diol is a solved used in the production of paint and a major component of antifreeze. Based on the
same naming you did for hydrocarbons and halogenated hydrocarbons draw the chemical structure of
ethan-1,2-diol.
Science 30 – Section 1 Organic Chemistry
Page 22
5. Shown below is lactic acid (Notice H C is the same as CH )
3
3
Use different coloured pens/pencils to circle and label the
i. hydroxyl groups
ii. Carbonyl group
iii. Carboxylic acid
6. Go to page 271 of your textbook and draw out the procedure of how an ester forms  Copy the chemical
reaction in the middle of the page that shows methanol combing with ethanoic acid.
Science 30 – Section 1 Organic Chemistry
Page 23
7.
Draw the following reactants and products that undergo esterification. State the systematic names of the
products produced.
a. Propanol and ethanoic acid  _____________ + _____________________
b. Butanol and ethanoic acid  ___________________ + _____________________
c. hexanol and propanoic acid  ___________________ + _____________________
Science 30 – Section 1 Organic Chemistry
Page 24
8.
Use different coloured pens to identify the portion of the ester that came from the alcohol and the portion
that came from the carboxylic acid then name the ester
a.
b.
c.
Science 30 – Section 1 Organic Chemistry
Page 25
Section 1.4 – Exposure of Organic Chemicals in the Environment
Definitions
Volatile organic compounds (VOC’s): organic materials that can be hazardous to health. Both
natural and man-made organic compounds (methane gas, DDT, CFC, etc....)
Persistent Organic Pollutants – Toxic and unable to easily break down in the environment. CFC’s,
DDT, Polychlorinated biphenyls (PCB’s). Use can be for industry, coolants, pesticides, flame retardants,
glue.
Off-gassing: release of VOC’s from building materials (example: paint)
LD50 and LC50 – the dosage/concentration of a particular chemical that would kill about 50% of the
population during a given time interval.
o Example: for the pesticide 2,4-D found in frogs vs. ducks.
o Frogs – 359 mg/L
o Ducks – 2000 mg/kg
Biochemical oxygen demand (BOD) – measure of the amount of oxygen required for the
decomposition of organic material.

High levels of BOD differences means it takes a lot of oxygen (i.e. decomposers working) to
break down the organic material. This leads to a concern over lower oxygen levels for things
like fish and aquatic organisms and higher chances of things like algal blooms. (p.288)
Exposure Problems
Paints and Solvents


Off-gassing that evaporates into the air. The organic chemicals then get into people’s bodies by
breathing.
Major Concern: long-term exposure increases the level of these VOC’s (For example,
formaldehyde, Propylene glycol or ethylene glycol). Can affect people with asthma or allergies
in the short term.
Science 30 – Section 1 Organic Chemistry
Page 26
Pesticides

Used to eliminate specific types of pests. Insecticides, herbicides, and fungicides remove
unwanted insects, plants, and fungi/moulds respectively.

Major Concern:
1. Can be a broad-spectrum pesticide (eliminate more plants/organisms than intended).
2. Persistence over time – halogenated hydrocarbons and benzene rings have difficulty
breaking down – remain in the soil, food chain, and then onto organisms and people over
time…
http://archives.cbc.ca/environment/pollution/clips/8687/
#not working video link – need to fix
Sewage


Human waste matter that is released into the water system.
Major Concern: Disease causing viruses and bacteria entering the water system. (i.e. E. coli)
http://archives.cbc.ca/environment/pollution/topics/1672-11530/
#not working video link – need to fix
Fertilizers


Excess nutrients (nitrogen, phosphorus) from the fertilizers gets into the water supply. Run-off
of the chemicals enter lakes and river and large amounts of algae feed on the nutrients and
take-over the lake/river.
Major Concern: Death of fish and aquatic life due to increase in algae and bacteria in the water.
http://www.youtube.com/watch?v=AvigoZgYbT4
How they spread
Run-off – transfer through the water supply.
Drift – transfer by wind or air currents from the location sprayed
Grasshopper effect – transfer by evaporating in warm climates, and coming down as precipitation in
cooler climates. (p.286)
Science 30 – Section 1 Organic Chemistry
Page 27
Limiting Exposure
1. Continuing monitor of toxins and their concentration levels in the environmental (Albert
Environment, Environment Canada) http://www.envinfo.gov.ab.ca/AirQuality/
2. Reduce amount of POP’s (Persistent organic pollutants) – see the list of the “dirty dozen” on
p.298
3. Educate workers and those exposed to VOC’s on a long-term basis to exposure education and
protection (coveralls, gloves, etc.). Understand WHMIS symbols in the workplace.
Science 30 – Section 1 Organic Chemistry
Page 28
1.4 Homework
Read the following sections to supplement your notes from above. When you complete this you
can start on the homework for this section.
1.
What is the main concern with off-gassing in paint and what are some ways to reduce exposure
(p.280)?
2.
What are other building materials besides paint that can be manufactured from recycled
materials? (p.280)
3.
What is pesticides target specific and what is a broad-spectrum pesticide (p.283)
4.
Explain how the herbicide 2,4-D is affecting plant growth (p.283)
Science 30 – Section 1 Organic Chemistry
Page 29
5.
Sketch the grasshopper effect process below (p.285 – explanation and p. 286 for diagram)
6.
What is an algal bloom (p.288) and what is the concern with one?
7.
What is warfarin and explain why it is not used very much anymore for pesticide control (p.
289)
Science 30 – Section 1 Organic Chemistry
Page 30
8.
What are concerns with by-products of 2,4-D production (p.292)
9.
What are alternative strategies to control pests besides pesticides (p.294)
10. List the “Dirty Dozen” p.298 below:
Science 30 – Section 1 Organic Chemistry
Page 31