Science 30 Section 1 - Organic Chemistry and Pollution Workbook... · Section 1 - Organic Chemistry and Pollution ... Organic chemistry – the study of compounds composed of

Science 30 –Section 1 Organic Chem Page 1

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


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)


Chemical Bonding and Naming Review

Ionic Bonds

Molecular (Covalent) Bonds

Properties Form between metals and non-metals forming a crystal lattice.

Electrons are transferred (or stolen)

Form solids Very strong bonds / high melting

points Ex. NaCl, LiF, MgBr2

Form between two or more non-metals

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.


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)



Examples: Make each compound using the kits then name it.

a) b) c)

d)


e)

f)


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


Section 1.1 Homework

1. Name the following:

a)

b)

c)


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


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


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 Chemistry Page 13

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)

http://www.youtube.com/watch?v=I1wrEvc2URE


Other Halogenated Compounds • Many types of ________________________________________________________________

_____________________________________________________________________. (p. 259) • Have a tendency

____________________________________________________________________________________________________________________________________________________________


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.


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?


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


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


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.


1.3 Homework

1. Fill in the table below for alcohol:

Alochol with….

Drawing Systematic Name

1 carbon

methanol

2 carbon

3 carbons

4 carbons

5 carbons


2. Fill in the table below for carboxylic acids:

Carboxylic acid with….

Drawing Systematic Name

1 carbon

methanoic acid

2 carbon

3 carbons

4 carbons

5 carbons


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.


5. Shown below is lactic acid (Notice H3C is the same as CH3)

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.


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 ___________________ + _____________________


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.


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.


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)

http://archives.cbc.ca/environment/pollution/clips/8687/

http://archives.cbc.ca/environment/pollution/topics/1672-11530/

http://www.youtube.com/watch?v=AvigoZgYbT4


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.

http://www.envinfo.gov.ab.ca/AirQuality/


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)


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)


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:

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Science 30 Section 1 - Organic Chemistry and Pollution Workbook... · Section 1 - Organic Chemistry and Pollution ... Organic chemistry – the study of compounds composed of