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OCV
Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
Unit 2: Organic Chemistry
“Common knowledge” Kahoot!
In the food industry, “organic” means the product involves no synthetic fertilizers or pesticides. “Organic” means
“related to
life
.” Whether an organic food actually contains more nutrition or less harmful substances depends on
each product. In the beginning, organic compounds were believed to be produced only by naturally occurring living
organisms. Starting with urea, more and more organic compounds can be synthesized. Now, organic compounds
means
carbon-based compounds
(which very likely also contain
H
), which are characteristic to life on Earth.
Earth’s crust
is not particularly carbon-rich (0.2%), but about half of living organism’s dry mass is carbon. There are
two reasons why carbon is so life-friendly.
(1) Carbon makes up to 4 bonds.
It is capable of making tetrahedral,
trigonal planar, and linear shapes.
(2) Adequate bond (dissociation) energy.
Carbon is small enough so that its
bonds do not break easily. It also has a medium electronegativity
,
so that it does not form hard-to-break ionic bonds
with elements on the other end of the electronegativity spectrum. Carbon bonds with a variety of elements. These two
properties make carbon a versatile building block. Many carbon-based organic compounds are therefore large and
complex.
Exercise 0
: Oxygen is the most abundant element in Earth’s crust. Why is oxygen not the best building block for life?
Only 2 bonds; forms ionic compounds that are too hard to break
Extended topic:
❏
Are there silicon-based life?
1
OCV
Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
https://www.youtube.com/watch?v=fQCrrPohyts
Hydrocarbons - Alkane (suffix:
-ane
)
Hydrocarbons (H & C, nothing else) are the simplest type of organic compounds. And the simplest type of
hydrocarbons are
alkanes
(all names of alkane ends with -ane), which is solely made of sp
3
carbon saturated with
hydrogen. Alkanes have the chemical formula of C
n
H
2n+2
(the “+2” H are attached to the C and both ends).
Prefix
(# of carbon in the main chain)
1
2
3
4
5
6
7
8
9
10
meth-
eth-
prop-
but-
pent-
hex-
hept-
oct-
non-
dec-
Please use 2 minutes to memorize this list. We will play a Kahoot game!
Exercise 1
. What should we call C
6
H
14
?
hexane
Exercise 2.
There may be one or more carbon side
chains on a hydrocarbon. Draw one C
6
H
14
that
includes a carbon branch - a
side chain
. If you have a
molecular model building kit, build one.
How to draw: There are four frequently-seen ways to
draw an organic compound: (a) molecular/chemical
formula (C
6
H
14
), (b) condensed structural diagram, (c) line diagram, and (d) full structural diagram. Please draw all of
them for your side-chained C
6
H
14
.
It turns out there are five possible C
6
H
14
. The straight chain hexane is
n-
hexane (
n
= normal). The other four are:
2-
meth
yl
pentane
,
3-
meth
yl
pentane
,
2,3-
di
meth
yl
butane
, and
2,2-
di
meth
yl
butane
. Can you see the naming pattern
here?
❏
If the side chain grows on the second carbon of the
main chain, add “
2-
” before the side chain.
2
OCV
Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
❏
# of the same functional group on a side chain:
2 =
di
-, 3 =
tri
-, 4 =
tetra
-
❏
Length of carbon chain in the functional group:
1 = meth
yl
, 2 = eth
yl
, 3 = prop
yl
, 4 = but
yl
IUPAC (International Union of Pure and Applied Chemistry) is the agency that makes the rules of nomenclature. In
this course we will learn several key naming principles. Besides the three rules above, please know that:
(1)
The
longest continuous carbon chain
is the main chain.
(2)
Minimize numbers. 2,2-dimethylbutane is better than 3,3-dimethylbutane.
See Google slide for more explanation:
https://docs.google.com/presentation/d/1HoLRrlCGU5k-OcGFjVr5cMPsshc5ag6j48uNzueUujU/edit?usp=sharing
Exercise 3
. Name as many different C
5
H
12
as you can. (Try to rotate them to see if two
apparently different compounds are actually the same.)
n-pentane, 2-methylbutane, 2,2-dimethylpropane
Finally, name the alkane on the right:
2,2,3,3-tetramethylbutane
Isomers
You have learned isotopes - same element (same number of protons) but with different numbers of neutrons. Many
complex organic compounds have
isomers
, which share the same chemical formula (e.g. C
6
H
14
) but are structurally
different. We just found out that C
6
H
14
has 5 isomers and C
5
H
12
has 3.
Let’s appreciate the number of isomers for different alkanes.
https://i.stack.imgur.com/kAbs7.jpg
Exercise 4
. Name two isomers of the 8-carbon compound in exercise 3. How many isomers does it have?
3,4-dimethylhexane, 2,2-dimethylhexane
Properties of Alkanes
Under room temperature (25°C) and 1 atm, methane, ethane,
propane, and butane exist as gas. These make up
natural gas
(the C comes from anaerobically decomposed organisms and
100+ million-year-old organic compounds), in which
3
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OCV
Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
methane
is roughly 80% of the mixture. Natural gas is responsible for winter heating in cities. Propane is commonly
compressed and sold as a liquid.
Alkanes are highly non-polar because all carbons are saturated by
weakly δ
+
hydrogen. Larger alkanes have more intermolecular attractions
(induced transient dipole-dipole) among molecules, so that they are normally
liquids or solids. (Gravity is far weaker than electrostatic attractions at the
atomic scale, so we can safely ignore the fact that large alkanes are also
“heavier.”)
Exercise 6:
Which of the following alkanes are liquid at room temperature, 1
atm? (a) C
4
H
10
(b) C
8
H
18
(c) C
12
H
26
(d) C
100
H
202
Methane
is a potent greenhouse gas due to its four C-H bonds to absorb infrared rays in the atmosphere. (The bonds
will vibrate more as a result.) The global emission of methane is rising rapidly, contributing increasingly more
significantly to global warming. The livestock industry and the fossil fuel industry are the largest methane emitters.
Extended topics
Kurzgesagt - In a Nutshell: Fracking explained
https://www.youtube.com/watch?v=Uti2niW2BRA
Seeker: Onions Could Stop Cows From Farting The Planet To Death
https://www.youtube.com/watch?v=oH79CGm4u7s
Alkenes (suffix:
-ene
)
Alkenes are alkanes with one or more
double bonded
carbon. Their IUPAC names end with -ene. The simplest alkene is
ethene (old name: ethylene), C
2
H
4
. Compared to alkanes, each double bond in an alkene takes the place of two bonded
H. If there is only one double bond, the alkene has an easy chemical formula of C
n
H
2n
. If there are two double bonds,
the chemical formula becomes C
n
H
2n-2
, and so on.
4
OCV
Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
The name “butene” above is confusing. Please include the location of the double bond within the name, just before the
-ene, such as but
-1-
ene and but
-2-
ene (old: 1-butene, 2-butene). Use the first carbon on the main chain where the
double bond begins.
but
a
-1,3-
di
ene
prop
a
di
ene
If there are two double bonds, both carbons should be named. The suffix becomes
di
ene.
Exercise
7. Draw the line diagrams of a hex-1-ene, a hex-2-ene, and finally a 2,3-
di
methylbut-2-ene.
Recall that sp
2
bond hybridization produces flat molecules as atoms are coplanar (on the same plane).
A double
bond cannot rotate
because the π bond repels the sp
2
bonds. (On the other hand, a single bond can be rotated
freely.) It turns out that there are two isomers of but-2-ene.
There are two systems to distinguish these two isomers.
(1)
cis
-but-2-ene,
cis
= the
larger
functional groups are on the same side of the double bond
trans
-but-2-ene,
trans
= on opposite sides
(2)
(Z)
but-2-ene,
Z
- same side
(E)
but-2-ene,
E
- opposite sides
This system is preferred when there are multiple double bonds (2E, 4Z, etc.)
Exercise 8
.
Return to the hex-1-ene you drew. Does hex-1-ene have cis/trans (E/Z) isomers? Why (not)?
No. Both groups from the #1 carbon are hydrogen.
More practice for cis(Z) / trans(E):
5
OCV
Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
https://docs.google.com/presentation/d/1HoLRrlCGU5k-OcGFjVr5cMPsshc5ag6j48uNzueUujU/edit?usp=sharing
Exercise 9.
Name two different cis(Z) / trans(E) isomers of oct-2-ene. Supply the line diagram of each. Supply its chemical
formula.
cis
-oct-2-ene,
trans
-oct-2-ene,
(Z) oct-2-ene or (2Z) oct-2-ene, (E) oct-2-ene or (2E) oct-2-ene
C
8
H
16
Exercise 10.
Does 2,3-
di
methylbut-2-ene have cis/trans (E/Z) isomers? Why (not)?
No, all groups coming out from the double bond are identical (-CH
3
).
Exercise 11
. Name these two compounds.
1.
Longest continuous carbon chain - 5 carbons, so it is a pentane
2.
Has a double bond. Minimize number, so it is a pent-2-ene (old: 2-pentene)
3.
Has a methyl (1 C) side chain at #4 carbon on the mainchain, so it is 4-methylpent-2-ene
4.
Left is (Z) 4-methylpent-2-ene; right is (E) 4-methylpent-2-ene
Cis-fat vs. trans-fat
A fat molecule contains one relatively polar “head” and three highly non-polar hydrocarbon “tails.” The hydrocarbon
tail is either an alkane, a carbon chain
saturated with hydrogen
, or an alkene, a carbon chain with one or more
double bonds. Fats that contain an alkene tail are
unsaturated
(with hydrogen). Since each single bond can be
rotated to fit in an empty space, saturated fats pack quite tightly and generate a significant amount of intermolecular
attractions. The melting point of saturated fat is higher than room temperature.
6
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Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
Land animal fats are rich in saturated fat. For the past several decades, people have been speculating that ingested
saturated fat, during transportation in the blood vessel, could deposit within the blood vessel wall and narrow it.
Eventually the blood flow is blocked. If the coronary artery is blocked, the person suffers from heart attack. If an
important artery to the head is blocked (or ruptures), the person suffers from stroke. Heart attack and stroke are
among the most common causes of deaths in an industrialized society. (Cancer is the other top-3.)
As for unsaturated fat, there are
cis-
and
trans-
isomers. A
cis-
isomer introduces a rigid “bent” within the tail. The
extra space reduces intermolecular attraction so that cis-unsaturated fat is liquid at a lower temperature. Most
vegetable oil and fish oil contain a high amount of cis-fat.
Trans-fats are byproducts of the food processing industry, which
passes H
2
to unsaturated fat to saturate it (so that the product does
not drip liquid oil). The trans-isomer has the main chain on opposite
ends of the double bond, which again enables tight packing and
increases intermolecular attraction. However, the human body has not
evolved an enzyme to process trans-unsaturated fat. Trans-fats
therefore remain in our blood vessel for a longer period. Ingested trans-fat stays in the blood vessel and the person
has increased risk of heart attack and stroke.
Watch
: AsapScience: Butter vs. Margarine
https://youtu.be/KG_ybdk1VaE
Exercise 12.
During the break, examine a couple of nutrition labels on your household food products. Look for “trans
7
OCV
Chemistry, Grade 12 University Preparation (SCH4U-04/05)
Ottawa-Carleton Virtual Secondary School 2020-2021
Mr. Daniel Cho-En Lee (
daniel.cho-en.lee@ocdsb.ca
)
fat content” and “hydrogenated oil” in the ingredients.
Hydrogenation reaction: alkene → alkane
In grade-school science labs we have been working on relatively fast reactions. Slow reactions, such as the
hydrogenation reaction of alkene to make alkane, require a catalyst.
Let’s watch:
https://youtu.be/R27PkAWqSTc
Extended topic
: Fruit ripening experiment with ethene
https://www.youtube.com/watch?v=jzjBAAv9nxc
Kahoot!
8
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- LEARNING COMPETENCY: Describe some simple reactions of organic compounds; combustion of organic fuels, addition, condensation, and saponification of fats. (STEM_GC110Cllg-j-9). SITUATION: You are a Grade 12 research student in your school and you are researching on the potential of a certain plant that can be an additive in making a hand soap. Your task is to write the Methodology of the Research by indicating the step-by-step procedure of preparing a hand soap. TASK: Research for a procedure in the preparation of hand soap. Write the materials and procedures and answer the guide questions below. GUIDE QUESTIONS: 1. What are other oils, besides coconut, that are used to make bath soaps? 2. Based on your research, why is potassium hydroxide used instead of sodium hydroxide to make certain kinds of soaps? 3. Based on your research, what is a micelle? 4. What is the chemical name of the most common fatty-acid molecule found in coconut oil? 5. Describe the process of saponification of…arrow_forwardPolymers are often thought to be manufactured in immense chemical plants. Although many are, there is a large group of polymers which are natural. State 2 natural or synthetic polymers and describe how they are utilized in our society (1K, 2C).arrow_forwardInsoluble liquids have different chemical properties. We can predict which liquid will be on the top or bottom depending on their density. If you did not know the density of the liquids in your separatory funnel, how could you test to identify which layer is the organic and which is the aqueous?arrow_forward
- When a compound containing CC, HH, and OO is completely combusted in air, what reactant besides the hydrocarbon is involved in the reaction? Express your answer as a chemical formula including phase.arrow_forwardDraw structural formulas for organic products A and B in the window below. -CH₂CI Li pentane Cul B • Draw only products having the organic portion of the original alkyl halide. • Draw carbon-lithium bonds using the single bond tool. If a structure has a copper-lithium bond, do not draw the lithium. Separate products from different steps using the → sign from the drop- down menu.arrow_forwardQuestion 10 of 10 Organic Chemistry Loudon | Parise SEVENTH EDITION presented by Macmillan Leaning Calculate the number of pounds of CO, released into the atmosphere when a 25.0 gallon tank of gasoline is burned in an automobile engine. Assume that gasoline is primarily octane, C, H,3, and that the density of gasoline is 0.692 g mL- This assumption ignores additives. Also, assume complete combustion. CO, released: lb about us careers privacy policy terms of use contact us help 6:01 PM ) ENG 3/28/2021arrow_forward
- Draw structural formulas for organic products A and B in the window below. -CI Li pentane H₂O A B • Draw only products having the organic portion of the original alkyl halide. • Draw carbon-lithium bonds using the single bond tool. If a structure has a copper-lithium bond, do not draw the lithium. • Separate products from different steps using the →>> sign from the drop-down menu. ? n [ ChemDoodleⓇarrow_forwardPlease don't provide handwriting solutionarrow_forwardGive two examples of natural and synthetic polymers?arrow_forward
- Predict the organic products that form in the reaction below: HO- + H* X H+ Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure.arrow_forwardFill the blank for organic synthesisarrow_forwardcaq4 This is an Organic Chemistry problem. Please help. Thanks.arrow_forward
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