1
Day 1 ( pg 8 )( pg 93 )
Unit 2 Organic Chemistry
Organic compounds: carbon is the principle element

A functional group is any atom, group of atoms or organization of bonds that determines specific
properties of an organic molecule

The functional group generally is the most reactive part of a molecule and gives the molecule
predictable characteristics
o
o
o
Solubility in polar and non-polar solvents
Melting and boiling points
Reactivity with other molecules
There are three (3) main components (one or more of which make up a functional group) that determine
the properties of an organic molecule:
1. Carbon-carbon _______________ bonds


ethene
propyne
The second or third bond in a multiple bond is not as strong as the initial carbon-carbon
single bond, therefore, multiple bonds are ______________ reactive
Molecules containing multiple bonds are considered ______________ while molecules with
only single bonds are considered ____________________________
2. Single bonds between carbon and a more ______________________ element


methanol
chloromethane
These bonds are ____________ increasing melting and boiling points (more attraction
between the molecules)
If the bond contains O-H or N-H, then ___________ bonding occurs between adjacent
molecules and smaller molecules (less than 8 carbons) is soluble in water
3. ______________ bonded carbon and oxygen
methanal
This is a strong polar bond increasing melting & boiling points and solubility in polar solvents
2
2. Give the functional group for each of the following : alkanes _____________,
alkenes _______________
alkynes __________________, alcohols ___________
aldehydes ________________,
ethers ____________,
carboxylic acids ______________,
amides _________________,
amines _______________
esters ________________
ketones ______________________,chloro _____, fluoro _____, iodo ________, bromo _________
3.
4.
Account for the fact that compounds containing OH and NH are soluble in water
_________________________________________________________________
Review the nomenclature, properties and reactions of hydrocarbons
Hydrocarbons are carbon compounds that contain only carbon and hydrogen atoms.
Hydrocarbon Derivatives are carbon compounds in which any hydrogen atom has been
replaced by another atom (ex. F, P, Br, Cl, N).
Organic compounds generally share some common physical and chemical properties. Most carbon
compounds are _________ electrolytes or are very ________electrolytes, and tend to have _________
melting points. Hydrocarbons are usually _________ (polar/non-polar), whereas hydrocarbon derivatives
can be ___________ depending on what other atoms exist in the molecules.
a. Alkanes( pg 11 )
Alkanes are the simplest group of aliphatics. They are ___________ hydrocarbons; they contain only
single bonds with bond angles of ______________.The general formula for alkanes is __________
Memorizing the following list of alkanes is a crucial step in successfully naming organic compounds.
3
Number
of
Carbon
atoms
Chemical
Formula
1
CH4
Schematic
formula
Structural formula
3D View
Name
Boiling
Point
(oC)
methane
-162
ethane
-89
propane
-42
butane
0
pentane
36
hexane
69
heptane
98
octane
126
H
H C
H
H
2
C2H6
C3H8
3
C4H10
4
C5H12
5
C6H14
6
C7H16
7
C8H18
8
-
H
H
H C
C
H
H
H
H
H
H
H C
C
C
H
H
H
H
H
H
H
H
H C
C
C
C
H
H
H
H
H
H
H
H
H
H
H C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
for 9 carbons the name is nonane , the formula is ________________________
for 10 carbons the name is decane, the formula is ___________________________
Review Naming Hydrocarbons ( pg 12 )
CH3
CH3
H3C
CH3
1. Identify the longest chain, or main chain, of carbon atoms existing in the molecule. This will not
necessarily be the most obvious horizontal chain, however in our example, it is the _______________
chain.
2. If you are dealing with a branched hydrocarbon, identify any sidechains or sidegroups. Here is a list of
sidegroups you are responsible. You are given the name find out what their structure is ( pg. 13 )
methyl
__________
ethyl
isopropyl ________________________
_________
n – propyl
___________________________
butyl___________________________
4
sec-butyl ________________________
tert-butyl_________________________
Note that the prefix iso counts alphabetically but not sec or tert
2. In our example, there are two methyl groups.
3. Identify the location of the sidegroups by numbering the carbons from one end to the
other. In the example, the methyl groups appear on carbon numbers ____ and ____.
It is important to understand that the molecule in the example is the same as
CH3
CH3
CH3
H3C
because the methyl groups are attached to the same carbon numbers. In the example, we began
numbering from the left, in this case we begin numbering from the right.
Always begin numbering at the end of the carbon chain that gives the
lowest valued position for the sidegroup. If more than one of the same
sidegroup appears, assign the appropriate prefix to show how many are present (ex.
Di for 2, tri for 3, tetra, penta, and hexa). Prefixes are not considered for
alphabetical order.
4. Separate numbers from other numbers with commas, and separate numbers from
words with hyphens.
Example 1:
H3C
CH3
H3C
CH3
There are six carbon atoms in the longest chain. There are two methyl group branches on the ________
and _______- carbons. Thus, the name of this compound is ___________________________________
CH3
CH3
H3C
Example 2:
CH3
CH3
CH3
The main carbon chain consists of __________atoms; we are dealing with _________. There are three
________ sidechains and one _________ sidechain. Therefore, this molecule is called ;
__________________________________________________________________
5
Example 3:
CH3
H3C
C
H
CH3
The main carbon chain is ________________, so you may be tempted to call this molecule
__________________. This is, however, not necessary because there is no other place for the methyl
group to exist on the main chain without the molecule becoming butane. This particular molecule may be
called ____________________or simply iso_______________
Example 4
Draw the structural formula for 2-fluoro- 3,4-dimethylpentane.
1. The main carbon chain is pentane
H3C
CH3
2. Methyl groups appear on carbons 3 and 4
CH3
H3C
CH3
CH3
3. A fluorine atom appears on the 2nd carbon
CH3
F
H3C
CH3
CH3
Name the following :
1.
CH3
C3H7
CH3
\
/
/
C - C - C - C - C - C - C - C - ________________________________________________
\
CH3
2.
____________________________
3.
_________________________________________
6
Condensed Formulas :
- shortform representations of structural ; to name these first draw out the structural formula
1.
CH3CH2CH(CH3)CH2CH2C(CH3)(C2H5)CH2CH3
CH3
/
- C - C - C - C - C - C - C - C - __________________________________________________
\
\
CH3
C2H5
2.
CH3(CH2)4CH(n-C3H7)CH2CH2CH3
- C - C - C - C - C - C - C - C - C - _____________________________________________________

C

C

C
Properties(pg 22)
Members of the alkane family share some distinct chemical and physical properties. Due to their non-polar
nature, alkanes are _______in water. They generally have low boiling points, but boiling points
___________ as the number of carbon atoms in the molecule rises. This is due to the fact that when
more carbon atoms are present, more hydrogen atoms are present. Recall that hydrogen atoms are
bonded with carbon atoms covalently within organic compounds (intramolecular bonds). These hydrogen
atoms are constantly forming momentary and induced dipoles as the electron each one shares with carbon
moves closer to, or further away from it. These momentary dipoles help create intermolecular bonds
(bonds between molecules).
Therefore, more hydrogen atoms means more intermolecular bonds must be broken for boiling to occur,
and more energy (heat) must be added to the system.
Similar reasoning can be applied in determining the physical state of various carbon compounds at room
temperature.
Number of Carbon
Physical State
atoms in compound
<4
Gas
5 – 16
Liquid
>16
Waxy solid
Define fractional distillation(22) _
__________________________________________________________________________
__________________________________________________________________________
__________________________________________________________________________
7
THE FRACTIONAL
DISTILLATION OF CRUDE OIL
names of
fractions
C atoms boiling USES of the fraction
in the range
depends on its
molecule in oC
properties
-
methane gas fuel,
C3-4 easily liquefied,
portable energy
source bottled gas for
cooking (butane), higher
pressure cylinders
(propane)
Fuel Gas,
LPG,
Refinery
Gas
1 to 4
-160
to
20oC
Gasoline,
Petrol
5 to 11
easily vaporized, highly
20 to
flammable,
easily ignited,
60oC
car fuel
Naphtha
7 to 13
60 to
180oC
no good as a fuel, but
valuable source of
organic molecules to
make other things,
cracked to make more
petrol and alkenes
less flammable than
Paraffin,
120 to
10 to 16
petrol, domestic heater
Kerosene
240oC
fuel, jet fuel
Diesel oil,
15 to 25
Gas oil
220
to
250oC
Fuel and
lubricating
Oils and
Waxes
not so easily evaporated,
not as flammable, safe to
250 store for central heating
to
oil, quite viscous
o
350 C (sticky) and can also be
used for lubricating oils,
clear waxes and polishes
Bitumen
Asphalt
20 to
70
car and larger vehicle
fuel
forms a thick, black,
tough and resistant
adhesive on cooling, used
over
over 70
as waterproofing
350oC
material and to sticks
rock chips on roofs or
road surfaces
8
Fractional Distillation, Cracking And Polymerization
Find words in the grid and add them to
the
P O P O L Y P R O P E N E S N A V Y O D S E H M I I E
text below. Each letter is used just
O H L R O P E L A N O I T C A R F D F O I R E O R L T
once.
P P O L Y C H L O R O E T H E N E H S P U C T S W O P
L C I Y
N O I T A L L I T S I D R F U N U R T E D R
Y O B G S L U B R I C A N T T A G O D B G T M A F E O
E N I C H T A L K A N E S
S I N C E L L A A N R T L
T D T O T E Y A L K E N E S Y R I A L E E R L A A A R
H E U L O
R R S L E V E L L C K R C R G E N P C R E
E N M U P H O T E S H I P S A R C B Y E A P I H T A L
N S E M D R U G S N S G A B T A A O C W S M A T I P I
E E N N P O I N T S E P V C A F R N E O E E H H O E O
A L U M I N I U M O X I D E C T C S R T S T C A N S B
Crude oil is a vital fossil fuel for modern life. It is a mixture of _ _ _ _ _ _ _ _ _ _ _ _, mostly alkanes,
that is _ _ _ _ _ _ _ _ _ by an industrial process called _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _.
To start with, liquid crude oil is fed into a _ _ _ _ _ _ where it is vaporized. The _ _ _ mixture of gases
then passes into a fractionating _ _ _ _ _ _ and begins its journey upwards from the hottest region at the
bottom towards the coolest region at the top. Hydrocarbons with similar boiling _ _ _ _ _ _ condense at
different _ _ _ _ _ _ and flow into collecting trays. Each so called _ _ _ _ _ _ _ _ contains
hydrocarbons of a similar size. For example, the petrol fraction condenses at a _ _ _ _ _ _ _ _ _ _ _ of
about 40oC and contains hydrocarbons with five to ten carbon _ _ _ _ _. The lower the boiling point of a
hydrocarbon, the _ _ _ _ _ _ up the fractionating _ _ _ _ _ it must go before it can _ _ _ _ _ _ _ _ and
be tapped off.
The _ _ _ _ _ _ _ fraction is tapped _ _ _ at the bottom of the fractionating column. This material is
used in road building and as a protective roof covering. The _ _ _ fraction, used as a _ _ _ _ _ _ _ _ _
or as fuel for _ _ _ _ _ and central heating, condenses at the following level and next comes the diesel
fraction, a source of fuel for lorries and _ _ _ _. Kerosene, used as _ _ _ _ _ _ _ _ fuel, is followed by
the less well known fraction called _ _ _ _ _ _ _. This material plays a very important role in the
manufacture of medicinal _ _ _ _ _ and other chemicals. After the naphtha comes _ _ _ _ _ _, that well
known fuel for cars. Finally, the refinery _ _ _ _ _, including the camping stove fuels propane and
butane, never condense but are simply collected for bottling at the _ _ _ of the tower.
On the whole, smaller hydrocarbons are more useful and in greater demand than larger ones.
Fortunately, an industrial process called _ _ _ _ _ _ _ _ can be used to turn long chain alkanes into short
chain alkanes and equally useful _ _ _ _ _ _ _. In this _ _ _ _ _ _ _ decomposition reaction, vaporised
_ _ _ _ _ _ _ are heated to temperatures of 400-700oC in the presence of a powdered _ _ _ _ _ _ _ _ _
_ _ _ _ _ catalyst.
The alkenes produced by cracking can be made into polymers using addition polymerisation reactions. A
_ _ _ _ _ _ _ _ and high pressure are used to make thousands of unsaturated alkene molecules rapidly
join up to form long _ _ _ _ _ saturated molecules. During the process alkene carbon-carbon _ _ _ _ _
_ bonds break and _ _ _ _ _ _ bonds form. Addition polymers are commonly known as plastics.
Examples are: _ _ _ _ _ _ _ _ _ _ (used to make carrier _ _ _ _, bottles, buckets and bowls); _ _ _ _ _
_ _ _ _ _ _ _ _ _ _ _ (also called _ _ _ and used to make electric _ _ _ _ insulation, records and
clothes); _ _ _ _ _ _ _ _ _ _ _ (used to make foam packaging and _ _ _ _ ); and _ _ _ _ _ _ _ _ _ _ _
(used to make crates, _ _ _ _ and carpets). One problem with plastics is that they are nonbiodegradable, but they are often _ _ _ _ _ _ _ _ nowadays even though the cost of sorting and
reprocessing them is high.
Complete page 10 (2-4) and 1,2
9
Day 2 : Reactions: pg 24
Alkanes are relatively unreactive due to strong _________ bonds, though reactions do occur at higher
temperatures.
i.
Combustion: alkanes react with oxygen to form _________, __________, ____________and
water.
In complete combustion the products are ___________ and ____________. Consider the complete
combustion of propane : C3H8 + 5O2  4H2O + 3CO2
In incomplete combustion the major products are _____or________ and __________________.
Substitution: other atoms can replace hydrogen atoms in alkanes. Reaction below requires
________________________.
ii.
H
H
H
C
H
+

Cl2
H C
H
iii.
Cl
+
HCl
H
CH4
+
Cl2

CH3Cl
+
HCl
methane
+
chlorine

chloromethane
+
hydrogen
chloride
when heated to high temperatures in the absence of air, alkanes will
break down into smaller molecules.
Cracking :
H
H
H C
C
H
H
H
H

H
C
C
H
+
H2
H
(1)
butane
ethane
ethene.....or
(2)
butane
methane
propene
lots and lots of other possibilities! e.g.
(3)
(4)
C8H18 ===> C6H14 + C2H4 (making ethene)
C12H26 ===> C9H20 + C3H6 (making propene)
10
Complete the following reactions and name the type of reaction ; write balanced equations :
a)
propane + Br2 
b)
ethane + I2 
c)
octane + O2 
d)
pentane + O2 
e)
CH3CH3 + heat 
Cycloalkanes (pg 11)
-
alkanes can also be found as cyclic structures or closed ring
Try drawing cyclopropane below ; notice the bond angles are ____________; since the bond is strained
cyclopropane would be ___________ reactive than propane
Cyclic structure
Cyclopropane
Cyclobutane
Cyclopentane
Cyclohexane
Structural formula
11
Draw methylcyclopropane
If more than one side group is present use the same rules as you did for alkanes
With 2 side groups it is possible to make geometric isomers. If the side groups are on the same plane ( cis
); if opposite planes then trans
Draw : Rename if necessary
a.
1,2-dimethyl-4-propylcyclobutane
b.
1-ethyl-2-isopropyl-4-methylcyclohexane
c.
trans-1,3-dichlorocyclobutane
d.
1-ethyl-4,5-dimethyl-2-bromocyclohexane
e.
2-sec-butyl-3-isopropylcyclobutane
Name the following :
1.
__________________________________________
2.
_________________________________________________
12
3.
___________________________________________
Draw the structural formulas for the following compounds: Note the prefix cyclo counts
alphabetically. Rename if necessary
1.
3-ethyl-2-fluoro-4-methylhexane
2.
1,3-dimethyl-2-isopropyl-4-ethylcyclopentane
3.
2-ethyl-4-sec-butyl-6-propylnonane
4.
4-ethyl-4,5-dimethyl-2-propylheptane
5.
1-ethyl-2-methylcyclobutane
6.
3-cyclopropyl – 4 – tert-butyl – 3-iodocyclopentane
7.
cis-1-ethyl-3-methylcyclopentane
13
8.
3-bromo-4-propylcyclopentane
9.
2-cyclopropyl-3-tert-butylcyclohexane
10.
1-isopropyl-4-methyl-3-ethylcyclobutane
Complete pg 15 (1,2)
14
Name the following :
CH3
CH3
1
CH3
H3C
CH3
CH3
H3C
C
2
H3C
CH3
CH3
H
H
3
C
Cl
Cl
4
CH3
5
6
7
_________________________________________
________________________________________
8
9
Cl
F
________________________________________
10
_________________________________________
11
______________________________________
________________________________________
15
Structural isomers -
same ______________________ formula but different ________________
formula
Draw and name all the isomers for pentane and octane. Research how isomers differ in physical and chemical
properties referring to the octane isomers.
Day 3 b.
Alkenes( pg 16 )
Alkenes are the next family of hydrocarbons. They have similar structures to alkanes, however they are
called _________________hydrocarbons because they contain a double bond (C=C); they are not
saturated with hydrogen. The general formula is ______________________
H
H
C
C
H
H
C
C
H
H
C
C
CH3
H3C
H
CH3
H
CH3
H
H
ethene or ethylene
propene or propylene
1-butene
2-butene
Members of the alkene family also have distinct chemical and physical properties. They have lower boiling
points than their respective alkanes because there are less hydrogen atoms present to form intermolecular
bonds.
For naming alkenes the longest chain must contain the double bond and it is number to give the
lowest possible # for the double bond. If 2 double bonds exist #’s are needed to indicate position
e.g. 1,4-hexadiene. Draw ____________________________________
Draw :
a.
3-ethyl-4-isopropyl—5-methyl-2-octene
16
b.
2-chloro-3-methyl-5-propylcyclohexene
Geometric isomers
-
due to the restrictions of rotation about the double bond and the molecular geometry,
there exists 2 different geometric structures to 2 - butene. The adjectives cis and trans are
used to differentiate the isomers. Cis designates the isomer with the like groups or atoms
on the same side of the alkene linkage while in trans the groups or atoms are on the
opposite sides of the alkene linkage that is opposite planes.
I.
CH3
CH3
\
/
C=C
a.
b.
c.
d.
The
The
The
The
e.
The structural formula for cis - 3 - hexene is :
f.
Draw trans - 3 - hexene
g.
Draw 5- ethyl - 5 - methyl - trans - 3 - heptene
II.
CH3
\
C=C
\
CH3
cis isomer is represented by # ____________________________________
trans isomer is represented by # ___________________________________
name for # 1 is
______________________________
name for # 2 is ___________________________________
Reactions (pg 25)
Combustion: Like alkanes, alkenes undergo oxidation, or react with oxygen, to release carbon dioxide and
water. They will also undergo addition reactions.
i)
Hydrogenation: (hydrogenation is addition of hydrogen gas which breaks the double bond and
an alkane is formed ( requires a catalyst (Pt), heat and pressure
H
H
C
H
H2

H
ethene
ii)
+
C
+
hydrogen

H
H
H
C
C
H
H
H
__________________
Halogenation: halogenation is the addition of a halogen (F, Cl, Br, I) to break the double bond
and create a hydrocarbon derivative ; reaction at _________________ temperature
17
H
H
C
C
H
+

Br2
H
H
ethene
+

bromine
Br
Br
C
C
H
H
H
___________________________
State Markovnikov’s Rule ( pg 26 )
_______________________________________________________________________________
_______________________________________________________________________________
iii)
Hydration is the addition of ________________, which breaks the double bond and creates
an ____________________( _________________ is the catalyst)
H
OH
H
H
C
C
H
+
H2O

H
ethene
+
water

H
C
C
H
H
H
______________
(ethanol)
Complete : Propene + water  ________________________________
iv)
e.g.
Hydrohalogenation : addition of a hydrogen halide to a double bonded alkene
propene + HBr
Complete pg 27 ( 1-3 )
----------- ____________________________________
18
Write the IUPAC name for each of the following:
a)
b)
F
c)
d)
e)
f)
Cl
Br
C.
Alkynes
Alkynes are the final family of aliphatics. Like alkenes, they are unsaturated; they contain a triple bond
between carbons. Their general formula is _________________
HC
CH
ethyne or
acetylene
HC
CH3
CH3
propyne
HC
1-butyne
Name the organic below :
______________________________________________
19
Reactions
Alkynes undergo the same type of combustion and addition reactions as alkenes.
1. Predict how the boiling point of alkynes compares to those of alkenes and alkanes. ____________
2. Account for this trend. __________________________________________________
3. Name where possible and classify each of the following as alkanes, alkenes, or alkynes.
a) C4H6
b) C5H8
H3C
H2C
CH3
e)
4.
f)
c) C6H12
CH3
g)
HC
d) C3H4
CH3
h) CH3CH2CH3
Complete the following reactions and name the reactants, products and the type of reaction:
a) CH3CH2CH3 + Br2 
b) CH3CH=CH2 + I2 
c) CH3CCCH2CH3 + 2Cl2 
d) CH3CH=CH2 + H2O 
e). CH3CH2CH3 + heat 
f)
CH3CCCH2CH3 + H2O 
g) CH3CH=CH2 + O2 
20
Complete pg 37 ( 6 a-f )
1 Day 4 CFC's and Ozone Depletion ( pg 34 )
Chlorofluorocarbons (CFCs)

Chlorofluorocarbons (CFCs) are compounds containing carbon, chlorine and fluorine.

Chlorofluorocarbons (CFCs) are sold under the trade name of ________________.

Used as working fluids in refrigerators and air conditioners because they are gases at room
temperature wich can be easily liquified by compression and because they are stable and non-toxic

Used as foaming agents in the production of polystyrene and polyurethane foam plastics used for
insulation and packing materials

Used as a propellant in spray cans for paint, insect repellants, deodorants
21
Name
Formula
Code
Uses
trichlorofluoromethane
freon-11
CCl3F
CFC-11
refigeration, aerosols, foams
dichlorofluoromethane
freon-12
CCl2F2
CFC-12
refigeration, aerosols, foams, air conditioning
1,1,2-trichloro-1,2,2-trifluoroethane
freon-13
CCl2FCClF2 CFC-13
electronics, dry cleaning, fire extinguishers
1,2-dichloro-1,1,2,2-tetrafluoroethane
CClF2CClF2 CFC-14
freon-14
1,2,2-trichloro-1,1,2-trifluoroethane
freon-113
aerosols
CClF2CCl2F CFC-113 degreasing and cleaning printed circuit boards
Chemistry of Ozone Depletion by CFCs ; watch video www.teachersdomain.org Ozone Hole

CFCs destroy the ozone in the stratosphere (15 - 20 km above the earth's surface)
(Ozone concentrations are measure in Dobsen units, 1 Dobsen unit represents 1 molecule of O 3
for every 1 billion air molecules)
Ozone loss is greatest over _____________ where the ozone depletion has been recorded and is
commonly referred to as the "ozone hole".

Ozone (O3), an allotrope of oxygen, is poisonous to humans if breathed in, but is important to life
in that it filters out or absorbs short wavelength ultraviolet radiation (u.v) in the 280 - 320nm
range which can cause serious sunburn, skin cancer and eye disorders.

The inertness and lack of water solubilty of CFCs mean they are not destroyed nor are they
dissolved in rain water so they stay in the atmosphere for a very long time and diffuse up to the
stratosphere

In the stratosphere, CFCs come into contact with short wavelength ultraviolet radiation which is
able to split off chlorine atoms from the CFC molecules
CCl2F(g)

u.v radiation
--------------->
CCl2F(g)
+ Cl(g)
These chlorine atoms destroy the ozone layer
Cl(g) + O3(g) ------------->
ClO(g) + O2(g)

There are significant numbers of oxygen atoms in the stratosphere (since ozone undergoes a
natural photochemical decomposition producing oxygen atoms and molecules) which leads to the
regeneration of chlorine atoms in the stratosphere.

So, 1 CFC molecule can destroy many ozone molecules.
ClO(g) + O(g) ------------->
O2(g) + Cl(g)
Substitutes for CFCs (pg 34)

The only long term solution to solve the problem of depletion of the ozone layer is to phase out
the use of CFCs (Montreal Protocol of 1987 and subsequent modifications)

Some CFCs can be replaced by HCFCs (hydrochlorofluorocarbons), compounds containing at least
1 H atom. Most common used today is __________________________
The C-H bond makes these compounds more reactive in the atmosphere so they are destroyed
more quickly and so are less able to diffuse into the stratosphere
22
Name
Formula
Code
Uses
chlorodifluoromethane
CHClF2
HCFC-22
air conditioning, refrigeration, foams
1-chloro-1,1-difluoroethane
CClF2CH3
HCFC-142b
aerosols
1,1-difluoroethane
CHF2CH3
HCFC-152a
aerosols, refrigeration
Hydrocarbon Classification
Aromatic Compounds ( pg 19 )
Aromatic compounds are those that contain, or are derived from the __________molecule. __________ is
unique in that its chemical formula is C6H6 yet it contains no _____ or ________ bonds. Rather, benzene’s
bonds are formed by delocalized electrons, which are not fixed to any one atomthey resonate
throughout benzene’s ring structure. All bonds in benzene are considered __________________.
H
H
H
H
H
H
H

H
H
H
H
H

The symbol
for benzene
3D representation
Physically, benzene is a flat molecule. It has a ___________boiling point than corresponding cycloalkane,
alkane, alkene and alkyne because hydrogen atoms from one molecule are able to get closer to the
hydrogens from other molecules. This allows for stronger intermolecular attraction. Also, benzene is
_____________, it is ____________in water.
Distinguish between the prefixes ortho, meta and para ( see pg 20 )
____________________________________________
23
See rules for naming aromatic hydrocarbons ( pg 21 ). For one alkyl group no number is needed to
identify the sidegroup e.g. methyl benzene. If more than one sidegroup numbers are needed.
Draw 1-ethyl-3-methyl benzene
Sometimes benzene may be considered a sidegroup and is given the name ________________
Complete pg 21 ( 7,8 )
Reactions
Due to its cyclic structure, benzene is very stable. It will only undergo ________________reactions.
H
H
H
H
H
+
Cl2

+
chlorine

H
Cl
H
H
H
benzene
-
H
+
HCl
+
hydrogenchloride
H
chlorobenzene
the catalyst for the above reaction is iron(III) bromide
also undergo nitration reactions ( nitrogen dioxide is added in the presence of the catalyst )
In some cases, such as when benzene forms a compound with ethylene, or any other alkene,
alkyne or even a long chained alkane, the benzene part of the compound may be called the
phenyl group:
CH2
phenylethene
24
Draw the structural formula for
i.
1,2,3-trimethylbenzene
ii.
2-phenyl-4-isopropylpentane
iii.
toluene
iv.
phenol
v.
orthodibromobenzene
vi.
paradiflourobenzene
vii.
metadibromobenzene
viii.
1,3,5-trimethylbenzene
ix.
Complete the following reactions. Draw the structural formulas and balanced equations.
a)
benzene + Br2 
b)
benzene + O2 
c)
phenylethene + Cl2
Complete page 22 (2b,f,h,j,k,l) 3,4), page 31 (2,3a-d,4), page 37(2,3). È
25
1. Write the IUPAC name for each of the following
a)
Cl
b)
Br
F
c)
d)
e)
f)
Cl
2. Draw appropriate line structures for each of the following:
a) meta-dibromobenzene
b) 3,6,7-triphenyldecane
Physical & Chemical Properties of Aromatic Hydrocarbons ( pg 29 )
-
aromatic compounds are __________reactive as the aliphatic compounds due to the extra
strength associated with the delocalizing e's in the aromatic ring
do not readily participate in ________________ rxns because of this stability
however, aromatic compounds do undergo _____________rxns in which one or more hydrogen
atoms from the ring are replaced by another group
used as a good ______________ solvent
26
Practice naming and drawing hydrocarbons.
27
1. Draw structural diagrams for the following hydrocarbons. Rename if necessary
(a) 2-ethyl-3-phenylheptane
(b)
(c) 4-ethyl-5-isopropyl-2-hexyne
(d)
3-ethyl-2-methyl-4-propylbenzene
2-ethyl-3-cyclopropylcycloheptene
(e) 1-sec-butyl-2,4-diethylcyclohexane
2.Draw line structural diagrams for the following hydrocarbons.
(a) 3-ethyl- 4- methylcyclopentane
(b)
2,3,4,5-tetramethylhexane
(c) 1-isopropyl-2-sec-butylcyclohexane
(d)
2,6,7-triethyl-4-methyl-3-heptene
(e) 3-methyl-2,4-dipropylbenzene
3. Name the following hydrocarbons.
(a)CH3CH2CH═CHCH2CH2CH3 _________________________________________
(b)
(c)
_____________________________________________
28
Nomenclature Review Sheet
H
H
H
H
H
H
H
C
C
C
C
C
C
H
CH3 H
CH3 H
H
H
H
__________________________________________
H
H
H
H
H
C
C
C
C
C
H
CH2 H
H
C
H
CH3 H
H
H
________________________________
CH3
CH3
CH
CH2
CH
CH3
CH2
CH3
CH
CH3
CH3
C
CH3
CH2
C
CH3
CH3
CH3
CH3
_______________________________
________________________________
CH3
CH2
CH3
CH3
CH2
CH3
________________________________
H
H
H
H
C
C
C
H
H
‗
H
H
C
C
C
H
H
H
______________________________
H
H
H
H
C
C
‗
H
H
H
C
C
C
H
H
H
H
______________________________________
__________________________________
CH2
H
H
C
H
‗
H
‗
C
CH2
CH2
CH2
CH2
H
CH2
C
C
C
H
CH3
H
H
________________________________
______________________________________
CH3
29
CH2
______________________
CH3
CH
‗
__________________ ________________________
CH3
CH
CH
CH
CH
CH3
CH3
CH2
CH3
CH2
CH3
_________________________________
CH
≡
C
CH3
CH
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3
_____________________________________
CH2
CH3
CH3
CH
C
≡
C
CH3
__________________________________
CH3
CH
CH
CH3
CH2
________________________________
CH3
1. Draw the correct Structural formula for each of the following:
(a)
(d)
Benzene
1,2 – dimethylbenzene
(b) Cyclopentane
(e)
(c)
3-ethylcyclobutene
Cyclopentene
(f) 1,4 – diphenylbutane
2. Write the correct IUPAC name for each of the following:
(a)
(b)
CH3
CH2CH3
CH3 – CH2 – CH – CH2 – CH – CH3
|
CH2
|
CH3
CH3
30
Day 5 : Building organic molecules
Day 6
Hydrocarbon Derivatives
Functional Groups
Now that we have finished our look at hydrocarbons, we move on to hydrocarbon derivatives. Adding
other atoms to hydrocarbons generally forms these. Examples of such derivatives are alcohols, esters,
carboxylic acids and alkyl halides. Functional groups are the sites at which most chemical reactions occur.
They are generally polar and will react with other polar or ionic reactants, however the double and triple
bonds in alkenes and alkanes can also be considered functional groups. Organic compounds with the same
functional groups will behave similarly in chemical reactions. Some of the most common functional groups,
their general structures and examples are listed in the following table.
General Structure
R
O
Group
Name
Functional
group name
Example Structure
H3C
alcohol
O
H
methanol
H
H3C
R—O—R’
R
Example Name
O
O
H
CH3
ethoxyethane
O
carbonyl
methanal
H
H
R
H3C
O
O
2-butanone
R1
CH3
O
O
R
ethanoic acid
(acetic acid)
H3C
OH
O
OH
O
ethyl acetate
R
O
R1
H3C
O
CH3
H
R
NH2
amino
H
C
H
H
methylamine
N
H
Note: R and R1 symbolize a general hydrocarbon group. They may be the same or different. Amides are
missing from the table the functional group is ______________________
a.
Alcohols (pg 38 )
Alcohols are molecules with the _______________ functional group (______________). Due to their
____________ nature, alcohols are completely miscible (dissolvable) in water. They have relatively
___________ boiling points, due to ___________________________
Alcohols are named by replacing the –e on the corresponding alkane with –ol. The C attached to the OH
must have the lowest # possible.
31
Methanol is wood alcohol used in windshield washer anti-freeze, ethanol is grain alcohol found in
alcoholic beverages,2-propanol or isopropanol is rubbing alcohol and 1,2-ethanediol is ethylene glycol
found in car anti-freeze.
Name some other important alcohols (good and bad) ________________________________________
H3C
H3C
O
O
H3C
H
CH2
1-propanol
methanol
OH
HO
1,2-ethanediol
O
H
H3C
H
2-propanol
In naming cyclic alcohols the OH is considered position # 1 thus no number is needed in the name . try
drawing
2,3-dimethylcyclohexanol
Complete page 41 (1-3)
Classification of alcohols :
Type of alcohols
A primary alcohol is one in which
the hydroxide group is attached to
a carbon that is bonded to one
other carbon atom.
A secondary alcohol is one in
which the hydroxide group is
attached to a carbon that is
bonded to two other carbon
atoms.
A tertiary alcohol is one in which
the hydroxide group is attached to
a carbon that is bonded to three
other carbon atoms.
Example
OH
H3C
1-propanol
HO
CH3
H3C
2-propanol
CH3
H3C
C
CH3
OH
2-methyl-2-propanol
Draw and name the first degree, second degree and tertiary alcohols of butanol.
b.
Draw the following molecules . Rename if necessary. Classify the type of alcohol where possible.
1.
2 - pentanol
2.
5 – ethyl-2-methyl - 3 - hexanol
32
3.
3 - ethyl-5-propyl-2- methyl -3 - hexanol
4.
2,3 – dimethyl-4-tert-butylcyclohexanol
5.
1,2 - ethanediol ( ethylene gycol ) ( anti-freeze )
6.
1,2,3 - propanetriol ( glycerol )
7.
3 - bromo - 2,3 - diethyl - 2 - butanol
8.
3-chloro-2-cyclopentenol
9.
2,3 - dimethyl - 2 - cyclobutenol
10.
3,4-dimethylcyclohexanol
11.
6-ethyl-2-heptanol
12.
1,3 - pentanediol
13.
trans-2-chlorocyclopentanol
14.
4-methyl-3-penten-2-ol
15.
trans-cyclobutane-1,2-diol
33
Name the following:
1.
__________________________________________________
2.
___________________________________________________
3.
________________________________________________
4.
_______________________________________________________
5.
___________________________________________________
Day 7 : Properties (pg 42)
1.
2.
3.
4.
5.
6.
7.
8.
Clean burning fuels i.e. methanol and ethanol
Alcohols are prepared by adding _____________ to _________________. Reaction is called
___________
Methanol is prepared by adding ___________ to ________________
Primary alcohols can be oxidized to aldehydes then to carboxylic aicids
Secondary alcohols can be oxidized to ketones
Alcohols can be dehydrated forming _____________________ ; _______________ reactions
B.P. are
due to
. As the size of the molecule increases the B.P.
_____
____________ in water ; as the # of carbons increases the solubility __________________
34
, alcohol in cough syrups
windshield washer
9.
1.
Some common alcohols are : anti-freeze
and skin lotions
;rubbing alcohol
_________________
Preparation and Reactions (42-43)
Alcohols can be prepared by the addition of water ( ________________ reaction ):
H
H
H
C
+
C
H
--------------
H2O
H
H
ethene
+
Sulfuric acid
(catalyst)
water
H
O
C
C
H
H
H
ethanol
How was methanol originally obtained ? __________________________________________________
What is the modern method of preparing methanol ? ________________________________________
2.
Combustion : the same as for alkanes
3.
Mild Oxidation of a primary alcohol first yields an _____________________ (pg52)
oxidation refers to either loss of ___________, loss of ______________ or gain of __________________
Remember LEO the lion says GER
OH
H3C
K2Cr2O7
O
H3C
potassium dichromate
(oxidizing agent)
1-propanol
propanal
+
H2O
+
water
and with further oxidation, a carboxylic acid...
O
O
H3C
K2Cr2O7
H3C
C
OH
propanal
potassium dichromate
propanoic acid
Oxidation of a secondary alcohol yields a ketone, and tertiary alcohols can not be oxidized easily
since _____________________________________________
O
OH
+
K2Cr2O7
H3C
CH3
2-propanol
H3C
potassium dichromate
H2O
CH3
propanone
water
35
-
3. Elimination reactions ( __________________ )( pg 43 )
alcohols when treated with sulphuric acid produce ________________________________
4. Substitution Reactions
alcohols react with strong acids like HCl. The OH is removed and exchanged for a Cl.
2-methyl-2-butanol
i.
+
HCl
------ ______________________ + ____________________
Complete the following reactions and name the reactants and products:
a)
CH3CH2CH2OH + oxidizing agent 
b)
CH3CHOHCH3 + oxidizing agent 
c)
CH3CH2CH2CH2CH2OH + oxidizing agent 
d)
CH3CH2C(CH3)(OH)CH2CH3 + oxidizing agent 
e)
CH3CH=CH2OH+ O2 
f)
3-methyl-2-hexanol + HCl
-----------
Complete pg. 44(7,8)
Research : What are the advantages and disadvantages of methanol as a fuel, over more
conventional gasoline or diesel fuels ?
_____________________________________________________________________
_____________________________________________________________________
_____________________________________________________________________
Day 8 : Lab : Oxidation of alcohols : Demo pg 85
36
1.NAMING ALCOHOLS
FORMULA
TYPE
NAME
CH3 – CH2 – CH2 – OH
2 – butanol
CH3
|
CH3 – C – CH2 – CH3
|
OH
ethanol
CH3 – CH – CH – CH3
|
|
OH OH
OH
|
CH2 – CH – CH – CH3
|
|
OH OH
OH
OH
OH
2.Write the IUPAC name for each of the following
a)
OH
OH
b)
OH
37
c)
d)
OH
OH
OH
e)
f)
F
OH
Cl
OH
OH
Day 9 Ethers (pg 45)
An oxygen atom bonded between two carbon atoms characterizes ethers. To name ethers, the longer of
the two alkyl groups is selected as the main chain. It is left as it would appear as an alkane, etc.
Remove the –yl ending that would normally apply to the shorter of the two groups, and add –oxy.
O
H3C
CH2
CH3
methoxyethane
- the traditional name for the above is ethylmethylether
1. Write the structural formula for an ether with the formula: C4H10O
ii. What other isomers can you make and name?
Draw the following :
1.
1-ethoxypropane
2.
3-ethyl-2 - propoxypentane
3.
1,2 - dimethoxyethane
38
4.
2 - chlorobutyl - 2,2 - dimethylpentyl ether
5.
cyclobutoxycyclopentane
6.
1,3 - dichloro - 2 - methoxypropane
Complete pg 46(11)
Name the following :
1.
________________________________________________
2.
_________________________________________________
Properties :
1. Boiling points are _____________ than corresponding alkane but _______________ than corresponding
alcohol
2. Considered a ________________ molecule due to _____________________; very good solvent for both
polar and non-polar molecules .
3. Highly __________________________; diethyl ether was used as a ____________________________but
now has been replaced by _______________(pg 48)
4. What is the common use of diethylether nowadays ? ______________________________
39
Preparation :
ethers can be formed through an elimination reaction __________________________________
alcohol + alcohol ------------ _____________________ + __________________________
catalyst for the above reaction is ______________________
-
Complete pg 48 (2,3,4,6a,b,c,7)
1.Complete the following :
CH3 – CH2 – CH2 – O – CH3
2- ethoxy – 3 – methyl pentane
CH3CH2 – O – CH2CH2CHCH3
|
CH3
2. Write the IUPAC name for each of the following
a)
b)
O
O
O
O
O
c)
d)
O
O
O
OH
O
40
e)
f)
O
O
O
O
Day 10
Aldehydes and Ketones (pg 49 )
Aldehydes and ketones are similar in that they both contain a carbon atom that is double bonded to an
oxygen atom. The difference is that in an aldehyde, this carbon atom is attached to a hydrogen atom,
whereas in a ketone, it is bonded between two other carbon atoms.
R
O
H
aldehyde
R
O
R1
ketone
Here R and R1
would be carbon
groups and not
Hydrogen atoms
Both have relatively _____________ boiling points and are _______________ in water because the
carbonyl group is quite polar.
In naming aldehydes and ketones, locate the carbonyl carbon atom that contains the base name. For
aldehydes, remove the –e ending from the base name and replace it with –al. For ketones, remove the –e
and replace it with –one. It is important, when naming ketones, to use the number of the carbon to tell
exactly where the carbonyl group occurs.
CH3
O
C
CH3
H3C
____________________________________________________
x.
Write and name a structural formula for this aldehyde: C 3H6O
xi.
Write and name the structural formula for the ketone with the same chemical formula.
Common aldehydes and ketones :
1. formaldehyde IUPAC name is ______________; used as a __________________________
2. acetone IUPAC name is _____________________; found in _________________________
Name the following :
1.
-C-C-H

O
41
2.
-C-C-C-C-H
/ 
CH3 O
3.
C-C-C-C-C-C-C–H
/
\
\

CH3
CH3
CH3 O
4.
_________________________________________________________
Draw the following :
1.
methylpropanal
2.
3-ethyl-4-methyl - 2 - pentenal
3.
2,3 - dibromo - 4,6,7 - trichlorodecanal
4.
3 – bromo-3-cyclopropyl- 2,2 - dichlorobutanal
Name the following :
1.
C-C-C-C-C 
\
CH3 O
CH3
2.
-C-C-C-C-C 

O CH3 C2H5
3.
___________________________________
42
4.
______________________________________
Draw the following : Rename if necessary
1.
2 –ethyl-4-methyl - 3 - pentanone
2.
3 - cyclopropyl - 4 - methyl - 2 - pentanone
3.
5,7 - diethyl - 2,3,5 - trimethyl - 4 - nonanone
4.
2,4,4 - trimethyl - 3- heptanone
43
Independent Research
Name ____________________________
1. Assess the impact on human health, society and the environment of organic compounds in everyday
life(e.g. polymers, nutritional supplements, food additives, pharmaceuticals and pesticides. Consider the
following issue regarding the use of organic solvents which can dissolve substances such as paint , oil and
grease. They are also used to produce plastics, dyes, detergents, textiles and pharmaceuticals . In a risk
benefit analysis we must also consider the workers exposed to organic solvents may experience long-term
effects on their health. We must also consider industrial spills and leaks which can leach into the soil and
ground water posing serious health and environmental risks. Answer the following questions ;
a.
What methods should be used to safely dispose of volatile organic compounds.
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
b.
What WHMIS symbols or HHWS should appear on containers of pesticides.
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
c.
Why are organic compounds added to food products and what impact can these additives have on human
health.
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
44
2. Propose a personal course of action to reduce the use of compounds that are harmful to human
health and the environment ( e.g. weed lawns by hand rather than using herbicides, use cloth bags for
shopping to reduce the number of plastic bags in landfill sites, choose fuel-efficient or hybrid vehicles
to reduce fossil fuel emissions. Consider the following ; many communities have banned the use of
pesticides and as a consequence many homeowners are seeking alternative ways to control weeds.
Questions to consider :
a. How long does it take for plastic garbage bags to decompose in a landfill site.
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
__________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
b. What biodegrable materials can be used to replace polystyrene as a packaging material.
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
__________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
c.
What are some technologies and features that are making new cars more fuel-efficient.
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
__________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
d. Watch video www.teachersdomain.org : Carbon-Fiber Car of the Future

What are the environmental effects of so many cars on the roads, as seen in the beginning of the
video? Brainstorm ways to address some of these issues.
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
__________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________

45
From 1987 to 2007, the average fuel efficiency of all cars on the road actually decreased from
22.0 mpg to 20.2 mpg. Explain why this decrease occurred, even though engines today are more
efficient.
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
__________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________

List at least three ways you can think of to increase the efficiency of cars. Are there steps an
ordinary person can take to make this happen?
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
__________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________

Describe carbon fiber. What are the pros and cons of using it to make cars?
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
__________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________

What environmental impact would this technology have on our lives if it were available today?
How would the production of this prototype impact car manufacturing? What other options are
presently available to reduce the problems presented in the video?
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________
__________________________________________________________________________________________
___________________________________________________________________________________________
___________________________________________________________________________________________

Consider the following list of organic compounds with known safety, health, and environmental
concerns, (e.g., ether, carbon tetrachloride, PCB, CFC, leaded gas, saccharin, olestra, and
formaldehyde) that students can choose from, or allow the students to research an organic compound
of their choice. In the database activity, students produce a database on the product, its use, known
safety/health/environmental concerns regarding this product, alternate products used in response to
these concerns, and the reason for the use of alternates (Why is it better?) in table format as
suggested below:
Product
Uses
Concerns Due
Alternate
Reason for Use
(Organic
to Uses of
Product
of Alternate
Compound)
Product
Product
Complete pg 51-52 (1,3,4 )
46
Worksheet: Aldehydes
1. Write the IUPAC name for each of the following
a)
b)
O
O
c)
d)
OH
O
OH
Organic Worksheet
Name ________________________
1. Give the structural formula for the following compounds. The hydoxy group is OH. Rename if necessary.
a)
b)
2-chloro-4-propyl-3-methylpentanal
4-cyclopropyl-2,3-dimethylcyclopentanone
c)
3,4-dihydroxy-2-methylpentanal
d)
2-hydroxy-3-methylbutanal
e)
5-t-butyl-4-hydroxy-3-hexanone
47
3.
Name the following compounds with names suitable to the IUPAC nomenclature rules. Mix and Match.
O
a.
H3C
CH2
CH3
_______________________________
b.
___________________________________________________________
c.
____________________________________________________
d.
_______________________________________________
e.
_______________________________________________
48
ALDEHYDES
Name the compounds shown below:
CH3 – CH2 – C = 0
|
H
________________________________
CH3 – CH2 – CH – CH2 – C = 0
|
|
CH3
H
__________________________
CH2 – CH2 – CH2 –CH2 – C= 0
|
|
|
CH2 – CH3
CH3 H
Draw the structural formula for the following:
1.
methanal
2.
2 – chloropropanal
3.
2 – bromo – 4,4 – dimethylpentanal
4.
2,2 – difloro – 3,3,4 – trichlorobutanal
__________________________
Br
O
|
||
CH3 – C – CH2 –CH2 – C – H
|
Cl
__________________________
KETONES
Name the compounds shown below:
O
||
CH3 – CH2 – C – CH3
Draw the structural formula for the following:
1.
propanone
2.
2 – pentanone
3.
3,4 – dimethyl – 2 – hexanone
4.
4 – bromo – 2,2 – dimethyl – 3 – pentanone
Name:___________________________
CH3 – CH2 – C – CH2 – CH3
||
O
Name :__________________________
CH2 – CH2 – CO – CH2 – CH3
|
|
CH3
Br
Name : __________________________
Br
O
|
||
CH3 – C – CH2 – C – CH3
|
Cl
Name : __________________________
49
Day 11 : Preparation :
-
see section on alcohols
Properties :
aldehydes generally have a strong pungent smell; ketones smell sweet e.g. smell of a rose is
due to ketones ; aldehydes of higher molecular masses have pleasant smells e.g. smell of
cinnamon. Both are used to make perfumes. Both are _________ in nature thus _________ in
water. They are also used to dissolve non-polar solutes. Boiling points are high as far as
organics go but much less than ________________
Name the following ketones : male sex hormone _________________; female sex hormone
____________________; anti-inflammatory _______________________________
Oil found in almonds ____________________________
Reactions :
1. Addition ( hydrogenation )(Reduction)
Ethanal + hydrogen
---------------- ______________________________
Propanone + hydrogen ------------- ________________________________
Complete pg 56 ( 6,7 ); pg 57 ( 3,4 )
Carboxylic Acids (pg 58)
Carboxylic acids contain both the carbonyl group, and the hydroxyl group. Together these make up the
__________ group.
O
C
OH
They have _____________ melting and boiling points because there is _____________ bonding present
In naming carboxylic acids, replace the –e ending of the corresponding alkane with –oic acid. If sidechains are
present, begin numbering the carbon atoms with the end that holds the carboxyl group, or assign the smallest
number to this group.
50
O
H3C
i.
OH ______________ acid
Draw and name the structural formula for the following carboxylic acid: C2H3OOH.
-
methanoic acid is the IUPAC name for ____________________________
-
ethanoic acid is the IUPAC name for ______________________________
Name the following :
1.
C - C - C - C - COOH
2.
C - C - C - C - C – COOH
/
\
CH3
C2H5
3.
4.
________________________________
_____________________________________
C - C - C - COOH
/
\
\
CH3 Cl Cl
_________
CH3C(Cl)(Br)COOH
5.
_________________
_____________________________________
Draw the following :
1.
trifluoroethanoic acid
2.
3-chloro-4-isopropy-5-methyllbenzoic acid
3.
4,4,5-triodo-2-methylhexanoic acid
4.
3,4-dibromo-2,5,7-trichlorodecanoic acid
Name the common acid found in :
vinegar
, rancid butter _______________
fruits ____________________________
rhubarb : ethanedioic acid : draw structure
bee stings
.
51
Properties (60)
1.
2.
3.
4.
Relatively
boiling points as far as organics go due to _________ ; ________
than alcohols
Simple ones are
in water ( the first four )
Characteristic unpleasant odour
Turn litmus paper
; when ionized in water produces the
____________________ion.
Complete pg 60 (1,2)
Preparation :
-
-
______________ of primary alcohols produces _______________ which can be further
_____________ to ____________
Complete pg 63 (5,7,8)
52
CARBOXYLIC ACIDS
Name the compounds shown below:
Draw the structural formula for the following:
1. Ethanoic acid
CH3 – CH2 – CH2 – C = 0
|
OH
Name : ________________________
CH3 – CH – CH2 – CH2 – COOH
|
CH3
2.
3 – ethylpentanoic acid
3.
3,3 – dibromopropanoic acid
4.
2,2,4,4 – tetramethylhexanoic acid
Name : _________________________
Br
O
|
||
CH3 – C – CH2 –CH2 – C – OH
|
Br
Name : _________________________
F
O
|
||
F – C – CH2 – CH – C – OH
|
|
F
CH3
Name : _________________________
Day 12
E. Esters ( pg 64 )
One of the most important reactions carboxylic acids undergo is esterification.
In this reaction, an alcohol reacts with a carboxylic acid to form an ester and water.
O
O
+
H3C
OH
+

HO
CH3
H3C
O
CH3
H2O
ethanol
ethanoic acid
ethyl ethanoate
water
Esters consist of two hydrocarbon groups separated by the ester functional group. This group consists of one
oxygen atom doubly bonded to a carbon atom and another oxygen singly bonded between the same carbon
atom and the next hydrocarbon chain. In forming esters _______________ is removed from the alcohol and
________________ is removed from the acid. See page 64-65
Esters have lower boiling and melting points than alcohols or carboxylic acids because they cannot form
hydrogen bonds.
In naming use the alkyl portion of the alcohol name as the first name.
The - ic acid ending of the name of the carboxylic acid is replaced with - ate . Consider the example
below.
53
O
H3C
C
O
CH3
propyl ethanoate ( note 2 separate words )
a.
Write and name the structural formula for the following ester: C 2H5OOCH
Name the flavour _______________
b.
Write the reaction for methanol and butanoic acid. Name the product.
What flavour.
c.
Write the reaction for methanol and ethanoic acid. Name the product.
d.
Write the reaction for: Name the reactants and products.
O
H3C
CH3
OH
HO
e. Name the two chemicals that react to form the following: State the flavour of each. Note common names
are used.
a) isobutyl propionate
b) methyl butyrate
c) ethyl butanoate
d) 3-methyl butylacetate
e) octyl ethanoate
f)
pentyl butyrate
54
Name the following :
1.
C - C - C - C - O - C - C - _____________________________________________

O
2.
C- C - C - C - C - O - C - C - C - C

\
O
CH3
3.
_______________________________________
O

C-C-C-O-C-C-C-C-C\
\
\
CH3
C2H5 CH3
4.
_____________________
________________________________________
5.
________________________________________________
Draw the following
1.
2-methylbutyl propanoate
2.
2-propyl -2-methylbutanoate
3.
2 - chloroethyl -2-chloroethanoate
4.
2-chloropropyl - 2 - methyl butanoate
5.
isopropyl-2,2-dimethyl pentanoate
55
Properties of esters : Pg 66
1.
2.
3.
4.
Simple esters are in __________________ water due to _____________
Boiling points are relatively
compared to other organics of similar mass
Esters are used for ______________________________
Most esters have a pleasant fruity odour.
Complete pg 66 (11,12 ) , pg 68 ( 1,2,3,4 )
56
ESTERS
Name the compounds shown below:
Draw the structural formula for the following:
1. methyl ethanoate
O
||
CH3 – CH2 – C – O – CH3
Name: ________________________________________
CH3 – CH2 – CH2 – CH2 – CO – O – CH3
2.
methyl 3-methylbutanoate
3.
ethyl 2,2-dichloropropanoate
4.
2-methylpentyl propanoate
Name: ________________________________________
O
//
CH3 – CH2 – C
CH3
\
|
O – CH2 – CH2 – CH2 – CH3
Name: ________________________________________
F
O
|
//
F – C – CH2 – C
|
\
F
O – CH2– Cl
Name: ________________________________________
1. Write the IUPAC name for each of the following
a)
b)
O
O
O
O
c)
d)
O
O
e)
O
O
Cl
OH
O
O
57
Day 13 : Ester Lab
Day 14 :
Amines and Amides ( pg 69 )
Amines are organic compounds closely related to ammonia and have a “fish-like” odour. They occur when
organic compounds replace one or more of the hydrogens bonded to the central nitrogen in ammonia.
H
R1
N
H
-
Amine Group
amine is classified as Primary if it contains only one alkyl group, Secondary if it contains 2, and
Tertiary if it contains 3.
Classify these :
1.
C - C - C - NH2
____________________________________
2.
C - C- N- C - C- C____________________________________

C
3.
C - C- C- C - N - C - C____________________________________

H
Amides are produced when an amine or ammonia is treated with an organic acid. It looks like an acid with
the –OH group replace by the –NH2.
O
R
C
H
N
H
Amide Group
The basic structural group of proteins and enzymes is the amide linkage.
O
R
C
R1
N
H
Amide linkage
Naming Amines
Common Names:
Common names for amines are formed from the alkyl groups bonded to
the nitrogen, followed by the word amine. Di-, tri-, and tetra are used to
describe identical substituents.
Draw the following :
Methyl amine
Dimethyl amine
Trimethyl amine
58
IUPAC Names:
Naming of amines is very similar to the naming of alcohols. The longest chain containing the amine is
used as the root name. The -e ending in the naming of alkanes is changed to -amine, and a number gives
the position of the amino group along the chain. Other substituents on the carbon chain are given
numbers, and the prefix N- is used for each substituent on nitrogen.
Draw these :
2-butanamine
N-methyl butanamine
N,N-diimethyl-2-butanamine
2-chloro-N,N-dimethyl-4-aminohexane
Name the following :
1. - C - C - NH2
_______________________________________
2. - C - N - C -
________________________________________
3. CH3 - CH - CH2 - CH - CH2 - CH3 __________________________________
\
\
NH2
CH3
4. C - C - C - NH2
5. C - C - N - C 6. C - C- C- C - NH2
7. C - C - C - N - C - C -
_____________________________________
_______________________________________
_____________________________________
________________________________________________
8.
____________________________________________________
59
Draw these :
1. 2,3 - diamino - 2 - pentene
2. 3 – methyl-4-propylpentanamine
3. 1,4 - diaminocyclohexene
4.
N – ethy-2-chloropropanamine
5.
2-aminopentane
6.
N-methyl-2-butanamine
7. N,N-diethyl-3-aminoheptane
Practice pg 72 ( 2,3 )
Amides ( R - C = O ) ( pg 74 )

NH2
- amides are derived from carboxylic acids and ammonia, or from a primary or secondary amine
- named by dropping the E ending from the name of the parent hydrocarbon and adding the amide ending
- numbering of the C chain begins at the C atom of the amide group.
- if the Hydrogens on the amide group are replaced by hydrocarbon groups, precede the name of each
replacing group by " N " to indicate that the group is attached to a nitrogen atom.
60
C - C = O is called

NH2
____________________________________________
O
//
- C - C - N - C - is called _________________________________________

H
Name the following :
1.
2.
3.
4.
CH3CH2 C = O

NH2
H

- C - C - N - C - CH3

O
O

- C - C - N - C - CH3

CH3
___________________________________
__________
___
O

Cl - C - C - C - N - CH3

CH3
5.
___
___________________________________
Draw the following : Rename if necessary
1.
2 – methyl-3-propyl butanamide
2.
N-cyclopropyl -2-chloroethanamide
3.
N – methyl methanamide
4.
N - ethyl - N - methyl - 2 - chlorobutanamide
61
Complete pg 76 ( 4-6 )
Properties of Amines (pg 72 )
1.
2.
3.
4.
5.
Often have a fishy or foul odour smell
Organic bases and form salts when reacted with acids
Primary and Secondary amines exhibit
bonding thus
in water
Tertiary amines have
B.P. than the primary or secondary amines
Nicotine, Epinephrine and Histamine are common examples. Adrenaline is an example of a
secondary amine.
Properties of Amides
1.
2.
3.
4.
Very weakly basic
Normally insoluble in water
Relatively
boiling points due to ____________; primary amides have higher
B.P. than _______________________
Proteins and nylon are common polyamides. The amide acetaminophen is found in painkillers.
Name the following Amines and Amides
CH3
H3C
N
H
_______________________________________________
H3C
H
N
H3C
H
_________________________________________
H
N
________________________________________
H
H
H3C
N
H
O
________________________________________
62
H
O
N
H
H
N
O
H
________________________________
Draw the following Amines and amides . Rename if necessary
a) 3-methylpentylamine
b) methylethanamine
d) p-aminobenzoic acid
e) 2-isopropylpentanamide
e) N-ethyl-N,N-dimethyl-3-ethyl butanamide
Synthesis of Amines and Amides
-
primary amines are produced by adding ammonia to an _________________________________
amides are produced by reacting __________________________ with amines
Complete pg 78 (1-5,9) Complete pg 95 (1-15,pg 96 ( 1-6)
63
AMINES
Draw the condensed structural formula for the
following:
1. aminobutane
Name the compounds shown below:
CH3 – CH2 – CH2 – NH2
Name:
_______________________________________
Type of amine (1°, 2°,3°) : ________
CH3 – CH – CH – CH2 – CH3
|
|
CH3 NH2
Name :
______________________________________
Type of amine (1°, 2°,3°) : _______
CH2CH3
|
CH3 – CH2 – CH2 – CH2 – CH2 – N – CH2CH3
Name :
______________________________________
Type of amine (1°, 2°,3°) : ___________
Br
NH – CH2CH3
|
|
CH3 – C – CH2 – CH – CH3
|
Br
2.
2 – aminopentane
3.
N – methyl – 2 – aminobutane
4.
N,N – diethyl – 3 – amino – 3 – methylpentane
Name :
_________________________________________
AMIDES
Name the compounds shown below:
O
||
CH3 – CH2 – C – NH – CH3
Draw the condensed structural formula for the
following:
1. N – methyl ethanamide
Name:
________________________________________
CH3 – CH2 – CH2 – CH2 – CO – N – CH3
|
H
2.
N,N – dimethyl propanamide
3.
N – ethyl 3 - methylbutanamide
4.
N – methyl 3,3 – dibromopropanamide
Name:
________________________________________
O
//
CH3 – CH2 – C
\
N – CH2 – CH3
/
H
Name:
_______________________________
Cl
O
|
//
Cl – C – CH2 – C
|
\
Cl
N – CH3
|
CH2CH3
64
PROPERTIES OF ORGANIC FAMILIES
Family 2
Alcohols
Polarity
Hydrogen
bonding
Solubility in water
Melting and
boiling points
Additional
characteristics
O-H bond is very
polar; small
alcohols are
______polar than
large alcohols
Alcohols
experience Hbonding with
other alcohols
and water
Extremely soluble in
water due to Hbonding. Solubility
______________with
increasing number of
carbon atoms.
Due to Hbonding, most
have higher
melting and
boiling points
than alkanes
with same
number of
carbon atoms.
Most are
___________at
room
temperature.
Extremely
flammable
Ethers
______shape
around oxygen
means two C-O
dipoles do not
counteract each
other. C-O bond is
____polar than OH, ether is ____
polar than alcohol.
No H-bonding
due to no O-H
bond. Can
accept Hbonding from
water.
Usually soluble,
solubility decreases
with increasing size
of carbon chains.
Boiling points
much lower
than alcohols.
Extremely
flammable
Amines
C-N and N-H
bonds are polar.
Amines are usually
polar.
N-H bonds
allow Hbonding.
Amines with four or
less carbons are
miscible with water
(due to H-bonding).
Solubility decreases
as # C increases.
Primary and
_____boiling
points than
tertiary (which
do not contain
N-H bond).
-Widely found in
nature. Often
toxic. Many have
medicinal
properties.
-Low molecular
mass amines have
____smell.
-Act as weak
_________.
Aldehydes
and
Ketones
C=O bond is polar,
so both usually
polar
H-bonding
cannot occur
between
molecules
since no O-H
bond. H-bonds
can form with
water.
Those with low
molecular mass are
very soluble in water.
Those with large
molecular mass are
less soluble.
BP are
________than
corresponding
alcohols, and
________than
corresponding
alkanes.
-Aldehydes have
strong ______
smell, while
ketones smell
_______Aldehydes
with large
molecular mass
smell_______.
Both used to
make _________.
-Can act as polar
solvents, but also
as solvents for
non-polar
compounds.
Most are
poisonous
65
Carboxylic
Acids
Due to polar O-H
and C=O bonds,
are polar
compounds.
H-bonding is
strong, and
also occurs
with water.
Those with low
molecular mass are
very soluble.
Solubility decreases
with increasing #C
atoms.
Melting and
boiling are very
high.
-Often have
unpleasant
odours.
-OH group does
not behave like
basic hydroxide
ion (OH-).
-Melting and
boiling points are
very high due to
exceptionally
strong H-bonding.
Esters
Like carboxylic
acids, usually
polar.
Do not have OH bonds
therefore
cannot form Hbonds.
Can accept H-bonds
from water, so those
with low molecular
mass are soluble.
Esters with C chains
longer than 3 are not
soluble.
Low boiling
points due to
no H-bonds.
Usually volatile
liquids at room
temperature.
-Pleasant odour
and taste, used to
produce perfumes
and artificial
flavours.
-Taste of many
fruits come from
esters.
C-N and N-H
bonds are polar
and amides are
similar to
carboxylic acids.
Primary
amides have
stronger Hbonds than
carboxylic
acids due to
two N-H
bonds.
Secondary also
form H-bonds.
Soluble in water.
Solubility decreases
with increasing nonpolar HC part.
Primary amides
have higher
melting and
boiling than
carboxylic
acids. Many
are
_________at
room
temperature.
-Amide called
acetaminophen is
painkiller
-Urea (an amide),
made from carbon
dioxide and
ammonia, first
organic compound
synthesized.
Amides
66
Organic Compounds : Summary
GROUP
STRUCTURE
Alkane
NAMING
GENERAL
FORMULA
PROPERTIES
USES AND OCCURENCE
__________
Non-polar ; Insoluble
;
______ M.P. and B.P.
_____________ and
combustion
Fuels ; petrochemical
building blocks
Major source is
______________l
_________
Same as alkanes
__________and
combustion reactions
starting materials for
many polymers
produced from catalytic
cracking of _________
Same as alkanes
addition of 1 or 2
molecules of adding
agent
Combustion
_________; insoluble
in water
______________ and
combustion
DEHYDROGENATION OF
2 O ALCOHOL
SOLVENT
very diverse- antifreeze,
alcoholic drinks,
cosmetics, food
methanol from
destructive distillation of
wood
ethanol from distillation
of sugars and
industrially by hydrating
ethene
commonly occurs in
foods, waxes
present in fruits- sour
taste, animal fats and
vegetable oils
used as solvents and
artificial flavours ;
commonly occur in
animal fats and
vegetable oils
natural occuring fruits
etc.
antiseptics
anaesthetics
refrigerants
insect repellants
-ane
Alkene
- ene
Alkyne
- yne
____________
__
Aromatics
- benzene or
phenyl
C6HnR(6-n)
(variable)
R -OH etc.
-ol,diol,triol
CnH2n+1OHet
c.
higher B.P.; soluble in
water; many
reactions e.g.
esterfication,
combustion
Acids
R-C=O
\
OH
- oic acid
CnH2n+1COO
H
Esters
O
high B.P.
first 4 soluble
all inorganic
reactions;
esterfication
insoluble in water
react with water to
form acid and alcohol
CnH2n+1X
CnH2n-1X
C6H5X
Variable B.P.'s
generally insoluble in
water
intermediates in prep
of many organics
Alcohols
R' yl R oate
\\
-C
\
O --R'
Alkyl
halides
R - Xn
X= F,Cl, Br, I
flurochlorobromoiodo-
very diverse solvents,
foods, drugs, explosives
major source is coal tar
GROUP
STRUCTURE
(Draw the
simplest in
the family)
NAMING
ETHER
67
__________IN
WATER
__________B.P.
THAN ALCOHOLS
OXIDIZED TO
_____________
_______________OF
PRIMARY ALCOHOLS
PRODUCED FROM
ALKENES
SOMEWHAT
SOLUBLE IN
WATER
UNREACTIVE
DEHYDROGENATION OF
2 O ALCOHOL
SOLVENT
Drop e
from
alkane
add the
word
amine
_________ODOUR
ORGANIC BASES
____________IN
WATER
NICOTINE-3OAMINE
BIODEGRATION OF
AMINO ACIDS
Drop e
from
alkane
add the
word
amide
HIGH B.P.
INSOLUBLE IN
WATER
VERY WEAKLY
BASIC
SYNTHETIC
POLYMERS
PROTEINS
al
KETONE
- ONE
H-C-NH2
\\
O
USES AND
OCCURENCE
__________________
ALDEHYDE
AMIDE
PROPERTIES
________
__________IN
WATER
ORGANIC
SOLVENT
yloxyether
AMINE
GENERAL
FORMULA
QUICK START SPRAYS
68
Naming and Drawing Organic Compounds
Compound
3-ethyl-4-methyl-2-pentanol
3-isopropyl-2-heptanamine
2-ethyl-3-isopropyl-4-methylhexanal
1-chloro-3-methyl-2-propanone
2-sec-butyl-4-tert-butylpentanoic acid
2-chloroethyl-2-propyl butanoate
N-methyl-4-isopropylhexanamide
3-tert-butyl-4-cyclobutyl-2-pentanone
2-methyl-3-propylbenzene
2-methoxy-2,3-dimethylbutane
Structural diagram
Hydrogen
bonding
(yes/no)
69
N,N-dimethyl-3-methyl-4-heptanamine
Isopropyl- 2,3-dimethylhexanoate
3,4-octanediol
N-ethyl-3-methylbutanamide
2,3,4-trimethylpentanal
6-propyl-2,4,5,7-tetramethyldecanoic
acid
2-ethyl-3-methyl-4-octyne
N,N-dimethyl-2-methyl heptanamide
4,5-dimethylcyclohexene
1-methoxy-4-chloro-2-pentene
4-methyl-2-pentynamide
2-ethyl-5-butylcyclohexane
70
NAMING ORGANIC COMBINATIONS OF FUNCTIONAL GROUPS
2. Name the following organic compounds.
(a) CH3CH2COOH
(b) CH3C(O)CH2CH2CH2CH2CH3
(c) CH3CONH2
(d) CH3CH2CH(CH3)CH2OH
(e) CH3CH2C(CH3) 2CH2NH2
(f) CH3CH2CH2CH2OCH2CH3
(g) HCOOCH2CH2CH3
(h) CH3CH2CH(CH3)CH2CHO
71
Name the compounds shown below:
Draw the structural formula for the following:
NH2
O
|
//
CH3 – CH – CH2 – C
\
H
1.
2 – aminopropanioc acid
OH
O
|
//
CH3 – C – CH2 – CH2 – C
|
\
NH2
OH
2.
3,3 – dihydroxyhexanal
NH2
|
CH3 – C – CH2 – CH2 – CH2 – OH
|
NH2
3.
1 – amino – 2 – propanol
Br
OH
|
|
CH3 – C – CH2 – CH2 – CH – CH3
|
H – N– CH3
4. 1 – hexen – 3 – ol
H
|
CH3 – CH2 – C = C – CH3
|
OH
5. 3 – amino – 1 – buten – 2 – ol
NH2
|
CH3 – CH2 – CH = C – CH3
|
OH
6. 4 – amino – 4 – chloro – 2 – penten – 1 – ol
7.
OH
O
|
//
CH3 – CH – CH2 – C – O – CH2 – CH3
|
CH3
N – ethyl – N – methyl 2,2 – dihydroxybutanamide
Day 15 Polymerization pg 100
Polymerization is the building up of large chains of molecules from repeating sequences of basic units
called_____________. ______________ polymerization involves the build-up of monomers without the elimination of
atoms. ____________________ polymerization results in the elimination of atoms as polymers are built.
H
H
C
H
+
C
H
H
C
H
H
ethene

C
H
+
ethene

An example of condensation polymerization involves amino acids in the formation of proteins.
H
O
+
N
OH
H
glycine
O
H

N
OH
H
+
glycine
peptide bond created

i. Show the condensation polymerization of
O
HO
OH
HO
ethylene glycol
OH
O
terephthalic acid
Ii Show the condensation polymerization of : account for the name nylon 6,6
OH
NH2
H2N
O
O
1,6-diaminohexane
OH
adipic acid
Watch video : www.teachersdomain.org : The Impact of Technology: Nylon
materials have you come in contact with today? If synthetic materials didn't exist, what do you think
those things would be made of instead?
73
What are the monomers needed to make ;
____________________________________ and ___________________________________________
_______________________________ and ______________________________________________
Complete table below : ( see page 101 and 139 )
Monomer Name
Monomer
Structure
Polymer Name
Polymer Structure
Uses
Propene
(propylene)
polypropylene
indoor-outdoor carpeting
___________________
Chloroethene
(vinylchloride)
polywinylchloride
(PVC)
shower curtains, floor tiles,
siding
____________________
Vinyl benzene
polystyrene
styrofoam, insulation,
containers
____________________
tetrafluoroethene
polytetrafluoro
ethylene
(teflon)
non-stick pan coating
What monomer is needed to make :
_____________________________________________________
74
Research (see pages 110) : Kevlar
What are the monomers used to make Kevlar ? __________________________ and ______________________
Describe and account for its properties.
______________________________________________________________________________
______________________________________________________________________________
Research the artificial sweetener aspartame (pg 120)
Artificial Sweeteners: Health Risk or Health Benefit ?
-
can be used to decrease sugar consumption for overweight people, decrease tooth decay and increase food choices
for diabetics
aspartame – sweet, digests to form natural __________acids and __________________
___________ – oxidized to form _____________– formaldehyde – changes protein function!
______________oxidized to form ___________ acid – interferes with mitochondrial function in cells
__________and _____________acid build-up in ____________ nerves can cause irreversible damage – blindness
but: small amounts of methanol in fruits, vegetables, beer, wine
so: aspartame deemed “safe” if not too much is taken per day
So: what amount is safe?
Complete pg 107 ( 2,3,6 ) pg 111 ( 1-3 ) pg 113 ( 2,3,5 )
75
ADDITION POLYMERS
Draw the structures of polymers formed from each monomer:
Ethene
Polyethylene
H
H
\
/
C=C
/
\
H
H
Vinyl Chloride
Polyvinyl Chloride (PVC)
H
H
\
/
C=C
/
\
H
Cl
1,1 – dichloroethene
Saran
H
Cl
\
/
C=C
/
\
H
Cl
tetrafluoroethene
Teflon
F
F
\
/
C=C
/
\
F
F
cyanoethene
Orlon
H
H
\
/
C=C
/
\
H
CN
Propene
Polypropylene
CH2 = CH
|
CH3
Styrene
H
H
\
/
C=C
/
\
H
Polystryrene
76
CONDENSATION POLYMERS
MONOMERS
POLYMERS
O
\\
+
C
/
HO
CH2 – CH2
|
|
OH OH
O
//
C
\
OH
Dacron (a polyester)
HO
OH
+
H2N – (CH2) 6 – NH2
O
O
\\
//
C – CH2 CH2 – C
/
\
HO
OH
O
O
\\
//
+
C – (CH2) 4 – C
/
\
HO
OH
Nylon (a polyamide)
H2N
O
\\
NH2 + C
/
OH
O
//
C
\
OH
O
H
O
//
|
//
H2N – CH2 – C
H2N – C – C
+
\
|
\
OH
CH3 OH
glycine
alanine
Amino Acids
H
O
|
//
+
H2N – C – C
|
\
CH2 OH
|
phenylalanine
H
O
|
//
H2N – C – C
|
\
CH3 OH
alanine
Protein (a polyamide)
77
H
O
|
//
H2N – C – C
|
\
CH2 OH
+
O
//
H2N – CH2 – C
\
OH
|
|
OH
tryosine
glycine
Day 16 Summary : Organic Reactions (pg 80)
1.
Combustion
-
all organics ; products are ____________________ and ______________
2.
Substitution
-
Alkanes, Cycloalkanes and Aromatics : treated with halogens e.g. chlorine gas
Alcohols : treated with a hydrohalogen compound like HCl
3.
Addition-
Alkenes, Alkynes, cycloalkenes : treated with Hydrogen gas [ hydogenation ]
Alkenes, Alkynes, cycloalkenes : treated with halogens [ halogenation ]
Alkenes, Alkynes, cycloalkenes : treated with a hydrohalogen [ hydrohalogenation ]
Alkenes : treated with water [ hydration ]
Ketones and Aldehydes : treated with hydrogen gas [ reduction ]
-
Alcohols : treated with sulfuric acid form alkenes [dehydration]
Formation of ethers from alcohols eliminates water [condensation]
formation of esters from an alcohol and a acid eliminated water[condensation]
formation amides from amines and carboxylic acids[condensation]
4.
Elimination
5. Mild Oxidation -
primary alcohols undergo mild oxidation producing an aldehyde which can be
further reduced to a carboxylic acid
secondary alcohols when oxidized form ketone
tertiary alcohols cannot be oxidized easily
Classify the following reactions :
___________________________________________
___________________________________________
___________________________________________
_____________________________________________
78
Identifying Organic Reactions
Reaction 1
Reaction 2
Reaction 3
Reaction 4
Reaction 5
Reaction 6
Reaction 7
Reaction 8
yes
no
no
no
no
no
Hydrolysis: Does a large organic molecule such as an ester
or amide split in half to form two smaller organic molecules?
Condensation: Do two organic molecules combine to form a
large organic molecule such as an ester or amide?
Reduction: Does the product have more bonds to hydrogen
and fewer bonds to oxygen?
Oxidation: Does the product have fewer bonds to hydrogen
and more bonds to oxygen?
Substitution: Has an atom or group of atoms been
substituted for a different atom or group of atoms?
Elimination: Does the organic product have more double or
triple bonds than the reactant?
Addition: Does the organic product have fewer double or
triple bonds than the reactant?
79
no
Type of reaction
addition
80
ORGANIC REACTIONS
For each of the following reactions complete the word equations; write a balanced chemical equation
for any combustion reaction and state the type of reaction.
a)
n-hexane +
oxygen --------> carbon dioxide + ____________________
b)
methane
+
chlorine -------->
c)
propene
+
bromine -------->
d)
cyclopropene + chlorine ---------> _________________________
e)
butanal
_______________________
f)
K2Cr2O7
--------------------> _____________________________
[O]
[O]
2,4-dimethyl-3-hexanol ------------->
g)
3,3-dimethylhexanoic acid + propanol ------>
[O]
----------->
h)
1-propanol
i)
propanal
j)
benzene + chlorine --------->
+ _________________
[O]
----------> _____________________________
K2Cr2O7
K2Cr2O7
---------------> ------------------>
k)
ethanol
l)
1-butyne + 2moles iodine ------------>
m)
2-methylpropene + hydrogen --------->
n)
2-butyne + oxygen ------------> carbon monoxide + _______________
o)
propene
+ water -------------> _________________________
p)
2-propanol
q)
1-propanol
r)
butanal
[O]
------------------->
[O]
[O]
-----------------> ------------->
+ hydrogen -------------> ______________________________
s) propanone + hydrogen -----------> ______________________________
t) methanoic acid + 3-hexanol ------->
K2Cr2O7
u) 2-methyl-2-propanol ------------------>
81
Day 17 : Slime Lab
Day 18 : Review : Pg 82 (1a,c,1a,d,3) pg 96 (7a-j,8a-j, 10a-e)
Complete pg 145 ( 1,5,6,7,8 ), pg 146 ( 1,2,19,21 ) pg 150 ( 1-9, 11-14,16-24 ) pg 152 ( 1-11),
13,21,22
SCH4U1 UNIT 2 REVIEW
Multiple Choice
Identify the letter of the choice that best completes the statement or answers the question.
____
1.
What is the correct name for the above compound?
a. 2-methyl-3-butanol
d. 3-methyl-2-butanol
b. 2-pentanol
e. none of these
c. isobutanol
____
2. What results when a secondary alcohol is oxidized?
a. a ketone
d. an acid
b. an amine
e. no reaction
c. an aldehyde
____
3.
The correct name for the compound given above is which of the following?
a. 3-amino-3-hexanone
c. N-propylpropanamide
b. ethyl ethanamide
d. N-ethylethanamide
____
4.
The correct name for the compound given above is which of the following?
a. 2-cycloproproxylcyclobutane
c. 2-cyclobutoxycyclopropane
b. cyclobutylpropoxy ether
d. cyclopropoxycyclobutane
____
5. 1-amino-4,4-difluoro-2-pentanol is the correct name for which of the following compounds?
a.
c.
b.
d.
82
____
6. Which of the following is the correct name for the diagram below?
a. propylcyclohexylcyclohexanoate
b. 2-cyclohexoxycyclohexylpropanoate
____
7. Which of the reactions shown are reductions?
a. (1), (2), and (3)
b. (1) and (3) only
c. (2) and (4) only
____
d. (4) only
e. (1) and (4) only
8. What is the correct IUPAC name for compound below?
a. 2-ethyl-5-hexanone
b. 5-ethyl-2-hexanone
c. 3-methyl-6-heptanone
____
c. dicyclohexanylpropanoate
d. methylcycloxypropanoate
d. 5-methyl-2-heptanone
e. 2-heptanone
9. The correct name for the compound given below is which of the following?
a. 1-phenyl-1-butanone
b. phenylbutanal
c. 4-phenyl-4-butanone
d. butanonebenzene
____ 10. The polymer Torlon is used in automotive engines as a plastic replacement for steel parts. It is produced
from the monomers.
and
83
What is the formula of Torlon?
a.
c.
b.
d.
____ 11. What is the monomer for the polymer Kel-F shown below?
a.
c.
b.
d.
____ 12. Which of the following polymers is Nylon 6,4?
a.
b.
c.
d.
84
Completion
Complete each sentence or statement.
13. When a straight chain alcohol is reacted with
,
, and
are both formed.
The structure of the original alcohol was _________________________.
14. The correct IUPAC name for the structure given below is
_____________________________________________.
Short Answer
15. Propane can be used as starting material for either propanal or propanone. Explain how this is possible.
16. The structure given below is PenicillinG, an antibiotic. Circle the functional groups in the molecule and list
their corresponding names.
17. Write the reaction showing how the ester.
, can be prepared from a carboxylic acid and an alcohol. Provide the names
of all reactants below your equation.
18. Nomex is a polymer used to make flame-resistant clothing for firefighters. A portion of its structure is
provided below. Write a polymerization reaction showing its production from monomers. What type of
reaction is this?
85