Chemistry 30

Organic Compounds:
Naming

Summary Notes
and Problems

1
 ORGANIC CHEMISTRY
How It Relates to the Curriculum:
• define organic compounds as compounds
Original definition: The study of compounds found or produced containing carbon, recognizing
inorganic exceptions such as carbonates,
by living organisms cyanides, carbides and oxides of carbon.
• Identify and describe significant organic
Organic chemistry today is considered to be the study of carboubased compounds in daily life, demonstrating
compounds generalized knowledge of their origins

exception carbonoxides coC carbides Beal and applications

carbonatesfbcos.Nacodcy.anide.suwY3 ioeIYepfo
IIrogoIdsoxides
Organic Compounds in Daily Life:
Organic compounds constitute a major part of energy sources (petroleum, natural
gas, coal); food(carbohydrates, proteins, fats, vitamins, enzymes, hormones);
drugs (antibiotics, antiseptics) and materials such as fabrics, wood, perfume,
cosmetics, dyes.
Carbon- 1% of the earth’s crust
-the basis of life on earth
Yurt
- makes bonds usually CEO
4 covalent
- can foI large stable molecules by linking C C
qy y - intermolecular forces betweenmolecules usually weak
-
i organic compounds tendtohave low up andbp
-other elements common in organic compounds include O, N, H, Cl, F, Si
There are over 4 000 000 organic compounds known
There are less than 50 000 inorganic compounds known
2 3
arr
I
How are Organic Compounds Classified?
d t
Ø The ability of carbon atoms to form chains, rings, sheets, tubes, and spheres is
a very important feature of organic compounds and how they are classified.

HYDROCARBONS
Ø These compounds contain only
H and C
Ø They are the most important class of organic compounds to humans. Why,
you ask?
fossil fuels
Ø Hydrocarbons are classified into two main groups
1. Aliphatics – alkanes alkenes
alkynes containbranches not rings
2. Aromatic –
cyclichydrocarbons rings
basedaround benzene specialtype ofring
Ø Hydrocarbons can also be classified according to the types of carbon-carbon
(C-C) bonding they possess:
1. Saturated hydrocarbons - contain single bonds
only
can'tbondto any more atoms
2. Unsaturated hydrocarbons -
contain 2 or more double or triplebond
fats g
can be saturated 2
add more atoms bonds
by
 How This Relates to the Curriculum:
• Be able to draw structural,
Ways to Represent Organic Compounds condensed structural, line
diagrams and formulas for
Empirical Molecular Formula [shows the number and types of atoms present, saturated and unsaturated
but does not indicate structure]
ft
aliphatic and aromatic carbon
compounds.
Example: Heptane - C7H16
Note: (hept) 7 carbons (ane) all single bonded) H C It µ it
l H i r
H Hit It t C it
H c Hch
hc
H l ti
Cy heh i e e isomers if It 1 H
H
H HH H H H
H H C
heptane GH I't G His
Structural Formula [gives atoms and locations of the bonds] 2,3 dimethylpentane
H H

HG H C C H
Can you name it: ethane
H H

Condensed structural Formula [similar to structural but saves space; carbon

hydrogen bonds assumed]
H3C CH2
CH3 Can you name it:
C3H8 propane
Line formula [uses lines to represent chemical bonds. Each point, or bend in the
line, and each end of a straight line represents a carbon atom (unless otherwise
specified) and each carbon is assumed to have as many hydrogen atoms attached
to it as is necessary to give the carbon four bonds]
c
Ethane (C2H6) would be

Propane C3H8 would be none of H is drawn

2
3
I

3
Practice:
1. Complete the following chart:
Molecular Structural Formula Condensed Structural Line Structural
Formula/ Formula Formula
name

C6H14 HHH H H H
IYJgHJHK
d
H HH H H H
CHaCHaCHsCHs CH.gs

y6
H HH HH
G Hn H 4 4444 H CH3—CH2—CH2—CH2—CH3
µ
It It It It It

Hg CH CHICA N
H HH H
Hyo H 4 444 H CHzCHICHA CH
H HH H
H
H dH GHz
1 it
GHio H C C H HC CH
l
H fH Htt CH
HH HH 4h3
GHis H
44 H Gt3ChaCH CH
H H 424
H
H H
H H CH3

H HEH H
l I H
l H CH3—CH—CH—CH2—CH3 1
7h16 l i
H C CC C C H N
l s l l l CH3 l
H H
Hq
H

4
 ALIPHATIC HYDROCARBONS
ALKANES (CnH2n+2)
bonds
saturated containsonly single
Ø Alkanes are considered an aliphatic hydrocarbon (i.e. these are hydrocarbons that
contain chains of carbon atoms and contain no benzene ring – more on this later)
Ø They have only carbon-carbon single bonds (i.e. this means they are saturated
hydrocarbons)
Ø Many hydrocarbons are found in oil
Ø First oil well in North America was Oil Springs Ontario 1856 How This Relates to the Curriculum:
• Using the International Union of Pure and
Applied Chemistry [IUPAC] guidelines
name saturated and unsaturated aliphatic
and aromatic carbon compounds:
Properties of Alkanes: - containing up to 10 carbon atoms in

bp dependon size of
molecule due primarily the parent chain or cyclic structure
- containing one type of functional

to LDF themore electrons greatertheLDF's

the group (including multiple bonds,
simple halogenated hydrocarbons,

on molecule structure shape

alcohols, carboxylic acids, and
bpdepends water esters)

non polar molecules verylowsolubility in - containing multiple occurrences of

only halogen or alcohol functional
conductors no dissociation groups
poor
combusteasily with 02cg properties
mplbp very low
Practical Uses of Alkanes:
Methane (CH4): H
Ø the simplest alkane
C weak intermolecular forces
Ø Found in marsh gas
Ø 90% of natural gas is methane Ht H yougot in water
Ø used as a fuel
H
Ø CH4(g) + 2O2(g) ® CO2(g) + 2H2O(g)

Ø Propane à C348cg combustion

Ø Pentane à winter addaitefor gasoline
G H2cg
Ø Octane à
His part ofgasoline

5

• Using the International Union of Pure and
IUPAC SYSTEM OF NAMING HYDROCARBONS
The IUPAC name of any organic compound has three basic parts:
1. a rootà denotes the # of carbon atoms in the longest
continuous chain of carbon atoms
2. a prefixà gives the position and names of any branches
beginning from the main chain
3. a suffixà gives the series to which the molecule belongs.
Ex. For the alkanes the suffix is “ane”
end 4. The branches that are added off the main carbon chain are
called substituent or side groups
Ø Common substituents are halogens and groups containing
How This Relates to the Curriculum:
Applied Chemistry [IUPAC] guidelines name
saturated and unsaturated aliphatic and
aromatic carbon compounds:
- containing up to 10 carbon atoms in the
parent chain or cyclic structure
- containing one type of functional group
(including multiple bonds, simple
halogenated hydrocarbons, alcohols,
carboxylic acids, and esters)
- containing multiple occurrences of only
halogen or alcohol functional groups
• .

Ø DD
C, H, O, N, S, P.
Substituent groups containing C and H atoms are called
alkyl groups and are named after the alkane from which
they are derived.
Ø You will responsible for learning the root names for the H HH
first 10 carbon atoms: l I I
C C CH
H Hl H
Number of carbon atoms Root name Alkane Group Name Alkyl Group Name
(n= # carbons) General formula (Branch name)
CnH2n+2
1
Meth methane
Cha methyl CH
2
3
Eth ethane Catto ethyl GHS
Prop Prom a
II
4
5
6
II't
7
8
9
10
Ø Additional substituent halogen groups include Bromo à Br; Chloro à Cl; Fluoro à F

6
 Naming Alkanes with branches
1. Identify the “root” by determining the longest chain of C atoms (a
continuous line can be drawn through all of them). If this is 5, the
name would end in “pent”
2. Identify the “suffix.” For alkanes it would be “ane” - now we have
“pentane”
3. Identify the “prefix”
a. number the C atoms in the chain beginning at the end nearest the
branch
b. Use a number to indicate where the branch is found (one number for
each branch even if they are the same kind of branch or off the same C
atom). Note: use lowest total number combination when possible.
c. If there is more than 1 of the same kind of branch, use prefixes di,
tri, tetra etc. to indicate this.
d. Place branches in (alphabetical order) in the name (or order of
complexity)
e. Use commas to separate #s, and "–" to separate letters from #s.
H
HEH H
Example:
H his s
dashseparates H C C C C CH
fromword Il l't l t't l't
numberidentify HG H
2,3-dimethylpentane
lg.ggYraofhes M Hcit CHz
C numberthe Coma prefix CHCH CH2 CHz
suffix 1
attachto between
of sidebranch root alkane saturated CH
numbers
sidebraches longest
chain
2 methyl
groups f
Other examples:
mI
ecthyl
H3C
CH2
CH3

Q2 02,00
H3C H3C
CH2 CH CH2 CH3 C CH3
order H3C 2 CH
I s CH2 b CH2 8 C CH2 CH
alphabetically z 3 5 I
H3C
H3C CH2 CH3
4
CH3
meth CH3 CH3

If3
ethyl methyl octane 4 2,2 dimethylpentane 32,3 trimethylbutane
Do not confuse dimethyl (2 methyl groups each having 1 C) with 1 ethyl group having 2 C.

H3C
H3C CH3
CH CH2 CH
CH2 CH2 CH3
H3C CH3 H3C CH3 CH3 H3C CH2

2 methylbutane butane
propane 7
methylpropane
 because only location
possible for
Drawing Alkanes Using Condensed Structures: methylgroup
Step 1 Identify the root and the suffix of the name: This step gives you
the number of carbons in the main chain and the type of functional group
present. For 3-ethyl-3-methylhexane, the root and suffix are −hexane. The
root, hex, tells you there are six carbons in the main chain. The suffix, –ane,
tells you that the chain has only single carbon–carbon bonds (i.e. it is an
alkane)
Step 2 Draw the main chain first: Draw a straight chain containing six
carbon atoms with single bonds between the atoms. Do not include
hydrogen atoms yet.

Step 3 Choose one end of your carbon chain to be carbon number 1 and
number the rest of the chain in sequence. Add the indicated branches to
the appropriate carbon: In this case, add a methyl group and an ethyl
group both at carbon three. You may place the branches on either side of the
main chain.

CH
H
H H HH31 pH
61 15 4 ft H
HC C C C C C
l l l l
H H H H H
H
QH
H GH
H
Step 4 Complete your formula by adding the number of hydrogen
atoms beside each carbon that will give each carbon four bonds: Add
hydrogen atoms as shown below.

8
Practice:
1. Name each of the following compounds
a. b.
CH3
3,4 dimethylheptane
CH3
CH CH2 CH3
H3C HC H2C CH CH2

CH2 CH3 CH3 CH3

methylbutane
c. d.
H3C

CH2

H2C CH3
CH2 H3C CH2
CH2 CH2
C CH2 CH3 CH CH2
CH2
CH2 CH2
CH2 CH3
H3C H3C
4 ethylheptane
4,4diethyl octane
2. Draw structural formulas for the following compounds:
a. 3-ethylhexane

9 it it it it it it H
2 carbons HC C G C C C
t
my
I't H H H c it
b. 2,2,3,3-tetramethylheptane
HAYEK
H 4H H
it it it it
i 1 I Y
HG 2 G
f GHtt l't l't l't EGEH.hn
c.
k
3-ethyl-4-propylnonane
41 A
42h5

3 C CH CHz IH GH CHz CHz CHICK CH

d.
I
3-ethyl-4,5-dipropyloctane 4h
qtr it 4C
q CH3 Hel H
e.
incident
d
2, 4-dimethylhexane i
EH il
f I l C C C lc
l l
C CC C l
I l l l l l
It
I 9
H 4
C H
H
H KH
 double How This Relates to the Curriculum:
• Using the International Union of Pure
ALKENES (CnH2n) and Applied Chemistry [IUPAC]
Ø Are unsaturated hydrocarbons guidelines name saturated and
unsaturated aliphatic and aromatic
Ø not bonded to maximum ofatoms carbon compounds:
- containing up to 10 carbon atoms in
Ø contain at least one bond double the parent chain or cyclic structure
- containing one type of functional
Ø longest chain must contain bond double group (including multiple bonds,
simple halogenated hydrocarbons,
use a number show to location of double bond if alcohols, carboxylic acids, and
Ø Physical properties very similar to the alkane having the same neededesters)
number of C atoms, however, they tend to have fewer dispersion forces,- containing multiple occurrences of
which allows them to be liquids at room temp, rather than solids only halogen or alcohol functional
(in the range where oils and margarine exist – 17-19 carbon chains) groups
Ø • .
diltrietc if wehave morethan
bond hasprefix
one double bond
Chemical properties of Alkenes
reactivesite
there isstrain at location of double bond
undergo addition reaction add H halogens OH etc
test is toadd Br water Bir bramnlorage when addedto
unsaturated
compound the Br atoms addto structure and
colour disappears
Practical uses of Alkenes
1. Ethene [CH2=CH2]
o is used to prepare polymers (polyethelene and polyesters), engine
coolant, paints and drugs
o prepared by cracking (dehydrogenation) ethane at 500° C and
using Cr2O3 as a catalyst
o also can be formed by dehydration (using H2SO4) of ethanol
o promotes growth and development in plants. Farmers treat fruit
after it is picked, with a compound which breaks down to produce
ethene while the produce is in transit.

2. Rubber [2-methylbut-2-ene]
o tends to be elastic, waterproof and airtight making it a very
useful substance.
o It also tends to become soft when hot and brittle when cold.
o Goodyear (the tire guy) spilt rubber and sulfur on a stove and
discovered that the 2 combined to give rubber better
properties. (Less change at extreme temperatures). This is
due to the cross-links that form given rubber more strength.
o Vulcanization is what this process is now called (Vulcan –
Roman God of Fire).
o Today tires are softer (more traction) and also stronger.
nH2nt2
alkyne Cn 2
Han
alkane alkene ChH2n
HY H H H 10 C H
C C c H
i
H
H H
trigonalplanar
triplebond
tetrahedral
f
ALKYNES( CnH2n-2) How This Relates to the Curriculum:
•
Using the International Union of Pure and
Ø Alkynes are also examples of:
Tusaturated hydrocarbons Applied Chemistry [IUPAC] guidelines name
saturated and unsaturated aliphatic and
Ø have atleast one triplebond aromatic carbon compounds:
- containing up to 10 carbon atoms in the
Ø triple band is more reactive thandouble parent chain or cyclic structure
- containing one type of functional group

end numberto (including multiple bonds, simple

Ø name has yne a
use halogenated hydrocarbons, alcohols,
indicate bond
position - carboxylic
containing
acids, and esters)
multiple occurrences of only
Ø Ethyne is the most common alkyne (also called acetylene)
halogen or alcohol functional groups

oruse in
Ø Ethyne is a cheap starting material used to build up complex
molecules. It reacts with many other substances.
Ø It can be prepared by adding water to calcium carbide cuttingtorches

CaC2(s) + 2H2O (l) à Ca(OH)2 (aq) + C2H2(g)

Ø Common structural isomers will have the placement of the triple

bond vary, e.g. but-2-yne and but-1-yne (more on structural isomers
later)

Naming and Drawing Alkenes and Alkynes

1. Identify the longest continuous chain which includes the double or triple bonds.
2. Identify the suffix which for alkenes is ``ene`` and for alkynes is ``yne.`` The suffix must
also include the location of the double or triple bonds.
3. Number from the end that will give the location of the double or triple bond the lowest
value. The location of the double or triple bond is indicated by the number of the carbon
atom that precedes the bond.
4. Use a hyphen, a number, a hyphen and then the suffix ``ene`` or ``yne``
5. Name the side or substituent groups same as done with alkanes.

Guided example: double

1. Name the following alkene: fondtakes location
priorityin numbering ofbond
f
4 ethyl4,5dimethylhex ene

Identify the root: The longest chain that contains the double bond has six carbon
atoms. The root is :
Identify the suffix: The molecule has a double bond so the suffix ends with :
Assign position numbers: Numbering must begin at the right end of the molecule
because it is closest to the double bond. The position of the double bond is 1 so the
suffix is :
Identify the prefix: There is one methyl group on carbon atom number 4 and
another on carbon atom number 5. There is also an ethyl group on carbon atom
number 4. The prefix is :
Solution: The full name of the compound is :

11
Practice naming alkenes and alkynes
1. Name the following:
a. b.
4
CH2
2CH CH3 CH3
H3C 5 3
CH
CH2 CH3 CH C CH2 3,3dimethylpent l ene
hex 2 ene H2C CH3

c. d.

CH3 CH3 CH3

C
H3C C C HC CH C
H3C CH2
CH2 CH3

4 methythex 2 yue 5 mettylhex2

yn .ci
2. Draw the structural formula and the molecular formula for the following:
a. oct-3-ene

i i ci ci ci
b. 3,4-diethylhex-1-yne yc
4255
I
N c
g d44
C2H5 G
c. 5-ethyl-4-propylhept-2-ene K
43h7

re C2H5
d. 2,4-dimethylpent-2-ene

ft ft fitsft
H C C CEC C H
f l I i
CH H H
e. 2,5,7-trimethyloct-3-yne

E E c

EE ad 44 c fY
c
12
 ring
CYCLIC HYDROCARBONS
Ø Are essentially aliphatic hydrocarbons chains that have
no beginning and no end, but rather form rings; alkanes (CnH2n) ; - containing up to 10 carbon atoms in the
alkenes (CnH2n-2) and alkynes (CnH 2n-4)
Ø Cholesterol is an example of biologically important molecule
which consists of four connected hydrocarbon rings.
Ø We don’t see cyclic structures of 3 or 4 carbons because of
instability due to ring strain. Ex. cyclopropane and cyclobutane
How This Relates to the Curriculum:
•
Using the International Union of Pure and
Applied Chemistry [IUPAC] guidelines name
saturated and unsaturated aliphatic and
aromatic carbon compounds:
parent chain or cyclic structure
- containing one type of functional group
(including multiple bonds, simple
halogenated hydrocarbons, alcohols,
carboxylic acids, and esters)
- containing multiple occurrences of only
halogen or alcohol functional groups

Naming and Drawing Hydrocarbons

1. Root: determine the number of carbon atoms in the ring (do
not count those carbons that are part of a side group). The root name
would coincide with this number, preceded by “cyclo”
2. Suffix: determine if the compound contains all single bonds, at
least one double bond, or at least one triple bond. The suffix will
then be “ane” “ene” or “yne” respectively. There are no numbers
used to indicate the location of the double or triple bond because it is
assumed to be between carbons 1 and 2.
3. Prefix: Similar to naming the aliphatic hydrocarbons with a few
extra things to consider:
Ø if there are no side groups or only one side group on a
cycloalkane, atoms are not numbered.
Ø If a cycloalkane contains more than one side group, number
the C atoms to give you the lowest number in the name.
Ø If it is a cycloalkene or cycloalkyne, start numbering with the
carbons on either side of the double or triple bond assigning
the numbers, 1 and 2 (this takes priority over the side
groups).

Example :

CH3 Identify the root: The ring has six carbon atoms so the root
is :
cyclohexane
CH
3
Identify the suffix: The ring has one double bond so the
HC CH2 suffix is :
2
ene
Assign the position numbers: The carbon atoms beside the
HC CH2
1 double bond must be numbered 1 and 2. The numbering
CH2
must proceed in the direction of the side group. Therefore, the
lower left carbon atom must be number one and the numbering then goes
clockwise giving the side group the number 3. Because the numbering of carbon
atoms one and two is mandatory, the numbers are not included in the name.
Identify the prefix: The side group has one carbon atoms so the prefix is : methyl
Solution: The name of the compound is :

3 methylcyclohexane
f 13 Tdoublebond
ring
Practice:
C C C
1. Name the following:
a. C C b. 3
CH
H2C CH I I
cyclohex 1,3diene
HC CH2
2
CH CH C C H2C CH
Cl 3 CH2

c.
3 chlorocyclobutene d.
H3C
CH2 H3C CH
H2C CH2 2
CH
CH2
CH2
H2C CH2 H2C
CH2 CH2
CH CH
CH2 2
H3C
cyclohexane
1,34 trimethyleydononame

2. Draw a condensed structural formula for the following:

a. methylcyclopentane

q CH
nnoeendeqber

b. 1,3-diethylcycloheptane
s

c. 2-ethyl-3-propylcyclohexene

cuppa
n

d. 4-butyl-1,3-dimethylcyclohexane
Hz
l

14 CH
I
cotta
alkanes all single bonds

alkenes double bond

alkynes triple bond

cyclic hydrocarbons form ring
 STRUCTURAL ISOMERISM
How This Relates to the Curriculum:
Ø Structural Isomers have : sameempiricalformula • Define structural isomerism as compounds
having the same empirical formulas, but
Ø
butdifferentstructure
There are three ways we can bring together 5 C atoms and
with different structural formulas, and relate
the structures to variations in the properties
12 H atoms (see below). Each molecule has slightly of the isomers.
different properties. These molecules are isomers of C5H12.
Ø Because of their different structures, isomers have different
names, and will have different physical properties as well.
Cs
5412
G Haz H3C CH3

CH CH2 H3C C CH3

on
CH2 CH2
H3C CH2 CH3 H3C CH3 CH3

pentane methylbutane dimethylpropane

b.p. 309 K b.p. 301 K b.p. 282 K

Pentane has a higher boiling point, because there is more available surface area for intermolecular
attractions (dispersion forces). The more dispersion forces, the higher the boiling point.

As the number of carbon atoms increase the number of possible

isomers also increases:
LDF's
Hexane (C6H14)has 5 isomers
Heptane (C7H16) has 9 isomers
Nonane (C9H20) has 35 isomers
10 C atoms----75 isomers
i i
20 C atoms ---- 366 319 isomers out
30 C atoms ---- 4 111 846 763 isomers more spread
Ø Different structural isomers can be separated by their molecule haggreater
boiling points LDF's
CH3 Br

CH2 CH2 CH use bpmp to

E
H3C CH3 intermolecular
represent our
Br
1-bromopropane 2-bromopropane
b.p. 344 K b.p. 332 K
forces
Ø This is due to the different structural shapes. (1-bromopropane
would pack more closely together due to increased surface area; higherbp stranger1mF
so there would be more intermolecular attractions)

liquid
CHA
15f Cha there
 How This Relates to the Curriculum:
HOMOLOGOUS SERIES • Compare, both within a homologous
series and among compounds with
Compounds within the same homologous series:
same structure different functional groups, the boiling

but differ by
points and solubility of examples of
one CHz added
to length aliphatics, aromatics, alcohols and
carboxylic acids

similar chemicalproperties
physicalproperties IMF
change as change

mplbp M as molecule length 9

If not
Ex. Alkanes form a homologous series (this is a consistent increment of change
from 1 member of the group to the next. In this case the change is a -CH2 unit.)
used in lighters c polarez
CH4(g)
Methane IT C2H6(g)
Ethane
C3H8(g)
propane
C4H10(g)
butane
CH5 12(l)
pentane
CH 6
hexane
14(l)
it H
Bp(oC): -162 -87 -45 -0.5 +36 +69
e
Ø Most organic compounds are non-polar and therefore are insoluble in polar water.
Remember “like dissolves like,” so polar dissolves polar and non-polar dissolves in
non-polar.
If
Ø If however, an organic compound contains a functional group which allows it to Ceo very
hydrogen bond with water (i.e. alcohols) then, it will be water soluble provided that HEY polar
very the hydrocarbon chain is relatively short. The solubility decreases gradually as the

y
olar length of the chain increases.
Ex. ethanol CH3CH2OH will be miscible in water; hexan-1-ol CH3(CH2)5OH
dissolves only slightly in water.
I slightly
The classes of organic compounds ranked according to polarity/boiling points polar
would be:
Polarity/Boiling Point Organic Compound Explanation
Highest Carboxylic Acid H-bonding; presence of 2 oxygens COOH
Alcohol H-bonding; presence of 1 oxygen
Esters Partially charged dipole due to
carbon double bonded to oxygen at.io e

EEE.iq
Lowest Hydrocarbons Only London dispersion forces
Alkanes (C-H bonds relatively nonpolar)
Alkenes
Alkynes

TT0 homologous series

0 it It H HH
d
H COH H E OH it
H H
c ott Hq
H HH
o H

Hethanoic propanoic
butanoic
methanoic and
acid
acid acid 16
increase
bp
 polarity Freaky
solubility is water ase How This Relates to the Curriculum:
REFINING AND USING ORGANIC COMPOUNDS - Describe in general terms, the physical,
chemical and technological processes
BITUMEN RECOVERY (fractional distillation and solvent
Ø Tar sands or oil sands, found in Alberta are large deposits of bitumen extraction) used to separate organic
compounds from natural mixtures or
(a tarry residue or heavy oil, often found mixed with sand) solutions; example petroleum refinery
Ø The petrochemical industry has developed an efficient process to and bitumen recovery
separate the useful petrochemicals from the bitumen • .
Ø Hydrotransport pipelines carry oil sands and caustic hot water
(to prevent the sand from drying out making it difficult to extract the bitumen
from it), to the plant where it is physically separated based on density.
The bitumen floats to the top and is then skimmed off.
Ø Bitumen is about 20% alkanes and cycloalkanes and about 80% aromatic
compounds.
Ø Converting the bitumen into a useful product begins either with coking
(which removes carbon) and hydrocracking (adds hydrogen)

Hot
water

0
I

soil
ta gs

oil crudelmittIoffdrocarbonus

Ly

17
 between

FRACTIONAL DISTILLATION
towers at refineries
edmontonand
sherwoodpark
Ø First step in refining petroleum which involves heating, evaporation, cooling and
then condensation
Ø How the process works:
1. Petroleum is heated to very high temperatures and vaporizes
2. The vapor rises up the fractional distillation tower and then gradually
cools
3. Each hydrocarbon component has its unique boiling point and
4. density (the bp increases with the size of the molecule) and so will
condense at different times.
5. The larger molecules (with higher bp) condense in the hotter, lower
levels of the tower.
6. The smaller, lighter molecules remain as a gas until it moves up
the tower and condenses at cooler levels.
Ø This is a very energy intensive process

CHA
Hf Hs Coho
gasatroomtop
molecules
smallest
decrease
lowestfp ofcarbons
larger 20˚ C
Gas – 4 C
molecules
40˚ C Naptha – 8 C

higher 70˚ C Gasoline – 8 C

hgge 70˚ C dense Kerosene – 12 C

120˚ C Diesel/Light oil – 16 C

200˚ C Lubricating oil – 36 C

(To Cracking Unit)
300˚ C Heavy Gas oil – 44 C
600˚ C (To Cracking Unit)
_ Residual and Asphalt
Jvaporize – 36 C(80 C To Coker)

highestbp
Heat molecules
largest
Boiler – Super Heated Steam Distillation Column

Fractional Distillation Apparatus

18
 Diploma Examination Practice

1. What is the IUPAC name for the following compound?

CH3
H3C
CH2 CH
C CH2 CH3
H3C
CH3

A. 1,3-pentamethylpropane
B. 1,1,3,3-tetramethylbutane
C. 2,2,5,5-tetramethylpentane
D. 2,2,5-trimethylhexane

2. Which is a member of the same homologous series as the following molecule?

CH2 CH3
H3C CH2

CH2 CH3
CH2 H3C CH
A H3C CH3
C CH3

CH CH3 CH2 CH2

B H3C CH D H3C CH2 OH

Use the following information to answer the next question

CH3

CH2 CH3 CH CH2

I. H3C CH2 II. H3C CH3 III. H3C CH3

3. Which of the formulas above represent butane or its isomer?

A. I and II only
B. I and III only
C. II and III only
D. I, II and III
19
 4. What is the IUPAC name for the following molecule?
I
methyl butane
CH2 CH3
H3C
20
CH

CH3
A 1, 1-dimethylpropane
B 2-methylbutane
C 3-methylbutane
I
D ethyldimethylmethane

5. Which compound has the lowest boiling point?

GHis 4
505
Hy H3C
CH2
CH
CH2
mB.tt
CH3
C H3C
CH2
CH2
CH 2
CH3

LDF's A CH3
CH3
epeahiueBrbpthm
H3C
OTE
C
CH2 CH2
CH3
D H3C O CH3
dipoles
B H3C 0

5h12 gasHOO 42 stronger

IMF
go high
electronegativity higher
6. Which of the following is not pentane or one of its isomers?
H3C CH3 bp
CH CH2

CH2 GHis CH 2
C. H3C GHis
A. H3C CH2 CH3 CH3
H3C
CH3
C
CH3 GHd2
CH2 C H3C
D.
B. H3C CH CH3

His
Caitz

20
7. Which structural formula below represents pent-2-yne?

8. Which of the following hydrocarbons is saturated?

A. Propene
B. Ethyne
C. Butane
0 0
D. Pentene

9. Which of the following compounds is an isomer of pentane?

E
A. Butane
B. Propane catty
Q
C. 2- methylbutane
D. 1-methylpentane
c
c c c c
10. Which formula represents propyne?
A. C3H4
B. C3H6
C. C5H8
D. C5H10

11. Which of the following chemical compounds is not considered an organic compound?
A. C2H5COOCH3(l)
B. C6H5COOH(s)
C. CH3CH2OH(l)
D. NH4CN(s)

21
 Use the following information to answer the next question.

Chemical Compounds

CH2 H3C CH2 CH3

1. H3C CH3 5. CH2 CH2
O
OH
CH2
O
go
C
H3C CH2 OH H3C CH CH3
2.
O CH2 CH2
6.
CH2 C CH3 CH2 CH2 CH3
3. H3C CH2 CH2 7. H3C CH2 CH2

00 I
H3C CH CH CH2 CH3
4. CH CH CH3 8. H3C CH2

II
12. Order the following compounds into a homologous series:

__________, __________, __________, ___________

Use the following information to answer the next question.

Chemical Compounds I 0
1 CO2(g) 5 Co(OH)2(s) ioniccompound
2 CH3OH(l) 6 HCN(g) ltarbonate
3 H2CO3(aq) 7 CH3COOCH3(aq)
4 ClCH3(l) 8 HCOOH(l)

13. The chemical compounds numbered above that represent organic compounds are
______, ______, ______, and ______.

IMFL smallmolecule has low bp

LDF
dipole dipole
H
H bonding

IH H
0

22
 14. The structural diagram that represent 2,2-dimethylpropane is
A. B.

C. D.

Use the following structural diagram to answer the next question

H
H C H
H H H
H
H C C C C
H H
H H
H C H C C
H H
H H
H C C H
H H

15. The IUPAC name for the structural diagram above is

A. 2,2,5-trimethylheptane
B. 3,6,6-trimethylheptane
C. 2-ethyl-5,5-dimethylhexane
D. 5-ethyl-2,2-dimethylhexane
16. Which of the following line diagrams represent 2,4-dimethylpentane?

23
 A. B.

C. D.

Use the following information to answer the next question

He02

Hg02

211402

He02

17. Which of the following structural diagrams above represent isomers?

A. I and II
B. I and IV formula
C. II and III same structure
D. III and IV different
Diploma Examination Practice ANSWERS
1) D 5) B 9) C 13) 2478
2) A 6) B 10) A 14) B
3) A 7) 4 11) D 15) A
4) B 8) C 12) 1578 16) C
17) D

24
 AROMATIC HYDROCARBONS How This Relates to the Curriculum:
Ø All contain the benzene structure (C6H6) • Using the International Union of Pure and
Applied Chemistry [IUPAC] guidelines name
saturated and unsaturated aliphatic and
CH aromatic carbon compounds:
HC CH - containing up to 10 carbon atoms in the
parent chain or cyclic structure

Fiat HC
CH
CH - containing one type of functional group
(including multiple bonds, simple
halogenated hydrocarbons, alcohols,
Ø This is a planar molecule. carboxylic acids, and esters)
- containing multiple occurrences of only
Ø Not all aromatics (i.e. “aroma”) have a pleasant odour, but all have an halogen or alcohol functional groups
odour. Ex. woody odours, spearmint, musk, camphor, cinnamon, • .
anise, caraway
Ø Did you know? There are 40 000 000 receptor sites for smells in your
nose. Each site is a hole of a certain size and shape which will
accommodate a certain chemical. When a molecule fits a site it acts as
a key to trigger a nerve signal to the brain which registers the smell.
Ø Aromatic hydrocarbons are found naturally in petroleum.
Ø Benzene is considered to be carcinogenic so therefore the benzene
content has been reduced to contain <1% benzene.
Ø The structure can be described by a resonance theory. The resonance
theory suggests that whenever it is possible to draw 2 or more
structures differing only in the location of the electrons, neither
structure adequately represent the molecule. The electrons are said to
be “delocalized”
Ø To represent the 6 delocalized electrons benzene is often represented

EI FI
Ø The molecular formula suggests that the molecule is highly
unsaturated but benzene does not react like an unsaturated e.no
hydrocarbon. 0 is a 1.5
Ø Benzene will only undergo substitution reactions and will not break
any double bonds to undergo addition reactions. Remember those bond
double bonds are actually resonating, and are really a hybrid bond
between a carbon-carbon single and double bond, which means each notsingle or
bond is equal to 1.5 bonds. double
a

H aromatic

i 25
i in
 Naming and Drawing Aromatic Hydrocarbons
Ø The root name for the molecule is “benzene”
Ø The carbons are numbered to locate the presence of more than one side
group
Ø If more than one side group, start numbering at the carbon that
contains the side group with highest priority (-OH, -F, -Cl, -Br, -I) to
lowest priority (alkyl groups with 6 or fewer carbon atoms in
alphabetical order).
Ø When there are two substituents off a benzene ring, we can number
them 1,2 1,3 or 1,4. We do not number them 1,5 or 1,6 (these would side
really be 1,3 and 1,2 respectively if you flipped the molecule around). branch
IT
Ø Use phenyl when benzene is a branch (eg. 2-phenylbutane)
sb.EE
O
CH3
CH3
branch
AT
C
HC CH C CH3
HC C
methylbenzene
HC CH HC CH
CH CH

1,2 dimethylbenzene
Cl

C
HC a
CH

HC
CH
C3
Cl
butylbenzene

1,3 dichlorobeneene
Practice drawing these aromatic compounds:
f
parent
1. 1-methyl-3-propylbenzene
GAS

GH
2. 2,2-dimethyl-3-phenylhexane

xx
3. 1-methyl-3,4-diethylbenzene (what is wrong with this name?)
notalphabetical on
t 4 emethylbenzene side
branches
4 1,2diethyl 26
notusing smallest
numbers possible
 Hi

4. 1,2,4-tribromobenzene

Br G HzBr
Br

Br

27
 Naming and Drawing Hydrocarbon Structures

Provide the IUPAC names for each of the following compounds. Indicate whether the hydrocarbon is either an
aliphatic, cyclic, or aromatic hydrocarbon. If the hydrocarbon is aliphatic, or cyclic, indicate whether the
hydrocarbon is an alkane, alkene, or alkyne.

1 3 methyl pentane
Name: _________________________ CH3

CH2 CH2 H3C CH2 CH2HC

H3C CH CH3
CH2HC CH3

CH3 CH2 CH3

6
4 2
Name: _________________________
ethyl methyl heptane
2
2,4
dimethylpentane
Name: _________________________
H3C
CH2
CH2
CH
CH
CH2
CH3
H3C CH2 CH3
CH CH

CH3 CH3 7 kept3

ene
Name: _________________________

CH CH2 CH3
butane
3
2,2 dimethyl
Name: _________________________ H3C CH CH2

CH3

CH2 C CH3
8 hex
2 ene
Name: _________________________

H3C
H3C CH3 CH2
CH C CH2
H2C CH3 CH3
4 3ethyl4 methylheptane
Name: _________________________

CH3 CH3

CH2 CH CH2
9 3 3
ethyl methyl pentTene
Name: _________________________

H3C CH2 CH CH3

H2C CH3
H2C
CHHC
CH3
C CH2
HC H2C
CH2
H3C

10 3
ethyl methyloct4
Name: _________________________
tyne
5
3
methyl buttyne
Name: _________________________

28
 CH3
CH2
HC C HC
H2C CH
CH3

3 methylbuttyne
H2C CH
CH2

11 Name: _________________________
cyclohexane
H2C CH2

15 Name: _________________________
H2C CH2
CH CH3
cyclobutane HC C

12 Name: _________________________
HC CH
C
CH CH3 1ethyl3methyl
HC C H2C
benzene
CH3
HC C
CH CH3

1,2 dimethylbenzene 16 phenyl ethene

Name: _________________________

CH
13 Name: _________________________ HC CH

HC CH
CH C
HC
2 4
CH

C
CH
CH
CH2 H2C

14 Name: _________________________

cyclopent 1,3 diene

29
 Draw condensed structural diagrams for the following compounds:

1. 3-methylhexane 8. Methylpropene
Hz 443
CHzcltz CH CH2 CH2CH CHE CH

2. 2,3-dimethylhexane 9. 3,4-dimethylhept-1-yne

Gt3 443

CH CH CH CH CHz CHz CHIC CHCH CHIK CH

I CH3
Hz
3. 3-methyl-4-propylnonane 10. Cyclopentane

43h7 CH2
CHz Hz GH CH CHICK CHICK CH I f't
CH CATCH
4. 3,4-diethyl-3-methylheptane 11. Methylcyclobutane
HT
CH
CH3CH2 d CH CHz CH.CH D
C'Its d2H5
5. Dimethylpropane 12. pent-1,3-diene

4h3
Hz f CH CHECH CHECH CH
CH
6. hept-3-ene 13. 4-ethyl-2-methylcyclohexene

Gta
CH Cha CHIH CHICKCH
TITCH
7. 2,3-dimethylpent-2-ene 14. 1,2dipropylbenzene
Hz
Cfb 4h3
GH't
Hz CE CH CH
30
 15. Cyclohexyne 18. 4,6-dimethyloct-2-yne

I
am
16. 1,3-diethylbenzene 19. but-2-yne
C2H5

DOC2h5 E
20. 4,4-dimethylhept-2-ene
17. 1,2-diethylcyclohexane

v
m
DE't C2H5
The following compounds names may or may not be correct. If they are correct, please write the
condensed structural formula for the compound. If they are incorrect, please give the condensed
structural formula, and the proper IUPAC name.

1. 3,4-dimethylpentane 4. 1,1-dimethyl-2,2-diethylbutane

I TT
n l
w
3,3diethyl2 methylpenta
2.
AO
1,2,4-methyl-3-ethylcyclohexane 5. 1,2-dimethyl-4,4-diethyloctane

2 ethyl 43,4trimethyl 4
cyclohexane fN
5,5diethyl 3 methlmonane
3. 3-methyl-4-propylpentane 6. 1,3-dimethylpropane pentane

Hzl CHzChaCha CH

din 3,4dimethylheptane
31
Organic Reaction Multiple Choice/Diploma Practice Questions it
18. Which of the following rows identifies the structural
formula and the corresponding IUPAC name of the
compound with the chemical formula C8H10

0
A.

CgHio
n

X
B.

y 1 CgHis
n

X
C.

a CgHi
a T

X
D.

y e GHlo
x t

32
 19. Which of the following rows identifies the condensed
structural formula or line diagram and the correct IUPAC
name of an isomer for C6H12?

Row Structural Formula IUPAC Name

O A

e
Methylcyclopentane

j
B Cyclohexene

C 4-methylpent-1-yne

D Hex-3-yne

ChHIn2
20. Which of the following structural formulas represents the
compound with the lowest boiling point?

A.
0
B.
H H
H H H H
H C C H
H C C C C H
H H
H H H H

C. D.

H H H H H H H H H H H H H H

H C C C C C C H H C C C C C C C C H

H H H H H H H H H H H H H H

33
 Halogens H O HN H F
HALOCARBONS (Organic Halides) How This Relates to the Curriculum:
Ø R-X where the ``R` represents an alkyl chain; `X`` represents the • Using the International Union of Pure and
Applied Chemistry [IUPAC] guidelines name
halogen. carboncfain saturated and unsaturated aliphatic and
Ø Halocarbons are a class of organic compounds containing covalently aromatic carbon compounds:
bonded fluorine, chlorine, bromine or iodine. - containing up to 10 carbon atoms in the
Ø These compounds are not found in nature, but are used to a great parent chain or cyclic structure
extent by humans. - containing one type of functional group
(including multiple bonds, simple
Ø Trichloromethane (or chloroform) is no longer used as an anaesthetic halogenated hydrocarbons, alcohols,
because it is considered to be carcinogenic. carboxylic acids, and esters)
Ø cancercausiyagent
CFCs (chlorofluorocarbons) were once used as refrigerants but are - containing multiple occurrences of only
no longer used due to its effect on the ozone layer. halogen or alcohol functional groups
Ø We use them for plastics (PVC), chloroform (anesthetic), • . comparedlo

ethan toxarat
catalyst
T
dichloromethane (decafeinator), refreigerants (Freon-12 and Freon-
22), and a variety of pesticides. H H
O
E Foo
Ø Adding halogens to long hydrocarbons that are plastics will prevent
no
g
them from UV degradation. As plastics are exposed to UV light,
they get oxidized (O replaces H) and tend to become more brittle.
Fluorine and Chlorine have equal or greater electronegativity and
therefore resist getting oxidized, so plastics retain their properties
H H
molecule
and don’t become brittle or faded. polar interaction
Properties of Halocarbons: dipole dipole
Ø Organic halides are solvents that can dissolve non-polar and/or polar
hydrocarbons, since organic halides may be polar or non-polar (like
dissolves like).
f ofe 9mpbp
Ø Act as good solvents for organic materials such as fats, oils, waxes, gums,
resins and/or rubber
Ø Have very low solubility in water but higher solubility than similar
hydrocarbons
Ø They have higher boiling points than similar hydrocarbons.
H
Naming Halocarbons:
Ø Halocarbons are named after the alkane from which they are H C Cl
derived. H
Ø The name consists of the alkane name with the halogen branch
identified as a prefix. chloromethane
Ø Identify the position of the halogen group indicated by the
number in front of the branch name.
Cl H
Ø Naming: “ine” ending of the halogen is replaced by “o”. C
Ø It is considered to be like any other substituent and is named
alphabetically. C
H H
Ø If more than 1 halogen group, or if there is more than two carbons in the
chain – use prefix to indicate the number.

choroetheney

34
 Practice: nH2nt2
1. Draw two isomers of C2H4Br2. Name each isomer.
Br H
Hb
H
I I
H Br
H
Br
Br
it H
g
H H
1,2 dibromoethane
1,1 dibromoethane
2. Draw the condensed structural formula of the following organic halides.

a. 1,1,2-trichloroethene
Cl Cl
c
a CBH
u H
b. 2-iodo-2-methylpropane
I ft 443H
r
V H CCC H
HI H

c. 2-bromobutane
Br H Br H H
l I I 1
HCC C C H
N H I't t't H
d. iodocyclopropane
I I
I C
N H f
H
f
H
H

e. 3,3-dibromobut-1-ene

H it
9
Pr
Br Br It f it
Br IC
35
H H
 net
ALCOHOLS (R-OH)
hydroxide
How This Relates to the Curriculum:
• Using the International Union of Pure and
Ø Alcohols are organic compounds with an –OH group. Applied Chemistry [IUPAC] guidelines name
Ø The –OH functional group in alcohols is called a hydroxyl saturated and unsaturated aliphatic and
group or hydroxyl function. It is not a hydroxide ion because aromatic carbon compounds:
the oxygen is covalently bonded to carbon and not with an ionic - containing up to 10 carbon atoms in the
bond to a metal. parent chain or cyclic structure
- containing one type of functional group
Ø The hydroxyl group is a functional group (i.e. a group of atoms (including multiple bonds, simple
that gives organic compounds bearing them characteristic chemical halogenated hydrocarbons, alcohols,
and physical properties. carboxylic acids, and esters)
- containing multiple occurrences of only
Properties of alcohols halogen or alcohol functional groups
methane •
Ø The relatively high boiling points and high water solubility of .
alcohols are the result of intermolecular hydrogen bonding. H
bp 160C Ø Alcohols associate through hydrogen bonding – for this reason, the I
melting points and boiling points of the alcohols are higher than H
methanol
those of alkanes of corresponding molar mass.
H
Ø Short-chain alcohols are miscible in water in all proportions because H ofi
Hbond
bpi68C
of intermolecular hydrogen bonding – long-chain alcohols are only
slightly soluble in water. He
muststronger
IMF's
Structural Isomers
Ø Primary, secondary and tertiary alcohols refer to the number of
Hf0
carbons bonded to the carbon atom which is also bonded to the
oxygen atom of the hydroxyl group (1, 2, and 3 respectively)

CH2 OH CH3
H3C CH CH2
CH2 CH2 H3C C
H3C CH2 OH CH3 CH3
HO
butan l ol butan 2 ol methylbutane 2 01
2(tertiary
(primary alcohol) (secondary alcohol) alcohol)

OH on end OH in middle OH in middle

There are two isomers of propanol, C3H7OH:
propan-1-ol
used as a solvent for lacquers and
waxes, as a brake fluid, and in the
manufacture of propanoic acid
alkylsidebranch
propan-2-ol (isopropanol)
sold as rubbing alcohol and is used
to manufacture oils, gums, and
propanone (acetone).

Both isomers of propanol are toxic to humans if taken internally.

0K

NOH IN
36
 Methanol CH3OH
Ø Also called wood alcohol, methyl alcohol, methyl hydrate, methylated spirits.
Ø 35 times as intoxicating as ethanol.
Ø
0
30mL causes blindness (methanol is converted into methanal which destroys the
optic nerve)
Ø USES- to make formaldehyde, shellac thinner, fuels (releases 50% more energy
than gasoline), antifreeze, solvent

Ethanol C2H5 OH (CH3CH2OH)

Ø colorless, pleasant odor, sharp taste, burns with a colorless flame, poisonous
Ø Prepared from glucose C6H12O6® 2C2H5OH + 2CO2
In the fermentation process enzymes produced from yeast act as catalyst to
breakdown glucose to ethanol.
Ø Can also be made by an addition reaction by heating and using sulfuric acid as a
catalyst. C2H4 + H2O ® C2H5OH
Ø Starchy foods such as grains also ferment to produce ethanol in the form of beer
and ale
Ø Alcoholic beverages are 5-75% ethanol yeast digestionbyproduct
Naming Alcohols:
Ø they are named after the alkane from which they are derived.
Ø The name consists of the alkane name with the “e" dropped and replaced by `ol`` methane methanol
if you do not need to add ``di, tri, etc. (more than 1 OH group) to the ending.
Ø If it needs di, tri, etc. leave the “e” ending and follow with a dash.
Ø Identify the position of the hydroxyl group indicated by the number in front of the –ol.
Ø If more than 1 –OH group – use prefix to indicate the number.
.
OH

OH
CH2 CH2
H3C CH2 OH
OH

f
phenol butan-1-ol
(used to make dyes & drugs)
butane 1,1diol
benzene

37
 Practice:
1. Name and draw a line structure for each of the following:

O ol
a. CH2 CH2 OH
H3C CH2 CH2
pentan I
b.

HO
CH2
CH2
OH
ethane 1,2 diol
c.

CH2 OH
HO CH
propane 1,2
trial
CH2
HO

OH

d. butan 2 01 e. HO

H3C
CH2
CH
CH3 benzene
1,4diol
OH

2. Draw a condensed structure and provide the molecular formula for

each of the following:

a. butane-2,2-diol b. 2,4-dimethylcyclopentanol
o
H OH
e l I i 94 1
tie c

OH CHz
H
Hz CHz I CH gotta.at
TH CH T
CH
1

c. 3-ethyl-4-methyloctan-1-ol
by d. 2,4-dimethycyclopentanol
GHAO
CH
CzHqOx
OH I
C
g
un 38

Hs
 How This Relates to the Curriculum:
• Using the International Union of Pure and
CARBOXYLIC ACIDS (R-COOH) Applied Chemistry [IUPAC] guidelines name
Ø Carbonyl + hydroxyl groups 0 saturated and unsaturated aliphatic and

O go aromatic carbon compounds:

- containing up to 10 carbon atoms in the

C HE parent chain or cyclic structure

O R C

OH R ok
- containing one type of functional group
(including multiple bonds, simple
0 halogenated hydrocarbons, alcohols,
carboxylic acids, and esters)
Ø Bond angles of 120° around the C atom (trigonal planar) - containing multiple occurrences of only
halogen or alcohol functional groups
Properties of Carboxylic Acids • .
Ø Carboxyl group is polar and capable of forming hydrogen bonds.
Since it is very polar, dipole dipole interactions are possible as well.
Ø The polarity of the carboxyl group makes the small carboxylic acids soluble in
water. (i.e. those with 1-4 carbons are completely miscible in water; 5-9 are
less soluble; greater than 10 are insoluble)
Ø Those with 1-10 carbon atoms exist as liquids and greater than 10 exist as wax-

Ø
like solids
Cat
Due to its stronger intermolecular forces, carboxylic acids havetemp
room
higher boiling
points than other functional groups of the same molecular mass.
Ø React with alcohols to produce esters
Ø a
They are weak acids (weaker than inorganic acids) and possess
properties similar to inorganic acids (i.e. turn litmus red, and are
conductive)

Some Common Carboxylic Acids (found in your Data Book):

bog
Methanoic acid in bee stings HCOOH up
Ethanoic acid in vinegar
I
CH3COOH acetic acid
Propanoic acid an antifungal agent CH3CH2COOH
Butanoic acid in rancid butter CH3CH2CH2COOH
Benzoic acid C6H5COOH

Caproic, caprylic, and capric acids (C6, C8 , C10) are responsible for the DO
notorious odour of goats.
Caper is Latin for goats

Naming Carboxylic Acids

with carboxylgroup
parentchain is longest chain
acid
drop e from alkane marne and replace with oic
at end of chain so it is always
carboxyl group is
on C I no need tonumber
other functional groups
39 are numbered compared to carboxyl
 H H Gt3 H 11O
1 l I i
H C C C C C
15 A 13 12 I O
H H c H I
H

acid
3 chloro 3 methylpentanoic
 carboxylic How This Relates to the Curriculum:
ESTERS (RC(O)OR)
acid O • Using the International Union of Pure and
Applied Chemistry [IUPA] guidelines name
R C
alcohol
lmk 2 carbon saturated and unsaturated aliphatic and
aromatic carbon compounds:
O R chains - containing up to 10 carbon atoms in the
parent chain or cyclic structure
- containing one type of functional group
trigonal planar (including multiple bonds, simple
halogenated hydrocarbons, alcohols,
1200bondangle carboxylic acids, and esters)
- containing multiple occurrences of only
halogen or alcohol functional groups
• .
Practical Uses of Esters:
Ø artificial perfumes or scents as they emit a sweet smell.
Ø used in making artificial food flavours that are added in many edible items like
ice cream, soft drinks, candies…
Ø used as industrial solvents for making cellulose, fats, paints and varnishes.
Ø used as solvents in pharmaceutical industries
Ø used as softeners in plastic and molding industries

Naming Esters (Esterification reactions)

Ø there are 2 parts to the name 1st part tells us the alcohol which is used to make
the ester while the 2nd part tells us which acid is used:
alcohol + acid ® ester + water
Ø The name of the alkyl group of the alcohol is the prefix for the ester
Ø The ending is the parent acid replacing the "oic acid" for "oate"
Ø Example:
Ethanol + propanoic acid® ethyl propanoate + water
(heat and H2SO4 used)

carboxylic acid + alcohol ester + water

tH
R o
R o

esterlinkage

D
ethanoicacid ethanol ethylethanoate hunter
f f
alpsrooduced

alcohol carboxylic
40
length acid
length
Rules for Naming Esters
Identify the root:
Identify the part of the ester that contains the C–O group. This is the part of
the ester that came from the acid.
The root of the name of the ester is based on the name of the acid. Determine
the name of the parent acid.
Identify the suffix:
Remove the −oic acid from the name of the parent acid and replace it with −oate.

I
Identify the prefix:
To form the prefix, consider the part of the ester that is associated with the
alcohol.
Ignore the oxygen atom and use only the alkyl group.
Identify the name of the alkyl group.
The name of the alkyl group is the prefix for the name of the ester.
There is always a space between the name of the alkyl group and the root.

Sample Problem
side with doublebondto 0
Name the following ester: came from carboxylic acid
H H O f parent
H C C C H
O C H
H H m
H
propagated
methanol acid
propanoic
Identify the root:
The C–O is part of a three carbon group making
the parent acid a :
propanoic acid
Identify the suffix:
Remove the −oic acid from the name of the
parent acid and replace it with −oate. The root
plus the suffix is now :
propanoate
Identify the prefix:
The part of the ester that is associated with an
alcohol has one carbon atom therefore the prefix
is :
Solution:
methyl
The full name of the ester is :
methylpropanoate

41
Sample Question #1

Write an equation for the esterification reaction to produce the ester

CH3CH2CH2C(O)OCH2CH3 . Write IUPAC names for each
reactant and product.

i Ho i toi
Eid t b ate
Sample Question #2

Draw the formula equation and write the IUPAC name for the ester
formed in the reaction between propan-1-ol and benzoic acid.

t oe
1 01 benzoic acia propylbenzoate
propan

42
Practice:
1. Complete the following chart:

Name and Name and Name of ester Odour Structural formula of ester
structural formula structural
of carboxylic acid formula of alcohol acid alcohol
used
butanoicacid
alcohol used
ethanol f
ethyl pineapple
Iv d

iEfo4
butanoate

ioa it Tacia
pentyl apricot
pentam l ol butanoate
butanoicHo
acid lol X IN
ethanoic 3methylbutantol3-methylbutyl banana o If
ethanoate
ft's
acidcaz c.jo
CH CHIHOH
CH CCC j
41312 I
methanoicacid ethanol
ethyl rum

CH 412 0 EH
methanoate
AEffort CH CHOH
butanoicacid methanol methyl apple

CHEHCHIEO CH
butanoate
CHzCHICHI oH CHIH
salicylic acid methanol methyl
salicylate
wintergreen

it
octyl orange
o octan l ol ethanoate
0
ethenoic
OH acid MOH work
pentyl banana
o ethenoic Penton101 ethanoate
Now
Ikot acid
WH ethyl cherry
if
benzoic acid ethanol
benzoate o
EH CHCHOH 10
octyl orange
ethenoicacid octantol
Mork
ethanoate

that mat
ethyl pineapple
butomoicacid ethanol o
butanoate
19 11
Not CHIANA Aom

43
2. Name the following carboxylic acids:
a. b.
Lester
O
OH CH2 C pentanoicacid
CH2 CH2 OH
C
CH2 O H3C
H3C
acid
propennoic

c. d. O
moat
O CH C O
H2C O CH2 CH2 CH2 CH2
CH3 CH2 CH2 CH2 CH2
H3C CH3

at.im an.a
3. Draw the line structure for hexanoic acid

What
4. Draw the condensed structural diagram for
3,4-diethyl-2,3,5 trimethylheptanoic acid

NY
5. Identify the ester which would be made when the following are mixed and
heated in the presence of an acid?
o't

propylmetharoate
a. Methanioc acid + propan-1-ol

Hello Chay CH
HEY HO CHICKCH

b. Ethanoic acid + butan-1-ol butylethanoate

casino HoCHIH.CN
tzIyy.a
It
gHEHftB0q0

meTtFbeIoate
c. Benzoic acid + methanol
it
44
 Organic Reaction Multiple Choice/Diploma Practice Questions

Use the following structural diagram to answer the next question

21. Match the general structural diagrams numbered above with the class of
compound below

Carboxylic acid __________________(record in the first column)

Aromatic __________________(record in the second column)
Alcohol __________________(record in the third column)
Ester __________________(record in the fourth column)

Q o R
RTCYOJ.at
Use the information below to answer the next question

esterknka.ge
carbonyl
D hydroxyl

The structural diagram above represents an __i___that contains a __ii____and

an __iii___ functional group.

22. The statement above is completed by the information in row

Row i ii iii
A. aromatic carboxyl OOH alkene
B.
C.
aromatic
aliphatic
hydroxyl
carboxyl
O
ester
alkene
D. aliphatic hydroxyl ester

Use the information below to answer the next question

45
23. The method of separating hydrocarbon compounds in crude oil that is
represented in the diagram above is
A. titration
B. precipitation
C. solvent extraction
D. fractional distillation

46
 Answers for Multiple/Diploma Examination Practice:

1. D
2. A
3. A
4. B
5. B
6. B
7. 4
8. C
9. C
10. A
11. D
12. 1857
13. 2478
14. B
15. A
16. C
17. D
18. A
19. A
20. B
21. 2615
22. B
23. D

47
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