iIi i ie

suffix
Fifi.is
substituents
t.EE
C

fiii itiiiiiiii
group
one arm
anne
Iii ae in i and
E
methyl
Bends c E
b at g pen
I are
É o HCarboxyloff co é
Chapter 15
card
sing
omologousseries containmembers
I pt folate esters

8 Oct
Non

i it
iiTw
E.EE.ir
i ii
Organic Chemistry
Hydrocarbons it
tha o
yf.ec o21kIeo1
si6trifloroHef

SEEK ua it B have
might
in

Ei i f it

T.it
B
inett T.fi fiEi.io
needs
a.E i

Isomers 1 Alkanes Done

Branch
dito
I
if
2 Substituted Alkanes to
9199Bn
3 Alkenes c
4 Alkynes CE Propan 1 01 propan 2 01 1
H
Alkyne CnHan
5 Alcohols o
480 inHana
9460
Alcohols

6 Carabetidicon
car C an
Esters
CnHan
tartsfrom 3 carbons
cyclic Isom
cycloalkanes are Isomers to Alkenes
Cyclo Alkenes are Isomes
to Alkynes 4 4 44 4 straightchain

it c
L Branched chain
propene
Cultantz

i i
i d iii i
i Cotta

T.IE H 151

G E g
 Organic Chemistry
Organic: means derived or produced from a living organism.

Hydrocarbons is the main branch of organic that we will study.

Hydrocarbons means organic compound composed of carbon &
hydrogen only.

Propane

Methane

Ethane

Ethene

152
 NAME & MOLECULAR FORMULA OF HYDROCARBONS

ALKENES

ALK….. ALKANES
CnH2n+2 CnH2n
CH4 No comp
C1 Meth…..
Methane
C2H2
C2H6 Ethane C2H4 Ethene
C2 Eth…. acetylene
11
C3H8 Propane 11
C3H6 Propene
C3 Prop…..

C4 But……
11
C4H10 Butane C11
H Butene
4 8

C5H12 C5H10 Pentene

C5 Pent……
Pentane
C6H14 Hexane C6H12 Hexene
C6 Hex……
C7H16 C7H14
C7 Hept……
Heptane Heptene
C8H18 C8H16
C8 Oct….
Octane Octene
C9H20 Nonane C9H18
C9 Non…..
Nonene
C10H22 C10H20
C10 Dec…..
Decane Decene

N.B. In all hydrocarbon series, every member differs from the adjacent members by
multiples of (CH2)n.
To MrofCH2 14

Saturated Compounds Unsaturated Compounds

[Alkanes]
1. They are inactive compounds.
2. They react very slowly.
3. They cannot decolorize bromine
Est water. ( stays orange )
[Alkenes & Alkynes]
1. They are active compounds.
2. They react very rapidly
3. They can easily decolorize bromine
water. ( turns colorless )

saturation 153
 4. They react by substitution giving 4. They react by addition giving one
two products. product only.
Molecular Formula
ISO similar Same

Mers Units ISOMERS & ISOMERISM Different

structuralFormula

Isomers:
They are organic compounds of the same molecular formula and
different structural formulae.

Isomers differ in their physical properties (e.g. boiling points); they

can be separated by fractional distillation

1. Isomerism of alkenes (because of double bonds):

a) Butene : (C4H8)

But–1–ene But-2–ene

b) Pentene: (C5H10)

Pent-2-ene Pent-1-ene

Remember: There are no isomers for alkenes which contain less

than four carbon atoms.

Propene has NO ISOMERS

154
2. Isomers of alkanes:
Isomers of alkanes can be done by changing the length of the
main carbon chain by moving one of the methyl groups from the
side to the middle of the compound.

Pentante 2- methyl butante

3. Isomerism because of halogens:

c) Chloropropane: (C3H7Cl)

1-Chloropropane 2–Chloropropane

d) Dichloroethane (C2H4Cl2)

1,2 dichloroethane 1,1 dichloroethane 4.

Isomerism of alcohols (because of –OH group):

e) Butanol: (C4H9OH)

Butan-1-ol Butan-2-ol
155
 GeneralFormula

ALKANES [CnH2n+2]
AllBondsaresingle
They are saturated hydrocarbons. They are relatively inactive compounds
(compared with alkenes). They consist of neutral covalent molecules (pH = 7)
insoluble in water but soluble in organic solvents.
withoxygen
Reaction
A
It
Alkanes are inactive in their reactions except for combustion and substitution with
halogens( chlorine) onehydrogenatom replacedbyone
haloga atom Forming 2products

The first four members in this homologous series are :

Methane Ethane Propane Butane

1ˢᵗmember Fourthmember

The first member (methane) is the major constituent (≈ 95%) of natural gas; it is
also produced by vegetation decomposition & as a waste gas from animals. Butane
gas is called butagas and its used as a bottled as.

WE A- Physical Properties:
• The first four members (C1 to C4) are gases.

1
•
•
The next members (C5 to, C17) are liquids.
The heavy members (> C18) are either viscous liquids or solid at room
temperature.
Viscosity
Resistance of Liquids
toFlow
B- Chemical Properties:
1. Combustion: [Burning in Air]
complete
1120
021

a) Complete Combustion: Incomplete

cattle
Hydrocarbons burn completely in plentiful supply of air (excess
oxygen) with a blue flame. The products are carbon dioxide “CO 2”
and water “H2O”.

156
 inBalancing To
org write
IDI Italy in Products It
Noof Carbons No of ofCO2
Nooffline
Rules of combustion of hydrocarbons (alkanes & alkenes):
40 2 2 2 4
1CH4(g) + 2O2(g) 1CO2(g) + 2H2O(g)
3 7
1C2H6(g) + 3½O2(g) 2CO2(g) + 3H2O(g)
I
1C3H8(g) + 5O2(g) 3CO2(g) + 4H2O(g)

1C4H10(g) + 6½O2(g) 4CO2(g) + 5H2O(g)

s
1C5H10(l) + 7½O2(g) 5CO2(g) + 5H2O(g)
s

1C6H14(l) + 9½O2(g) 6CO2(g) + 7H2O(g)

c

1C8H18(l) + 12½O2(g) 8CO2(g) + 9H2O(g)

Excercise:
6 3 9
1 C3H6(g)
…… + ……
9
O2(g) ……
3 CO2(g) + …… H2O(g)
1 C4H8(g)
…… + 6
……
02 O2(g) …… 4 H2O(g) 12
4 CO2(g) + ……
1 C5H12(l)
…… +
8
…… O2(g) …… 6 H2O(g)
5 CO2(g) + …… 716
1 C6H12(l)
…… + 9 O2(g)
…… …… 6 H2O(g)
6 CO2(g) + …… 18
1 C7H16(l)
…… + 11 O2(g)
…… 2 CO2(g) + ……
…… 8 H2O(g) 22

y C7H14(l)
…… + …… O2(g) 7 CO2(g) + ……
…… 7 H2O(g)
w
b) Incomplete Combustion: 21
1- Alkanes: They burn in limited supply of air with a luminous flame producing a
I
mixture of carbon monoxide “CO” and water vapour “H2O”
2- Alkenes: They burn in limited supply of air with a sooty (smoky) flame producing
a mixture carbon monoxide “CO” and water vapour “H2O”

All organic compounds are flammable & used

as fuels except organic acids.
2 ene Alkane Cultana

92426 1 81
157
 c) Effect of Pollutants:
Most of the products resulted from the combustion of hydrocarbons are pollutants
and have some harmful effects on the environment. The major pollutants are CO 2 ,
CH4 , CO & unburnt hydrocarbons

tttiff am
Eithne
g
*****************
Inactive
Lowenergy
III Cracking of Alkanes
Lefave Cracking ismthe breaking down of organic compounds of big molecular
mass into others of smaller molecular mass. This is one of the most important
processes used in petroleum refiners in order to get better products out of the heavy
fractions. Upon cracking a heavy alkane, the products are one alkane and alkenes.

C17H36
Gas Oil fghenerg .tt
Cracking 500°C, SiO2 C8H18 +
Octane
……………………..

C15H32 Cracking 500°C, SiO2 C8H18 + ……………………..

Gas oil Octane

it H
VII
• The Conditions of Cracking. Cracking can also produce hydrogen
1- Using high temperature (about 500°C). gas in case of cracking small alkanes

v81 2- Using high pressure.

3- Using of a suitable catalyst (SiO2 or Al2O3).
The advantages of cracking are:
C2H6
ethane
C2H4 +
ethene
H2

1- Changing large alkanes to small alkanes & alkenes

2- Changing heavy useless solid fuels to light useful compounds
3- Changing cheap inactive alkanes to valuable active alkenes

Many products can be resulted from the cracking of octane. The choice of any of
which depends on the applied conditions.
C8H18 C4H10 + C4H8

C8H18 C5H12 + C3H6

C8H18 C3H8 + C5H10

C8H18 C6H12 + ………

C8H18 C2H4 + ………

C8H18 C7H14 + ………

158
 • Cracking alkanes in the lab:

6 catalyst

waterinsoluble collectedover
IMP Brawater
Boiling
Eve decolonized

CwÉ at

Revision questions:
1- What is the purpose of broken tile?
➢ Used as catalyst.
2- Why are small pieces of broken tiles used?
➢ To increase the rate of reaction (bigger surface area).
3- What is the purpose of the mineral wool?
➢ To hold the liquid alkane.
4- Why ethene is collected over water?
➢ Because it is a neutral gas insoluble in water.
5- Explain why the delivery-tube should be removed from the water trough before
stop heating?
➢ To prevent back-suction of water as the gases contract by cooling.
6- Describe a test to show that alkenes have been made?
➢ Add bromine water; it decolorizes.

Explain why testtube should be

16
heated gently then
strongly

To prevent cracking of testtube

Sudden change in tempdue
by 159

to very strong heat

 Fraffiation
Crude oil
alkanes
Refining Of Petroleum Oil Mainly
Crude oil is a mixture of miscible liquid hydrocarbons it includes molecules of
Muhr
many shapes and of different molecular masses. Crude oil is related to fossil fuels
containing sulphur as impurities
The refining of petroleum oil includes two main processes: Fractional Fractions useful
Distillation & Cracking.

A- Fractional Distillation: The crude oil is

boiled/evaporated/vaporized and its vapour is passed through the
bottom of a fractionating column. The different fractions are separated
according to their boiling points. The lightest fractions are collected
from the top of the tower whereas the heaviest fractions from the
bottom. Each fraction is not a pure substance and has therefore a
range of boiling point (not a fixed temperature).

Fractionating Column Tower

Vapour
THE

DIFFERENT FRACTIONS OF CRUDE OIL

160
 As we move
Fraction Uses
down the column
1 Gases Refinery
gases
nd
Bottled gas (butagas)
(ethane, methane)
1. Boiling
point increases
2 Petrol [gasoline] Petrol for vehicles and solvent 2. Viscosity
3 Naphtha Making chemicals increases
4 Paraffin [Kerosene] Aircraft fuel 3. Chain
5 Diesel oil [Gas oil] Diesel engine fuel Buses Trucks length increases
mm mmmm
Fuel for power station and 4. Volatility
6 Fuel oil
mn ships decreases
Lubricating oil Used as lubricant,waxes and Volatile LowBP
7
[mineral oil] polishes. Candles
8 Asphalt [Bitumen] Road making, roofing material
mm mm
Fraction: Useful pure part of hydrocarbon resulted from fractional
distillation of crude oil. B- Cracking:
The heavy fractions are cracked in order to change:-
1- One heavy alkane into some light alkenes
2- The heavy low energy value fuels into light high energy value
fuels.
1 k it d it
3- Inactive alkanes into active alkenes. H feel
Chemical Properties of alkanes (continued): GHG 02 k gAge 1
2. Substitution reaction of alkanes: photochemical reaction
As all alkanes are inactive; they react under special conditions (UV
light or heat ) by substituting one hydrogen atom with one halogen
atom in which two products are formed.

111

161
 GeneralFormula
Nometh
ALKENES [CnH2n]

en dsmtemb.es
Ethene Propene SEmber
A- General features of alkenes: Containsdoublebond
1- They are unsaturated hydrocarbons. made CH sins kyle
upof y
2- They contain double bonds between 2 successive carbon atoms 3-
Efron
takesPartin
They are active compound, readily react by addition. only one product isformed
mn
4- They can decolourize bromine water (test for unsaturation)
chemicalreaction
orange to colourless
B- Test of unsaturation / alkenes:
• Add bromine water (reddish brown)
• If unsaturated (alkenes): bromine water decolorizes.
• If saturated (alkanes): color remains.

C- Preparation Of Ethene: [C2H4] 1- Preparation Of Ethene

In Industry:
It is prepared by cracking of heavy alkanes at high temperature and high
pressure using a suitable catalyst.
Cracking

C17H36 C8H18 + C3H6 + 3C2H4

Gas oil 500°C SiO2octane propane ethene

2- Preparation Of Ethene In Laboratory:

A B C

Caltgott GHa H2O

ethanol ethene watercg

162

a
 Alcoholdehydration producesthe
Correspondingly

cyst GE Alkene sifications

It is prepared by the dehydration of ethanol (C2HsOH) either by:-

medalist
1- Passing ethanol vapour through conc. H2SO4 at 180°C.
2- Passing ethanol vapour over hot Al2O3 at 360°C

it it it I
C2H5OH dehydration C 2 H4 + H 2 0 H CIC 1

Revision questions:
conc H2SO4 or Al2O3 E it it
Ethanol
1- What is the purpose of aluminium oxide? Ethene

➢ Used as catalyst.
2- Why aluminium oxide is used as a very fine powder?
➢ To increase the rate of reaction (bigger surface area).
3- What is the purpose of the glass wool?

1
➢ To hold the liquid ethanol.
4- Although aluminium oxide is heated, yet ethanol is evaporated. Explain why.
➢ Because ethanol is a volatile liquid.
5- Why ethene is collected over water?
➢ Because if is a neutral gas insoluble in water.
6- Explain why the delivery-tube should be removed from the water trough before
stop heating?
➢ To prevent back-suction of water as the gases contract by cooling.
D- Chemical Properties:
The following reactions show that ethene is an unsaturated
compound. It therefore, is an active compound, which reacts fast by
ADDITION producing only one product.
part

1- With Hydrogen: (hydrogenation)

ego
ftfef.in
Hydrogen is added to the alkenes by heating in presence of nickel
as a catalyst and temp 150 to 300C . Vegetable oils (unsaturated
fats) are also
hydrogenated into saturated solid fats (margarine)
Alkene + hydrogen Alkane

iiEEiii
itii
Hydrogen Alkane
Alkene
Acid

Br B Disy

163
 2- With Steam: (hydration): Catalytic addition of steam to ethene
Ethanol is manufactured from ethene. It reacts with steam
using phosphoric acid (H3PO4) as a catalyst, high
temperature 300C & 60 atm or 6000 kpa pressure.

H3PO4
C2H4 (g) + H2O (g) 60 atmosphere C2H5OH
(g)

H3PO4
60 atmosphere
56

+ H-OH
Ethene Water vapour Ethanol

H3PO4
56 atmosphere

But-1-ene Water vapour Butan-1-ol

C4H8 (g) + H2O (g) C4H9OH (l)

+ H-OH

Butan-2-ol
In such a reaction 2 isomers are produced

3- With Acids of Halogens:

C2H4 + HCl C2H5Cl

164
 + H-Cl

Ethene Hydrogen chloride

Chloroethane

C4H8 (g) + HCl (g)

C4H9Cl (l)

+ H-Cl

But-1-ene Hydrogen chloride

1-chlorobutane

2-chlorobutane
In such a reaction 2 isomers are produced

4- With Halogens:(halogenations)
Ethene and other unsaturated compounds react readily with
halogens by addition. They can decolourize bromine water or
iodine water (red/brown).
This is the simple test for unsaturation.

C2H4 + Br2
C2H4Br2

+ Br-
Br

Ethene Bromine water 1,2

dibromoethane
(reddish brown) (colorless)

165
c o it Ef.io i o a
Alcohol
nu
 oi
1 17
HIII
General Formula
ALCOHOLS [CnH2n+1OH]
Alkyl group – O – H

The hydroxyl group (-OH) is the functional group (active group) of alcohols. It is
attached with the alkyl group (CnH2n+1)
The name of an alcohol is given by "alkanet" or "alkyl alcohol".
The ending “.... ol" means an alcohol. Alcohols are neutral compounds pH=7 The
a are:
first three members in this homologous series

CH3OH C2H5OH C3H7OH

methanol ethanol propanol

• Preparation Of Ethanol:[C2HsOH] 1-
East By Hydration of Ethene: Catalytic addition of steam to
100 yield
This hydration reaction has been discussed early.
001 pureethanol
C2H4(g) + H2O(g) C2H5OH(g)
H3PO4 /60 atmosphere
cheaptrfossifel Ethene water vapour at 300°C
Ethanol The only
onreni.it
L to make ethanol from hydrocarbons is by adding water 2- By
way
Fermentation of Glucose:
Ethanol can be also manufactured (or prepared in the laboratory) by fermentation of
carbohydrates.
Yeast is added to slurry of 10% sugar (glucose C6H12O6) and the mixture is kept at
warm temperature (≈32°C) until all CO2 is given off (no further froth).
In industry it is expensive to start with glucose as a source of carbohydrate. Actually
potato (as a source of starch) is hydrolyzed by dilute sulphuric acid at 60°C to
produce glucose.
FfEskese
ofoxygen.tt
Absence
sos
CHED yeast

Bteria
C6H12O6(aq)
enzymm2C2H5OH(l) + 2CO2(g)
otatoes
[zymase]
Ii L Glucose at 35°C
ethanol Carbon dioxide Extfin
e Froth Bubbles
fat
a_
avant
Definitions:
1- Fermentation: It is a breakdown of a carbohydrate by the action of yeast
producing alcohol and carbon dioxide.
2- Respiration: The breakdown of food to produce energy
3- Carbohydrates: They are compounds containing carbon, hydrogen and oxygen
in which the ratio of hydrogen to oxygen is 2: 1 (as that in water).
4- Hydrolysis: It Is breakdown of an organic compound by adding water.
166
 Conditions for fermentation:
1- Add water to form either solution, paste or
slurry of glucose. Water is essential for the
living of bacteria.
2- Water is used as a coolant to avoid any
further rise in temperature (This is because
fermentation is an exothermic process).
3- Add yeast, which produces the enzyme
zymase which acts as a biological catalyst.
4- Warm temperature should be used (30-35°C).
• Lower temperatures slow down the rate of reaction.
• Higher temperature would kill the bacteria (denaturing).
5- The process should be carried out in absence of air to prevent the oxidation of
ethanol into ethanoic acid.
C2H5OH + O2 by bacteria (from air) CH3COOH + H2O

6- Yeast is removed from the wash by filtration whereas pure alcohol is separated
from the filtrate by fractional distillation.
Ii t.EE tethii
Fermentation may stop for 3 reasons 1-

isYf
Glucose is used up. Filteration Factotal
distillation

2- Ethanol produced kills the yeast.

explain
3- Temperature rise kills the yeast. Na
2m
ing189
Condensate
L
A- Physical Properties Of Ethanol: [C2H5OH]
Alcohols are neutral colourless liquids. They are volatile liquids.
LOWBI
B- Chemical Properties Of Ethanol: [C2HsOH]
1- Oxidation:
Ethanol can be oxidized into ethanoic acid by:-
a. Oxygen of air through the action of certain bacteria present in air.
b. An acidified solution of potassium manganate(VII), This is accompanied by a
color change(pink into colorless)

2- Combustion:
C2H5OH + 3O2 2CO2 + 3H2O
Ethanol always burns by complete combustion producing CO 2 & H2O
b

3- Dehydration or an alcohol gives the corresponding alkene.

Dehydration
Done Alcohol Alkene + water
a Hydration

167

a
 Conc. H2SO4
C2H5OH(l) C2H4(g) + H2O(g)
at 180°C
Ethanol Ethene water
Conc. H2SO4

C3H7OH(l) C3H6(g) + H2O(g)

Propanol Propene water
at 180°C
C4H9OH(l) Conc. H2SO4 C4H8(g) + H2O(g)
Butanol Butene water

at 180°C
C- Uses Of Ethanol
1- It is used as an organic solvent (e.g tincture iodine & in chromatography).
Is
2- Although expensive it is a good fuel (produces less pollutants than petrol). 3-
It is the major constituent of wine and beer.
___

D- Test for ethanol: (paper 6) Test Lightedsplint

It is a neutral flammable liquid which burns & catches fire with a blue or yellow
flame & has an aromatic (antiseptic/sweet/ fruity /distinctive) odour.
Perfumes

Ethanol production by Ethanol production by

hydration of ethene fermentation
Cheap Expensive
Produces high concentration of Produces low concentration of ethanol
ethanol
Catalyst needed Biological catalyst (enzyme) needed
Non renewable (as ethene is Renewable (as starch is renewable)
produced from petroleum)
GeneralFormula
Cult Butane
ORGANIC ACIDs [CnH2n+1COOH] Cutty
Butene

Carboxylic acids cult Butyne

O Catty
Butanol

Alkanoic acids: Alkyl group - C acid

GHgCooltPedanoic
O–H

The carboxylic group (-COOH) is the functional group (active group) of organic
acid. It is attached with the alkyl group (CnH2n+1).
The name of an organic acid is given by "Alkanoic acid". The ending “…….oic" means
an organic acid.

The first three members in this homologous series are:

Inorganicacid salt acid
Organic salt

III metha o H
met 168
HCOOH
Ethy Ethanate
 Hydrogen
Magnesium ethic
1,1 yet
HE
I 2
Aug Iff dg

HCOOH CH3COOH C2H5COOH

Methanoic acid ethanoic acid propanoic acid
Remember: Smede
Ammonia PH77
1- Ethanoic acid (CH3COOH) is called "vinegar" with strong acidic / pungent
smell. T ethanoicacid P 7

2- The name of the salts of organic acids is ended by the word "alkanoate". For
example, methanoate, ethanoate, propanoate, butanoate, etc…..

A- Preparation Of Ethanoic Acid:

By oxidation of ethyl alcohol (ethanol)

KMnO4
C2H5OH + O2 CH3COOH + H2O
(oxidizing agent)

B- Properties of organic acids:

1- Typical properties of acids
It reacts (as an acid) with alkali, base, carbonate and
metals.

+ Na NaOH
+ + H2O

Ethanoic acid [alkali] sodium ethanoate

CH3COOH + NaOH CH3COONa + H2O

[alkali] sodium ethanoate

2CH3COOH + CaO (CH3COO)2Ca + H2O

[base] calcium ethanoate

2CH3COOH + Mg (CH3COO)2Mg + H2
169
 [metal] Magnesium ethanoate

2CH3COOH + Na2CO3 2CH3COONa +

H2O + CO2
[carbonate] sodium ethanoate

2- Special Properties Of Organic (carboxylic) Acids:

a- They are weak acids (not completely ionized). They produce low number of
ions upon ionization. The concentrations of H+(aq) ions is very low and thus
they react slowly. Their pH value is about 4.

CH3COOH (l) ionization

CH3COO- (aq) + H+ (aq)
Ethanoic acid ethanoate ion
React
A
b- Organic acids react with alcohols in the presence of concentrated reacted
sulphuric acid. The products are esters and water. acid
carboxylic

oc oa

ii E
Alcohol
carboxylic
ESTERS [R.COO.R’] Cark
Alcohol
O
fi
alcohol
fffffgffwaterrehoval o

Alkyl Group – C
Aldol
O – Alkyl Group Carabylic

The ester linkage is [-COO-].Fats and vegetable oils (including butter and margarine)
as well as most perfumes are ester. Some polymers (such as Terylene) are
polyesters
Esters are made (synthesized) by the reaction between an organic acid and
an alcohol. The process is called "esterification" in which the reaction is
reversible at equilibrium. The reagents are gently heated in the presence of
concentrated sulphuric acid (acting as catalyst), where the resulted ester is
separated from the final mixture by fractional distillation.
N.B. All fats are esters; when they are heated with an alkali, soap is
formed & glycerol (saponification)
Esterification
R.COOH + R'.OH R.COO.R' + H2O
Hydrolysis
Organic acid Alcohol Ester Water

1. Naming:
170
 The name of the ester is composed of two parts, the first from the alcohol & the
second from the acid

Ethanol + Methanoic acid Ethyl methanoate + Water

Methanol + Propanoic acid Methyl propanoate + Water

Exercise 1:
Solve the following word equations

Propul Butanoale water

a) Propanol + Butanoic acid
41 Foale
b) Pentanol + Ethanoic acid pentyl ethanoate water
71 Take

c) Propanoic acid + Ethanol ethyl propanoate

water
Fate F
d) Methanoic acid + Methanol Methyl Methanoak
water
2. Drawing:take x̅
Esters can be drawn by drawing their building units (acid and alcohol), Then
connecting both units by removal of water (condensation)

PHIbutanoate

Exercise 2: startTith linkage

Draw the following esters:
ethyl AI Alcohol
etterate
a C 171

CH 100 CH
 e 1 Butanoate

a) Propyl methanoate:

it it
it
it
it
CHz CHz 00C cha CHz CH
b) Ethyl butanoate:

c c C
Co c c

c) Methyl pentanoate:

s c c c
Co c

d) Propyl propanoate:
o
c C E o c c c
Exercise 3:
Name the following esters:

a)

Ethanoate + Propyl Propyl ethanoate

Acid
oate b)

Butyl ethanoate

Alcohol 71 172
 propyl Methanoate
c)

Acid Alcohol
d) CH3CH2CO2CH2CH3 Propanoate
Ethyl

e) CH3CH2CH2CO2CH3 Methyl Botanoate come

Isomersofesters card
pa

f iiiii HOMOLOGOUS SERIES iii

CE.PE
n 9,4
The homologous series is a group of organic compounds having
the same functional group, similar chemical properties & same
Hy general formula.
02162 Consecutive members differ
by_CHz group
3H22 Theyshow a trend intheirphysical properties

Homologous series Functional group General Formula

Alkanes (single bond) CnH2n+2
Alkenes (double bond) CnH2n
Alcohols OH (Hydroxyl) group CnH2n+1OH
COOH or CO2H CnH2n+1COOH
O
Organic acids
- C – OH (carboxylic)
(carboxylic acids)
group

O R-COO-R’
Esters - C – O – (ester linkage)

oly Many POLYMERIZATION

One
It is a process in which small molecules (monomers) are built up
no
together by linking to from a giant macromolecule (polymer).
er unit
Bonding
zation
Prof Monomer: It is a small molecule that can be joined up to form a giant
macromolecule (polymer).
173
 Polymer: It is a macromolecule which is formed by linking of small
molecules (monomers).

There are & types of polymerization :

1- Addition polymerization. Monomer is Alene
2- Condensation polymerization.
gqp.pe
Addition Condensation
It produces one product It produces 2 product one of
them is water
Linking is by breaking double Linking is by removal of
bonds water
1. ADDITION POLYMERISATION
The Polymerisation reaction:
In this type of reaction the monomer is an alkene (containing the bond C=C).
During polymerisation. The double bond is broken leaving a single bond and the
monomers are linked together. Each of the symbols (♣,♥,♠,♦) represents either
an atom or a group of atoms.

♣ ♥ ♣ ♥
n C = C C - C Polymerization

♠ ♦ ♠ ♦ n
Example:
1- Poly-ethene

Conti

n Esea

Monomer
ftn.net
Ethene
p
Alkene Alkane
2- Poly-chloroethene (poly vinyl chloride PVC)

fi i iii
3- Poly-propene: i e
CH at at at
fit
174

t.si
t.fi
 it

Exercise 1:
Draw the structure of the monomer for the following polymers

a)
it

Easy
c
I
H As

b)

I
Monomer Polymer
1. Unsaturated (double bond) 1. Saturated
2. Reacts fast 2. unreactive
3. Decolorize Bromine water 3. Can’t decolorize Bromine water

Uses of polymers (Plastic)

➢ Polyethene : Bags
➢ Polypropene : sterilized bottles
➢ PVC : insulator for electrical wires
➢ Nylon: Making clothes, ropes & strings
➢ Terylene: Making clothes

Advantages of polymers : (plastic) ➢

Heat & electrical insulator.
➢ Doesn’t rust.
➢ Unreactive with good strength.

Disadvantages of polymers : (plastic)

175
 ➢ Non-biodegradable: so they cause accumulation of waste &
visual pollution. synthetic
➢ When burnt they produce toxic gases as HCl (g) carbon
monoxide. g It
Ét
2. CONDENSATION POLYMERIZATION
➢ It is the linking of monomers together to make a big polymer by
removal of water molecules.
removal of water Condensate

1. Natural polymers (Food constituents): COOH Carboxylicacid

a) Starch (polysaccharide) .. (read only) E 1 ir

no H NHz Amino group

Single monomer: Glucose new ÉÉ Amidelinkage

Polymer: Starch

-H2O -H2O -H2O

Starch … read only Complex

carbohydrates:
Monomer : Glucose
Polymer : Starch
Test for starch : Iodine which gives blue black colour
N.B. Iodine + hydrocarbons purple color
Iodine + ethanol red / brown color

b) Proteins:

Monomer: Different
amino acids

176
 Polymer: Protein

Poly amide (peptide):

Monomer : Amino acids (different in
structure)
Polymer : Protein
Separation of amino acids : By
chromatography using a suitable locating
agent (e.g.
ninhydrin)
-H2O -H2O -H2O -H2O

amide linkage
Protein

O
C – O – (ester linkage)

Found naturally in fats & in man-made terylene (poly ester)

O

C–N (Amide / peptide linkage)

H Found naturally in proteins & in man-made nylon

These constituents of food can all be hydrolysed by boiling with acid or

alkali.
constituents of food Linkage Product of hydrolysis
Protein Amide linkage Amino acids
Fat Ester linkage Fatty acids (soap) &
glycerol
Complex starch Glucose
Carbohydrate

177
2. Synthetic (man-made) polymers:
a) Polyamide (Nylon)

2 different monomers:

-H2O -H2O -H2O -H2O

building units

amide (peptide) linkage

Nylon

Protein Nylon
Natural Synthetic
Composed of many different Composed of only 2 building
building units units
Each building unit carry 2 Each building unit carry 2
different functional groups similar functional groups;
(carboxylic group COOH) & either 2 carboxylic groups
(amino group NH2) COOH or 2 amino groups NH2
Biodegradable Non-biodegradable

b) Polyester (Terylene)

2 different monomers:

-H2O -H2O -H2O -H2O

178
 building units

ester linkage
Terylene

Q: Draw the formula of the polymer formed by condensation of the 2

following monomers:

HOOC-(CH2)6-COOH & HO-(CH2)4-OH

A: -OC-(CH2)6-COO-(CH2)4-O-

Remember: For every organic compound, there is a molecular,

structural, general & empirical formula

Exercise: Find the empirical formula of the following:

a) Hexene
b) Methyl propanoate
c) Butanoic acid

Best wishes

179
 Condensation hydrolysis
Condensation Polymerization
DilAcid
Done by removal ofwater
Catalyst
Conf u
Polymer Monomer
Monomer polymer

condensation
Natural Condensation synthetic
Polymen
polymers
Starch Carbohydrates

onomer glucose to oH D

Typeof linkage Saccharide linkage 0

Polymer
Natural Polysaccharide
Tpe
Draw 0 11 0 11 0 1 0
11

20230
Name of Polymer
Fats PE T Terylene

Nooner F glyceroo
Meter Ii carboxylicacid Di alcohol Dio

Typeoflinkage Esterlinkage Eo a o I o it III t

Type of polymer Natural PolyEster

Typeoflinkage Ester linkage do
Typeofpolymer synthetic
Polscothed
Drag Nomad Ds I 11 o o one repeatunit

F proteins it.nl i o it
fÉmerNylon

Motomers 21 aminoacids Monomer

fi IIi DicarkYic

a.dz qE
ot
typeoflinkage Amidelinkage
PolyPePtide

epgEi Dew
eofpolymer NatuualPolyamide
amj.tn f
I Iti i EI_its
BE It I1 1 I i i.FI
 Of It'd I
fd
H
Dipeptide o
it

Ñ Aminoacid
2 Amingacid
B
V
remove
one
It it o H

water

ni.EE
molecule
nt
only H o i II
H

No
Continuation
Bond

Catches
Removal
2504
of water
1802

Dehydration Drying Condensation

Chemical changes Physical change chemical changes

Removal of water Remove water From Removal of waterfrom

From same structure a mixture 2 diff molecules Monomer

Htand 0HFrom
same structure
A larger structure
Products smaller
is produced
structure

a out

H H
1
Nov
16
E Q1
only

180