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Whole Organic
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Chapter 15
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Organic Chemistry
Hydrocarbons it
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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.
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
N.B. In all hydrocarbon series, every member differs from the adjacent members by
multiples of (CH2)n.
To MrofCH2 14
saturation 153
4. They react by substitution giving 4. They react by addition giving one
two products. product only.
Molecular Formula
ISO similar Same
Isomers:
They are organic compounds of the same molecular formula and
different structural formulae.
a) Butene : (C4H8)
But–1–ene But-2–ene
b) Pentene: (C5H10)
Pent-2-ene Pent-1-ene
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.
c) Chloropropane: (C3H7Cl)
1-Chloropropane 2–Chloropropane
d) Dichloroethane (C2H4Cl2)
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 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
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)
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”
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
……………………..
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
Many products can be resulted from the cracking of octane. The choice of any of
which depends on the applied conditions.
C8H18 C4H10 + C4H8
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.
Vapour
THE
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.
A B C
162
a
Alcoholdehydration producesthe
Correspondingly
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
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
+ H-OH
Butan-2-ol
In such a reaction 2 isomers are produced
164
+ H-Cl
+ H-Cl
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
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
• 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- Combustion:
C2H5OH + 3O2 2CO2 + 3H2O
Ethanol always burns by complete combustion producing CO 2 & H2O
b
167
a
Conc. H2SO4
C2H5OH(l) C2H4(g) + H2O(g)
at 180°C
Ethanol Ethene water
Conc. H2SO4
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.
___
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.
III metha o H
met 168
HCOOH
Ethy Ethanate
Hydrogen
Magnesium ethic
1,1 yet
HE
I 2
Aug Iff dg
2- The name of the salts of organic acids is ended by the word "alkanoate". For
example, methanoate, ethanoate, propanoate, butanoate, etc…..
KMnO4
C2H5OH + O2 CH3COOH + H2O
(oxidizing agent)
+ Na NaOH
+ + H2O
2CH3COOH + Mg (CH3COO)2Mg + H2
169
[metal] Magnesium ethanoate
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
Exercise 1:
Solve the following word equations
PHIbutanoate
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)
Acid
oate b)
Butyl ethanoate
Alcohol 71 172
propyl Methanoate
c)
Acid Alcohol
d) CH3CH2CO2CH2CH3 Propanoate
Ethyl
O R-COO-R’
Esters - C – O – (ester linkage)
♣ ♥ ♣ ♥
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
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
b) Proteins:
Monomer: Different
amino acids
176
Polymer: Protein
amide linkage
Protein
O
C – O – (ester linkage)
177
2. Synthetic (man-made) polymers:
a) Polyamide (Nylon)
2 different monomers:
building units
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:
178
building units
ester linkage
Terylene
A: -OC-(CH2)6-COO-(CH2)4-O-
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
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
F proteins it.nl i o it
fÉmerNylon
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
Htand 0HFrom
same structure
A larger structure
Products smaller
is produced
structure
a out
H H
1
Nov
16
E Q1
only
180