Organic chemistry

Chemical compounds

Berzelius divided all compounds into

Inorganic compounds Organic compound

Coming from Vital force : Berzelius considered that organic
mineral source compound are formed by vital force which is
found in living cells of the body and it is
impossible to synthesized them in lab
The scientist Wohler destroyed the vital force theory when he
prepared urea by heating an aqueous solution of 2 inorganic
compounds, ammonium chloride and silver cyanate.
NH4Cl + AgCNO AgCl + NH4CNO

NH4CNO H2N – CO – NH2

ammonium cyanate urea

* What are the reasons of the abundance of organic

compounds?

- This is due to he ability of carbon atom to combine with

itself or with other atoms by different kinds of bond, it
might connect through single, double , triple bonds.

Triple bond Double bond Single bond

|
–C  C– C=C -- C --
|

* carbon atoms can join together with different methods, either

straight chain , branched chain , homocyclic or heterocyclic

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 Organic chemistry

Note:
The number of covalent bonds around the atom indicates it's
Valency

e.g.
Element H Cl O N C
Valency 1 1 2 3 4

* The difference between organic and inorganic compounds.

property Organic compound Inorganic compound

1- Chemical - must contain - may contain carbon
structure carbon atom atoms in addition to
other elements
2- solubility - most are insoluble - most are soluble in
in water but soluble water
in organic compound
solvent
3- Melting point - low high
4- Boiling point - low high
5- The odor - most have Most are odorless
characteristic odor

6- Inflammability - inflammable and Not inflammable , if

produce CO2 , H2O it is inflammable it
produces other gases

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 Organic chemistry
7- kind of bond - covalent bond Ionic bonds
8- conductivity - don’t conduct elec. Conduct elec.
9- rate of chemical - slow - fast
reaction
10- plymerization Can be polymerized Can not be
polymerized
11- Isomerism - it’s found among No isomers
many compounds

Classification of hydrocarbons

The molecular and structural formula of organic compounds.

Molecular formula
It is the formula which indicates the no. and kind of elements which
form the chemical compound.
e.g.

C2H4Cl2 , C2H2 , CH3OH

Structural Formula
It is the formula which indicates the no. and Kind of each element
in the molecule, and the kind of linkage between the atoms by
covalent bond.
e.g.
H–C  C–H
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 Organic chemistry

An Empirical formula is the simplest whole number ratio of the atoms in a

compound as found by experiment like chemical analysis.

The Molecular formula of a glucose molecule is C6H12O6

but its empirical formula is CH2O

The Molecular formula of a Propane molecule is C3H8

its empirical formula is itself C3H8

A skeletal formula e.g. in which none of the H atoms bonded to

carbon atoms are shown. The lines represent either carbon-carbon bonds
(single, double or triple), but other lines are needed to show bonds to other
atoms which are NOT carbon or hydrogen

e.g. C-Cl in and hydrogen atoms are shown if they are bonded to non-
carbon atoms

e.g. the C-OH in .

Hybridization is the concept of mixing atomic orbitals into new hybrid

orbitals (with different energies, shapes, etc., than the component atomic
orbitals) suitable for the pairing of electrons to form chemical
bonds in valence bond theory. Hybrid orbitals are very useful in the
explanation of molecular geometry and atomic bonding properties.

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 Organic chemistry

Hybridization and molecule shape

Hybridization helps to explain molecule shape, since the angles between bonds are
(approximately) equal to the angles between hybrid orbitals.
Examples are given in the table below:
Classification e.g. Main σ and π hybridizat Angle Shape
group bonds ion
Alkane CH4 Single All σ sp3 (109.5°) Tetrahedral
bond
Alkene C2H4 Double 1σ &1π sp2 (120°) Triagonal
bond planar
Alkyne C2H2 Triple 1σ&2π sp (180°) Linear
bond

Isomerism

Structural Isomers and Stereoisomers

Isomers are compounds with different physical and chemical
properties but the same molecular formula.
In organic chemistry, there are many forms of isomerism.

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 Organic chemistry

Chain Isomers :
The formula C4H10 represents both butane and 2-methylpropane.

postion Isomers :

Functional group Isomers :

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 Organic chemistry

Stereoisomers have identical molecular formulas and arrangements

of atoms. They differ from each other only in the spatial orientation
of groups in the molecule. The simplest forms of stereoisomers are
cis and trans isomers, both of which are created by the restricted
rotation about a double bond or ring system.

Butene, C4H8, exists in both cis and trans forms.

Optical isomers are named like this because of their effect on plane
polarized light.

Detection of carbon and hydrogen in organic compounds:

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 Organic chemistry

Organic
substance +
black copper
oxide White copper
sulphate

Lime water

- Procedure:
1- Heat organic compound with (CuO) in test tube
2- Pass the resulting gases over white anhydrous copper sulphate
(CuSO4) then through clear lime water
-Observations:
1- The white colour of anhydrous copper sulphate turns into blue
2- The clear lime water becomes turbid.
-Conclusion:
Organic compounds contain mainly carbon and hydrogen elements.

Hydrocarbons: They are organic compounds consist of carbon

and hydrogen only
The nomenclature of organic compounds (IUPAC system)
1- First suffix indicates the number of carbon atoms

No.of No.of
carbon suffix carbon suffix
atoms atoms
C1 Meth C6 Hex
C2 Eth C7 Hept
C3 Prop C8 Oct
C4 But C9 Non
C5 Pent C10 Dec

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 Organic chemistry

2-the second suffix indicates the type of hydrocarbon

Bonding
Single bond Double bond Triple bond
ane ene yne

A-Saturated hydrocarbon

Alkanes

General formula (CnH2n + 2)

1- Each compound exceeds the previous one by ( - CH2)

2- They are inactive compounds due to presence of sigma bond
3-they are homologous series

Structural Formula Alk

CnH2n+2 anes
Name
All bonds are sigma bond
H
|
CH4 H - C - H C1 Methane
|
H

H H
| |
C2H6 H - C -C- H C2 Ethane
| |
H H

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 Organic chemistry

Homologous series

it is a series of related organic compounds having the same general

formula , chemical properties and graduated physical properties

Alkyl Radical (R)

1- It is an organic atomic group which does not found alone.

2-it is derived from the corresponding alkane by removing on
hydrogen atom
3- Alkyl radicals are given the symbol “R”. Their general formula
(CnH2n + 1)
4- Its name is derived from the corresponding alkane replacing the
suffix (ane) by (yl).
Ex.

- CH3 - C2H5 - C3H7 - C4H9 - C5H11

Methyl Ethyl Propyl Butyl pentyl

The nomenclature of alkanes (IUPAC)

1- The name of hydrocarbon is determined according the longest

continuous carbon which may be linear or branched.
2- The carbon atoms are given numbers in the longest chain.

3- If the side group is repeated in the hydrocarbon chain we use

prefix Di – or Tri – or Tetra – to indicate the number of repetition

4- if the branch is a halogen atom such as chlorine or bromine or a

group such as NO2- , the name is ended by the letter (O) so we say
chloro , bromo or nitro.

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 Organic chemistry

Ex.
The name Compound
CH3 Cl
6 5 4| |
2-chloro-4,4 Di methyl Hexane CH3-CH2-C-CH2-CH-CH3
| 3 2 1
CH3
4 5 6 7
CH3-CH-CH2-CH2-CH3
|
3,4 Di methyl heptane 3
CH3-CH2-CH
1 2 |
CH3
CH3 CH3
| |
3,4,4,5 Tetra methyl octane CH3-CH2-CH- C - CH-CH2-CH2-CH3
| |
CH3 CH3

CH3-CH-CH-CH3
2- bromo 3- methyl butane | |
CH3 Br

Write the name of each compound according IUBAC

CH3- CH – CH2-CH-CH3 CH3- CH - CH-CH3
| | | |
CH2 CH2 C2H5 CH3
| |
CH3 CH3

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 Organic chemistry

Methane CH4
1- It is the first member and the simplest organic compound

2- Forms about 90% of natural gas

Preparation of methane in lab

By dry distillation of anhydrous sodium acetate with soda lime

(mixture of NaOH/CaO)
CaO
CH3COONa + NaOH CH4 + Na2CO3

Function of (CaO ) quick lime

1- Help in reducing the melting points of the reaction mixture

CH4

CH3COONa
+
NaOH/CaO

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 Organic chemistry

The physical properties of alkanes

1- The first 4 members are gases. methane can be used as a fuel in

homes, while the mixture of propane and butane, is filled in
cylinders and is used as a fuel , since propane more volatile ( less
b.p) than , butane so we find that the ratio of propane is more in
cold countries , while in warm countries the cylinders contain larger
ratio of butane .

2- Alkanes , which contain 5 – 17 carbon atoms are liquids

e.g gasoline and kerosene which are used as liquid fuel

3-the compounds which contain more than 17 carbon atoms are

solid. e.g. paraffin wax
4- alkanes are non polar compound insoluble in water , so the
metals are covered by heavy alkanes to protect them against rust

The chemical properties of alkanes

Alkanes are inactive . due to presence of strong sigma bond

1- Burning: all alkanes burn giving water vapour and carbon

dioxide
CH4 + 2O2 CO2 + 2H2O + E

2- the reaction with halogens (I2, Br2, Cl2)

a-) in direct sunlight: -
if methane reacts with chlorine or fluorine in the direct sun light,
black carbon is remained. This reaction is accompanied by
explosion ( this reaction is called elimination reaction)
D.S.L
CH4 + 2Cl2 C + 4HCl

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 Organic chemistry

b-) in indirect sunlight: -

alkanes react with halogens in indirect sun light in a series of
substitution reaction these are:-
I.S.L
CH4 + Cl2 CH3Cl + HCl
Methyl chloride
CH3Cl + Cl2 I.S.L CH2Cl2 + HCl
Dichloro methane
I.S.L
CH2Cl2 + Cl2 CHCl3 + HCl
Trichloro metane )chloroform(
CHCl3 + Cl2 I.S.L CCl4 + HCl
)carbon tetrachloride( Tetrachloro methane

THE REACTION BETWEEN METHANE AND CHLORINE

A Free Radical Substitution Reaction

This is free radical substitution reaction between methane and chlorine

This is a good example of a photochemical reaction - a reaction by light.

CH4 + Cl2 CH3Cl + HCl

The organic product is chloromethane.

One of the hydrogen atoms in the methane has been replaced by a chlorine
atom, so this is a substitution reaction. However, the reaction doesn't stop
there, and all the hydrogen in the methane can in turn be replaced by
chlorine atoms.

The mechanism is known as free radical chain reaction.

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 Organic chemistry
Chain initiation
The chain is initiated (started) by UV light breaking a chlorine molecule into
free radicals.

Cl2 2Cl

Chain propagation reactions

These are the reactions which keep the chain going.

CH4 + Cl CH3 + HCl

CH3 + Cl2 CH3Cl + Cl

Chain termination reactions

These are reactions which remove free radicals from the system without
replacing them by new ones.

2Cl Cl2

CH3 + Cl CH3Cl

CH3 + CH3 CH3CH3

Uses of halogenated derivation of alkanes:

1- Chloroform was used for a long time as anesthetic substance but

its uses stopped because the inaccurate estimation of the dose for
each patient causes the death

2- Halothane is used now as anesthetic substance with more safety

and its formula is CHBrCl – CF3
(2-bromo 2- chloro -1,1,1 triflouroethane)
Br F
| |
H–C–C–F
| |
Cl F
Halothane
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 Organic chemistry

3- The compound 1,1,1 trichloro ethane is used in the dry cleaning

4- Freons were used in air conditions and fridges, also as a rushed

substance to liquid and perfumes and as a cleaner of electronic sets.

The famous one of Freons is dichloro , difloromethane CF2Cl2

How ever Freon’s causes the decay of ozone layer which protect the
earth against harmful effect of ultra violet rays.

3-Thermal catalytic cracking: -

This process usually takes place during the refining of petroleum oil
to convert the heavy long petroleum chain to the daily used lighter
short chain products.

- This process takes place by heating the heavy petroleum products

under high pressure and temperature in the presence of catalyst to
produce two kinds of products

a-) Short chain alkanes which are used with gasoline .

b-) short chain alkenes as ethane and propene which are used in
many chemical industries such as manufacture of polymers.

C8H18 C4H8 + C4H10

Octane Butene Butane

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 Organic chemistry

Alkenes

Unsaturated open chain aliphatic hydrocarbons.

1- Olefins are hydrocarbons in which, one double bond or

more are found between the carbon atoms of their compound

2- They are considered as alkanes derivatives by removing two

hydrogen atoms from the corresponding alkane

3- They are a homogeneous series

4-their general formula is CnH2n

CnH2n π + σ Alkene Name

H H
| |
C2H4 C=C ethene
| |
H H
H H H
| | |
C3H6 H–C–C=C–H Propene
|
H

Nomenclature of alkenes

1- By using the same way in case of alkanes where we choose the

longest continuous carbon chain . the suffix (ane) is replaced by the
suffix (ene) in the name of alkene , preceding by the number of
carbon atom nearest to the double bond

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 Organic chemistry

2-Numbering the carbon chain starts from the nearest side to the
double bond regardless the position of other group

CH2 = CH-CH-CH2-CH3 Cl
| |
CH3 CH2-CH2-CH = CH2
3-methyl – 1 – pentene 4- chloro – 1- butane

Ethene C2H4

Preparation in lab

By removing water from Ethyl alcohol by using hot conc. H2SO4 at

180 oC

80 oc
CH3 – CH2 – OH + HOSO3H CH3 – CH2 – OSO3H + H2O
o
180 c
CH3 – CH2 – OSO3H H2C = CH2 + H2SO4

Properties of alkenes:

1- the physical properties

1- The first members are gases (from C1 – C4)

2- The alkenes contain C5 – C 15 are liquid

3- The alkenes contain more than C15 are solids

4- Alkenes are non- polar compounds, insoluble in water but they

can dissolve in organic compounds .

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 Organic chemistry

Chemical properties

- alkenes are more active than alkanes due to presence of weak (pi)
bond , which are easily broken

1- burning:
Alkenes burn to form H2O/CO2
C2H4 + 3O2 2CO2 + 2H2O + E

2- Addition reaction :
a- addition of hydrogen ( Hydrogenation ):-
Ni or Pt / 150 – 300oc
CH2 = CH2 +H2 CH3 - CH3

N.B: the hydrogenation of unsaturated compound is considered the

fundamental reaction of the preparation of artificial fats.

The hydrogenations of this oil in the presence of (Ni) make them

solidify due to the conversion of unsaturated compounds to
saturated one.

b- Halogenation (I2, Br2, Cl2):

this reaction is used to detect unsaturated alkenes. When bromine
in carbon tetrachloride is added to ethane , the red colour of
bromine is removed and acolour less 1,2 dibromoethane is formed
.
H H Br Br
| | | |
C = C + Br2 H–C–C–H
| | | |
H H H H

1,2 dibromoethane

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 Organic chemistry

c- the addition of hydrogen halide (HX):

1- if the alkenes is symmetrical (i.e. the two carbon atoms which are
attached to the double bond carry the same number of hydrogen
atoms)
H H H Br
| | | |
C = C + HBr H–C–C–H
| | | |
H H H H
Bromo ethan
2- if the alkene is asymmetrical (the two carbon atoms which
attached to the double bond carries different number of hydrogen
atom) the hydrogen atom is added to the carbon atom rich in
hydrogen atoms, whereas the halogen atom is added to the other
carbon poor in hydrogen. This is known as:” Markownikoff’s rule.”

Markownikoff’s rule:
“ On adding an asymmetric reagent (HX) to an asymmetric
alkene, the positive part of reagent is added to the carbon
atom which carries a large number of hydrogen atoms and the
negative part is added to the carbon atom which carries less
number of hydrogen atoms”

H H H H H H
| | | | | |
H – C – C = C – H + HBr H–C–C–C–H
| | | |
H H Br H
2- bromopropane

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 Organic chemistry

d)- Addition of water:

-since water is weak electrolyte, the the concentration of hydrogen

ions is very weak and is unable to break down the double bond,

therefore, the reaction should proceed in the presence of strong acid

to increase the concentration of hydrogen ions.

3-Oxidation:

- alkenes are oxidized by oxidizing agent as hydrogen peroxide

(H2O2) or KMnO4 forming dihydroxy compounds known as
glycols

- Baeyr’s reaction :

It is reaction between ethane and (KMnO4 ) in alkaline medium

where the purple color of (KMnO4 ) is discharged . this reaction
very important to detect the double bond.
H H H H
| | KMnO4 | |
C = C + H2O H–C–C–H
| | (O) alkaline medium | |
H H OH OH
Ethylene glycol
N.B: -
- ethylene glycol is used as antifreeze substance which
prevents the freezing of water in care radiators where it
form hydrogen bond with water molecule and prevent their
combination with each other in the form of ice crys tals

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 Organic chemistry

4- polymerization
is the combination of large number unsaturated simple molecules to
form large molecule.
H H H H H H H H
| | | | | | | |
C=C + C=C C–C + C–C
| | | | | | | |
H H H H H H H H
– CH2 – CH2 – CH2 – CH2 –

Poly ethylene

Commercial polymer
uses property Monemer
name
Flexible | |
Plastic –C–C– CH2 = CH2
and Poly ethylene
shhets,bags | | n ethene
tolerate
H H
Carpets, Strong | | | |
polypropylene –C –C– C=C
cases and and
P.P | | n | |
cans. tolerate
CH3 H CH3 H
propene
poly chloro
ethene H H
Drainage tube Poly vinyl H H | |
Plastic tube Strong | | C=C
Shoes
chloride
and solid –C –C– | |
hoses P.V.C
| | n H Cl
chloro ethene
H Cl
poly tetra F F
flouro ethene | |
Cooking
Resist F F
utensils – C=C
haet and teflon | | | |
surgical
threads
insulator –C –C– F F
| | n Tetra flouro
ethene
F F

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 Organic chemistry

Alkynes ( Acetylenes )

1- They are unsaturated open chain hydrocarbons

2- They contain triple bond
3- General formula (CnH2n - 2)
5- On of the triple bond is strong sigma , while the other two bonds
are weak (pi)bonds, therefore, alkynes are very active compound
Nomenclature of alkynes
1- by using the same method used in the nomenclature
H H H H H
| | | | |
H–C  C–C–C–H H–C–C  C–C–C–H
| | | | |
Br H H H Cl
3-bromo – 1- butyne 5- chloro – 2- pentyne

Ethyne (acetylene ) C2H2

Preparation in lab:

1- water dropped on calcium carbide

C C + 2H.OH Ca (OH) 2 + H – C  C – H
Ca

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 Organic chemistry

Properties of ethyne
1- burning

a) In limited amount of air ethyne burn with smoky flame because

carbon does not completely burnt
2C2H2 + 3O2 2CO2 + 2H2O + 2C (smoke)

b) In excess amount of air ethyne completely burned , producing

3000 °C this heat used in welding and cutting metals (oxyacetylene
flame)
2C2H2 + 5O2 4CO2 + 2H2O + 3000 °C

2- Addition reactions:

Because Ethyne contain two (pi) bonds , it reacts by addition into

two steps .
a) Hydrogenations:
H H H H
| | | |
H–C  C–H 2H/Ni C = C 2H/Ni H–C–C–H
| | | |
H H H H
ethyne ethene ethane

b) Halogenations:
Ethyne reacts vigorously with halogens.
when ethyne is passed through bromine water dissolved in carbon
tetrachloride , the red colour of bromine is discharged . this
reaction is used to detect the unsaturation of ethyne .

+ Br2
C2H2 + Br2 C2H2Br2 C2H2Br4

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 Organic chemistry

3- The addition of hydrogen acids (HX)

H H H H
| | | |
H – C  C – H + HBr C=C HBr H – C – C – Br
| | | |
H Br H Br
1.1dibromo rthane

4- Addition of water ( catalytic hydration)

H OH
H2SO4 40% | |
H–C  C–H + H2O H–C=C–H CH3 C HO
HgSO4 60% vinyl alcohol acetaldehyde

By oxidation of acetaldehyde we obtain acetic acid

[O]
CH3CHO CH3COOH

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 Organic chemistry

Cyclic hydrocarbons

a) Saturated cyclic hydrocarbons (cycloalkanes)

HH H H H H
H C H | | C
H C C H H–C–C–H H H
| | C–C
H C C H
H C H H–C–C–H H H
| | cyclopropane
HH H H
cyclohexane cyclobutane

1-Hydrocarbons which contain three or more carbon atoms may found in

cyclic structure. The general form of cycloalkanes is CnH2n which is the same
as the molecular formula of aliphatic alkenes. So we have to differentiate
between them on writing their molecular formula.

2-Nomenclature of cyclic alkanes is similar to open chain alkane but we put

the prefix "cyclo" in case of cyclic alkanes.

3- The angles between the bonds in cyclopropane equal 60

while they are 90 in cyclobutane and in open chain alkanes =109.5o.

4-The small angles lead to weak overlap between the atomic orbitals.
Therefore ,the combination between carbon atoms are very weak. They are
very active for example cyclopropane forms with air an extremely burning
mixture , while normal propane ( linear propane ) is less active.
Cyclopentane and cyclohexane are stable because the angles between the
bonds near 109.5 , so the overlap between the atomic orbitals becomes more
strong therefore a strong sigma bonds are formed.

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 Organic chemistry

Unsaturated cyclic chain hydrocarbons (aromatic hydrocarbons)

The structural formula of benzene:

Benzene reacts by addition and by substitution. The bond length

between the carbon atoms are intermediate between the length of
single and double bond. the German scientist kekule discovered the
hexagonal cyclic shape in which single and double bonds are
alternated.

The ring in figure indicates that the 6 electrons are delocalized at

certain carbon atoms .

Note.: Fuel is used in cars is gasoline which is completely

Different from aromatic benzene .

Aromatic benzene Naphthalene

C6H6 C10H8

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 Organic chemistry

Aromaticity
a cyclic (ring shaped), planar (flat) molecule with alternate single bonds & double
bonds that has much stability.

Characteristics of aromatic (aryl) compounds:

An aromatic compound contains a set of covalent bond with specific
characteristics:

1. A delocalized conjugated π bonds , of alternating single and double bonds

2. planar structure, all the atoms in the same plane
3. atoms arranged in one or more rings
4. the molecule must have [4n+2] pi electrons (Huckle rule)

Benzene and cyclooctatetraene are both cyclic and conjugated, but benzene is
aromatic and cyclooctatetraene is not.

The difference is that benzene has 6 pi electrons, and cyclooctatetraene has 8.

benzene has [4n+2] pi electrons and cyclooctatetraene does not.

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 Organic chemistry

Preparation of benzene in industry

1- From coal tar :

During destructive distillation of coal (heating in absence of air ) it gives coal
tar By fractional distillation of coal tar, we obtain Benzene .

2- From aliphatic petrolume derivatives :

a-From normal hexane

normal hexane is passed at high temperature on the surface of platinum as a
catalyst . This method is called catalytic reforming method

heat/Pt
CH3-CH2-CH2-CH2-CH2-CH3 + 4H2

b- Polymerization of ethyne: ( Trimerization )

By passing ethyne vapor in a red hot nickel tube

Red hot nickel tube

3C2H2

3- From phenol :
By passing phenol vapors on the surface of hot zinc powder which reduces to
benzene .
OH
Zn + ZnO

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 Organic chemistry

Preparation of benzene in lap.

By dry distillation of sodium benzoate with soda lime. ( as in case the

preparation of methane in lab).

COONa CaO
+ NaOH + Na2CO3

Nomenclature of benzene derivatives:

1- The name of mono-substituted benzene is derived from the name of the
Atom or group which is attached to benzene ring
2-
NO2 Cl

N.B. The entering atom or the group attacks any carbon atom of benzene
Since the six carbon atoms in benzene ring are identical

The aryl radical ( Ar)

(Ar)
It is the radical which produce by removing one hydrogen atom from the
Aromatic compound ( its symbol is Ar )
For example when we remove a hydrogen atom from benzene the produced
Radical is phenyl radical ( C6H5- )

EX.: Nomenclature of some aromatic compound

CH3-CH-CH3

(C6H5 - C6H5 Diphenyl) 2-phenyl propane

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 Organic chemistry

2-The disubstituted benzene may be represented by three isomers which are:

ortho ( o- ) , meta ( m- ) and para (p-).

The product depends on the nature of substituent group which is

Mainly found (A) . There are some groups direct the new substituent to
Ortho and para positions and other direct to meta position.

From groups which is directed to ortho and para positions are:

R- , OH , NH2 and halogen X.

CH3 CH3 CH3

Fe Cl
2 + 2Cl2 + + 2HCl

Cl
Toluene ortho- chloro toluene para- chloro toluene

From the meta directing groups are:

CHO , CO Ketone group , COOH and NO2.

NO2 NO2

Fe
+ Cl2 + HCl
Cl
Nitrobenzene m.chloro nitro benzene

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 Organic chemistry

Note: nomenclature by the IUPAC system, considers only the

numbering of Benzene ring.
Cl
4 NO2
5 3
6 2
1
Br
1- bromo – 4 – chloro – 3- nitro benzene

Physical properties of benzene

1- immiscible with water
2- it has a pleasant smell
3- It burns in air with a black smoky flame, this mean that its
molecule contain a large number of carbon atoms

Chemical properties
Benzene reacts by two kinds of chemical reactions ( addition and
substitution )

a) Addition reaction :
Although the molecule of benzene contains double bonds but its reactions by
addition is difficult and takes place under certain conditions.

1 – The addition of hydrogen

Benzene reacts with hydrogen under pressure and temperature , in the
Presence of catalyst to give cyclohexane

Heat + Pressure
+ 3H2 C6H12 cyclohexane

C6H6 Benzene

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 Organic chemistry

2 – Halogenation :
Benzene reacts with chlorine in direct sun light to form hexachloro
cyclohexane, used as insecticide is called Gamixane .
H Cl
Direct sun light
+ 3Cl2 Cl C H
H C C Cl C H Cl Gamixane
6 6 6
Cl C C H
H C Cl
Cl H

b ) Substitution reaction :
1 – Halogenation

Cl
FeCl3
+ Cl2 + HCl
I.D.S.L

chlorobenzene

2. Nitration:

NO2
Conc. H2SO4
+ HO – NO2 + H2O
o
50 c
Nitobenzene

T.N.T (trinitrotoluene) is one of the explosive. This compound is prepared by

the reaction between toluene and mixture of concentrated Nitric and
sulphuric acids ( 1 : 1 ratio).
CH3
H2SO4
+ 3HNO3 CH3 + 3H2O
O2N NO2
2,4,6 trinitrotoluene
NO2
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 Organic chemistry

3. Alkylation ( friedel – craft's reaction ) :

Benzene reacts with alkyl halides ( R X ) in presence of anhydrous
aluminum chloride (AlCl3) as a catalyst.

CH3
AlCl3
+ CH3Cl HCl +
Heat )Toluene)

4. Sulphonation:
In this process the hydrogen atom of benzene ring is replaced by a
sulphonic acid group ( SO3H ). where benzene sulphonic acid is formed.

SO3H
H2SO4
+ HO – SO3H H2O +
Conc Benzene sulphonic acid

The detergent industries depend mainly on the aromatic sulphonic acid

compounds after the treatment with caustic soda obtain the water soluble
sodium salt.

R SO3H + NaOH R SO3-Na+

Alkyl benzene sulphonic acid Sodium salt of alkyl benzene

The molecule of detergent is composed of two parts (tail), it is a long carbon

chain which is hydrophobic and the other part ( head ), is an ionic group
which is hydrophilic.

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Hydrocarbon derivatives
Functional group:
It is an atom or group which is responsible for the physical and
chemical properties of the organic compound.

The following table illustrates the classes of the organic compounds

and the functional group of each class:

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Priority of functional groups in Naming

Alcohols and phenols

They are organic compounds which contain one or more hydroxyl group,
attached to alkyl group (as in alcohols) or aryl group (as in phenol)

Alcohols and phenols as hydrocarbon derivatives:

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Organic chemistry

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Preparation of ethanol
1- Fermentation of sugars:
Ethanol is prepared from molasses (sucrose). The fermentation process takes
place by the addition of yeast to molasses where ethanol and carbon dioxide
gas is formed as:

3- from catalytic hydration of ethylene gas:

3- Hydrolysis of alkyl halides:

- By heating alkyl halides with aqueous solution of strong alkalies ,
where the halide radical is replaced by hydroxyl group

Notes:

Primary alcohols:
- They are oxidized on 2 steps due to the presence of two hydrogen
atoms attached to the carbinol (R – CH2 – OH).

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 Organic chemistry

Secondary alcohols:
They are oxidized in one step due to the presence of one hydrogen
atom attached to the carbinol ((R)2 – CH – OH)

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 Organic chemistry
Uses of ethanol:
1- Solvent for oils & fats.
2- Manufacture of drugs, paints & polish.
3- Used in sterilizing mouth and teeth also it is used as disinfectant which
has a great effect on microbes
4- Manufacture of perfumes & alcoholic drinks.
5- Used as a fuel in some countries.
6- Converted alcohol contains (85% ethanol – 5% methanol – 1% another
additive color, odor and the rest of water).
7- Used in filling thermometers which are used to measure low
temperatures.

Dihydric alcohols * Ethylene glycol:

CH2 – CH2
OH OH
Viscous liquid - It contains 2 hydroxyl group, so it is miscible with water

Uses of ethylene glycol:

1- Anti freezing substance which prevents the freezing of water in car
radiators in a cold region as it is non volatile.
2- Used in hydraulic brakes fluids.
3- Organic solvent.
4- Manufacture of lnk.

Tihydric alcohols (Glycerol)

CH2 – CH – CH2
OH OH OH

Uses of glycerol:
1- Used in the manufacture of creams and cosmetics as a moisturizer of
skin.
2- It is used in the manufacture of textiles, since it make them soft and
flexible.
3- It is used in the preparation of explosive substance, nitroglycerine
4- Nitroglycerine is also used to widen arteries in the treatment of heart
problem.

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 Organic chemistry

Phenols
Phenols are hydroxyl compounds in which one or more hydroxyl group
is directly attached to the carbon of the benzene ring.

-phenol react with alkalis such as caustic soda , and considered as an acid
(carbolic acid). Because the polarity of hydroxyl group increases in the case
of phenol due to the presence of benzene ring in phenol as it attracts the
electrons from oxygen. So that the length of (O –H) bond increase and
become weak which facilitate the separation of hydrogen ion.

- phenol does not react with hydrogen halides under normal while alcohols
react easily with acids.
Due to the presence of benzene ring in phenol as it attract the electrons
from oxygen.

So the bond between benzene ring and the oxygen atom of the hydroxyl
group become shorter and stronger so it is impossible to eliminate the
hydroxyl group.

Esters
Esters are produced from a reaction between carboxylic acids with alcohols.

Most of the esters are characterized by a pleasant smell which is responsible

for the odour and flavour of fruits and flowers.

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 Organic chemistry

Nomenclature of ester
- They are named according to the alkyl or aryl group of the alcohol followed
by the name of the acid by replacing the suffix (ic) by the suffix (ate).

Physical properties:

1- Their boiling points are less than those of acids and alcohols of the same
molecular weight approximately. And this is due to the absence of hydroxyl
group in esters.

2- They are sparingly soluble in water.

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Important uses of esters in our life:

1- Ester as flavor:
Ester are characterized by pleasant smells and tastes so they are used in food
industries as flavors .
2- Esters as fats and oils:
- Fats and oils are esters produced from the reaction between acids and glycerol.
- Their molecules are called triglyceride because each molecule is formed from the
reaction of one molecule of glycerol (trihydric alcohol) and three molecules of
fatty acids. The acid molecules may be similar or different, saturated long chain or
unsaturated short chain.

Aspirin:
- Reduces the headache pains and temperature.
- Reduces the blood clotting and prevents the heart crises.
- The active substance in aspirin is salicylic acid however, the addition of acetyl
group to the acid decreases its acidity effect and becomes tasteless.
- Aspirin is hydrolysis in the body to produce salicylic acid and acetic acid.

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