STEM Chemistry Marathon

ORGANIC CHEMISTRY
Carbon Chemistry
PART-1

PREPARED BY: A. RAAFAT

LO.3.19

Essential Question:
What do detergents, proteins, hormones, plastics,
most of food, dyes and pigments, soaps, fertilizers,,
insecticides, smells, tastes, addictive substances,
genetics, bitumen(road surface), perfumes, fuels,
cosmetics, tires, drugs, liquors, anesthetics,
preservatives, beer, win, and digestive enzymes,
nicotine, fibers,…etc. have in common?
Skills:
Distinguish between organic and inorganic compounds
Differentiate between molecular and structural formulas
Using IUPAC nomenclature
Experimentally determine the carbon and hydrogen in organic
material
Identify aromatic compounds
concepts:
1. Isomers (geometric and optical)
• 2. Simple preparation of methane (dry distillation of sodium
acetate)
• 3. Reactions of hydrocarbons:
o a. combustion in limited and excess amount of oxygen for
hydrocarbons
o b. halogenation of alkane and alkene by free radical
mechanism (Methane and propane)
o c. catalytic hydration of alkene
 o d. addition of HX (alkene only)
o e. polymerization of ethene
o f. catalytic hydration of alkyne
o g. polymerization- trimerization, aromaticity, and
benzene structure
o h. preparation of aromatic benzene (from acetylene –
hexane)
• 4. Reactions of Benzene
o a. mono substituted benzene
o b. di-substituted benzene
• 5. Distinguish practically between Ethane, Ethene and
Acetylene.
 Importance of carbon in living organism

• 25 elements make up all living things

• About 97% of your body’s mass is made of just 4
elements: oxygen, carbon, hydrogen, & nitrogen
• If you take away the water, the rest of the human body
is 53% carbon, because of its ability to bond with
other atoms
• Silicon is similar to carbon-tetravalent-. Why are
there no life forms based on silicon like carbon?
Because silicon-silicon covalent bond is not strong
enough for it to form long stable chains. So, it can not
form molecules of the complexity needed to make up
cells like carbon can!
 Vital force theory

■ The scientist Brezelius divided all the compounds into two categories:
1) Organic compounds:
They are the compounds that are extracted from animal or plant
origin.
2) Inorganic Compounds:
They are the compounds that originate from mineral sources in Earth.
Brezelius considered that organic compounds are formed by vital
processes that are found in living cells of the body and it is impossible to
be synthesized in the lab.
The destroy of the vital force theory

■ In 1828 the German scientist ‘Wöhler’ destroyed the vital

force theory when he prepared organic compound (Urea) by
heating an aqueous solution of two inorganic compounds
(silver cyanate and ammonium chloride)

■ The organic materials become known according to their

structure not according to their sources. This is because most
of organic compounds which were prepared in laboratories are
not formed in living organisms.
 What are the reasons of the
abundance of organic compounds?
■ The abundance of organic compounds is due to
Carbon is tetravalent element can bind with 4 bonds
1.carbon combines together or with others elements (H – N – O –
S …) by different kinds of bond forming endless chains.
2. Carbon atoms can join together with different methods, either
straight chains, branched chains, homocyclic or heterocyclic.
Comparison between the organic and inorganic compounds
Qualitative analysis of organic compounds

CARBON AND HYDROGEN ARE PRESENT IN ALMOST ALL

THE ORGANIC COMPOUNDS. OTHER COMMONLY PRESENT
ELEMENTS IN ORGANIC COMPOUNDS ARE OXYGEN,
NITROGEN, HALOGENS, SULPHUR AND SOMETIMES
PHOSPHORUS.
DETECTION OF CARBON AND HYDROGEN
CARBON AND HYDROGEN ARE DETECTED BY HEATING THE
ORGANIC COMPOUND WITH CUPRIC OXIDE (CUO)
STRONGLY, WHERE CARBON IS OXIDIZED TO CARBON
DIOXIDE AND HYDROGEN TO WATER. CARBON DIOXIDE IS
TESTED BY LIME WATER TEST, WHERE AS WATER IS TESTED
BY ANHYDROUS COPPER SULPHATE TEST.
1- The Saturated aliphatic acyclic Hydrocarbons (Alkanes)
They have general molecular formula CnH2n+2
-yl R
 Nomenclature of Alkanes

The parent name indicates the number of carbons in the longest

continuous carbon chain in the molecule.
• The suffix indicates what functional group is present.
• The prefix tells us the identity, location, and number of substituents
attached to the carbon chain.
HOW TO Name an Alkane Using the IUPAC System
■ Step 1: Find the parent carbon chain and add the suffix.
• Find the longest continuous carbon chain, and name the
molecule using the parent name for that number of
carbons, add the suffix -ane for an alkane. Each functional
group has its own suffix.
• The longest chain may not be written horizontally across
the page. Remember that it does not matter if the chain
is straight or has bends. All of the following
representations are equivalent.
■ Step 2:
Number the atoms in the carbon chain to give the first substituent the lower
number.

■ Step 3: Name and number the substituents.

• Name the substituents as alkyl groups, and use the numbers from
step [2] to designate their location.
■ NOTE → If two or more identical substituents are bonded to the
longest chain, use prefixes to indicate how many: di- for two
groups, tri- for three groups, tetra- for four groups, and so forth.

■ Step 4: Combine substituent names and numbers + parent +

suffix.
• Precede the name of the parent by the names of the
substituents. Alphabetize the names of the substituents, ignoring
any prefixes like di-. For example, triethyl precedes dimethyl
because the e of ethyl comes before the m of methyl in the
alphabet.
• Precede the name of each substituent by the number that
indicates its location. There must be one number for each
substituent.
• Separate numbers by commas and separate numbers from
letters by dashes.
 Examples

Use punctuation
- use commas to separate numbers
-hyphens to separate numbers with words.
■ To derive a structure from a name, first look at the end of the name to
find the parent name and suffix.
■ From the parent we know the number of C’s in the longest chain, and
the suffix tells us the functional group; the suffix -ane = an alkane.
■ Then, number the carbon chain from either end and add the
substituents.
■ Finally, add enough H’s to give each C four bonds.

■ Example: 2,3,3-Trimethylpentane
 ■ (those which are
Complex alky groups branched
themselves) are
named as if they
were alkanes,
but the name
ends in -yl and is
enclosed in
parenthesis. The
carbon from
which the
substituent
attaches to the
main chain is
automatically
number 1 .
 NB
AS THE BRANCHES INCREASE THE B.P. DECREASE. WHY?
BECAUSE THE CONTACT SURFACE AREA DECREASES, SO THE DISPERSION
FORCE DECREASES.
Primary, Secondary, And Tertiary Carbons.
■ Another bit of terminology associated with common names
refers to the connectivity of sp3 carbons in alkanes and alkyl
groups. A primary carbon is one that is covalently attached to
only one other carbon. A secondary carbon is one attached to
two other carbons. A tertiary carbon is attached to three other
carbons. This definition implies that methane cannot have any
such carbons, since it consists of only one carbon atom.
Likewise, this terminology applies only to sp3 carbons. Other
types are not defined in this way. In the following examples the
carbons in question are indicated as dots.
How many primary, secondary, tertiary carbon atom?
 Trivial Nomenclature(common)
■ In chemistry, a trivial name is a nonsystematic name for a chemical
substance. That is, the name is not recognized according to the rules of
any formal system of chemical nomenclature such as IUPAC
inorganic or IUPAC organic nomenclature. A trivial name is not a formal
name and is usually a common name eg. Sec, neo, tert, iso,… are trivial
naming
■ Generally, trivial names are not useful in describing the essential
properties of the thing being named. Properties such as the molecular
structure of a chemical compound are not indicated. And, in some
cases, trivial names can be ambiguous or will carry different meanings
in different industries or in different geographic regions. (For example, a
trivial name such as white metal can mean various things.) On the other
hand, systematic names can be so convoluted and difficult to parse that
their trivial names are preferred. As a result, a limited number of trivial
chemical names are retained names, an accepted part of the
nomenclature.
■ Iso, neo only are alphabetic order
Branching in Alkyl Groups

■ Sec. is used with propyl, and butyl only..WHY?

■ Tert. is used with butyl and pentyl only..WHY?
■ Bec. There will be more than one option!
Collection!
Take Care!!
■ Make sure you’ve identified the longest continuous carbon chain correctly. Otherwise
you might end up with the wrong name. The longest continuous carbon chain doesn’t
always have to be a horizontal row of carbons. It can take twists and turns. That’s why
one must get used to visualize molecules from different angles and perspectives. The
following example illustrates the correct name and an incorrect name based on a
horizontal row of carbons.
Give another name!

5-ISO-BUTYL NONANE
■ If there are several options for choosing the longest continuous carbon chain, choose the
one that yields the simplest name. That means:
(a) The longest continuous carbon chain has the greatest number of substituents, and
(b) The name has the lowest set of numbers indicating the substituent positions.
SUMMARY
Alkanes: Common Names.
■ Like alkyl groups, alkanes can also have common names. Common, or “trivial” names
are rarely used for straight chain alkanes, but are frequently used for branched
alkanes.

■ ISOALKANES and ISOALKYL GROUPS:

The iso structural unit consists of two methyl groups attached to a common carbon.
When this unit is present in an alkane or alky group, the common name starts with the
prefix iso.
■ When this unit is present in alkanes, the molecule is named according to the total
number of carbon atoms present, but the name starts with the prefix iso. The smallest
possible isoalkane is then isobutane.

■ The same rules apply to isoalkyl groups, but their names end in -yl. The smallest
possible isoalkyl group is the isopropyl group, because alkyl groups are always
attached to another carbon chain.
 Neo Alkanes
■ The prefix "neo" is used when all but two carbons form a continuous
chain, and these two carbons are part of a terminal tert-butyl group.
The most common example for alkanes is Methane (CH4)

■ Methane is the first member, it is considered as the simplest

organic compound and forms about 90 % of natural gas found under
the earth’s crust or accompanied to crude petroleum. Also, it is
found in cool mines that may be exposed to an explosion as a result
of its illumination .It is sometimes called the Gas of swamps
because it goes out as bubbles from the bottom of these swamps as
a result of decaying of the organic matters.
■ Preparation of Methane in lab.
BY dry distillation of anhydrous sodium acetate with soda lime is a
mixture of NaOH and quick lime CaO
Soda lime doesn’t take part in the reaction,
CaO is a drying agent that helps in reducing the melting points of
the reaction mixture and helps in decomposition of sodium acetate.
 Physical properties of alkanes
1) They are all non- polar compounds (pure covalent bonds) they are
insoluble in water (but soluble in organic solvents) & also have low b.p.
2) Usually, C1 to C4 : gases
C5 to 17 : liquids as kerosene and gasoline (fuel),
Longer chains greater than C17 : solids
Chemical properties
Alkanes are less reactive than unsaturated compounds because of the
strong sigma bond therefore alkanes are not affected by conc. mineral
(inorganic) acids at room temp , or by regular oxidizing agents such as
potassium permanganate or potassium dichromate . but it may
undergo the following reactions:
1-Burning
■ All hydrocarbon burn in excess of O2 produce CO2 and H2O through
an exothermic reactions.
 2-A Halogenation of methane:
■ In indirect sunlight :
Alkanes react with halogens by heating to 400ºC or in presence of
U.V in a series of reactions called substitution reactions.
The product of reaction depends on % (Percentage) of methane and
halogen in reaction mixture.

Write the name(s) of each compound, and their uses?

•The function of ultraviolet light is to provide energy for the
homolytic cleavage of halogen (Cl-Cl or Br-Br) to form free radicals

•The products are haloalkanes (RX) and hydrogen halides (HX)

•The halogenation of alkanes is a free radical substitution reaction

•The mono substitution of alkanes refers to the substitution

reaction where there is only one hydrogen atom in alkanes
substituted by halogen free radical.
 FREE
RADICAL
MECHANISM:
 2-B Halogenation of propane: Selectivity in Free Radical Reactions:
Bromine vs. Chlorine in the halogenation of propane

“Why is bromine more “selective” for the secondary carbon than

chlorine?”.
Uses of halogenated derivatives 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. Halothane (its
common name) is used now as anesthetic substance with
safety and its formula

2) The compound 1,1,1 trichloro ethane

is used in the dry cleaning.
3) Freons were used in air conditions and fridges, also as a rushed substance
to liquid and perfumes and as a cleaner of electronic sets

Freons are considered as halogenated derivative of alkanes as CH4 ,tetra

flouro methane, but the famous one is dichloro, diflouromethane CF2Cl2.
Freons are used by large quantities due to its sheep price, easily to be
liquefied, non poisonous and non corrosive for metals
However Freon’s cause the decay of the ozone layer which protect the earth
against harmful effect of ultra violet rays

There is an international agreement to prevent their uses starting from 2020.

Exercise:

Write the skeletal formula of 7-(1,2-diflurobutyl)-5-ethyl tri decane.

Is it right?
3- Thermal Catalytic Cracking

■ This process takes place by heating the heavy petroleum

products under high pressure and temperature in the
presence of a catalyst to produce two kind of products.

1) Short chain alkanes: which are used with gasoline to fulfill

the permanent world needs.
2) Short chain alkenes: as ethene and propene which are used
in many chemical industries such as manufacture of polymers .
The Economic Importance of Alkanes:
1- To obtain finely divided carbon, (black carbon ). The black carbon
is produced by heating methane to 1000˚C in the absence of air.
Black carbon is used in the manufacture of car tires, black painting,
polishes, and printing ink .

2- To obtain “water gas”. This is a mixture of hydrogen and carbon

monoxide which is used as reducing agent or as a flammable fuel.

3- Home fuel in houses Propane & butane are used as fuel in

butagas cylinders.
 Saturated cyclic hydrocarbons (Cycloalkanes)
■ 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 structural formula.
■ Nomenclature of cyclic alkanes is similar to open chain
alkane but we put the prefix “cyclo” in case of cyclic alkanes.

■ It is observed that the angles between the bonds in

cyclopropane equal 60˚ while they are 90˚ in cyclobutane.
They are less than 109 ˚ which is found in open chain
alkanes. These small angles lead to weak overlap between
the atomic orbitals. Therefore ,the combination between
carbon atoms is very weak. They are very active compared
with linear alkanes, 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˚, so
the overlap between the atomic orbitals becomes more
strong therefore a strong sigma bonds are formed.
Alkenes (olefins)
■ Unsaturated hydrocarbons that contains double bonds.
■ Nomenclature of alkenes:
1- the longest continuous carbon chain + (ene) , proceeding by
the number of the carbon atom nearest to the double bond.

2- Numbering starts from the nearest side to the double bond

preparation of ethylene from alcohol by dehydration
■ Ethene can be prepared by removing water (dehydration) from ethyl
alcohol by using hot concentrated (H2SO4) at 180˚C or aluminum
■ Before collecting the gas, the acidic remains removed by NaOH
■ This reaction takes place in two steps:
1- Ethanol reacts with conc. heated sulphuric acid , to form ethyl
hydrogen sulphate .

2- Ethyl hydrogen sulphate thermally decomposed to give ethene .

Physical Properties
■ 1- Alkene from C1 to C4 are gases and from C5 to C15 are liquids.
2- Alkene are non polar insoluble in water and dissolve in organic
compounds as ether and CCl4
Chemical reactions
 Oxidation:
a. By burning:
b. By using an oxidizing agent (Bayer’ reaction)
■ Oxidizing agent Such as purple potassium permanganate KMnO4
oxidizes ethylene into glycol which is alcohol contains two OH groups
on two adjacent carbon atoms and the colour of permanganate is
discharged. This reaction is called Bayer’s reaction.
■ Bayer’s reaction: Is used to test for double bond or pi bond where
purple KMnO4 (in alkaline medium) is decolorized through the
reaction(differentiate between ethane and ethylene)
 Addition Reactions
■ a. Hydrogenation:
Is adding of hydrogen to produce corresponding alkane each pi bond
needs one mole of hydrogen gas to be broken.
 b.Halogenation :

■ Halogens react with alkenes by

additions, this reaction is used to
detect unsaturated alkenes.
When bromine in carbon
tetrachloride is added to ethene, the
red color of bromine is removed and
a colorless 1, 2 dibromo –
ethane(ethene dibromide) is formed
 c. With hydrogen halides (H - X ):
■ Alkenes react by addition with hydrogen halides where the
(Pi) bond break down. The hydrogen atom is added to one
carbon atom of the double bond and the halogen atom is
added to the other one, giving the corresponding alkyl
halide. The addition products depend on the type of alkene.
a) If the alkene is symmetrical
i.e. the two carbon atoms which are attached to the double bond carry
the same number of hydrogen atoms, the hydrogen atom is added to any
carbon atom and the halogen atom is added to other one .
b) If the alkene is asymmetrical
■ (the two carbon atoms which attached to the double bond
carries different number of hydrogen atoms) 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 rule is known as “Markownikoff’s
Rule”.
■ Markownikoff’s rule :
“On adding an asymmetric reagent (HX) or (H – OSO3H) to an
asymmetric alkene, the positive part of the 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 “.
d. Addition of water(catalytic hydration):
■ Water is a weak electrolyte contains very small ratio of proton can’t break down the
double bond so water is added to alkene in the presence of strong acid as sulphuric
acid???
Sulphuric acid reacts with ethylene forming ethyl hydrogen sulphate which hydrolyze
into ethanol and sulphuric acid. This method is considered as industrial method for
preparation of ethanol from petroleum: that is why ethanol is petrochemical
compound
TO be continued. The Chemical properties.. In part-2
 Polymerization
■ Combination of a large number of small unsaturated molecules called monomers to form a
large molecule called polymer. Both monomer and polymer have the same empirical
formula.
■ Number of monomers forming the polymer ranges from 100 to 1000000 units.
■ There are two principal methods for polymerization process:
1- Addition polymerization :
It takes place by adding a huge number of unsaturated small molecules to each other to form a
very large molecule such as formation of polyethylene.
2- Condensation polymerization :
Condensation takes place between two different monomers and accompanied by losing a
simple molecule such as water . The copolymer formed is considered as the basic unit which
continues the polymerization process.
■ Example for addition polymerization (polyethylene) when ethene is heated under high
pressure (about 1000 atmosphere) in the presence of oxygen or hydrogen peroxide as
initiator, poly ethylene is formed its molecular mass reach to about 30,000 ( notice that the
molecular mass of ethene = 28 only). In the addition polymerization of ethene (pi) bond is
broken, the electrons of this bond are liberated .Each carbon atom now has a free electron,
then the carbon atoms of each molecule combine by their free electrons with those of
other molecules by a single covalent bond to form a long chain of the polymer molecules .
■ Ethylene is the gas that ripens fruit, and a ripe fruit emits
the gas, which will act on unripe fruit. Thus, a ripe tomato
placed in a sealed bag with green tomatoes will help
ripen them.
Lots of carbon compounds seem to be isomers.
What is an isomer?
■ In organic chemistry, there are many examples of different
compounds which have the same molecular formula as each
other,
■ But different arrangements (structures) of the atoms in
their molecules.
■ These are called isomers.
What is an isomer?
■ These compounds
are said to be isomers
of one another.
■ Isomerism also occurs
in inorganic
chemistry, but it is
less common.
If isomers have the same atoms in them, surely
they have the same properties, so what's the point?
■ In fact, these small changes in structure can
have significant effects on the properties of
the substance!
■ But, it is important to realize that this can
have significant effects in a living system.
■ One optical isomer of glucose, for example,
can be used by a living cell, but the other
isomer cannot.
■ This is because the enzyme in the cell which
recognizes glucose is sensitive to only one
form.
There are two types of isomerism common in
organic chemistry:

1. structural isomerism
■ Which have the atoms of their
molecules linked in a different
order.
■ This can come about in one of
three ways:
Chain Isomerism

■ Chain isomers of the same compound are very

similar.
■ There may be small difference in physical properties
such as melting or boiling point due to different
strengths of intermolecular bonding.
■ Their chemistry is likely to be identical.
Positional Isomers

■ Positional isomers are also usually similar.

■ There are slight physical differences, but the chemical
properties are usually very similar.
■ However, occasionally, positional isomers can have
quite different properties
 Positional Isomers

■ A simple example of isomerism is given by propanol:

■ it has the formula C3H8O (or C3H7OH) and two isomers propan-1-ol
(n-propyl alcohol; I) and propan-2-ol (isopropyl alcohol; II)
■ Note that the position of the oxygen atom differs between the
two: it is attached to an end carbon in the first isomer, and to the
center carbon in the second.
■ The number of possible isomers increases rapidly as the number of
atoms increases; for example the next largest alcohol, named
butanol (C4H10O), has four different structural isomers.
Functional Group Isomers

■ Functional group isomers are likely to be both physically and chemically

dissimilar.
You Try It!
How
did
you
do?
Alkynes (acetylenes)
■ They are unsaturated hydrocarbons containing triple bonds (one is strong sigma and
the others are weak pi bonds), between carbon atoms.
■ Alkynes are characterized by the following:
1) Unsaturated hydrocarbons, its general formulae ( CnH2n-2 )
2) Named according to the I.U.P.A.C from corresponding alkanes , by Replacing “ane“ by
“yne“ numbering carbon atom from the terminal nearer to the triple bond
3) First member are gases, then liquids.
4) Chemically more active than alkanes due to presence of two weak pi bonds which
can be easily broken, therefore it reacts by addition.
5) Alkynes are insoluble in water, but dissolve in organic solvents.
Preparation of acetylene (Ethyne)(C2H2) in
lab:
1. In lab: From calcium carbide CaC2, by dropping water on calcium carbide.

The role of copper sulphate is

to remove hydrogen sulphide
and phosphine which are
produced from the impurities
in calcium carbide
■ 2. In industry: From natural gas which contains high % of methan by heating to more
1400ºC and cooling suddenly .
Reactions of Alkynes
Combustion
■ Alkynes are highly inflammable in oxygen producing heat energy, its amount
depends on quantity of oxygen (oxy acetylene flame).

■ This reaction is used in welding and cutting metals and called oxy acetylene flame
Oxy acetylene
Addition reactions

1) Hydrogenation [ add. of hydrogen ] :

2) Halogenation :add of halogen (Cl2 –Br2 , I2)
Acetylene (ethyne) reacts vigorously with halogen , the reaction is accompanied with
heat and flame in case of chlorine but with bromine water dissolved in carbon
tetrachloride, the red colour of bromine is reduced so this reaction is used to test
unsaturation (pi bond) in ethyne.
3) With halogen acids [ HCl - HBr - HI ]
• Addition of halogen acids to acetylene takes place according to MarkoniKoff’s rule
Addition of water (catalytic hydration)
■ Catalytic hydration of acetylene gives acetaldehyde.

■ This reaction is used to prepare acetic acid (ethanoic) from acetaldehyde (Ethanal)by
oxidation
■ Also is used in preparation ethyl alcohol
 4. Metamerism

In this type of isomerism, isomers differ in structure because of differences in the

distribution of carbon atoms about the functional group. Ether and secondary amines
are the best examples of metamerism. For example; ethoxypropane and 1-
ethoxypropane are metamers of each other.

CH3CH2CH2-O-CH2CH3 and CH3-CH2-O-CH2-CH2-CH3

Ethoxypropane 1-Ethoxypropane

5. Tautomerism

It is also called as keto-enol isomers as in this type of isomerism,

isomers are in dynamic equilibrium and converts in keto and enol form due to
 AROMATIC
COMPOUNDS
Benzene ring
Aromatic Compounds

■ Aromatic compounds, originally named because of their fragrant properties, are

unsaturated hydrocarbon ring structures that exhibit special properties, including
unusual stability, due to their aromaticity. They are often represented as resonance
structures containing single and double bonds. However, the bonding is stronger
than expected for a conjugated structure, and it is more accurately depicted as
delocalized electron density shared between all the atoms in the ring.
■ Aromatic compounds are cyclic structures in which each ring atom is a participant
in a π bond, resulting in delocalized π electron density on both sides of the ring. Due
to this connected network of π bonds, the rings are planar, unlike the boat or table
structures typical of cycloalkanes.
Physical properties of aromatic
compounds
■ Aromatic compounds are generally nonpolar and immiscible with water. As they are
often unreactive, they are useful as solvents for other nonpolar compounds. Due to
their high ratio of carbon to hydrogen, aromatic compounds are characterized by a
sooty yellow flame.
Reactivity of aromatic compounds

■ The double bonds in aromatic compounds are less likely to participate in addition
reactions than those found in typical alkenes. Instead, cyclic aromatic compounds
undergo electrophilic substitution reactions (reactions in which the ring acts as an
nucleophile to a suitable electrophile). When benzene participates in such
substitution reactions, the product retains the stability associated with the aromatic
π electron system. This stability is lost in electrophilic addition because the product
is not aromatic.
 Structure of Benzene
■ Kekulé Structure
Kekulé (1866) bravely proposed that benzene had a cyclic structure with three alternating
C=C double and three C-C single bonds.

Whilst this is reasonably close to accurate, it cannot be

exactly correct since this would require that 1,2-
dichlorobenzene existed as two isomeric forms, yet it was
known that it did not
Resonance structure

■ The Kekulé structure would have the single bonds of longer length than the double
bonds, and thus an irregular hexagonal shape.
■ But spectroscopy had shown that benzene had a planar ring, with all the carbon-
carbon bond distances the same 1.397Å (C-C typically 1.48Å, C=C typically 1.34Å).
■ Since the atoms are the same distance apart, and the only difference is the location
of the pi electrons in the two Kekulé structures, they are in fact resonance
structures of one another.
■ Because of the delocalization of the π electrons, often the double bonds are represented
by a circle in the middle of the hexagon.
■ This resonance description lets us draw a more realistic representation of
benzene, with 6 sp2 hybrid carbons, each bonded to one hydrogen atom.
■ All the carbon-carbon bonds are of equal length, and all the bond angles are
120°.
■ Each carbon has an unhybridized p orbital, which lies perpendicular to the
plane of the ring.
■ These p orbitals each have 1 electron inside.
■ There are therefore 6 electrons in the circle of p orbitals.
 Unusual behavior of Benzene
■ Benzene has much more stability than
predicted by the simple resonance
delocalized structure. For example, we
know alkenes can be oxidized to syn
diols (KmnO4) and undergo electrophilic
additions with halogens (Br2).
■ Yet the same reactions do not work with
benzene.
■ Benzene does not react - benzene is
more stable than normal cyclo-alkenes.
■ When a catalyst is added to the benzene bromination reaction, reaction does occur,
but the reaction is not an addition, but rather a substitution (a ring hydrogen is
substituted for a ring bromine).
■ All three double bonds are retained in the product.
Failures of the Resonance Picture for
Aromatics
■ If having these identical resonance structures were the sole cause of this
pronounced stability, then ALL structures with conjugated systems of alternating
double and single bonds should show analogous enhanced stabilities.
■ These cyclic hydrocarbons with alternating double and single carbon carbon bonds
are called Annulenes
■ Benzene is the 6 membered annulene, and is
called [6] annulene.
■ For the double bonds to be totally conjugated,
the molecule must be planar so that the p
orbitals of the pi bonds can overlap.
Cyclo-octatetraene does not exist in
■ However, molecules like cyclobutadiene and
a planar structure like this.
cyclo-octatetraene DO NOT exhibit this
increased stability - in fact quite the opposite!
■ Cyclobutadiene has never been isolated and
purified because it is so unstable - it reacts
with itself to form dimers even at low
temperatures.
■ Cyclo-octatetraene has been shown to not
exist in a planar structure, but instead it
adopts a 'tub' like conformation. Rather, It exists like this
MO’s of benzene
■ Benzene's extra stability cannot be explained by resonance alone, and so we must turn to
Molecular Orbital theory for a fuller answer.
■ Benzene has 6 planar sp2 carbons, and therefore each carbon has an unhybridized p orbital.
■ These p orbitals are perfectly aligned for overlap (i.e. bonding, just like for a pi bond).
■ These p orbitals create a continuous ring of orbitals above and below the plane of the carbon
atoms.
■ The 6 overlapping p orbitals create a cyclic system of molecular orbitals (i.e. a three
dimensional system).
■ Even though we have only seen two dimensional MO's previously (ethene, allyl systems, the
same basic rules apply.
■ 1) Six p orbitals are used in the benzene pi system, therefore six MO's are created.
■ 2) The lowest energy MO is entirely bonding (constructive overlap between all adjacent p
orbitals; no nodes).
■ 3) The number of nodes increases as the MO's increase in energy.
■ 4) The MO's must be divided between bonding and antibonding, with the possibility on non-
bonding MO's in some cases.
 Energy Level Diagram of Benzene
• MO's ∏ 4*, ∏5* and ∏6* are all overall
antibonding, and lie above the level of an
isolated p orbital (non-bonding line).

• Each p orbital contributes one electron, which

means we have 6 electrons to accommodate
(this is the same number of electrons as 3 ∏
bonds in the Kekulé structure).

• The 6 electrons fill the three lowest MO's, which

happen to be the bonding MO's. This electron
configuration of all the bonding MO's filled, is a
very stable arrangement, and explains the high
stability of benzene. This electron configuration
is sometimes referred to as a 'closed bonding
shell'.
 The MO Picture of Cyclobutadiene
■ Although it is possible to write resonance
structures for cyclobutadiene, experimental
evidence indicates that it is very unstable.
■ Again, MO theory provides an explanation for
this (unexpected) instability.
■ Cyclobutadiene contains four sp2 hybridized
carbons, which leaves four p orbitals for the
bonding.
Aromatic, Antiaromatic and
Nonaromatic Compounds.
■ In a more specific, chemical sense, aromatic compounds are defined as those which
meet the following criteria:
■ 1) The structure must be cyclic, and contain some number of conjugated pi bonds.
■ 2) Each atom in the ring must have an unhybridized p orbital.
■ 3) The unhybridized p orbitals must overlap to form a continuous ring of parallel orbitals.
This is usually achieved through a planar (or almost planar) arrangement, allowing for
the most efficient overlap.
■ 4) Delocalization of the pi electrons over the ring must result in a lowering of the
electronic energy.
■ An antiaromatic compound is one which meets the first three criteria, but delocalization
of the pi electrons over the ring results in an increase of the electronic energy.
■ Aromatic compounds are more stable than their open chain counterparts. For example,
benzene is more stable than 1,3,5-hexatriene

■ An antiaromatic compound is less stable than its open chain counterpart. For example,
cyclobutadiene is less stable than butadiene.

■ A cyclic compound that does NOT have a continuous, overlapping ring of p orbitals cannot
be aromatic or antiaromatic.
■ The electronic energy is similar to its open chain counterpart. For example 1,3-
cyclohexadiene is about as stable as cis,cis-2,4-hexadiene.
 Hückel Aromaticity
■ Hückel developed a quick way to predict which of the annulenes would be aromatic, and
which would be antiaromatic.
■ If (and only if) the molecule in question meets the criteria for being either aromatic or
antiaromatic (i.e. it must have a continuous ring of overlapping p orbitals, arranged in a
planar, or almost planar fashion), then Hückel's rule applies.
■ Hückel's Rule states that if the number of pi electrons in the cyclic system is equal to
(4N+2), where N is a whole number integer, then the system is aromatic.
■ If the number of pi electrons in the cyclic system is equal to 4N, where N is a whole number
integer, then the system is antiaromatic.
■ Thus systems with 2, 6, 10, 14, … pi electrons are aromatic.
■ Systems with 4, 8, 12, … pi electrons are antiaromatic.
 Preparation of benzene in industry
■ (1) From coal tar:
■ During destructive distillation of
coal( heating in absence of air), it
decomposes into gases and liquids.
The most important of these liquids
is a heavy black substance known
as “ coal tar”. By fractional
distillation of coal tar, we obtain very
important organic compounds
economically. Benzene is obtained
at 80-82 C.
2- Preparation of benzene from
aliphatic petroleum derivatives.
■ A) from normal hexane:
In this method, normal hexane is passed at high temperature on the surface of
platinum as a catalyst. This method is called catalytic reforming method
■ B) polymerization of ethyne
By passing ethyne in red hot nickle tube

Red hot nickel ball

3- From Phenol

■ By passing phenol vapors on the surface of hot zinc powder which reduces phenol to
benzene
Preparation of benzene in the lab

■ By dry distillation of sodium benzonate with soda lime

Naming benzene derivatives
What are aromatic hydrocarbons?

✓ Aromatic means having a smell, and hydrocarbons means that they are composed
only from hydrogen and carbon.
✓ A special class of cyclic unsaturated hydrocarbons is known as the aromatic
hydrocarbons. The simplest of these is benzene (C6H6)
 Reactions
• benzene undergoes substitution
reactions in which hydrogen atoms are
replaced by other atoms.
 Nomenclature
 It is similar to the nomenclature for saturated ring systems.

 Another nomenclature system uses the prefix ortho- (o-) for two
adjacent substituents, meta- (m-) for two substituents with one
carbon between them, and para- (p-) for two substituents
opposite each other. 1,2-dichlorobenzene
o-chlorobenzene
 When benzene is used as a substituent, it is called the phenyl
group.
Practice :
Addition reactions of benzene

■ In the presence of ultraviolet light (but without a catalyst present), hot benzene will
also undergo an addition reaction with chlorine or bromine. The ring delocalization is
permanently broken and a chlorine or bromine atom adds on to each carbon atom.
For example, if you bubble chlorine gas through hot benzene exposed to UV light for
an hour, you get 1,2,3,4,5,6-hexachlorocyclohexane.
Addition of hydrogen ( hydrogenation)

■ Hydrogenation is an addition reaction in which hydrogen atoms are added all the
way around the benzene ring. A cycloalkane is formed. For example: With benzene:
• These reactions destroy the electron delocalization in
the original benzene ring, because those electrons are
being used to form bonds with the new hydrogen atoms.
Although the reactions are exothermic overall because of
the strengths of all the new carbon-hydrogen bonds
being made, there is a high activation barrier to the
reaction. The reactions are done using the same finely
divided nickel catalyst that is used in hydrogenating
alkenes and at similar temperatures (around 150°C),
but the pressures used tend to be higher.
Benzene reactions
Electrophilic attack substitution (EAS)

■ Step 1: An electrophile attacks the pi electrons of the aromatic benzene ring which
results in the formation of a resonance stabilized carbocation. This carbocation is
called the arenium ion and has three resonance contributors. Electrophilic attack is
a very slow process. It is endergonic and has high activation energy due to the loss
of aromaticity
■ Step 2: The carbocation intermediate is attacked by a base and loses a proton. These
electrons are used to reform a pi bond and restore aromaticity. As opposed to the first step,
this step is fast and exergonic because aromaticity is regained. It is important to note that
the carbocation loses a proton where the electrophile attacked the benzene ring.
Aromatic Halogenation

■ Functional groups: halides (Br, Cl, I)

Chlorine mechanism example
Uses of aryl halides

■ Aryl halides are produced in large scales and are used as insecticides, the most
important one is DDT which is dichloro diphenyl, trichloro ethane. Its poisonous
effect is due to the presence of the group ( CH- CCl3) in the molecule which
dissolves in the fatty tissue of the insect and kill it. It was called the ugliest
compound in the history of chemistry for its environmental problems
Aromatic nitration
Nitration mechanism
1- dissociation of H2SO4
2-HNO3 reaction with H2SO4
3-Electrophile attack of hydronium ion
4- nucleophile attack of water and
restoring aromaticity
Poly nitro organic compounds are
explosive
■ They are explosive beacuase theycontain their own fule, carbon besides oxygen
which is the oxidizing agent. These compunds burn rapidly, and a great amount of
heat and gases are produced accompanied by explosion. This is due to the
weakness of the bond between N and O (N-O), to form the strong bonds, between C
and O (C-O) in carbon dioxide and the bond between (N-N) in nitrogen molecule.
TNT ( trinitrotoluene)
■ It is one of the explosive nitro organic compounds which was produced by millions of
tons through the second world war, and still produced until now. This compound is
prepared by the reaction between toluene and a mixture of concentrated nitric and
sulfuric acid ( ratio 1:1)
Aromatic sulfonation
Mechanism
Detergents

■ The detergent industries depend mainly on the aromatic sulphonic acid compounds
after the treatment with caustic soda to obtain the water soluble sodium salt.
■ 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.
Friedel -Crafts alkylation
Freidel acetylation reaction
Mechanism
Question

This reaction will give us iso propyl

benzene not propyl benzene.
This is because the positive charge will form on the
secondary carbon not the primary carbon.
Naming di substituted benzene ring
Ortho, para directing activators (
electron donating groups)
■ First, we have to know the resonance structure of the carbocation intermediates for
ortho, meta and para locations.

The red dots represent the

positions of carbonations in
the resonance intermediates
Ortho, para directors

Both ortho and para locations are

more preferable as they bring the
positive charge ( carbocation) near
the electron donating substituent.
 Meta directors

Meta directing groups include

The middle structure is

the most preferable one
Important links

■ http://www.endmemo.com/chem/compound/hno3.php
■ http://www.chemguide.co.uk/organicprops/arenes/other.html
■ http://web.chem.ucla.edu/~harding/notes/notes_14D_EAS02.pdf
■ https://www.youtube.com/watch?v=PUypbJ8LNjM&index=10&list=PLaySzQJTCO1nJ
5uMZeVTM_cSb3NeDswlM
LO.3.20 Connect functional groups with chemical and physical
properties of organic compounds. Identify and describe aliphatic
alcohols and will be able to prepare them and test for their
presence. Conduct research on their industrial applications.
Key Concepts:

• 1. Nomenclature
• 2. Classification of alcohols according to the functional group,
and according to carbinol group.
• 3. Prepare experimentally by fermentation
• 4. Preparation theoretically from alkanes and alkyl halides
• 5. Oxidation reactions to determine the presence of ethanol
• 6- Industrial application of:
o a. methanol
o b. ethanol
o c. glycerol
o d. ethylene glycol
• 7. Differentiate between phenols, methanol, and NaOH
Skills: Students will go to Cairo Univ. to learn the detection of
functional groups by spectral analysis.
Essential Questions: How can rice straw be converted from an
environmental disaster to an economic value?
LO.3.21 Study esters and will be able to prepare esters,
determine their presence. Conduct research on their
industrial application.
Key Concepts:
• 1. Nomenclature according to the origin
• 2. Preparation of aspirin
• 3. Reactions:
o a. acidic hydrolysis of ethyl acetate
o b. alkaline hydrolysis- preparation of saponification
• 4. Application of esters in perfumes and food industry.
Skills: Students will produce an ester in the laboratory,
write the formula and structure and create a three
dimensional model of the molecules.
Essential Questions:
How are flavours, food, oils, polymers, fabrics, plastics
related and what do they have to do with Egyptian
industry?
■Hydrocarbon Derivatives
■ Introduction
– Hydrocarbon derivatives are formed when one or more hydrogen atoms is
replaced by an element or a group of elements other than hydrogen.
– Halogens (F2, Cl2, Br2, I2,) can all add to a hydrocarbon to form am alkyl
halide.
■ When naming the halogen the –ine ending is replaced by –o
■ Fluorine becomes fluoro
■ Chlorine becomes chloro
■ Bromine becomes bromo
■ Iodine becomes iodo
■ Common examples of organic halides.
– Alkenes can also add to each other in an addition reaction to form long
chains of carbon compounds.
■ this is called polymerization
– The atom or group of atoms that are added to the hydrocarbon are called
functional groups.
■ Functional groups usually have multiple bonds or
lone pairs of electrons that make them very
reactive.
 Alcohols
 An alcohol has a hydrogen replaced by a hydroxyl (-OH) group.
 The name of the hydrocarbon that was substituted determines the name of
the alcohol.
 The alcohol is named using the hydrocarbon name and adding the suffix –
ol.
○ If methane is substituted with an OH group it
becomes methanol
○ If a pentane group is substituted with an OH group it
is pentanol.
○ For alcohols with more than two carbon atoms we
need the number the chain so as to keep the alcohol
group as low as possible.
■ Four different alcohols. The IUPAC name is given
above each structural formula, and the common
name is given below.
 Gasoline is a mixture of hydrocarbons (C8H18 for
example) that contain no atoms of oxygen. Gasohol
contains ethyl alcohol, C2H5OH, which does contain
oxygen. The addition of alcohol to gasoline, therefore,
adds oxygen to the fuel. Since carbon monoxide forms
when there is an insufficient supply of oxygen, the
addition of alcohol to gasoline helps cut down on carbon
monoxide emissions. An atmospheric inversion, with
increased air pollution, is likely during the dates shown
on the pump, so that is when the ethanol is added.
– The OH group is polar and short chain alcohols are soluble in both
nonpolar alkanes and water.
– If an alcohol contains two OH groups it is a diol (sometimes called a
glycol).
– An alcohol with three OH groups is called a triol (sometimes called a
glycerol).
■ Common examples of
alcohols with one, two, and
three hydroxyl groups per
molecule. The IUPAC name
is given above each
structural formula, and the
common name is given
below.
■ Ethers, Aldehydes, and Ketones
– An ether has a general formula ROR’
■ Diethyl ether for example would have the formula CH3CH2OCH2CH3
– An aldehyde has a carbonyl group (carbon double bonded to an oxygen)
attached to a terminal carbon atom
– A ketone has a carbonyl group attached to an internal carbon atom.
■ The carbonyl group (A) is present in both
aldehydes and ketones, as shown in (B).
(C) The simplest example of each, with
the IUPAC name above and the common
name below each formula.
 AROMATIC
HYDROCARBONS
22.3
Chapter Twenty-Two Organic and Biological Molecules
 Organic chemistry

Hydrocarbons Derivatives of hydrocarbons

Aromatic Aliphatic

Acyclic
Cyclic
(open chain)

Saturated Unsaturated

Alkanes Alkenes Alkynes

What are aromatic hydrocarbons?

✓ Aromatic means having a smell, and hydrocarbons means that they are composed
only from hydrogen and carbon.
✓ A special class of cyclic unsaturated hydrocarbons is known as the aromatic
hydrocarbons. The simplest of these is benzene (C6H6)
 Reactions
• benzene undergoes substitution
reactions in which hydrogen atoms are
replaced by other atoms.
 Nomenclature
 It is similar to the nomenclature for saturated ring systems.

 Another nomenclature system uses the prefix ortho- (o-) for two
adjacent substituents, meta- (m-) for two substituents with one
carbon between them, and para- (p-) for two substituents
opposite each other. 1,2-dichlorobenzene
o-chlorobenzene
 When benzene is used as a substituent, it is called the phenyl
group.
Practice :
❖ Benzene is the simplest aromatic molecule. More complex aromatic systems can be
viewed as consisting of a number of “fused” benzene rings.

☺☺☺
Reference:
 Zamdahl 7th edition
Sources:

■ https://socratic.org/chemistry/the-mole-concept/empirical-and-molecular-
formulas/1013-distinguish-between-empirical-molecular-and-structural-formulas-ib-
chemistry-sl
■ https://socratic.org/chemistry/the-mole-concept/empirical-and-molecular-
formulas/125-determine-empirical-formula-from-the-percent-composition-or-from-
other-data-ib-chemistry-sl
Question

■ Carbon shows a very strong tendency to form:

■ a.ionic bonds.
■ b.covalent bonds.
■ c.hydrogen bonds.
■ d.highly polar bonds
answer :B
■ How many covalent bonds can a carbon atom usually form?
■ a.2
■ b.3
■ c.4
■ d.5
■ Answer : C
■ Carbon atoms readily join with atoms of:
■ a.metals.
■ b.carbon only.
■ c.both other elements and carbon.
■ d.nonmetals.
■ Answer : C
■ Organic compounds are defined as all covalently bonded compounds containing
carbon except
a.oxides and carbonates.
b.alcohols and acids.
c.ethers and esters.
d.aldehydes and ketones.
■ ANSWER : A
■ The diversity of organic compounds is so great because carbon
a.has many allotropes.
b.has many isotopes.
c.compounds have many isomers.
d.compounds are very reactive.
■ ANSWER : C
In which of the following are the atoms bonded in a different order?
a.structural isomers
b.geometric isomers
c.three-dimensional models
d.organic compounds
■ Answer :A
■ In which of the following are atoms bonded in the same order but arranged
differently in space?
a.structural isomers
b.geometric isomers
c.three-dimensional models
d.organic compounds
■ Answer : B
Saturated v. Unsaturated fats

Saturated with H)
CARBOXYLIC ACIDS
AND ESTERS
Carboxylic acids

■ They are the most acidic organic compounds, but they are still weaker than the
inorganic acids like: hydrochloric acid and sulfuric acid.
■ They are known by the presence of a carboxylic group. They are aromatic or
aliphatic carboxylic acids.
■ The carboxylic group which is COOH is composed mainly from 2
functional groups: the carbonyl group(C=O) and the hydroxyl group (-
OH).
■ The monocarboxylic aliphatic acids are named fatty acids because they
present in fats in form of esters with glycerol.
 Examples of carboxylic
acids

Phthalic acid

Benzoic acid
Oxalic acid
Nomenclature of carboxylic acids

■ Common names:-
The carboxylic acids are usually named by common names which are derived from the
Latin name.
IUPAC Nomenclature

■ The IUPAC system of nomenclature assigns a characteristic suffix to these classes.

The –e ending is removed from the name of the parent chain (the corresponding
alkane)and is replaced -oic acid.
■ Since a carboxylic acid group must always lie at the end of a carbon chain, it is
always is given the #1 location position in numbering and it is not necessary to
include it in the name.
Acetic acid

■ It is a monocarboxylic aliphatic acid.

■ Preparation of acetic acid in industry:
➢ biological method:-
■ The oxidation of diluted alcoholic solutions by the atmospheric oxygen in the
presence of vinegar bacteria.
➢ Chemical method:-
■ Also by the catalytic hydration of acetylene where acetaldehyde is produced and
then easily oxidized to the acid.
General prosperities of
carboxylic acids
Physical properties of carboxylic acids

■ The physical properties of organic compounds are graduated by increasing the

molecular weight.
■ The first four members are corrosive liquids and they have a pungent irritating odor.
■ They are completely miscible with water.
■ The following members are oily and sparingly soluble in water.
■ As the molecular weight increases they become solids, odorless, and insoluble in
water.
The boiling point

■ The boiling point of the carboxylic acids compared to those of alcohols which have
the same number of carbon atoms is higher due to the presence of the hydrogen
bond as each acid molecule is attached to another by the hydrogen bond.
Chemical properties of carboxylic acids

■ The acidic property of the carboxylic acids appears in their reactions with metals
above hydrogen in the electrochemistry series, hydroxides, carbonate, and
bicarbonate salts to form organic salts.
■ The react with alcohols and form ester and water.
Reactivity of carboxylic acids

■ They are reduced by hydrogen in the presence of copper chromate as a catalyst at

200 degree Celsius.
■ Ethanol can be prepared by this method which is the opposite the oxidation of
alcohols to produce acids.
Detection of carboxylic acids

1. Acidity test
When the acid is added to sodium carbonate or bicarbonate, effervescence takes place
and CO2 gas is produced and turbid the lime water.
2. Ester formation test
Acids react with alcohols to produce esters which have a pleasant odor.
Aromatic carboxylic acids

■ They contain one or more carboxylic group attached to a benzene ring.

■ They are more active and less volatile and soluble in water.
Organic acids in our life

■ Formic acid:
Produced by ants to defend themselves.
■ Acetic acid:
(100%) colorless corrosive liquid which has a pungent odor.
(4%) vinegar in homes.
■ Benzoic acid:
Sparingly soluble in water.
It can be converted to its sodium or potassium salts to be soluble in water.
Sodium benzoate(1%) prevents the growth of fungi in food.
■ Citric acid:
It is found in fruits like: orange and lemon. It prevents the growth of
bacteria by decreasing the PH.
It’s also used to retain the color and the taste of some fruits
■ Lactic acid:
Found in milk as a result of secretion of some enzymes by certain bacteria
in milk sugar.
It is also produced by the human body as a result of herd work.
■ Ascorbic acid (Vitamin C):
Humans need this vitamin in small quantities. It can be found in fruits and
vegetable.
The lack of this vitamin leads to Escrapot disease, which decreases the
biological functions in the human body.
■ Salicylic acid:
It is used in the formation of aspirin but it causes stomach bleeding.
■ Amino acids:
They are organic acids derivatives.
It is formed by replacing one hydrogen atom in the alkyl group by amino
group (-NH3).
There are only 20 amino acids found in natural proteins.
Proteins are considered as a polymers of amino acids.
ESTERS

■ They are the products of the reaction between carboxylic acids and alcohols.
■ They have pleasant smell which is responsible for the odor and flavor of fruits and
flowers.
■ The odor of the ester decreases by increasing the molecular weight of the alcohol
and the acid used in the formation.
■ They can be liquids or odorless waxy solids.
■ Fats and oils are derived from high fatty acids and trihydric alcohols.
Nomenclature of Esters

■ Esters
Systematic names of esters are based on the name of the corresponding carboxylic
acid.
The alkyl group is named like a substituent using the -yl ending. This is followed by a
space. The acyl portion of the name (what is left over) is named by replacing the -ic
acid suffix of the corresponding carboxylic acid with -ate.
Physical properties of esters

■ Most of esters are liquids which is much lower boiling point than those of
corresponding acids and alcohols due to the absence of the polar hydroxyl group.
Chemical properties of esters

■ 1-hydrolysis: (reverse of ester formation)

Alcohol and acid can be produced from hydrolysis of ester.
Methods of hydrolysis:
1- (acid hydrolysis)use the dilute mineral acids as a catalyst.
2-(alkaline hydrolysis): by heating the ester with aqueous alkali to produce alcohol and
salt of the acid.
Ammonolysis

■ Esters can react with ammonia and give alcohol and acid amide.
Esters as flavor

■ Esters have pleasant smell and taste, so they are used in food industries as flavors.
Esters as oil and fats

■ Fats and oils are esters produced from the reaction between 3 molecules of fatty
acids and glycerol which is trihydric alcohol.
■ Saponification is the hydrolysis of fat or oil in the presence of strong alkali which is
principle reaction in the manufacturing of soap and glycerol.
Esters as polymers

■ Polyesters are polymers produced from the condensation of 2 monomers, one of

them is dibasic acid and the other is dihydric alcohol.
■ The most common ester is Darcon fibers which is prepared by the reaction between
terphthalic acid and ethylene glycol.
Esters as medical drugs
references

■ Ministry book of chemistry.

■ http://www.chem.uiuc.edu/GenChemReferences/nomenclature_rules.html