Organic chemistry

In 1806, Berzelius divided all the compounds into two categories, which are: inorganic
compounds which can be obtained from mineral sources in the earth's crust and organic
compounds which are extracted from a plant or an animal origin.

Berzelius established the vital force theory, where it states that the organic compounds are
formed inside the cells of the living organisms by vital forces, and cannot be synthesized in the
laboratories. In 1828, Wohler managed to prepare urea in the laboratory by heating the aqueous
solutions of two inorganic compounds which are ammonium chloride and silver cyanate.

The organic material has become known on the basis of its structure and not its origin, because
most of the synthetic organic compounds that prepared in the laboratories are not necessarily
found in the bodies of the living organisms.

Organic chemistry: the science which studies carbon compounds except carbon oxides,
carbonate and cyanide salts. The number of the organic compounds exceeds ten million
compounds and is increasing daily but he inorganic compounds do not exceed half a million
compounds.

The possibilities for diversity of compounds are increased by the presence of atoms other than
carbon in organic compounds, especially hydrogen, oxygen, nitrogen, halogens, and sulfur.
Sulfur is the enormous potential for variation in chemical properties that has made organic
compounds essential to life on Earth.

Carbon atoms have the ability to bind to each other or to other elements with different types of
bonds: single, double, or triple bonds. They can bind to each other in different forms: chains
and cycles. Chains can be straight or branched. Cycles can be homocycles or heterocycles.

Organic compounds don’t dissolve in water, but dissolve in organic solvents, their melting
points and boiling points are low, are inflammable producing carbon dioxide and water vapor,
mostly have characteristic odors, are mostly nonelectrolytic, mainly contain carbon element,
have covalent bonds, their reactions are slow, can be polymerized, and have isomers.

Inorganic compounds mostly dissolve in water, their melting and boiling points are high, are
mostly noninflammable, are mostly odorless, some of them are electrolytic, may contain carbon
in addition to other elements, have covalent and ionic bonds, their reaction are fast, can’t be
polymerized, and don’t have isomers.
Molecular formula: a formula which exhibits the number and the kind of the atoms of each
element in the compound. Structural formula: a formula that exhibits the number and the kind
of the atoms of each element in the compound, in addition to the kind of linkage between the
atoms by the covalent bonds. Empirical formula: the simplest integer numerical ratio of the
atoms of the elements composing the compound.

Each element in the molecule of the organic compound has a specific and a constant valency; it
is indicated by the number of the covalent bonds surrounding each element's atom. There are
many methods to express the structural formula of an organic compound. Kekule structural
detailed formula provides a detailed picture of all of the atoms and the bonds in the molecule.
Repeated units are compiled together with removing the bonds in most of cases in condensed
structural formula.

The structural formula does not represent the actual shape of the molecule. To illustrate the
actual shape of the molecule, the molecular models can be used, where they represent the atoms
of each element by a certain color and volume. Molecular models include ball-and-stick model
and the space-filling model.

Isomerism: a phenomenon that many organic compounds are different in physical and
chemical properties and also in structural formulae but they have the same molecular formula.

There are many steps to detect carbon and hydrogen in the organic compounds. A small amount
of an organic material is heated with copper (II) oxide. Produced gas and vapor are passed over
the white anhydrous copper (II) sulphate powder, then through clear limewater. As a result, the
white color of anhydrous copper (II) sulphate powder turns into blue and the clean limewater
becomes milky.

This happens because hydrogen present in the organic material reduces copper (II) oxide,
producing water vapor which is absorbed by anhydrous copper (II) sulphate white powder, so it
turns into blue. Carbon present in the organic material reduces copper (II) oxide, producing
carbon dioxide gas which turns clear limewater milky.

Organic compounds can be classified as hydrocarbons and hydrocarbon derivatives.

Hydrocarbons: organic compounds which contain only carbon and hydrogen elements.
Hydrocarbon derivatives: organic compounds which contain carbon and hydrogen elements in
addition to other elements.

There are three forms of hydrocarbons: straight chain, branched chain, and homocyclic.
Hydrocarbons are divided into aliphatic and aromatic hydrocarbons. Aliphatic hydrocarbons
contain open chain and saturated cyclic. Open chain is divided into saturated and unsaturated.
Saturated are alkanes. Unsaturated contain alkenes and alkynes. Saturated cyclic are cyclic
alkanes. Aromatic hydrocarbons are unsaturated cyclic.

Alkanes (paraffins): open chain hydrocarbons in which the carbon atoms are linked together
with a sigma bond. Sigma bond is single, strong, and difficult to be broken. Alkanes are
relatively chemically inactive. Their general formula is CnH2n+2.

Common names: the names that mostly indicate the sources from which organic compounds
were extracted. The IUPAC system (International Union Pure and Applied Chemistry) helped to
identify the structure of any organic compound accurately. Straight chain alkane nomenclature
is accomplished by adding the suffix –ane to the prefix which indicates the number of carbon
atoms in the compound. If two different chains of equal length are present, the one with the
larger number of branch points are chosen.
Homologous series: a group of members which are characterized by having similar chemical
properties while their physical properties change gradually.

Alkyl radical (R-): an organic atomic group which is not found alone and it is derived from the
corresponding alkane by removing one hydrogen atom. Its general formula is CnH2n+1. It ends
with the suffix –yl. When naming alkyls attached to compounds, the nonhyphenated prefix iso-
is considered part of the alkyl-group name for alphabetizing purposes, but the hyphenated and
italicized prefixes sec- and tert- are not.

There are two ways to name the halogenated alkane derivatives, which are: the common name:
Alkyl halide or IUPAC name: Haloalkane.

Water molecule is polar, because its molecule has an angular shape in which the angle between
the two bonds is 105°, hence the molecule has a partial positive pole which is concentrated in
the region between the hydrogen atoms, and a partial negative pole which is concentrated at the
oxygen end.

Water is one of the most important polar solvents, for its high ability to dissolve enormous
numbers of ionic, covalent and some nonpolar substances which can form hydrogen bonds with
water.

Each carbon atom in the alkane binds with four sigma bonds of sp³ type, and the angle between
each two bonds of them is 109.5°. Alkanes are nonpolar compounds, and this is for many
reasons: the geometry of the molecule, the similarity of the values of the angles between bonds,
and the difference in electronegativity between C and H atoms is 0.4.

Alkanes are found in large quantities in the crude oil, they are separated by fractional
distillation. Methane is the simplest organic compound on earth. Methane gas represents more
than 90% of the natural gas that is present deep in the earth or accompanying the crude
petroleum oil. It is also found in coal mines which are prone to explosion as a result of its
burning. Methane gas is called gas of swamps because it goes out as bubbles from the bottom of
swamps as a result of decaying organic matter.

Methane gas is prepared in the laboratory by dry distillation of anhydrous sodium acetate salt
with soda lime (a mixture of caustic soda NaOH and quick lime CaO). Soda lime is used instead
of caustic soda on preparing methane gas in the laboratory because calcium oxide which is
present in soda lime with sodium hydroxide reduces the melting point of the reaction mixture.

Gaseous alkanes contain 1:4 carbon atoms, which are methane, ethane, propane, and butane.
Liquid alkanes contain 5:17 carbon atoms like gasoline and kerosine. Solid alkanes contain
more than 17 carbon atoms like paraffin wax and grease. Alkanes are nonpolar substances and
insoluble in polar solvents.

When two compounds have the same number of carbon atoms, the most straight one will have
higher boiling point. Because it has larger surface area and stronger W.V.F. When two
compounds have different number of carbon atoms, the one with higher molar mass and number
of carbon atoms will have higher boiling point. Because it has stronger W.V.F.

For alkanes, the odd number alkanes have lower melting point than the even number alkanes.
Even number alkanes are packed well and organized straight which requires more energy to be
broken. With increasing the symmetry of the compound, the melting point increases.

Alkanes are relatively chemically inactive, because carbon atoms are bound with single strong
sigma bonds which are difficult to be broken, except under certain conditions.

Once any hydrocarbon burns completely, it produces carbon dioxide gas and water vapour
through an exothermic reaction, so alkanes are used as fuel. When alkanes undergo incomplete
cobustion reaction, carbon, carbon monoxide, carbon dioxide, water vapor, and smoky flame
are produced. Each methylene group requires 1.5 mole of oxygen gas to undergo complete
combustion reaction.

Thermal catalytic cracking process is carried out during the refining of petroleum oil to convert
the heavy long chain petroleum products into lighter and smaller molecule. The process is
carried out by heating the heavy petroleum products under high pressure and temprature in the
presence of catalysts to produce two kinds of product: short chain alkanes that are used as car
fuel and short chain alkenes that are used in many chemical industries.

Alkanes react with halogens by heating to 400 or in the presence of ultraviolet rays in a series
of substitution reactions and the product depends on the proportion of each of alkane and the
halogen in the reaction mixture. Ease of Substitution of alkanes with halogens depending on
reactivity order. The reaction is carried out by free radical mechanism (radical chain reaction).

Radical chain reactions have three distinct phases: initiation, propagation, and termination.
Initiation phase: the step that initially creates a radical species. This is a homolytic cleavage
event, and takes place very rarely due to the high energy barriers involved. The influence of
heat, UV radiation, or a metal-containing catalyst is necessary to overcome the energy barrier.

Propagation phase: the chain part of chain reactions. Once a reactive free radical is generated,
it can react with stable molecules to form new free radicals. These new free radicals go on to
generate yet more free radicals. Propagation steps often involve hydrogen abstraction or
addition of the radical to double bonds.

Chain termination occurs when two free radical species react with each other to form a stable,
non-radical adduct. It is very rare due to the low concentration of radical species and the small
likelihood of two radicals colliding with one another.

Ease of substitution of saturated hydrocarbon is tertiary, secondary, then primary hydrogen.

When the halogen replaces a secondary or tertiary hydrogen atom, it is a major substitution. But
when it replaces primary hydrogen, it is a minor substitution.
Chloroform (trichloromethane) was used as an anesthetic in surgical operations but it is stopped
because the inaccurate estimation of its dose required for each patient may cause death.
Halothane (2-bromo-2-chloro-1, 1, 1-trifluoroethane) is used as a safe anesthetic.

1, 1, 1-trichloroethane is used in dry clean processes. Halogenated alkane derivatives (freons)

are used in fridges and air conditioners, as a rushed substance to liquids and perfumes, and as a
cleaner of electronic sets. Freons are cheap, easy to be liquefied, non-poisonous, and non-
corrosive for metals. They cause the decay of the ozone layer.

Grignard reagent: an organomagnesium compound which can be described by the chemical

formula RMgX where X is a halogen and R is an alkyl or aryl group. They are produced by
reacting an aryl halide or an alkyl halide with magnesium. The reaction is catalyzed by ethers.

Grignard reagents react with carbon dioxide in two stages. In the first, you get an addition of the
Grignard reagent to the carbon dioxide. The product is then hydrolyzed in the presence of a
dilute acid. A carboxylic acid is produced with one more carbon than the original Grignard
reagent.

Wurtz reaction: coupling of haloalkanes using sodium metal in solvent like dry ether to yield a
longer alkane chain. The reaction is catalyzed using heat.

For elimination reaction, methane is heated to 1000 and black carbon is formed. It is used in
car tyres, black ink, paintings, and polishes. Water gas is formed by heating methane gas to
725 with vapor in the presence of a catalyst. It is used as a reducing agent and as a fuel. For
quenching reaction, methane is heated 1500 then rapidly cooled. Ethyne is produced.

Catalytic reforming happens in presence and absence of air. In absence of air, hexane is
converted into benzene and isoheptane (2-methyl hexane) is converted into toluene.
Pi bond ( ) is weaker than sigma bond, because pi bond is formed by the collateral overlapping
of the atomic orbitals, while sigma bond is formed by head-on overlapping between atomic
orbitals.

Alkenes (olifenes): unsaturated open chain aliphatic hydrocarbons which contain at least one
double bond in their carbon chains. Their general formula is CnH2n. Alkene is derived from the
corresponding alkane by removing two hydrogen atoms from it. The first molecular formula
which can have isomers is C4H8.

The nomenclature is accomplished by determining the longest carbon chain that contains double
bond, naming the longest carbon chain with the name of the prefix which represents the number
of carbon atoms and the suffix –ene is added to the end of the root chain, numbering the root
chain starting from the side nearer to the double bond, determining the position and the name of
the branch.

Alkenes can be prepared by removing a water molecule from the corresponding alcohol and
aluminum is used as a catalyst. Ethene (ethylene) is the first member in alkene series. Ethene
gas is prepared in the laboratory by removing water from ethyl alcohol (ethanol) by using conc.
sulphuric acid which is heated to 180°C.

Ethanol reacts with the hot concentrated sulphuric acid forming ethyl hydrogen sulphate. Ethyl
hydrogen sulphate is thermally decomposed forming ethene. The product is passed on sodium
hydroxide solution, to eliminate the traces of the fumes of concentrated sulphuric acid evolved
with ethene gas. Ethene gas is collected over water surface, because the density of ethene gas is
lower than that of water, in addition to being insoluble in water.
Gaseous alkenes contain 2:4 carbon atoms. Liquid alkenes contain 5:15 carbon atoms. Solid
alkenes contain more than 15 carbon atoms. They don’t dissolve in water but in organic
compounds. The boiling and melting points are lower than the corresponding alkanes of the
same number of carbon atoms. Because the approaching clouds causes repulsion between two
chins,so the intermolecular force Wanderval force decreases.

Alkenes are chemically more active than alkanes, because alkenes contain double bonds which
are formed of strong sigma bond and weak pi bond which can be broken easily, while alkanes
contain single bonds which are all of the strong sigma bond type which is difficult to be broken.
It is difficult for alkenes to react by substitution.

Alkenes combust in air through an exothermic reaction producing carbon dioxide gas and water
vapour. The addition reaction is to add atoms or atomic groups to two adjacent carbon atoms
bound together with an unsaturated bond to convert it into saturated compounds. Alkenes are
characterized by their ability to share in addition reactions forming saturated compounds.
Addition reactions include hydrogen, halogens, hydrogen halides, and water.

Hydrogenation reactions of alkenes: reactions of addition of hydrogen to alkenes.

Hydrogenation reactions of alkenes take place in the presence of catalysts with heating to form
the corresponding alkanes. It requires 1 mol of hydrogen molecules to break each 1 mol of pi
bond in the alkene, to convert it into a saturated compound. This reaction is used to convert
unsaturated oil into saturated fats.

Halogenation reactions of alkenes: reactions of addition of halogens to alkenes. Halogenation

reaction is used in the detection of alkenes. On passing ethene gas in bromine water, the red
color of bromine water disappears gradually, due to the consumption of bromine in breaking the
double bond of ethene forming colorless 1, 2-dibromoethane. Alkenes halogenation reactions
by addition don’t require ultraviolet rays, but alkenes halogenation reactions by substitution do.

In the reaction, if the alkene is limiting, the color of bromine doesn’t change. If the alkene is
excess or both are stoichiometric equivvalent, the color of bromine will be discharged.
Alkenes react with hydrogen halides, where pi bond is broken and the hydrogen atom becomes
attached to one of the two carbon atoms of the broken pi bond, and the halogen atom attaches to
the other carbon atom to form the corresponding alkyl halide, the product of this addition
reaction depends on the type of alkene.

Symmetric alkenes: alkenes in which the two carbon atoms which are attached to the double
bond carry the same number of hydrogen atoms. Asymmetric alkenes: alkenes in which the
two carbon atoms which are attached to the double bond carry different numbers of hydrogen
atoms.

On adding hydrogen halide to a symmetric alkene, one of carbon atoms of the double bond
accepts a hydrogen atom and the other carbon atom accepts the halogen atom to form the
corresponding alkyl halide (haloalkane).

On adding hydrogen halide to an asymmetric alkene, the reaction proceeds following a rule
which is Markovnikov's rule, and it states that on adding an asymmetric reagent to an
asymmetric alkene, the positive part of the reagent is added to the carbon atom which carries the
larger number of hydrogen atoms and the negative part is added to the carbon atom which
carries less number of hydrogen atoms.

The same reaction can proceed but following the anti Markovnikov's rule. On adding an
asymmetric reagent to an asymmetric alkene, the negative part of the reagent is added to the
carbon atom which carries the larger number of hydrogen atoms and the positive part is added
to the carbon atom which carries less number of hydrogen atoms. The catalyst is H2O2 peroxide
or any peroxide reagent which has the formula R O O R.

Elimination reaction: a reaction in which two or more atoms, one of which is usually
hydrogen, are removed from adjacent atoms in the reactant, resulting in the formation of a
multiple bond. For an elimination reaction of alkyl halides, the major product alkene is
produced together with the small hydrogen halide molecule. Alcoholic KOH or alcoholic NaOH
is used.

Reaction of addition of water to alkenes in the presence of conc. sulphuric acid as a catalyst to
form the corresponding alcohol is known as catalytic hydration reaction of alkenes. Conc.
sulphuric acid is used because water is a weak electrolyte, so the concentration of hydrogen ions
produced from its ionization is weak and insufficient to break the pi bond between the two
carbon atoms. Ethene reacts with cone. sulphuric acid at 80°C forming ethyl hydrogen sulphate.
Ethyl hydrogen sulphate is hydrolyzed at 110°C forming ethanol. The only alkene that gives
primary alcohol by catalytic hydration is ethene. Other alkenes give secondary or tertiary
alcohol.

Alkenes react with hydrogen halide following Markovnikov's rule producing alkyl halide. The
alkyl halide reacts with aqueous KOH through hydrolysis producing secondary alcohol.

Alkenes react with hydrogen halide following anti Markovnikov's rule producing alkyl halide.
The alkyl halide reacts with aqueous KOH through hydrolysis producing primary alcohol.

Alkenes are oxidized by the oxidizing agents, like: hydrogen peroxide and alkaline purple
potassium permanganate (KMnO4) forming dihydroxy compounds called glycols. On heating
alkenes with potassium permanganate in an acidic medium, ketones or carboxylic acids are
formed.

On passing ethene gas in potassium permanganate solution, in an alkaline medium at room

temperature, the purple colour of potassium permanganate is discharged and ethylene glycol
compound is formed. This reaction is the Baeyer's reaction (hydroxylation). It is used to detect
the presence of the double bond by discharging the purple colour of permanganate. It takes
place in a basic medium, as the formed alcohol cannot react with the alkali, but it can react with
the acid. Hydroxylation can be carriedd by H2O2.
Ethylene glycol is the essential antifreezing substance that is used in car radiators, because it
forms hydrogen bonds with the molecules of water, so it prevents their combination together in
the form of ice crystals.

Ozonolysis (ozonolysis-reduction): the treatment of an alkene with ozone followed by a

suitable reducing agent to break down complex double-bond-containing compounds into
smaller and more easily identified products. Molozonide: is an unstable, cyclic intermediate
that is initially formed when an alkene reacts with ozone.

Alkenes can also be cleaved by potassium permanganate. However, KMnO 4 will carry the
oxidation further than ozonolysis, so products can be slightly different. Ozonolysis produces
aldehydes and ketones, while KMnO4 can oxidize all the way to to carbon dioxide and
carboxylic acid. When the bond is terminal, the products are carboxylic acid, carbon dioxide,
and water. When the bond is internal, the products are alkenes and ketones.

Polymerization process: the combination of a large number of compound molecules, where

their number ranges between 102 to 106 molecules, to form a huge molecule with a very large
molecular mass. The small primary molecule is a monomer. The huge molecule produced from
the polymerization process is a polymer. The polymer and the monomers have the same
empirical formula.

Addition polymerization: the process of adding a huge number of unsaturated small molecules
to each other to form a very large saturated molecule. Alkenes are characterized by their high
ability to form polymers by addition. On heating ethene under high pressure in the presence of
peroxides as initiators, polyethylene is formed.

On heating ethene under high pressure, the pi bond is broken and the two electrons of this bond
are liberated, therefore each carbon atom has a free electron. Each two carbon atoms bind to
each other with a single covalent band. The process continues to form long chains of polymer
molecules.

The polymer formed by addition is similar to the forming monomer in the masses and the
empirical formulae of both the used substances and the produced substances. It is different from
the forming monomer in the molar mass, the boiling point, the density, and the molecular
formula.
Polyehtylene is soft and resists the effects of chemicals. It is used in hoses, plastic bottles,
plastic sheets, and bags. Polypropylene is hard and strong. It is used in cases, cans, plastic
sacks, and carpets.

Polychloroethene (polyvinyl chloride) is soft and strong. It is used drianage tubes, hoses, shoes,
floor insulators, and oil bottles. Vinyl group (a radical) is a group derived from ethene by
removing one hydrogen atom. Polytetrafluoroethene (teflon) resists heat and adhesion. They are
inert and electrical insulators. They are used in surgical threads and cooking utensils.

Condensation polymerization: condensation process which takes place between two different
monomers to form a common polymer that represents the basic unit with which the
polymerization process continues.

A polymer is a macromolecule that is composed of a large number of repeating units. Polymers

have different physical properties depending on their structures. Their morphology varies from
crystalline to amorphous structures. They can rupture when a pressure is applied. Most except
elastomers are stiff and rigid.

Elastomer: a type of polymer having the specific characteristic feature of elasticity. They have
the unique physical property of elasticity. They are amorphous polymers. They can withstand
high pressures due to elasticity. They are flexible.

Alkynes (acetylenes): unsaturated open chain aliphatic hydrocarbons which contain at least one
triple bond in their carbon chains. Alkynes are called acetylenes, because the first member in
this series is ethyne whose common name is acetylene. Their general formula is CnH2n-2.

The nomenclature is accomplished by determining the longest carbon chain that contains Triple
bond, naming the longest carbon chain with the name of the prefix which represents the number
of carbon atoms, then the suffix –yne is added to the end of the root chain, numbering the root
chain starting from the side nearer to the triple band, determining the position and the name of
the branch, and the branches are arranged alphabetically according to their latin names.

Ethyne gas is prepared in the laboratory by dropping water on calcium carbide. Ethyne gas is
passed on copper (II) sulphate solution in dilute sulphuric acid before collection, to remove
phosphine gas (PH3) and hydrogen sulphide gas (H2S) produced from the impurities found in
calcium carbide. Ethyne gas is collected over water surface, because the density of ethyne gas is
lower than that of water, in addition to being water insoluble.
Ethyne gas is prepared in industry by heating the natural gas which contains a high percentage
of methane gas to a high temperature then fast cooling the product.

The products of burning of ethyne gas depend on the amount of oxygen gas. Ethyne gas burns
in air giving a smoky flame, because the amount of oxygen in the atmospheric air is insufficient
to burn all carbon found in ethyne.

Ethyne gas burns completely in excess of pure oxygen gas through an exothermic reaction.
Complete burning reaction of ethyne produces a flame with a temperature reaches 3000°C, this
flame is known as oxyacetylene flame which is used in cutting and welding metals.

Acetylene is used in welding purposes, even though its heat of combustion is lower than those
of both ethane and ethene. The amount of heat required to activate oxygen in the beginning of
the reaction, and that required to evaporate the produced water are the least in case of acetylene.

Ethyne is an unsaturated compound, so it reacts mostly by addition. The addition reactions in

this case take place in two steps, because ethyne gas molecule contains two pi bonds in addition
to the sigma bond, so the triple bond becomes double bond in the first step, then it becomes a
single bond in the second step.

Hydrogenation reactions of alkynes: addition reactions of hydrogen to alkynes in the presence

of catalysts to form the corresponding alkanes. Each 1 mol of alkyne which contains a triple
bond requires 2 mol of hydrogen molecules to break the pi bonds found in this alkyne to
convert it into a saturated compound.

Ethyne reacts with halogens vigorously, the reaction is accompanied by a flame when it reacts
with chlorine. Halogenation reaction of alkynes is used in the detection of their unsaturation, so
when ethyne gas is passed in bromine water, the red colour of bromine water disappears
gradually.

Methane reacts with chlorine gas in the presence of ultraviolet rays. It does not react with
bromine water. Bromine dissolved in carbon tetrachloride can not be used to differentiate
between ethene and ethyne, as it reacts with both of them by addition.
Hydrogen halides react with ethyne in two steps. The first step does not obey Markownikoff's
rule, because ethyne is a symmetric alkyne. The second step obeys Markownikoff's rule,
because bromoethene is an asymmetric compound.

Catalytic hydration of ethyne: reaction of ethyne with water by addition in the presence of
catalysts at 60°C to form ethanal (acetaldehyde). Vinyl alcohol is unstable and rearranged to be
converted into acetaldehyde. Because the two free pairs of electrons present on the oxygen atom
of the hydroxyl group –OH repel the two electrons of the weak pi bond found between the two
carbon atoms. This effect is called keto–enol tautomerism.

Keto–enol tautomerism: a chemical equilibrium between a keto form (a ketone or an

aldehyde) and an enol in organic chemistry. Tautomers are claimed to exist between the keto
and enol forms. Tautomers are isomers that differ solely in moving a hydrogen atom from one
atom to another. Tautomers exist between enols and their keto isomers. The keto tautomer is
often significantly more stable than the enol form.

Aldehydes are oxidized by oxidizing agents, such as: acidified potassium permanganate
forming the corresponding carboxylic acids. Aldehydes are reduced by reducing agents forming
the corresponding primary alcohols.

Alkynes are more acidic than alkenes and alkanes. This is because the S sublevel has high
penetrating power and low shielding effect. As a result, the hydrogen atom is lost easily. The
alkynes have acidity only when the triple bond is terminal.

The hydrogen on a terminal alkyne is somewhat acidic, with a pKa of approximately 26. When
there is a strong enough base, a terminal alkyne can be deprotonated, yielding a powerful
carbanion nucleophile called an acetylide or alkynide. Sodium amide (NaNH2) (in liquid
ammonia) or sodium hydride (NaH) are often used as the base.

Acetylide anions are strong bases and strong nucleophiles. Therefore, they are able to displace
halides leaving groups in substitution reactions. The product is a substituted alkyne.
When alkanes, alkenes, and alkynes are added to a solution of red bromine, the red color
discharges with alkenes and alkynes only. When alkanes, alkenes, and alkynes are added to a
solution of violet potassium permenganate, the violet color discharges with alkenes only. When
alkanes, alkenes, and alkynes are added to a solution of copper sulphate, the alkyne only reactes
with it forming reddish brown precipitate of copper acetylide. Acetyline gas can be got from
copper acetylide by reaction with conc. H2SO4.

Cycloalkanes: saturated cyclic hydrocarbons whose molecules contain at least three carbon
atoms, they are found in cyclic shape. Their general formula is CnH2n. The molecular formula
cannot be relied on to differentiate between the cycloalkane und the aliphatic alkene
corresponding to it, because they both have the same general formula. IUPAC nomenclature of
cycloalkanes does not differ from that of the corresponding straight chain alkanes, except in
adding the prefix cyclo- to the name of the alkane.

Chemical properties of cycloalkanes differ from one to another according to the value of of the
internal angle between each two carbon bonds.
Chemical properties of cycloalkanes depends on the value of the internal angle between each
two carbon bonds, because as the value of this angle decreases, the overlapping between the
atomic orbitals becomes weaker, therefore the combination between carbon atoms becomes
very weak and the chemical activity hence increases, and vice versa.

Aliphatic compounds are derived from fatty acids. They are characterized by containing a
higher number of hydrogen atoms. Methane is the first member of these compounds. Aromatic
compounds are derived from some resins and some natural products and they have characteristic
aromas. They are characterized by containing a lower number of hydrogen atoms. Aromatic
benzene is the first member of these compounds.

Aromatic compounds may contain one, two, or more benzene rings. Gasoline is completely
different from aromatic benzene. Aryl radical (Ar-): the radical produced by removing one
hydrogen atom from the aromatic compound. Benzyl radical is produced by removing one
hydrogen atom from the methyl group of toluene.

Halogenated monosubstituted benzene derivatives are named according to IUPAC

nomenclature halobenzene and common name phenyl halide. If the substituent is an atomic
group, the name of this group is mentioned first followed by the word benzene. If the benzene
ring is attached to a complicated name group, the benzene ring will be dealt with as the
substituent, so it will be called phenyl.

If one hydrogen atom in the benzene ring is substituted by an active functional group, the name
of the resulting compound will be related to benzene according to IUPAC nomenclature, or it
will have a new common name.

On substituting two hydrogen atoms in the benzene ring by two atoms or groups either similar
or different, the nomenclature is done by the same way as in aliphatic hydrocarbons which
considers the numbering of substituents that provides the least summation for the branches
numbers, as well as considering their alphabetical order.

In case of substituting a hydrogen atom in phenol, toluene or benzoic acid, the main group is
given the number 1, and the other groups are numbered according to their positions in relation
to the essential group. The presence of two substituent atoms or groups attached to the benzene
ring is accompanied by the probability of the presence of three located isomers.

On substituting two hydrogen atoms in a benzene ring with two methyl groups, the compound
name according to IUPAC system will be xylene. It isn’t related to toluene. On substituting two
hydrogen atoms in a benzene ring with a hydroxyl group and a methyl group, the compound
name according to IUPAC will be cresol. It is related to phenol not toluene.
For multi-substitued benzene derivatives, carbon atoms of the ring are numbered in order to
provide the least summation for the branches numbers. The groups are ordered alphabetically
according to their latin names regardless their positions numbers.

Identification of the structural formula of benzene had provoked so much controversy because
benzene reacts by substitution, as well as by addition and it is a perfect hexagon, where its six
carbon bonds lengths are equal and are in between the single bond length and the double bond
length.

Kekule suggested two formulas to represent benzene. Benzene molecule is a ring of 6 carbon
atoms form a perfectly regular hexagon. The six carbon atoms are linked together with 3 single
bonds and 3 double bonds, exchanging with each other. All the six bond lengths are equal. Each
carbon atom has a hydrogen atom attached to it. The ring inside benzene hexagon represents the
delocalization of the six electrons at certain carbon atoms.

Hückel proposed a theory to help determine if a planar ring molecule would have aromatic
properties. His rule states that if a cyclic, planar, fully conjugated (p orbitals at every atom in
the ring) molecule has 4n+2 π electrons, it is considered aromatic. n is the number of
subsequent energy levels.

According to Hückel's Molecular Orbital Theory, a compound is particularly stable if all of its
bonding molecular orbitals are filled with paired electrons. This is true of aromatic compounds,
meaning they are quite stable. With aromatic compounds, 2 electrons fill the lowest energy
molecular orbital, and 4 electrons fill each subsequent energy level, leaving all bonding orbitals
filled and no anti-bonding orbitals occupied.

Hückel's Rule applies to ions. As long as a compound has 4n+2 π electrons, it does not matter if
the molecule is neutral or has a charge.
Benzene is not oxidized by potassium permanganate. It reacts mostly by substitution, and
hardly by addition. It does not react with bromine water or hydrogen halides. It is more stable
than alkenes. It reacts hardly by addition because of the delocalized electrons, and so this
reaction if it occurs would involve producing less stable products.

Destructive distillation of coal: heating coal in absence of air to decompose it into gases,
liquids and coke. On carrying out a fractional distillation to the coal tar at: 80°C to 82°C,
benzene will be obtained, and at other temperatures, other organic compounds are obtained
which have high economic importance. Fractional distillation: the process of separation of
some mixed liquids from each other depending on their boiling points.

The catalytic reforming method is used in the conversion of the aliphatic petroleum derivatives
which contain straight carbon chains of 6 to 8 carbon atoms into compounds which contain
benzene ring. On passing ethyne gas in a red hot nickel tube, each 3 molecules of ethyne will be
polymerized forming one molecule of benzene. This process is called trimerization.

On passing phenol vapours on the surface of hot zinc powder, phenol is reduced to aromatic
benzene. Pure benzene is prepared in the laboratory by dry distillation of sodium benzoate with
soda lime. Sodium benzoate is prepared by reacting benzoic acid with sodium hydroxide.

Benzene is transparent liquid with a characteristic pleasant odour. Its boiling point is 80°C. It is
immiscible with water, but miscible with most of the organic solvents. Benzene burns in air
forming a black smoke, due to the high content of carbon in it.

Benzene reacts with hydrogen under temperature and pressure in the presence of a catalyst to
produce cyclohexane. Hydrogenation reaction of aromatic benzene takes place in the presence
of nickel as a catalyst at a temperature ranging from 100°C to 200°C and the pressure of the
used hydrogen gas is 100 atm.

Benzene reacts with chlorine gas or bromine fumes by addition in the sunlight, by the effect of
the ultraviolet rays, forming hexahalocyclohexane.
Substitution reactions of benzene produce compounds of very high economic importance. They
are more common than addition reactions, where one or more hydrogen atoms are replaced by
other atoms or groups, according to the reaction conditions and the type of the used catalyst.

Halogenation of benzene: a process of replacing one or more hydrogen atoms in benzene ring
by one or more halogen atoms in the presence of a suitable catalyst. These reactions produce
aryl halides in large amounts, to be used as insecticides.

The most important aryl halide used as insecticide is DDT (Dichloro Diphenyl
Trichloroethane). The toxicity of DDT is attributed to the part CH-CCl3 in this molecule which
dissolves in the fatty tissue of the insect, so it kills it. This compound is described to be the
ugliest chemical compound ever, due to the environmental problems arising as a result of its
usage.

Benzene reacts with alkyl halides through a reaction known as Friedel - Craft's reaction
(Benzene alkylation) which is a process of replacing one hydrogen atom in benzene ring with an
alkyl group in the presence of a catalyst as anhydrous aluminum chloride AlCl3 to form alkyl
benzene.

If the ring of benzene has alkyl, hydroxyl, halogen, or amino (NH2) group, the substitution
reaction will take place at ortho- and para- positions. If the ring has carbonyl (CO), ether
(CHO), carboxyl (COOH), and nitro (NO2) group, the substitution reaction will take place at
meta- position.

On chlorinating toluene, three products are going to be produced but in different percentages:
ortho-chlorotoluene in 39%, meta-chlorotoluene in 1%, and para-chlorotoluene in 60%. The
sum of the percentages of ortho- and para- chlorotoluene represents 99% of the total products,
so the methyl group is said to be ortho- and para- directing group. When toluene is oxidized,
benzoic acid is formed.
Nitration process: a process of replacing one hydrogen atom in benzene ring with a nitro group
in the presence of a catalyst. Nitration of nitrobenzene is more difficult than nitration of
aromatic benzene, as group has an electron withdrawing nature, which leads to the decrease of
the electron cloud on the benzene ring, consequently the reaction becomes slower.

Trinitrotoluene is a very explosive polynitro organic compound. Polynitro organic compounds

are very explosive because they burn quickly producing great amounts of gases and heat. Their
molecules contain their own fuel and the oxidizing agent. The bond in the nitro group is weak
compared with the strength of the bonds formed in the products. The released amount of energy
produced from the formation of the bonds is very large compared to the absorbed amount of
energy during the breaking of the bonds.

Sulphonation process: a process of replacing a hydrogen atom in benzene ring by a sulphonic

(-SO3H) group. Sulphonation process takes place by the reaction of aromatic benzene with
concentrated sulphuric acid to form benzene sulphonic acid. Detergents industry depends
mainly on the aromatic sulphonic acid compounds.

The detergent is obtained by treating the aromatic sulphonic acid compounds with caustic soda.
Deteregent molecule is formed from a head and a tail. The head is ionized polar group and
hydrophilic. The tail is nonpolar long hydrocarbon chain and hydrophobic.

Hydrogen bonds between water molecules causes what is known as surface tension, which can
explain the walking of the insects on the surface of water without sinking. Adding detergents to
water decreases the number of those hydrogen bonds between water molecules causing its
surface tension to decrease.

Adding the detergent to water decreases its surface tension, therefore its ability to wet the textile
increases. The tail is directed towards the greasy spot. The head is directed towards water, so
the greasy spot becomes covered by the detergent molecules. The mechanical friction during
rubbing leads to the separation of the greasy spot and its breaking into small balls. The balls are
separated from the textile as a result of the repulsion between heads of the detergent molecules
and become suspended in water in the form of emulsion which is removed by rinsing.
Carbon atoms in any organic compound are classified according to the number of other carbon
atoms that are bound to them. Primary carbon atom is bound to only one other carbon atom.
Secondary carbon atom is bound to two other carbon atoms. Tertiary carbon atom is bound to
three other carbon atoms. Quaternary carbon atom is bound to four other carbon atoms.
Primary, secondary, and tertiary hydrogens are attached to primary, secondary and tertiary
carbon atoms.

Removing a hydrogen atom from a primary carbon atom makes propane to produce propyl
group. Removing a hydrogen atom from a secondary carbon atom makes propane to produce
secondary propyl group.

Removing a hydrogen atom from a primary carbon atom makes butane to produce butyl group.
Removing a hydrogen atom from a secondary carbon atom makes butane to produce secondary
butyl group. Removing a hydrogen atom from a primary carbon atom makes isobutane to
produce isobutyl group. Removing a hydrogen atom from a tertiary carbon atom makes
isobutane to produce tertiary butyl group.

Functional group: a group of atoms that combine together in a certain way, to form a part of
the molecule. Its activity affects the properties of the whole molecule.

Organic compounds that contain carbon, hydrogen, and oxygen are alcohols, phenols, ethers,
aldehydes, ketones, carboxylic acids, and esters. Organic compounds that contain carbon,
hydrogen, and nitrogen are amines. Organic compounds that contain carbon, hydrogen, oxygen,
and nitrogen are amides.

Alcohols are compounds attached to hydroxyl group. They are derived from water by replacing
a hydrogen atom in a water molecule with alkyl group. Alcohol is derived from the aliphatic
hydrocarbon by replacing a hydrogen atom in the aliphatic hydrocarbon molecule with a
hydroxyl group. On removing one hydrogen ion, a group is formed which is alkoxide group.
The carbon atom which is attached to the hydroxyl group is called carbinol group.

Phenols are compounds attached to hydroxyl group. They are derived from water by replacing a
hydrogen atom in a water molecule with aryl group. Phenol is derived from the aromatic
hydrocarbon by replacing a hydrogen atom in the aromatic hydrocarbon molecule with a
hydroxyl group.

Ethers are compounds attached to an oxygen atom. Two groups can attach to it. If the two
groups are similar, the name ends with the word ether preceded by di alkyl group name. If the
two groups are different, the name ends with the word ether preceded by the two names of the
two alkyl groups arranged alphabetically.

Aldehyde (formyl group) are compounds attached to a group of carbon, hydrogen, and oxygen.
Many aldehydes are famous for their common names. The suffix –al is added to the end of the
alkane name instead of –e.

Ketones (carbonyl group) are compounds attached to a group of carbon and oxygen. Two
groups can attach to it. If the two groups are similar, the name ends with the word ketone
preceded by di alkyl group name. If the two groups are different, the name ends with the word
ketone preceded by the two names of the two alkyl groups arranged alphabetically. The suffix –
one is added to the end of the alkane name instead of –e.

For the common name, the word alcohol is added at the end of the name preceded by the name
of the alkyl group. For the IUPAC nomenclature, the suffix –ol is added to the name of the
alkane instead of –e, considering that the numbering of the carbon chain starts from the side
nearer to hydroxyl group.

Naming the alcohol which contains four carbon atoms as just butanol is inaccurate, because
butanol has more than one isomer, consequently the number of the carbon atom which carries
the alcoholic hydroxyl group must be determined.

Alcohols are classified according to the nymber of hydroxyl groups into monohydric, dihydric,
trihydric, and polyhydric alcohols. Monohydric alcohols are classified according to the
attachment of the carbinol group to the alkyl groups and the hydrogen atoms into primary,
secondary, and tertiary alcohols.

Primary alcohols: alcohols in which the carbinol group is attached to a primary carbon atom.
Secondary alcohols: alcohols in which the carbinol group is attached to a secondary carbon
atom. Tertiary alcohols: alcohols in which the carbinol group is attached to a tertiary carbon
atom.

Isoalkyl alcohols: alcohols which contain a carbon atom attached to one hydrogen atom and
two methyl groups. Ethers are isomers of the alcohols which have the same number of carbon
atoms.

About 20% of ethanol production worldwide is produced through the alcoholic fermentation
processes of sugary and starchy materials especially in the countries which are rich in
cultivating sugar-cane, maize and beet. Ethanol is prepared in Egypt from the remaining sugary
solution after extracting sugar from sugar cane, which is known as molasses.

Fermentation is carried out by adding yeast, which secretes zymase enzyme, to molasses
(sucrose). Hydrolysis of sucrose happens in an acedic medium, then glucose is fermented by
zymase enzyme giving ethanol and carbon dioxide gas.

The petroleum materials are thermally cracked to obtain ethene, and then by catalytic hydration
of ethene in the presence of dilute sulphuric or phosphoric acid as a catalyst, ethanol is
obtained. Ethene is the only alkene that gives a primary alcohol by catalytic hydration.

Secondary and tertiary alcohols can be prepared by catalytic hydration of alkenes, these
reactions obey Markownikoff's rule. 2-propanol is prepared from propene. 2-methyl-2-butanol
is prepared from 2-methyl-2-butene.

Pure ethanol is highly taxed, in order to minimize its use in making alcoholic liquors because of
their harmful effects on health and social aspects. Ethanol is traded in an economic price after
adding: some toxic substances like methanol which causes madness and blindness, pyridine
which has an unpleasant bad odour, and colouring dyes. These additives can not be easily
separated from ethanol except through complicated chemical processes besides being illegal.

Among the impure alcohols which are used as fuels in houses and in some chemical industries
is the converted alcohol (the red spirit), it is composed of 85% ethanol, 5% methanol, 1% dyes
and 9% colours, odour and water.

Alcohols are prepared in the laboratory by the hydrolysis of alkyl halides in a strong alkaline
medium, where the hydroxyl group replaces the halide radical to form the corresponding
alcohol. Halogens are sorted in order of their ability to be replaced as follows: iodine > bromine
> chlorine > fluorine.

Alkyl iodide is more preferable than alkyl chloride in preparing alcohols through the general
method, as the hydrolysis of alkyl iodide in a strong alkaline medium is easier than that of alkyl
chloride. With increasing the atomic number in group 7A, the atomic radius of the halogen
increases, and the electronegativity decreases, consequently the bond strength in alkyl halide
decreases, which leads to an easy hydrolysis in alkaline medium.
Primary, secondary and tertiary alcohols can be prepared through the general method. Ethanol
can be prepared from bromoethane. 2-propanol can be prepared from 2-bromopropane. 2-
methyl-2-propanol can be prepared from 2-chloro-2-methyl propane.

Pure alcohols are colorless. Their effect on litmus is neutral. First members are light liquieds,
middle members are oily liquids, and higher members are waxy solid substances. First members
of alcohols are characterized by being completely miscible with water, due to the presence of
the polar hydroxyl group which forms hydrogen bonds between water molecule and the alcohol
molecule causing its miscibility with water.

Solubility of alcohols in water decreases by increasing its molar mass. due to the weak
influence of the polar part of the molecule with increasing the mass of the nonpolar part of the
molecule.

The first three members of alcohols are characterized by having higher boiling points than their
corresponding alkanes, due to the presence of the polar hydroxyl group which forms hydrogen
bonds between alcohol molecules, that leads to increasing the energy required to separate these
molecules from each other, hence their boiling points increase. Increasing the branches causes
decreasing the boiling point.

Increasing of the number of hydroxyl groups in the alcohol molecule leads to increasing its
solubility in water, and increasing its boiling point. The molecules of an amine bind together
with hydrogen bonds just like in alcohol molecules.
Despite being neutral, alcohols shows a weak acidic character, because the pair of electrons
which binds the hydrogen atom to the oxygen atom in the polar hydroxyl group is shifted
towards the more negative oxygen atom, leading to weakening the covalent bond between
hydrogen and oxygen, so it becomes easy to be broken, resulting in the removal of hydrogen
ion.

The weak acidic character of alcohols is conspicuously visible in their inability to react with
strong alkalis, neverthless, they react with the active metals, these metals replace the hydrogen
atom of the hydroxyl group.

When sodium ethoxide solution is evaporated, sodium ethoxide will precipitate in the form of a
white solid substance. Sodium ethoxide is hydrolyzable, it can be hydrolyzed giving ethanol
and sodium hydroxide.

Alcohols react with carboxylic acids to form esters. The source of the produced water is a
hydrogen atom from the hydroxyl group of the alcohol molecule and a hydroxyl group from the
carboxyl group of the carboxylic acid molecule.

On treating ethanol which contains the heavy oxygen isotope with ethanoic acid which contains
the normal oxygen isotope it was found that oxygen of the produced water is normal not heavy
oxygen. Concentrated sulphuric acid is added to the reactions of alcohols with carboxylic acids
to eliminate the produced water, hence preventing backward reaction and increasing the forward
reaction rate.

Alcohols react easily with halogenated acids, where the halogen replaces the hydroxyl group
forming alkyl halide and water.

Alcohols are oxidized by oxidizing agents, such as: potassium dichromate and potassium
permanganate acidified with conc. sulphuric acid. Oxidizing agent effect is focused on the
hydrogen atoms attached to the carbinol group, it converts them into hydroxyl groups. The
product of oxidation of alcohols varies according to the alcohol type.

Due to the presence of two hydrogen atoms attached to the carbinol group of the primary
alcohol, the oxidation process takes place in two steps: one of the carbinol group hydrogen
atoms is oxidized, and an unstable compound is formed which loses one molecule of water
being converted into an aldehyde and the other hydrogen atom attached to the carbinol group is
oxidized to form a carboxylic acid.

Oxidation reaction of ethanol by acidified potassium dichromate solution is used to detect the
driver's intake of alcohol. The driver blows a balloon through a tube containing silica gel
saturated with potassium dichromate acidified by concentrated sulphuric acid. The balloon is
left to allow the driver's exhalation air to go out through the tube once more, so if the driver is
drunk, the colour of potassium dichromate will be changed from orange into green colour.

Due to the presence of one hydrogen atom attached to the carbinol group of the secondary
alcohol, the oxidation process takes place in one step forming a ketone.

Tertiary alcohols are not oxidized with the regular oxidizing agents, because the carbinol group
in the tertiary alcohol is not attached to any hydrogen atom.

When alcohols react with concentrated sulphuric acid, the reaction product depends on the
number of reacting molecules of alcohol and reaction temperature. When ethanol reacts with
conc. sulfuric acid at 180 , one water molecule is eliminated from one molecule of alcohol to
form an ethene molecule. But when the reaction happens at 140 , one water molecule is
eliminated from two molecules of alcohol to form a diethyl ether molecue.
During dehydration of secondary alcohol, the source of water hydrogen is carbon atom which is
adjacent to carbinol group that carries lower number of hydrogen atoms. Ethanol is used in
alcoholic liquors manufacture.

Ethyl alcohol (monohydric alcohol) is used as a solvent for organic substances and in chemical
industries. It is used in mouth washes which sterilize mouth and teeth, and as a disinfectant due
to its ability to kill microbes. It is used in perfumes. It is used as a car fuel after mixing with
gasoline. It is the main component of the converted alcohol which is used as a domestic fuel and
in some chemical industries. Used in filling the thermometers that measure the low
temperatures due to its low freezing point.

Ethylene glycol (1,2-dihydroxy ethane) is used as an antifreezing substance in car radiators in

cold regions. It is used in hydraulic break, pin ink, and printing inks due to its high viscosity. It
is used in preparing dacron fibers. It is used in preparing the polymer called polyethylene glycol
which is used in the manufacture of photographic films and cassette tapes. It is used as a skin
moisturizer in cosmetics and creams. It is used in textile manufacture , as it renders tham soft
and flexible.

Nitration of glycerol by a mixture of concentrated nitric and sulphuric acids gives

trinitroglycerine compound (Nitroglycerol). Trinitroglycerine is used in preparation of
explosive substances and manufacture of the drugs that widen arteries used in the treatment of
the heart problems.

Phenols: aromatic hydrocarbon derivatives in which one or more hydroxyl groups are attached
directly to carbon atom of benzene ring. Phenols are classified as monohydric, dihydric, and
trihydric phenols. Phenol is used as a starting material in the preparation of polymers, picric
acid, dyes, disinfectants, and salicylic acid derivatives.

Phenol is prepared by the fractional distillation of coal tar. Phenol is prepared by the hydrolysis
of chlorobenzene in an alkaline medium at 300°C and under 300 atm pressure.
Phenol is a solid corrosive substance. It has a characteristic odour. Phenol melts at 43°C. It is
sparingly soluble in water, its solubility increases by increasing temperature ,at 65°C it becomes
completely miscible with water. Phenol behaves in some chemical reactions in a manner that
resembles alcohols, however, some of reactions differ completely from alcohol reactions.

Phenol resembles alcohols in conntaining a polar hydroxyl group. The polarity of O – H bond
of hydroxyl provides an acidic character to both phenol and alcohol which is manifested in their
reactions with the strong metals.

Despite being a weak acid, phenol is still more acidic than alcohols. Because benzene ring in
phenol increases O – H bond length, and hence weakens it more. This is why phenol is known
as carbolic acid. High acidity of phenol compared with alcohols is evidenced by the ability of
phenol to react with strong alkalis while alcohols can’t participate in this kind of reactions. The
pH values of the different aqueous solutions of phenol are less than 7 (exactly between 5:6).

Phenol , unlike alcohols, doesn’t react with halogenated acids, because the attachment of the
hydroxy group to the benzene ring leads to shortening the C – H bond and hence increaing its
strength.

Phenol reacts with concentrated nitric acid in the presence of concentrated sulphuric acid
forming trinitrophenol which is known as picric acid. Picric acid is used as explosive substance.
It is used as antiseptic in treatment of skin burns. It stains the skin yellow which is difficult to
be removed and it remains several days until the skin is renewed.

Copolymers: the polymers produced by condensation polymerization. They are produced by

the combination of two types of monomers with the elimination of a small molecule.
Phenol reacts with formaldehyde in an acidic or basic medium to form a copolymer and by
continuing the condensation polymerization process of the copolymer, bakelite polymer is
formed. Each formaldehyde molecule reacts with 2 molecules of phenol to form one copolymer
molecule with losing one water molecule. Copolymer molecules combine to form bakelite
polymer.

Bakelite is a type of crosslinked plastics. These plastics are thermosetting. Bakelite has dark
brown color. It is a good electrical insulator, so it is used in manufacturing some electric
instruments. It can withstand heat, so it is used in manufacturing ash trays.

Phenol can be detected by adding drops of iron III chloride to an aqueous solution of phenol.
This results in violet color. It can be detected by adding drops of bromine water to an aqueous
solution of phenol. This results in wite participate.

Carboxylic acids are the most acidic organic compounds. Functional group of the carboxylic
acid is the carboxyl group, its name is derived from being a combined group of two groups
which are the carbonyl group and the hydroxyl group. Caboxylic acids: a homologous series of
organic compounds, characterized by the presence of one or more carboxyl group, they are
derivatives of aliphatic and aromatic hydrocarbons.

The organic acids can be aliphatic or aromatic acids. The general formula for alihpatic acids is
R – COOH, where R is an alkyl group and can be replaced by a hydrogen atom. The general
formula for aromatic acids is Ar – COOH, where Ar is an aryl group.

Basicity of the acid: the number of carboxyl groups which are present in one molecule of the
organic acid. Organic acids are classified into monocarboxylic and dicarboxylic acids. Aliphatic
monocarboxylic acids are called fatty acids, because a large number of these acids are found in
fats and oils in the form of esters with glycerol. There are organic acids contain other functional
groups in addition to the carboxyl group. Hydroxy acids contain hydroxyl group in addition to
the carboxyl group. Amino acids contain amino group in addition to the carboxyl group.

Salicylic acid behaves as an acid or a phenol in chemical reactions. Because in some reactions it
reacts as an acid due to the presence of carboxyl group, and in other reactions it may react as a
phenol as well due to the presence of a hydroxyl group.

Carboxylic acids are usually named by the common names which are derived from the latin
names of the sources from which they were firstly prepared. For IUPAC nomenclature, the
name ends with the word acid preceded by the name of the alkane ending with -oic instead of -
e, to be alkanoic acid.

Vinegar (4% acetic acid) is prepared through the oxidation of dilute solution of ethyl alcohol by
the atmospheric oxygen in the presence of a certain type of bacteria known as vinegar bacteria.
Acetic acid is prepared in industry by the catalytic hydration of acetylene producing
acetaldehyde which is easily oxidized to form acetic acid.

Physical properties of aliphatic acids change gradually with increasing their molar masses, these
properties depend on three factors, which are polarity of the carboxyl group, hydrogen bonds
between acid molecules and those between acid molecules and water molecules, and number of
carbon atoms of the root chain.
The physical state and the odour of aliphatic acids change gradually with increasing their molar
masses. Water solubility of aliphatic acids decreases by increasing their molar masses. The
complete miscibility of the first four members with water is due to their polarity, and their
ability to form hydrogen bonds with water.

On comparing the boiling points of aliphatic acids with those of alcohols which have the same
number of carbon atoms or the same molar mass, it is found that the boiling point of the
carboxylic acid is always higher, because each molecule of the acid is linked to the other acid
molecule with two hydrogen bonds which provide stability for the acid higher than that of the
alcohol in which each two molecules are linked with one hydrogen bond.

Acetic acid reacts with metals that precede hydrogen in the electromotive series forming the
acid salt and hydrogen gas evolves. Acetic acid reacts with metal oxides forming the acid salt
and water. Acetic acid reacts with metal hydroxides forming the acid salt and water. Acetic acid
reacts with metal carbonates or bicarbonates forming the acid salt and water and carbon dioxide
gas evolves.

Aliphatic acids react with alcohols forming ester and water. Carboxylic acids are reduced by
hydrogen in the presence of a catalyst. This reaction is the reverse of the oxidation reaction of
primary alcohols to form carboxylic acids.
On adding acetic acid to sodium carbonate or bicarbonate, an effervescence takes place and
carbon dioxide gas evolves which turns clear limewater milky. Organic acids react with
alcohols forming esters which are characterized by their pleasant odours.

Benzoic acid is prepared by oxidation of toluene in the atmospheric air at 400°C in the presence
of vanadium pentoxide as a catalyst.

On comparing aromatic acids with aliphatic acids, it is found that aromatic acids are slightly
stronger acids than aliphatic acids, less soluble in water, and less volatile than them.

Aromatic acids react with metal hydroxides forming salt of the acid and water. Aromatic acids
react with alcohols forming esters and water. Concentrated sulphuric acid can’t be used as a
dehydrating agent in the esterification reaction of benzoic acid with ethanol because it reacts
with the benzene ring of the acid by substitution.

Formic acid is naturally secreted by ants to defend themselves. It is used in manufacturing dyes,
insecticides, perfumes, plastics, and drugs.

Pure acetic acid has a pungent odour, and is called glacial acetic acid, because it freezes in the
form of crystals at 16°C. Acetic acid is used as a starting material in the preparation of many
organic products such as: synthetic silk, dyes, insecticides, and nutritional additives. The diluted
solution of acetic acid is used as vinegar in houses.

Benzoic acid can not be absorbed in the human body, because it is sparingly soluble in water, so
to facilitate its absorption, it is converted into sodium or potassium salt to be soluble in water.
Sodium benzoate (0.1%) is used as a food preservative, because it prevents the growth of fungi
in food.

Citric acid is one of the tribasic acids found in citrus fruits, such as: lemon and orange. Citric
acid is added to the frozen fruits to retain their colour and taste. Citric acid is used in food
preservation because it decreases pH of the food, so it prevents the growth of bacteria in it.
Lactic acid is a hydroxy aliphatic acid. It is known as milk acid, as it is found in yogurt due to
the effect of the enzymes secreted by a certain type of bacteria on milk sugar. It is formed in
human muscles as a result of exerting hard effort, causing muscle contractions.

Ascorbic acid is known as vitamin C, which human body needs in small amounts, it is found in:
citrus fruits, fruits, and vegetables. Ascorbic acid decomposes by heat and the effect of air.
Deficiency of ascorbic acid in the human body leads to the deterioration of some biological
functions, and causes the scurvy disease Escarporn. which among its symptoms are: gum
bleeding and joint swelling.

Salicylic acid is one of hydroxy aromatic acids. It is used in elimination of skin warts and acne,
preparation of skin cosmetics, because it gives the skin softness and protects it from the rays of
sun, and preparation of drugs such as aspirin and Marookh oil.

Amino acids are amino derivatives of organic acids. The simplest member of amino acids is
glycine, it is formed by replacing a hydrogen atom in the methyl group present in acetic acid
molecule with an amino group. Amino acids which exist in nature are numerous, but only 20 of
them are found in natural proteins. Amino acids found in proteins are characterized by being
alpha amino acids in which the amino group is attached to the alpha carbon atom which is
directly attached to the carboxyl group. They act as monomers of natural proteins composition.

Esters are widely spread in nature, they are found in all plants and animal materials. They are
used either alone or mixed with natural products in making different fragrances and flavours.
Their general formula is R–COO–R. The two R groups can either be alkyl or aryl, similar or
different groups, and the R group of the prefix of the ester can be replaced by hydrogen atom.

The common name of any ester is composed of two parts. The first part is the name of the alkyl
group which is attached to the oxygen atom of the alcohol molecule. The second part is derived
from the common name of the acid by replacing the suffix –ic with the suffix –ate.
Ester name according to IUPAC is composed of two parts. The first part is the name of the alkyl
group attached to the oxygen atom of alcohol molecule. The second part is derived from IUPAC
name of the acid with replacing the suffix –ic with the suffix –ate.

Esters are prepared by reactions of carboxylic acids with alcohols. It is a necessity to use a
dehydrating agent in esterification reactions, like concentrated sulphuric acid and dry hydrogen
chloride gas. To eliminate produced water, consequently preventing the backward reaction and
increasing the rate of the forward reaction in this reversible reaction according to Le Chatelier's
principle.

Most of esters are liquids. Most of esters are characterized by pleasant odours, esters are
responsible for odours and flavours of fruits, flowers and essential oils. The gradual increase in
the molar masses of the carboxylic acids and the alcohols that are used in forming the esters
changes the physical properties of the esters from being pleasant smelling liquids to waxy
almost odourless solids. Beeswax is a high molar mass ester.

Boiling points of esters are much lower than those of carboxylic acids or alcohols with the same
molar masses, due to the absence of the polar hydroxyl group found in both carboxylic acids
and the alcohols which results in the absence of the hydrogen bonds among molecules.

Hydrolysis of an ester produces a carboxylic acid and an alcohol. It is the reverse of the
esterification reaction, hydrolysis of esters may take place in acidic or alkaline medium. Ester is
hydrolyzed in an acidic medium forming an organic acid and an alcohol. Ester is hydrolyzed by
heating in an alkaline medium forming organic acid salt and alcohol. Ammonolysis: the
reaction of ester with ammonia to form carboxylic acid amide and alcohol.
Esters are characterized by pleasant odours, this makes them very important as flavours in many
of food industries. Fatty acids are monocarboxylic aliphatic acids (saturated in fats and
unsaturated in oils) react with glycerol, forming esters. Organic acids forming fats and oils are
sometimes of one type, but mostly they are of different types. The carbon chains of these acids
may be long or short and saturated or unsaturated.

Fats and oils can be defined as esters produced from the reaction between fatty acids and
glycerol. Fat and oil molecules are called triglycerides, because each molecule of them is
formed from the reaction of one molecule of glycerol with three molecules of fatty acids.

The hydrolysis of fats and oils in an alkaline medium to form soap and glycerol is known as
saponification, because it represents the principal reaction for the preparation of each of soap
and glycerol in industry. Soap is a sodium salt of fatty acids. Detergent is a sodium salt of an
alkyl benzene sulphonic acid.

Esters act as monomers in the preparation of polyesters which are polymers produced from the
condensation of two monomers, one of them is a dibasic acid and the other is a dihydric
alcohol. The most famous polyester is dacron. Dacron polymer is produced from the reaction of
terephthalic acid with ethylene glycol.

The condensation process continues to proceed through attacking the hydroxyl group of the
alcohol end of the molecule by a carboxyl group of an acid molecule, attacking the carboxyl
group of the acid end of the molecule by a hydroxyl group of an alcohol molecule, and by
continuing the condensation process, a very long chain molecule is formed known as polyester.
Dacron is an inert nontoxic substance, so it is used in manufacturing substitute for the spoiled
arteries and artificial heart valves.

Esters are used as active ingredients in many drugs like marookh oil and aspirin. Salicylic acid
is used in the preparation of these two drugs, this acid contains the carboxyl group and the
hydroxyl group both in one molecule.
Marookh oil is prepared by the esterification reaction of salicylic acid with methanol. Marookh
oil is used as a topically applied oil to relieve rheumatic pain, where it is absorbed through the
skin.

Aspirin is prepared by the esterification reaction of salicylic acid with acetic acid. The active
substance in aspirin is salicylic acid, however, the addition of acetyl group to the acid decreases
its acidity effect, and it becomes tasteless. Aspirin is one of the most important drugs that is
used in relieving headache, antipyretic, and reducing heart crises possibilities, because it
decreases blood clotting.

Aspirin tablet should be crushed before swallowing or to be dissolved in water, because aspirin
is hydrolyzed in the stomach giving salicylic acid and acetic acid, these acids cause excitation
of stomach wall, and may cause stomach ulcer. Some kinds of aspirin are mixed with an alkali
like aluminum hydroxide, to neutralize salicylic acid and acetic acid effects that are produced
from the hydrolysis of aspirin.

There are two primary types of isomerism, which can be further categorized into different
subtypes. These primary types are structural isomerism, stereoisomerism, and conformational
isomers.

Structural isomer (constitutional isomer): an isomer in which two or more organic

compounds have the same molecular formulas but different structures. They have same
chemical properties and slightly different physical properties.

In position isomers, the positions of the functional groups or substituent atoms are different.
This isomerism involves the attachment of the functional groups to different carbon atoms in
the carbon chain. They have similar chemical properties and and different physical properties.
Functional Isomerism (functional group isomerism): the compounds that have the same
chemical formula but different functional groups attached to them. They have different
chemical and physical properties.

Stereoisomers: isomers that have the same connectivity and molecular formula in their atoms
but a different arrangement in three-dimensional space.

Geometric isomers (cis-trans isomers): isomers in which the order of atom bonding is the
same but the arrangement of atoms in space is different. These isomers can happen only for
alkenes and cycloalkane. Because they have restricted rotation. The double bond in an alkene is
not free to rotate because of the nature of the bond. Single covalent bonds can easily rotate.
What appears to be a different structure is not. Structures are the same.

Each carbon around the double bond should has different substitution. Once there are two
similar atoms or groups attached to one end of a double bond, there can’t be geometrical
isomerism.

The cis isomer (Z) has the two single hydrogen atoms on the same side of the molecule, while
the trans isomer (E) has them on opposite sides of the molecule. In cis ismoers, hgih priority
atoms or groups are on the same side of the double bond. In trans isomers, hgih priority atoms
or groups are on opposite sides of the double bond. The priority of the groups are defined for
the higher in molar mass. Trans isomers have more stability than cis isomers because they have
less steric repulsion.

Optical isomers: isomers that feature similar bonds but different spatial arrangements of atoms
forming non-superimposable mirror images. If all the attached groups to the central carbon
atom are different, then there is no plane of symmetry and the carbon atom is chiral. If all the
groups attached to the central carbon atom are not different, then there exists a plane of
symmetry and the carbon atom is achiral. The number of optical isomer for any compound is
2n, where n is the number of chiral center.
Enantiomers: a type of stereoisomers in which two molecules are a non-superimposable mirror
image of each other. Diastereomers: stereoisomers that are not mirror images. It occurs when
more than one chiral centre are present in a molecule.

In ordinary light, the oscillation is randomly oriented in an infinite number of planes. When
ordinary light is passed through a polarizer, all planes of oscillation are filtered out except one,
resulting in plane-polarized light. A beam of plane-polarized light, when passed through a
sample of a chiral compound, interacts with the compound in such a way that the angle of
oscillation will rotate. This property is called optical activity.

The specific rotation of a pure chiral compound is = , where is the observed

rotation, is the wavelength of light, T is the temperature in celicius, L is path length in
decimeters, and C is the concentration of the sample in grams per 100 mL.

If a compound rotates plane polarized light in the clockwise or right direction, it is said to
be dextrorotatory, while if it rotates light in the counterclockwise or left direction it
is levorotatory. Racemic mixture: a 50:50 mixture of two enantiomers. The mixture will have
no observable optical activity, because the two optical activities cancel each other out. Meso
compounds: achiral compounds that has multiple chiral centers. It is superimposed on its
mirror image and is optically inactive.