ORGANIC CHEMISTRY

Organic Chemistry
• Organic chemistry is the branch of chemistry in which
covalent carbon compounds and their reactions are studied.
• A wide variety of classes of compounds such as vitamins,
drugs, natural and synthetic fibres, as well as carbohydrates,
peptides, and fats consist of organic molecules.
Organic Chemistry
• Organic chemists determine the structures of organic
molecules, study their various reactions, and develop
procedures for the synthesis of organic substances.
• An organic compound is a compound that contains
carbon and, in nearly all cases, also contains hydrogen
in a covalently bonded structure.
• Other elements such as oxygen, nitrogen , sulphur and
chlorine are also present, but it is carbon that is the
key.
Organic Chemistry
• Carbon is able to form a large number of compounds
than all the other elements put together.
• This is because carbon forms four strong covalent
bonds with other carbon atoms or with other
elements, especially hydrogen.
• Carbon’s ability to link to itself to form chains and
rings, known as catenation, is one of the main reasons
for the vast number of organic compounds that exist.
• The simplest organic chemicals, called hydrocarbons,
contain only carbon and hydrogen atoms.
Classification of Organic Compounds
Homologous series:
• Organic compounds are classified into families of compounds
known as homologous series.
• The members of each homologous series possess certain
common features, which are described below
Types of homologous series
1. Alkanes
2. Alkenes
3. Arenes
4. Alkynes
5. Halogen alkanes
6. Alcohols (including primary, secondary and tertiary) and phenols,
aldehydes and ketones
7. Carboxylic acids and esters
8. Amines (primary only), amides and amino acids.
Properties of homologous series
1. Successive members of a homologous series differ by a – CH2 –
group. This means that the molecular mass increases by a fixed
amount as we go up a series.
2. Members of a homologous series can be represented by the same
general formula. Other homologous series are charecterised by the
presence of a particular functional group, for example the
homologous series of alcohols possess the functional group –OH–
3. Members of a homologous series show a gradation in the physical
properties. This is because the carbon chains become longer as we
go up a series.
4. Members of a series have similar chemical properties.
Nomenclature for organic compounds: IUPAC
system
• For over a hundred years chemists have recognised the need for a
specific set of rules for the naming of organic compounds.
• IUPAC names are logically based on the chemistry of the compounds,
and so give information about the functional groups present and the
size of the molecules.
Nomenclature for organic compounds: IUPAC
system
Rule 1: Identify the longest straight chain of carbon atoms.
• The longest chain of carbon atoms gives the stem of the name as
follows.
Number of carbon atoms Stem in IUPAC name Example of compound
in longest chain
1 meth- CH4, methane
2 eth- C2H6, ethane
3 prop- C3H8, propane
4 but- C4H10, butane
5 pent- C5H12, pentane
6 hex- C6H14, hexane
7 hept- C7H16, heptane
8 oct- C8H18, octane
Nomenclature for organic compounds: IUPAC
system
Rule 2: Identify the functional group
• The functional group usually determines the specific ending or suffix
to the name.
• The suffixes for some functional groups are shown below.
 Class Functional Name of functional Suffix in Example of compound General
group group IUPAC name formula
alkane - - -ane C2H6, ethane CnH2n+2
alkene ∖ ∕ alkenyl -ene 𝐻2 𝐶 = 𝐶𝐻2 , ethene CnH2n
∕𝐶 = 𝐶∖
alkyne −𝐶 ≡ 𝐶 − alkynyl -yne 𝐻𝐶 ≡ 𝐶𝐻 CnH2n-2
alcohol −𝑂𝐻 hydroxyl -anol 𝐶𝐻3 𝐶𝐻2 𝑂𝐻, ethanol CnH2n+1OH
aldehyde ⫽𝑂 aldehyde(carbonyl) -anal 𝐶2 𝐻5 𝐶𝐻𝑂, propanal R – CHO
−𝐶\𝐻
ketone /𝑅 carbonyl -anone 𝐶𝐻3 𝐶𝑂𝐶𝐻3 , propanone R – CO – R’
𝑂= 𝐶\𝑅′
carboxylic ⫽𝑂 carboxyl -anoic 𝐶𝐻3 𝐶𝑂𝑂𝐻, ethanoic acid CnH2n+1COOH
−𝐶\𝑂−𝐻
acid
ester ⫽𝑂 ester -anoate 𝐶2 𝐻5 𝐶𝑂𝑂𝐶𝐻3 , methyl propanoate R – COO – R’
−𝐶\𝑂−𝑅
amide O carboxyamide -anamide 𝐶2 𝐻5 𝐶𝑂𝑁𝐻2 , propanamide
C H
N
H
amine −𝑁𝐻2 amine -anamine 𝐶2 𝐻5 𝑁𝐻2 , ethanamine
arene phenyl -benzene 𝐶6 𝐻5 𝐶𝐻3 , methylbenzene

𝐶6 𝐻5−
 Nomenclature for organic compounds: IUPAC
system
Rule 3: Identify the side chains or substituent groups
• Side chains or functional groups in addition to the one used as the
suffix, are known as substituents and are given as the first part or
prefix of the name.

Class Functional Name of Prefix in IUPAC Example of compound

group functional group name
alkane - - methyl, ethyl, 𝐶𝐻3 𝐶𝐻 𝐶𝐻3 𝐶2 𝐻5 , 2 – methylbutane
propyl, etc. 𝐶𝐻 𝐶2 𝐻5 3 , 3 – ethylpentane
𝐶𝐻 𝐶3 𝐻7 3 , 4 – propylheptane
halogenoalkane - F , - Cl, - Br, halogeno flouro, chloro, 𝐶2 𝐻5 𝐶𝑙, chloroethane
-I bromo, iodo 𝐶𝐻3 𝐶𝐻𝐵𝑟𝐶𝐻3 , 2 - bromopropane
amine - NH2 amine amino 𝐶𝐻2 𝑁𝐻2 𝐶𝑂𝑂𝐻, 2 – aminoethanoic acid
Amines
• Some examples of amines are given in the table
below:

Compound formula
methylamine CH3 – NH2
ethylamine CH3 – CH2 – NH2
propylamine CH3 – CH2 – CH2 – NH2
butylamine CH3 – CH2 – CH2 – CH2 – NH2
HALOALKANES
Production of haloalkanes from
alkanes
 MANUFACTURE OF CHLOROALKANES FROM ALKANES

• Chloroalkanes can be made from alkanes in a reaction

known as a free radical substitution reaction.
• e.g. CH4 + C𝑙2 → CH3 Cl + HCl

• A substitution reaction is one in which one atom or group

of atoms on the organic molecule is directly replaced by
another.
MANUFACTURE OF CHLOROALKANES FROM ALKANES

• In this reaction the H atom on the alkane is replaced by

a Cl atom.
• Since all the carbon atoms in alkanes are attached to
four other atoms, it is not possible to add another
species to an alkane unless another species leaves.
• Thus addition reactions are not possible and alkanes
can undergo substitution reactions only.
• A free radical is a species which contains an unpaired
electron.
• Free radicals are very reactive species and will bond with
almost anything they come into contact with.
• In this reaction the free radical which starts the reaction
is a chlorine atom, formed when a chlorine molecule
breaks up in the presence of ultra-violet light:
• Free radicals are represented by a dot next to the atom
containing an unpaired electron.
• They are caused by homolytic fission of covalent
bonds.
• Homolytic fission is the breaking of a covalent bond in
such a way that one electron goes to each atom.
 Mechanism 1: free radical substitution
• Free radical substitution reactions proceed in three
stages: initiation, propagation and then termination.
1.Initiation
• Initiation is the production of free radicals by homolytic
fission of a covalent bond.
• Most bonds do not undergo homolytic fission under
normal conditions. Generally, UV light is required.
• UV
2.Propagation
• Propagation is the reaction of a free radical with a
molecule to produce another free radical.
• The reaction involves two propagation steps:
3.Termination
• Termination is the combination of two free radicals
to form a single molecule.
• Note that the Cl radicals are recycled during the
propagation steps, so the reaction only requires a very
small number of Cl-Cl bonds to undergo fission for the
reaction to proceed.
By-products in free radical substitution:
• Chloromethane is not generally the only organic product
of this reaction.
• Free radical reactions tend to result in a variety of
different products.
1.Different propagation steps
• The propagation steps can continue beyond the
formation of methane, and can result in the formation
of dichloromethane, trichloromethane or
tetrachloromethane:
•
• These further propagation steps are likely if excess
chlorine is used.
• If excess methane is used, then chloromethane is likely
to be the major product.
2.Different termination steps
• It also possible to get other products from alternative
termination steps:
•
• Thus when methane reacts with chlorine, a variety of
products are formed including chloromethane,
dichloromethane and ethane.
• In order to ensure that chloromethane is the major
product, it is important to use excess methane.