Overview of Organic

Chemistry
By Kamila Singh
Introduction
 What is Organic Chemistry? - The chemistry of carbon compounds, excluding
carbonates, cyanides, carbides, cyanates and other carbon-containing ionic
compounds.
 All organic compounds contain carbon, nearly always bonded to itself and to
hydrogen, and often to other elements as well.
 Organic has a biological connotation, implying that it involves the chemistry
of living systems.
 Industrial importance of Organic Chemistry: polymers, pharmaceuticals and
insecticides.
 Huge variety of organic compounds: Over ten million estimated.
Unique properties of Carbon

 Tetravalent – forms 4 bonds due to 4 electrons in outer shell.

 Catenation – ability to bond with other carbon atoms to form straight chain,
branched chain and ring compounds.
 Hybridization – ability to mix and rearrange the 4 orbitals in the outer shell:
sp3 hybridization: 2s orbital + 3 2p orbitals = 4 sp3 hybrid orbitals (allows for
single bonds)
sp2 hybridization: 2s orbital + 3 2p orbitals = 3 sp2 hybrid orbitals + 1
unhybridized p orbital (allows for double bonds)
sp hybridization: 2s orbital + 3 2p orbitals = 2 sp hybrid orbitals + 2
unhybridized p orbital (allows for triple bonds)
Homologous Series – Group of organic
compounds with certain characteristics
 Same general formula – common relationship exists between numbers of
atoms, e.g. Cn H2n+2 (alkanes).
 Each member differs from its nearest neighbor by –CH2 or molecular mass of
14.
 Same functional group, e.g. Alcohols contain –OH group.
 Similar chemical properties – due to same functional group.
 Gradual change in physical properties down group – increase in melting and
boiling points as number of carbons increase.
Examples of homologous series

 Alkanes
 Alkenes
 Alkynes
 Alcohols
 Aldehydes
 Ketones
 Halogenoalkanes
 Carboxylic Acids
 Esters
 Aromatic compounds
Types of Formulae

 Empirical formula: the simplest whole number ratio of atoms in compound.

 Molecular formula: the actual number of each kind of atom in a molecule.
 Condensed formula: the placement of atoms in the molecule.
 Displayed formula: all the bonds are clearly shown in the molecule.
 Skeletal formula: only the carbons (points) and the bonds in between are
shown.
IUPAC Nomenclature

 Look for the longest unbranched chain in the molecule.

 Look for the branches/side groups attached to the main chain and locate
which C atoms they are attached to.
 Number the substituents.
Isomerism

 Structural isomers – chain isomers, positional isomers, functional group

isomers.
 Stereoisomers – geometric (cis – trans) isomers, optical isomers – chiral
carbon, enantiomers, racemic mixture.
Reactions and Mechanisms
 Free radical substitution (alkanes)
 Electrophilic addition (alkenes) – Markovnikov’s rule
 Oxidation and hydration of alkenes
 Oxidation and dehydration of alcohols
 Esterification and hydrolysis of esters
 Hydrolysis of halogenoalkanes
 Nucleophilic addition (carbonyl compounds)
 Halogenation and nitration of benzene
 Reactions of phenols.
 Polymerization: addition and condensation, including natural polymers such as
proteins and polysaccharides.