Functional Groups and

Reaction Mechanisms
 Classes of carbon and Hydrogen
• Primary carbon : CH3-CH2-CH3
• Secondary carbon : CH3-CH2-CH3
• Tertiary carbon : (CH3)2-CH-CH3
• Hydrogens are also referred to as 1º, 2º or 3º
according to the type of carbon they are bonded
to.
Homologous Series
A homologous series is a group of compounds which have the same
functional group. Eg alkanes or alcohols

Characteristics of a Homologous Series

● Members contain the same functional group
● Members have similar chemical properties
● Members show a gradation of physical properties
● Successive members differ by CH2 formula units or 14 mass units
 Functional Groups
A functional group is an atom or group of atoms
which take part in chemical reaction.

● The functional groups in a compound determine its

chemical reactivity.
R-Fg
R is the unreactive hydrocarbon section
Fg is the functional group
Important Functional Groups in Organic Compounds
Important Functional Groups in Organic Compounds
 Alcohols
● The alcohol functional group consists of a carbon bonded to
an –OH group.

● Alcohols are named by replacing the –ane at the

end of the parent hydrocarbon name with the
suffix –anol.
● Alcohols have high melting and boiling points.
Why?
 Haloalkanes
● Haloalkanes or alkyl halides contain a halogen atom bonded
to carbon.

● Haloalkanes are named by identifying the halogen

with a prefix on the hydrocarbon name. The C
bearing the halogen must be numbered.
 Amines
● The amine functional group contains a N atom.

● The systematic name for an amine is formed by

dropping the final –e of the alkane and adding
the suffix –amine.
● Common names that use the name of the alkyl group
followed by the suffix –amine are also widely used.
 Alkenes
● Alkenes contain the C=C double bond:

● Alkenes typically undergo addition reactions.

● The systematic name for an alkene is formed

by dropping the final –ane of the alkane and
adding the suffix –ene.
 Aldehydes and Ketones
● Aldehydes and ketones both contain the carbonyl
group, C=O.
R and R′ indicate
hydrocarbon groups.

● Aldehydes are named by replacing the final –ane of the

alkane name with the suffix –anal.
● Ketones have the suffix –one and the position of the
carbonyl must be indicated.
 Carboxylic Acids
● Carboxylic acids contain the functional group –COOH, or

● Carboxylic acids are named by replacing the –

ane of the alkane with the suffix –anoic acid.

● Carboxylic acids are weak acids in water, and react

with strong bases:
 Esters
● The ester group is formed by the reaction of an alcohol and a
carboxylic acid.

● Esterification is a dehydration-condensation reaction.

● Ester groups occur commonly in lipids, which are
formed by the esterification of fatty acids.
 Amides
● An amide contains the functional group:

● Amides, like esters, can be hydrolyzed to give a carboxylic

acid and an amine.
● The peptide bond, which links amino acids in a protein, is
an amide group.
Bond Fission
Homolytic Bond Fission (Homolysis)
The breaking of the covalent bond such that the bonding
electrons are equally shared between the atoms in the bond.
Radicals are formed in the process.
Bond Fission
Heterolytic Bond Fission (Heterolysis)
The breaking of the covalent bond such that the bonding
electrons are unequally shared between the atoms in the bond.
Ions are formed in the process.
carbocation
Initiating Species
We will look at three species which
initiate reactions in organic chemistry:
● Radicals
● Electrophiles
● Nucleophiles
 RADICALS
• This is an atom or group of atoms that has an
unpaired electron.

• Radicals (sometimes called free radicals) are

highly reactive, and are intermediates in many
reactions of alkanes.

• They have the same number of protons as

electrons hence they are electrically neutral.
 ELECTROPHILE- electron deficient
• this is an atom or group of atoms that reacts
with electron rich centres in other molecules.

• Electrophiles possess either a positive charge,

an empty orbital in their valence shell or they
contain a polar bond producing an atom with
a partial positive charge.
.
 NUCLEOPHILES- electron rich
• this is an atom or group of atoms that reacts
with electron deficient centres in other
molecules.

• Nucleophiles possess lone pairs of

electrons and many are anions
.
The Inductive Effect
This is the polarizing effect of a covalent
bond i.e, a process whereby electrons are
pulled along a bond to make it polar.

OR

The effect on electron density in one

portion of a molecule due to electron-
withdrawing or electron-donating groups
elsewhere in the molecule.
 REACTION
MECHANISMS
Reaction Mechanisms
● These show the stepwise process by which an overall
reaction takes place. It shows the sequence of bond
breaking and formation.

● The name of the mechanism gives the initiating species

and the reaction type. Eg Electrophilic Addition

● Reaction Types to be explored include: Addition,

Substitution, Oxidation, Reduction, Elimination,
Hydrolysis,
 Substituition

This is a reaction
which one atom
or group
replaces another
 Addition
This is a reaction which
an organic molecule
(usually with a double
bond) react with another
molecule to give only one
product.
 Hydrolysis

This is a reaction which

a molecule is split into
two by the action of
water.
 Condensation
This is the opposite of
hydrolysis. Two molecules
come together to form a
bigger molecule, with the
elimination of water
molecule or any other
small molecule.
 Elimination
Reaction

This is a reaction that

forms an alkene by the
removal of water from
an alcohol or HCl from a
chloroalkane.
Combustion Analysis
Combustion Analysis and Chemical
Formulae
A known amount of an organic compound is burned
completely [in excess oxygen] and the amount of
products determined.
For unit 2 we will carry this out using volume
measurements and apply Avogadro’s law to determine
the mole ratio of reactants and products and hence
deduce the molecular formula of the organic compound
Combustion Analysis Problem 1
20 cm3 of a gaseous hydrocarbon were mixed with 62
cm3 (an excess) of oxygen. The mixture was exploded
and, after cooling to room temperature, the residual
volume of gas occupied 52 cm3. On adding concentrated
KOH the volume of the excess oxygen was 12 cm3.
Determine the molecular formula of the hydrocarbon
Combustion Analysis Problem 2
10 cm3 of a gaseous hydrocarbon were mixed with
33cm3 (an excess) of oxygen. The mixture was exploded
and, after cooling to room temperature, the residual
volume of gas occupied 28 cm3. On adding concentrated
KOH the volume of the residual gases decreased to 8
cm3.
Determine the molecular formula of the hydrocarbon
Combustion Analysis Problem 3
10 cm3 of a gaseous hydrocarbon were mixed
with 60 cm3 of oxygen. The mixture was
exploded and, after cooling to room
temperature, the residual volume of gas
occupied 45 cm3. On adding concentrated
NaOH the volume decreased to 15 cm3.
Determine the molecular formula of the
hydrocarbon.
Combustion Analysis Problem 4
20 cm3 of a gaseous hydrocarbon were mixed with
150cm3 of oxygen. The mixture was exploded and, after
cooling to room temperature, the residual volume of gas
occupied 100 cm3. On adding concentrated KOH the
volume decreased to 20 cm3.All measurements were
taken at the same temperature and pressure.

Determine the molecular formula of the hydrocarbon.