Homologous Functional Functional Example General name Name

series / class name group group name

alkane alkyl H H H H alkane butane
H C C C C H

H H H H

alkene C=C alkenyl H H H H alk-x-ene but-1-ene

H C C C C H (or x-alkene) (or 1-butene)
H H

alkynes C C alkynyl H H alk-x-yne but-1-yne

H C C C C H (or x-alkyne) (or 1-butyne)
H H

alcohol –OH hydroxyl H H H H alkan-x-ol propan-1-ol

H C C C O (or x-alkanol) (or 1-propanol)

H H H
H H H H H H
ether O ether O alkoxyalkane methoxyethane
C C C C
H C O C C HH C O C C H

H H H H H H
aldehyde O H H O alkanal propanal
C H C C C
H H
H H
carbonyl
ketone O H O H H H alkan-x-one pentan-2-one
C H C C C C C H (or x-alkanone) (or 2-pentanone)
C C
H H H H

carboxylic acid O carboxyl H H O alkanoic acid propanoic acid

C
H C C C
O H
H H O H

halogenoalkane –X halo (chloro, H Br H H x-haloalkane 2-bromobutane

X = Cl/Br/I bromo, iodo) H C C C C H

H H H H
amine –NH2 amino H H H H alkylamine or propylamine
–NHR H C C C N x-aminoalkane or or
–NR2 alkan-x-amine 1-aminopropane or
H H H H
(or x-alkanamine) propan-1-amine
(or 1-propanamine)
ester O ester O H H alkyl alkanoate methyl propanoate
H
C C C C H
C O H C O
H H
H

a –C N nitrile H H alkanenitrile propanenitrile

H C C C N (C of C N
included in chain)
H H

amide O carboxamide H H O alkanamide propanamide

C H C C C
NH2 H H NH2

Table 10.2  Functional groups that you are likely to meet. ‘R’ can be used to represent an alkyl group – so a general carboxylic acid may be
represented as ‘RCOOH’ and an aldehyde as ‘RCHO’. ‘R’ is occasionally also used to represent a phenyl group (–C6H5).

10 ORGANIC CHEMISTRY 425

 Summary
carbon compounds, specifically
containing a C–H bond
aromatic compounds –
contain a benzene ring
undergoes electrophilic
substitution
HL
nitration of benzene
occurs with conc.
HNO3 and conc. H2SO4
isomers – compounds with
the same molecular formula
Structural isomers have the
same molecular formula but
different structural formulas.
Branched-chain isomers have
lower boiling points than
straight-chain isomers.
have different physical
properties; may
also have different cis = same side
chemical properties trans = opposite sides
E/Z notation may also
be used
π component of double
bond prevents rotation of
groups around the C=C bond
For isomerism to exist
there must be two different
groups on both sides of the
double bond.
ORGANIC hydrocarbons – organic
COMPOUNDS compounds that contain only
C and H
named according to the IUPAC system
To HOMOLOGOUS names based around the longest
SERIES on next page continuous carbon chain
HL conformational isomers can
be interconverted by rotation
about a sigma bond
contain at least one
carbon atom that has four
different groups attached
Stereoisomers have the same – a chiral centre
structural formula but different
arrangements of groups in space.
configurational Optical isomers are non- do not have a plane
isomers superimposable mirror of symmetry
images of each other.
cis–trans isomers have groups
arranged differently around a
double bond or ring. distinguished
using a
polarimeter
enantiomers are mirror
images of each other,
diastereomers are not
mirror images
Individual optical isomers racemic mixture –
are enantiomers. equimolar mixture of
two enantiomers
ring structure in cyclic
compounds prevents
rotation around bonds identical chemical identical physical
properties, except has no effect on
properties except
rotate plane of plane- plane-polarised light
when they react
with something polarised light in
For isomerism to exist else that is chiral. opposite directions
there must be two
different groups on at light that vibrates in
least two carbon atoms. one plane only
10 ORGANIC CHEMISTRY 505
 Summary – continued
boiling point increases as
chain length increases
members of a series have
similar chemical properties
complete incomplete
products: CO2, H2O products: CO, C, H2O
combustion
CnH2n+2 alkanes –
hydrocarbons
with only
single bonds
hydrogenation –
H2 is added, forms
an alkane
react with halogens
in presence of
sunlight or UV light
through free radical
substitution
Cl2 splits into
chlorine free radicals.
homolytic fission –
each atom gets
one electron from
the bond that splits
506
HOMOLOGOUS SERIES functional group – atom or group of
– series of compounds with the atoms that gives an organic molecule
same functional group, in which its characteristic chemical properties
each member differs from the
next by a –CH2– group.
position
primary – group secondary – group tertiary – group
attached to carbon attached to carbon attached to carbon
that is attached to that is attached to two that is attached to
one other carbon other carbons three other carbons
CnH2n for alkenes – contain CnH2n+2O alcohols – contain esterification –
compounds with one or more C=C a hydroxyl group: a carboxylic acid
one double bond bonds –OH and an alcohol join
to form an ester
are unsaturated
with Cr2O72−/H+ Primary and secondary
decolorise colour change from alcohols can be oxidised using
addition reaction orange to green acidified K2Cr2O7 or KMnO4.
bromine water – molecule X–Y is
added either side with MnO4–/H+
HL of a C=C bond
electrophilic addition colour change from
mechanism purple to colourless
A primary alcohol is Secondary alcohols are
oxidised first to an oxidised to ketones.
aldehyde and then to a
hydration – H2O addition carboxylic acid CnH2nO2.
is added, forms polymerisation – HL
an alcohol alkene monomers ketones can
join together in be reduced to
polymer chain secondary alcohols
Aldehydes and ketones are
substitution – an
HL carbonyl compounds –
atom or group is Aldehydes and carboxylic they contain a C=O group.
replaced by another acids can be reduced to
atom or group primary alcohols. HL
steric effects prevent more stable
SN2 mechanism carbocation
Nucleophile – molecule
or negative ion with a lone
pair of electrons which is rate not affected
free radical – a attracted to regions of low by nature or faster with
species with an electron density. concentration protic polar
unpaired electron
of nucleophile solvents
tertiary
The free radicals Undergo nucleophilic SN1 mechanism halogenoalkane
react with the alkane substitution. The two steps
secondary
molecules to form nucleophile replaces
halogenoalkane
halogenoalkanes. the halogen. SN2 mechanism
one step primary
halogenoalkane
contains a halogen
atom as functional faster with
group aprotic polar
solvents
reactions rate:
R–I > R–Br > R–Cl > R–F faster with ions than stereospecific
with neutral nucleophiles