Professional Documents
Culture Documents
C=C
C C
H C Cl
H
-OH
H H
H C C O H
H H
H C C
H
H O H
H C C C H
H
H C C
H
H
O H
H C C
O C H
H
H C N
H
Page 1
Aliphatic:
Alicyclic:
Saturated:
Unsaturated: containing carbon-carbon double or triple bonds, and the bonds found in
benzene rings (aromatic compounds are unsaturated)
empirical formula :
molecular formula :
displayed formula :
H H H H H H
H C C C C C C H
H H H H H H
Page 2
structural formula :
To draw a structural formula, first identify the longest chain of carbon atoms. Then for each
carbon in the longest chain, write the C and then what is connected to it. If anything
connected consists of more than one atom, put it in brackets unless it is the last carbon in
the chain. e.g. for methyl propane the structural formula would be CH 3CH(CH3)CH3 and
for propane-1,3-diol the structural formula could be written as CH 2(OH)CH2CH2OH or
HO(CH2)3OH
skeletal formula
If unsure about drawing skeletal formulae, start with the displayed formula. Remove all C
atoms, make the chain a zig-zag so that you can see where one bond ends and the next
starts. Remove all C-H bonds and the H atoms on them, but leave any other groups
containing H atoms such as OH. Look at examples carefully to see how they work.
Naming organic molecules
IUPAC nomenclature is standardised to precisely describe the structure of molecules
Basic rules apply:
1:
stem of the name comes from the longest carbon chain (which may be bent !)
methane
CH4
hexane
C6H14
ethane
C2H6
heptane
C7H16
propane
C3H8
octane
C8H18
butane
C4H10
nonane
C9H20
pentane
C5H12
decane
C10H22
2:
H
H
methyl-,
propyl-
H H
H H H
H C
H C C
H C C C
H H
H H H
H
C
ethyl-,
H H H H H
H H H H H H H
H C C C C C C C H
H H
H H H H
H C H
H C H
H H H H H H H
H C C C C C C C H
H H H
H H H
H C H
H
Page 3
ii)
iii)
3:
If we have more than one of the same side group we use a di-, tri- etc. prefix and
position numbers in the form 2,3- where needed
e.g. 2,3-dimethylhexane
2,2,4-trimethylpentane
H
H C H
H C H
H C H
H H H H
H C C C C C C H
H H
H H H
H
H C
H
C
C H
H C H
H C H
iv)
4:
If different alkyl groups are present they are named in alphabetical order
H
e.g. 3-ethyl-2-methylpentane
H C H
H
H C
C H
H C H
H C H
H
5:
If the carbon skeleton forms a ring rather than a chain we use a cyclo- prefix
e.g. cyclopentane,
cyclohexane
H
H H
H
H
H H
H
C
H C
C H
H
H C
C H
C
H
H
H H
NOTE: when writing structural formulae for rings we need to show that
they are not chains, so the formula becomes semi-displayed e.g. for
cyclohexane we might write:
H2C
H2C
H2
C
C
H2
CH2
CH2
Alkenes use the same stem, followed by an -ene ending. If the position of the C=C
is ambiguous, an position number is used, referring to the carbon in the chain
where the double bond starts
Page 4
e.g.
but-2-ene
CH3CH=CHCH3
propene
H
H
H C
C H
H
C C
H
H
H
H H
C C C H
H
if we have more than one C=C then the name ends with diene or triene etc. and
we need numbers to show where the double bonds are.
e.g. buta-1,3-diene
7:
C C
H
H
C C
H
H
bromoethane,
1,1,1-trifluoroethane
H H H H
H H
H C C
1-chlorobutane,
Br
H H
H C C C C H
Cl H H H
Check your
understanding:
vi)
Name the isomers of dibromopropane. (It may help to draw them first).
8:
propan-1-ol,
H H H
H H H
H C C C H
H C C C H
O H H
H O H
If there is more than one OH group we have a diol or triol etc. and need
numbers to show where these groups go. We also include the "e" from the alkane
name, which we didn't do when only one OH group was present.
e.g.
H H H
ethane-1,1-diol
propane-1,2,3-triol.
O H
H C C C HH C C H
9:
O O O
O H
H H H
propanone,
pentan-3-one
Page 5
H H O H H
H C C C C C H
H H
10:
H H
H O H
H C C C H
H
Aldehyde (-al endings) and carboxylic acid (-anoic acid endings) functional groups
can only occur on the end of a carbon chain, so they do not need a number. There
is only one possible butanoic acid, or butanal. The number of carbon atoms for the
stem- name includes the carbon atom in the functional group. Numbering starts
from that C when needed to show the position of other functional groups.
e.g.
H H H
butanoic acid,
O
H C C C C
H H H
H H H
butanal
2-methylbutanal
H C C C C
O H
H H H
ISOMERS
1) STRUCTURAL ISOMERS
Defined as having the same molecular formula but different structural formulae. We are
familiar with the straight chain alkanes, but alkanes can also be branched so there can be
several different structures.
Check your understanding:
vii) Which is the shortest chain-length alkane to have structural isomers?
2) STEREOISOMERS
Defined as having the same structural formulae but with a different arrangement in space
(i.e. it can't just be rotated to make them the same)
e.g. but-2-ene has two
stereoisomers
These are not the same because there is no free rotation around the double bond.
E/Z ISOMERISM
This is a form of stereoisomerism that we see with alkenes. Because the C=C bond cannot
twist round (we say it has restricted rotation), when we have different groups attached to
each carbon atom there are two ways in which they can be attached.
e.g. Z-but-2-ene
E-
but-2-ene
Cahn-Ingold-Prelog (CIP) rules determine which is the Zand which is the Eisomer. We will examine these rules further when we study the alkene homologous series.
Page 6
CIS-TRANS ISOMERISM
This is a special case of E/Z isomerism in which one of the groups on each C in the C=C is
the same. The cis- isomer has these on the same side, and the trans- isomer has them on
opposite sides across the double bond
e.g. cis-1,2-dichloroethene
C C
C C
H
Cl
trans-1,2-dichloroethene
Cl
Cl
Cl
H x
BrH
xx
xx
Homolytic fission:
When we break the H-Br bond each element can take one of the electrons from the bond.
Each element now has a single unpaired electron. Atoms or groups of atoms with
unpaired electrons are known as RADICALS. Breaking in this way is known as homolytic
fission.
If a bond is broken homolytically, the energy to do this is
xx
usually provided by ultraviolet light or high temperature
xx
BrH
H
x
xx
Page 7
Unpaired electrons are represented by a single dot. As an example, the homolytic fission
of chloromethane to form a methyl free radical and a chlorine free radical may be
represented as follows:
CH3-Cl
CH3 + Cl
Heterolytic Fission:
Alternately the bond may be broken so that one element takes both the covalent bond
electrons, hence forming ions. This is heterolytic fission. The more electronegative
element is the one which takes both the electrons.
xx
+
H
BrH
xx
xx
The movement of two electrons from the bond to the same atom is shown using a curly
arrow. For example, the heterolytic fission of bromomethane to form a positive methyl ion
and a bromide ion may be represented as:
H3C - Br CH3+ + :Br
Note: Care with curly arrows. Must come from the bond and go to the atom.
Note: Two dots may be used to show an unbonded (lone) electron pair
-
Page 8
2-methylpentane,
2,2-dimethylbutane,
3-methylpentane,
2,3-
dimethylbutane
vi)
vii)
viii) Draw all the isomers of C4H8 you can think of. Which can have cis-trans isomers ?
but-1-ene; no cis- trans- isomers becuase 2 x H on the first C
but-2-ene; yes, has cis- and trans- isomers
Page 9
methylpropene
cyclobutane
ix) Draw skeletal
formulae of:
cis-hex-3-ene
trans-hex-3-ene
Page 10