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number of C atoms 1C 2C 3C 4C 5C 6C
H H H H
H H H
F Br
fluoro / chloro
halogenoalkane H C C C H 2-bromopropane
Cl I / bromo / iodo
H Br H
H H H
H H O
O
aldehyde * al H C C C H propanal
C H
H H
H H O H
O
ketone oxo one H C C C C H butanone
C
H H H
H O
O
carboxylic acid * oic acid H C C O H ethanoic acid
C O H
H
H H
H H H
H ethanamine
amine amino amine H C C N H
N H (ethylamine)
H H
H O
O
acyl chloride * oyl chloride H C C Cl ethanoyl chloride
C Cl
H
H O O H
O O
acid anhydride oic anhydride H C C O C C H ethanoic anhydride
C O C
H H
H H O H
O
ester oate H C C C O C H methyl propanoate
C O
H H H
H O H
O H
amide amide H C C N H ethanamide
C N H
H
* indicates this the C atom in this functional group is defined as carbon-1 in the chain
shading indicates that this prefix is only used if the suffix cannot be used
1 Longest C chain
• look at the molecule to find the longest C chain – if there is a functional group it must be the longest C
chain containing the functional group
• note that alkyl groups (e.g. methyl, ethyl, propyl) are not functional groups.
• number the longest C chain (that contains the functional group) from the end that gives the functional
group(s) the lowest numbers
• note that some functional groups (labelled * in the chart, e.g. aldehyde group) are carbon-1 in the chain by
definition (and do not need a number themselves therefore), and define which end the numbers start for
other groups
• note that we should only include numbers in names when they are necessary – but we usually only omit
numbers in the simplest molecules where it is obvious that no number is needed
• groups that come off the C chain are given a number to show which C atom they are on (if necessary)
• when we write the name, these groups are listed in alphabetical order
• if there are several groups that are the same, then the prefix di (for two the same), tri (for three the same),
tetra (for four the same), etc are added first (note that the prefix di/tri/tetra/etc is ignored when we work out
alphabetical order)
Note
H H H C H
H H
H
H H C H H
H H
H
H C C C C C H
H H H C H
H H
H
CH3 CH C CH2 CH3 If the chain is counted from the left end, then we
have 2-methyl, 3-ethyl and 3-methyl. If it is
numbered from the right we have 3-methyl, 3-ethyl
CH3
and 4-methyl. We get lower numbers if we number
from the left end.
Displayed formula
5 The groups are listed in alphabetical order, but we
H
H
H
ignore the di of the dimethyl. Therefore, ethyl comes
before dimethyl alphabetically.
H H
H H 3-ethyl-2,3-dimethylpentane
H
H C C H H
H C C C C C H
H H C H H
H H
H
CH3
If the chain is counted from the left end, then we
have 4-methyl. If it is numbered from the bottom we
Displayed formula have 3-methyl. We get the lower number if we
number from the bottom.
6
H H H H H 3-methylhextane
H C C C C C H
H H H C H
H H
C
H H
H
Name
CH3 CH3
8
CH2
CH3
Name
H C H
H H
H
H H H H H H 3-ethyl-5-methylhex-1-ene
CH2 CH CH3
12
Name
CH3
13
CH3 C CH CH3
Name
CH3 CH2 F There is only one functional group (methyl and ethyl
are not functional groups), and to give the F group
F
the lowest number it is numbered from the right end,
CH3 CH CH CH2 CH CH3
so it is 2-fluoro.
There is a methyl group on carbon-5, so it is
Displayed formula 5-methyl, and an ethyl group on carbon-4, so it is
14 H
4-ethyl.
H H In alphabetical order, it goes 4-ethyl then 2-fluoro
C and then 5-methyl.
H H
H H C H F H 4-ethyl-2-fluoro-5-methylhexane
H C C C C C C H
H H H H H
H H
H
CH3 CH2 Br
15
Name
Cl I
CH3 CH C CH3
16
I
Name
Br Cl CH3
CH3 C CH C CH3
17
Br Br
Name
Cl
18
CH3 CH CH CH2
Name
H C H H 3-methylbutan-2-ol
H C C C C H
H H O H
CH3 CH3
OH
Name
CH3
CH2 CH CH CH CH3
22
OH
Name
CH3
CH OH
23
CH3 CH2 CH2 CH CH2 CH3
Name
H H H
25
CH3 CH2 C H
Name
CH3 O
CH3 C CH CH2 C H
26
Br Br
Name
KETONES
28
CH3 CH2 C CH3
Name
H H O propanoic acid
H C C C O H
H H
CH3 C CH C OH
30
CH3 CH2
CH3
Name
NITRILES
H H H 4-bromobutanenitrile
CH3
32
CH3 CH CH2 CH2 CN
Name
AMINES
H H H
The group bonded to the N is an ethyl group.
It can be thought of as ethane but with an amine
H C C N H group in place of an H.
ethanamine
H H
ethylamine or aminoethane also used
CH3 CH2 CH NH2 NH2 This molecule can be thought of as butane with an
amine group on carbon-2. The amine group does
CH3 need a number because it could also be on
carbon-1.
Displayed formula butan-2-amine
34
H H H H
1-methylpropylamine or 2-aminobutane also used
H C C C N H
H H C
H H
H
H C C C N C H
N-methylpropan-1-amine
N-methylpropylamine also used
H H H H
H C N C H
H H
CH3
37
CH3 CH2 CH2 CH NH2
Name
CH3 CH CH NH CH3
38 CH3 CH3
Name
CH3
39
CH3 CH2 CH2 N CH3
Name
H C C C C Cl
H H H
41
CH3 CH2 C Cl
Name
ACID ANHYDRIDE
H C C C O C C C H
propanoic anhydride
H H H H
O O
43 CH3 C O C CH3
Name
ESTERS
O
O There are two parts to the name. Esters can be
thought of as being similar to carboxylic acids but
with an alkyl group on the O instead of an H.
CH3 CH2 CH2 C O CH3
O
This ester could be thought of as propanoic acid with
44 a methyl group in place of the H on the O.
Displayed formula
The part of the molecule that is like propanoic acid
H H H O H without the H is propanoate. This propanoate has a
methyl group attached.
H C C C C O C H
methyl propanoate
H H H H
45
CH3 CH2 C O CH2 CH3
Name
46 H C O CH2 CH3
Name
AMIDES
H H O
H C C C N H
H H H
49
CH3 CH2 C NH CH3
Name
50
CH3 CH2 CH2 C NH2
Name
CYCLIC COMPOUNDS
Note - it is normal to draw skeletal (or sometimes displayed) formulas for cyclic compounds – it is quite hard to draw anything else
54
OH
55
Br Br
halogenoalkanes 2,3-dibromopentane
CH3 CH CH CH2 CH3
OH OH
alcohols propane-1,3-diol
CH2 CH2 CH2
O O
aldehydes butanedial
H C CH2 CH2 C H
O O
ketones pentane-2,4-dione
CH3 C CH2 C CH3
O O
carboxylic acids propanedioic acid
HO C CH2 C OH
O O
acyl chloride propanedioyl dichloride
Cl C CH2 C Cl
O O
amide propanediamide
H 2N C CH2 C NH2
• In terms of numbering the chain, there is an order of priorities with the highest priority groups taking the
lowest number – you are not generally expected to know this order as an A level student, but it is useful to
be aware of it – some common groups are shown here:
carboxylic acid > nitrile > aldehyde > ketone > alcohol > amine > alkene > halogenoalkane
• If there are two groups that have suffixes, then the lower priority group becomes a prefix.
59 O
Br O
60
CH3 CH CH C CH3
Br
CH3 CH3 In this molecule, the longest C chain that contains the functional
6 5 4 3 2 1 group has 6 C atoms (and so the name has hex in it.)
CH3 CH CH CH CH2 CH3
In order to give the functional group (iodo, I) the lowest number, the
I C chain is numbered from the right hand end. This makes it 3-iodo
rather than 4-iodo.
3-iodo-4,5-dimethylhexane There are also two methyl groups, on carbon-4 and carbon-5,
making it 4,5-dimethyl.
When writing the name, we put the 3-iodo before the 4,5-dimethyl
the as i comes before m in the alphabet (we ignore the di in the
dimethyl when doing this).
Note that the we would get a lower set of numbers if this was
numbered from the other end, but we have to number the C chain to
give the functional group the lowest number(s), and the only
functional group here is the iodo group (methyl and any other alkyl
groups are not functional groups).
CH3 O In this molecule, the longest C chain that contains the functional
group has 4 C atoms (and so the name has but in it.)
CH3 CH CH2 C H
4 3 2 1 The aldehyde group (CHO) is by definition carbon-1 and so the name
has al at the end (note that no number is needed as the C in an
aldehyde is on carbon-1 by definition). This means that the methyl
3-methylbutanal group is on carbon-3 and is 3-methyl.
CH3 In this molecule, the longest C chain that contains the functional
group has 6 C atoms (and so the name has hex in it.)
O CH2
There are two functional group (C=O and I). We number it from the
CH3 C CH CH CH2 CH3 end to give the ketone group the lowest number (as ketone groups
1 2 3 4 5 6 have higher priority than halo groups). Therefore we number it from
I the left making it 2-one and 3-iodo.
There is also one ethyl group on carbon-4, making it 4-ethyl.
4-ethyl-3-iodohexan-2-one
When writing the name, we put the 4-ethyl before the 3-iodo the as e
comes before i in the alphabet.
CH3 CH3 In this molecule, the longest C chain that contains the functional
6 5 4 3 2 1 group has 6 C atoms (and so the name has hex in it.)
CH3 C C CH CH CH3
There are two functional group (alkene C=C and bromo Br). We
CH3 Br number it from the end to give the alkene group the lowest number
(as alkene groups have higher priority than halo groups). Therefore
we number it from the right making it 2-ene and 4-bromo.
4-bromo-4,5,5-trimethylhex-2-ene
There are also three methyl groups, two on carbon-5 and one on
carbon-4, making it 4,5,5-trimethyl.
When writing the name, we put the 4-bromo before the
4,5,5-trimethyl the as b comes before m (ignore the tri) in the
alphabet.