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IUPAC nomenclature

Dr Margaret A.L. Blackie

This very brief draft document is intended to help to clarify some of the confusion which
currently around the area of IUPAC nomenclature. A fuller outline will be included in our
Organic Chemistry notes. If there is anything I have omitted (or any errors!) please let René
Toerien know.

Terms in italics are discussed in full below

1. Identify principal functional group

2. Identify longest continuous carbon chain or ring containing principal functional group –
this is the parent

3. Number chain to give principal functional group lowest possible locant (i.e. locating
number)

4. Identify substituents and position of attachment to main chain or ring

5. Use replicating prefixes (di-, tri-, tetra-) according to the number of identical
substituents attached to the main chain

6. List substituents in alphabetical order preceded by locant: eg 3 –methyl… (do not


alphabetise di-, tri-, tetra- etc)

7. If both groups on same C atom, repeat the number separated by a comma

[locant] [prefix] [parent] [suffix]

numbers indicating identify identifies the size identifies the principal


where substituents substituents – of the main chain functional group and
are located on the atoms or groups or ring therefore the class to which
main chain attached to main the molecule belongs. A
chain locant is needed if the PFG
is not necessarily at Carbon-
1

Principle Functional Group:

The principle functional group is the most important functional group in the molecule. It will
establish the suffix of the name and will establish the numbering of the molecule. In the
table below the functional groups are arranged from highest to lowest priority. The functional
group with the higher priority will be the parent. So a carboxylic acid will always provide the
suffix. Some principle functional groups will always be at carbon 1 e.g. carboxylic acid, ester,
amide, aldehyde, when this is the case, it is not necessary to give a locant between the
parent and the suffix. In all other cases, unless there is only one possible position for the
functional group (usually limited to 1, 2, sometimes 3 and very occasionally 4 carbon atoms)
it is necessary to give a locant. For example, propanone and butanone are correct, but
pentanone is not. Pentan-2-one or pentan-3-one are possible, so the locant associated with
the suffix is necessary.

When you have a principle functional group which necessarily will be in position 1 –
aldehyde, carboxylic acid etc. It is redundant to give the locant, so it is technically not
correct to give the locant. For example, propan-1-al (or 1-propanal) will not be correct. The
correct name is propanal.

Subsituent:

A substituent is general term meaning any functional group present in the molecule, or any
alkyl branches on the longest continuous carbon chain. The term substituent normally does
not include the principle functional group. In the name of the molecule substituents normally
refer to those elements which are given as prefixes.

General name General structure Name when Name when


suffix (i.e. when prefix (i.e.
PFG) substituent)
Carboxylic acid O -oic acid carboxy
C
R OH

Carboxylic ester O -oate alkoxycarbonyl


C
R OR'

Amide O -amide
C
R NH2

Aldehyde O -al oxo


C
R H

Ketone O -one oxo


C
R R'

Alcohol R OH -ol hydroxy

Amine R NH2 -amine amino

Alkene R R' -ene


C C
R'' R'''

Alkyne R C C R' -yne


Note: R is usually used to denote any alkyl group. R’ also means any alkyl group which may
or may not be the same as R. (R’’ is any alkyl group which may or may not be the same as R
and/or R’ etc.) The use of R, R1, R2 etc is also accepted.

Longest Continuous Carbon Chain:

This is the longest possible chain of carbon atoms (the chain may be straight or bent) – no
heteroatoms should be considered. A heteroatom is any atom other than carbon or
hydrogen.

If there are two possible choices for the longest continuous carbon chain – the more
substituted chain is chosen as the parent i.e. the chain which has more substituents.

Locant:

Basically means the number given to a particular position. The word is similar to location,
and the numbers are used to indicate the exact location of a principle functional group or
subsituent in a molecule.

Once the longest continuous carbon chain has been identified, it numbered to give the
principle functional group the lowest possible locant. However, in the case of alkanes where
there is no principle functional group number the substituents to give the lowest locant to
the first substituent. If this makes no difference, apply the rule to the second subsituent etc.
If there is still no obvious choice, the lower locant will be given according to alphabetical
order of the first substituents. Again if the first substituents are identical, the process is
repeated with second substituents etc. until a point of difference is reached. In alkenes and
alkynes, the double bond is considered the principle group and the compound is named to
give the lowest possible locant to the multiple bond. If there is no difference in the position
of the bond if named from both sides, then the rules for numbering subsituents applies. In
the case of an enyne (a compound with a double bond and a triple bond) the double bond
has a higher priority, so the compound is named to give the double bond the lowest possible
locant.

Two important guidelines

1. Avoid ambiguity: If the name you have generated is ambiguous is incorrect. That is to
say, if you can draw more than one constitutional isomer from your name it is
ambiguous. A correct name will only ever apply to a single structure.

2. Minimise redundancy: If the position of a functional group is implied by the nature of


the functional group it is not necessary to give it a locant.

Example 1: butene is an ambiguous name. We can draw two different constitutional


isomers from that name:
H2 4 H2 4
C CH3 C CH3
H2C C 3 H3C C3
H2 1 H
1

But -1-ene and but-2-ene are two different molecules. In this case, the locant is
important.

2H 4 2H 4 4
C CH3 C CH3 2H
C
2
CH2
H2C C 3 H3C C H3C C
H2 1 H3 H 3
1 1
Incorrect

If asked to draw all the constitutional isomers of butene, students may be tempted to
draw ‘but-3-ene’. Notice though that ‘but-3-ene’ is simply but-1-ene drawn in a different
way.

Example 2: propene is unambiguous. In ‘prop-1-ene’, the ‘1’ is redundant (i.e. not


necessary).

2H
C 2 H
C
H2C CH3 H3C CH2
1 3 3 1

Following rule 3 above, both molecules are numbered in such a way that the double bond
starts at position 1. There is no such thing as ‘prop-2-ene’. Propene is therefore a more
correct name than prop-1-ene.

When you have a principle functional group which necessarily will be in position 1 –
aldehyde, carboxylic acid etc. It is redundant to give the locant, so it is technically not
correct to give the locant. For example, propan-1-al (or 1-propanal) will not be correct.
The correct name is propanal.

Note the difference between the two paragraphs above - because the locant of the
alkene is not defined by the nature of the functional group using the name prop-1-ene is
still acceptable. The 1 is only redundant in the case of propene and ethene – all longer
chain alkene will require a locant. In the case of other principle functional groups which
necessarily take position 1 – there is no ambiguity and the use of a locant is always
superfluous.

Common names and IUPAC names

One of the principle confusions around nomenclature is the fact that common names are
still accepted. So whilst the IUPAC name is ethanoic acid for example, the name acetic
acid is still commonly used and is accepted as being unambiguous. If asked for the name
of the molecule CH3COOH – both acetic acid and ethanoic acid are acceptable answers.
However, if asked for the systematic IUPAC name of the same molecule the correct
answer is ethanoic acid.

Another problem is that organic chemistry is, at least partly, a spoken language. This
means that names that are easier to say have also been retained. For example, 1-butene
is easier to say than but-1-ene or 1-propanol is easier to say than propan-1-ol. According
to IUPAC rules, the locant associated with the suffix should come immediately prior to
the suffix i.e. but-1-ene, not 1-butene. 1-butene then is the equivalent of slang. It is not
incorrect, the meaning is unambiguous, but it is not ‘grammatically’ correct and
shouldn’t be used in writing.

Examples: See Powerpoint presentation

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