IUPAC Nomenclature of Organic Chemistry
IUPAC Nomenclature of Organic Chemistry
The main idea of IUPAC nomenclature is that every compound has one and only one name, and every name
corresponds to only one structure of molecules (i.e. a one-one relationship), thereby reducing ambiguity.
For ordinary communication, to spare a tedious description, the official IUPAC naming recommendations are
not always followed in practice except when it is necessary to give a concise definition to a compound, or when
the IUPAC name is simpler (viz. ethanol against ethyl alcohol). Otherwise the common or trivial name may be
used, often derived from the source of the compound (See Sec 14. below)
Contents
[hide]
1 Basic principles
2 Alkanes
4 Functional groups
o 4.1 Alcohols
o 4.2 Halogens (Alkyl
Halides)
o 4.3 Ketones
o 4.4 Aldehydes
o 4.5 Carboxylic acids
o 4.6 Ethers
o 4.7 Esters
o 4.8 Amines and Amides
o 4.9 Cyclic compounds
names
o 6.1 Ketones
o 6.2 Aldehydes
7 Ions
o 7.1 Hydron
o 7.3 Cations and
substitution
8 See also
9 External links
10 References
[edit]Basic principles
In chemistry, a number of prefixes, suffixes and infixes are used to describe the type and position of functional
groups in the compound.
2. Identify the functional group, if any (If more than one, use the one with
highest precedence as shown here)
3. Identify the side-chains and number them. Side chains are the carbon
chains that are not in the parent chain, but are branched off from it.
If there is more than one of the same type of side-chain, add the prefix
(di-, tri-, etc.) before it. The numbers for that type of side chain will be
grouped in ascending order and written before the name of the side-
chain. If there are two side-chains with the same alpha carbon, the
number will be written twice. Example: 2,2,3-trimethyl...
4. Identify the remaining functional groups, if any, and name them by the
name of their ions (such as hydroxy for -OH, oxy for =O , oxyalkane for
O-R, etc.).
Different side-chains and functional groups will be grouped together
in alphabetical order. (The prefixes di-, tri-, etc. are not taken into
consideration for grouping alphabetically. For example, ethyl comes
before dihydroxy or dimethyl, as the "e" in "ethyl" precedes the "h" in
"dihydroxy" and the "m" in "dimethyl" alphabetically. The "di" is not
considered in either case). In the case of there being both side chains
and secondary functional groups, they should be written mixed together
in one group rather than in two separate groups.
5. Identify double/triple bonds. Number them with the number of the carbon
atom at the head of the bond (i.e. the carbon atom with the lesser number
that it is attached to). For example a double bond between carbon atoms
3 and 4 is numbered as 3-ene. Multiple bonds of one type (double/triple)
are named with a prefix (di-, tri-, etc.). If both types of bonds exist, then
use "ene" before "yne" e.g. "6 13 diene 19 yne". If all bonds are single,
use "ane" without any numbers or prefixes.
7. Add punctuation:
For simplicity, here is an image of the same molecule, where the hydrogens in the parent chain are removed
and the carbons are shown by their numbers:
2. The functional groups with the highest precedence are the two ketone
groups.
3. There are two double bonds: one between carbons 6 & 7, and one
between carbons 13 & 14. They will be called 6,13-diene. There is one
triple bond between carbon atoms 19 & 20. It will be called 19-yne
[edit]Alkanes
Straight-chain alkanes take the suffix "-ane" and are prefixed depending on the number of carbon atoms
in the chain, following standard rules. The first few are:
Numbe
r of
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 20 30
carbon
s
Prefix Meth Eth Prop But Pent Hex Hept Oct Non Dec Undec Dodec Tridec Tetradec Pentadec Eicos Triacont
For example, the simplest alkane is CH4 methane, and the nine-carbon alkane CH3(CH2)7CH3 is named
nonane. The names of the first four alkanes were derived from methanol, ether,propionic acid and butyric acid,
respectively. The rest are named with a Greek numeric prefix, with the exceptions of nonane which has
a Latin prefix, and undecane and tridecane which have mixed-language prefixes.
Cyclic alkanes are simply prefixed with "cyclo-", for example C 4H8 is cyclobutane and C6H12 is cyclohexane.
Branched alkanes are named as a straight-chain alkane with attached alkyl groups. They are prefixed with a
number indicating the carbon the group is attached to, counting from the end of the alkane chain. For example,
(CH3)2CHCH3, commonly known as isobutane, is treated as a propane chain with a methyl group bonded to the
middle (2) carbon, and given the systematic name 2-methylpropane. However, although the name 2-
methylpropane COULD be used, it is easier and more logical to call it simply methylpropane - the methyl group
could not possibly occur on any of the other carbon atoms (that would lengthen the chain and result in butane,
not propane) and therefore the use of the number "2" is not necessary.
If there is ambiguity in the position of the substituent, depending on which end of the alkane chain is counted as
"1", then numbering is chosen so that the smallest number is used. For example,
(CH3)2CHCH2CH3 (isopentane) is named 2-methylbutane, not 3-methylbutane.
If there are multiple side-branches of the same size alkyl group, their positions are separated by commas and
the group prefixed with di-, tri-, tetra-, etc., depending on the number of branches (e.g. C(CH 3)4 2,2-
dimethylpropane). If there are different groups, they are added in alphabetical order, separated by commas or
hyphens: 3-ethyl-4-methylhexane. The longest possible main alkane chain is used; therefore 3-ethyl-4-
methylhexane instead of 2,3-diethylpentane, even though these describe equivalent structures. The di-, tri- etc.
prefixes are ignored for the purpose of alphabetical ordering of side chains (e.g. 3-ethyl-2,4-dimethylpentane,
not 2,4-dimethyl-3-ethylpentane).
Alkenes are named for their parent alkane chain with the suffix "-ene" and an infixed number indicating the
position of the double-bonded carbon in the chain: CH2=CHCH2CH3 is but-1-ene. Multiple double bonds take
the form -diene, -triene, etc., with the size prefix of the chain taking an extra "a": CH 2=CHCH=CH2 is buta-1,3-
diene. Simple cis and trans isomers are indicated with a prefixed cis- or trans-:cis-but-2-ene, trans-but-2-ene.
More complex geometric isomerisations are described using the Cahn Ingold Prelog priority rules.
Alkynes are named using the same system, with the suffix "-yne" indicating a triple bond: ethyne (acetylene),
propyne (methylacetylene).
[edit]Functional groups
Alk is the prefix of the group (Meth, Eth, Prop, etc.)
R—x
Halogens Halo'alkane - Alkyl halide
(halogen)
Carboxylic
(Alk + 1)anoic acid Cycloalkanecarboxylic acid -
acids
Alk(1)yl Alk(2)yl
Ketones Alkanone -
ketone
[edit]Alcohols
Alcohols (R-OH) take the suffix "-ol" with an infix numerical bonding position: CH 3CH2CH2OH is propan-1-ol.
The suffixes -diol, -triol, -tetraol, etc., are used for multiple -OH groups: Ethylene glycol CH2OHCH2OH is
ethane-1,2-diol.
If higher precedence functional groups are present (see order of precedence, below), the prefix "hydroxy" is
used with the bonding position: CH3CHOHCOOH is 2-hydroxypropanoic acid.
Halogen functional groups are prefixed with the bonding position and take the form fluoro-, chloro-, bromo-,
iodo-, etc., depending on the halogen. Multiple groups are dichloro-, trichloro-, etc, and dissimilar groups are
ordered alphabetically as before. For example, CHCl3 (chloroform) is trichloromethane. The
anesthetic Halothane(CF3CHBrCl) is 1-bromo-1-chloro-2,2,2-trifluoroethane.
[edit]Ketones
In general ketones (R-CO-R) take the suffix "-one" (pronounced own, not won) with an infix position number:
CH3CH2CH2COCH3 is pentan-2-one. If a higher precedence suffix is in use, the prefix "oxo-" is
used: CH3CH2CH2COCH2CHO is 3-oxohexanal.
[edit]Aldehydes
Aldehydes (R-CHO) take the suffix "-al". If other functional groups are present, the chain is numbered such that
the aldehyde carbon is in the "1" position, unless functional groups of higher precedence are present.
If a prefix form is required, "oxo-" is used (as for ketones), with the position number indicating the end of a
chain: CHOCH2COOH is 3-oxopropanoic acid. If the carbon in the carbonyl group cannot be included in the
attached chain (for instance in the case of cyclic aldehydes), the prefix "formyl-" or the suffix "-carbaldehyde" is
used: C6H11CHO is cyclohexanecarbaldehyde. If a aldehyde is attached to a benzene and is the main
functional group, the suffix becomes benzaldehyde.
[edit]Carboxylic acids
Main article: Carboxylic acids
In general carboxylic acids are named with the suffix -oic acid (etymologically a back-formation from benzoic
acid). As for aldehydes, they take the "1" position on the parent chain, but do not have their position number
indicated. For example, CH3CH2CH2CH2COOH (valeric acid) is named pentanoic acid. For common carboxylic
acids some traditional names such as acetic acid are in such widespread use they are considered retained
IUPAC names, although "systematic" names such as ethanoic acid are also acceptable. For carboxylic acids
attached to a benzene ring such as Ph-COOH, these are named as benzoic acid or its derivatives.
If there are multiple carboxyl groups on the same parent chain, the suffix "-carboxylic acid" can be used (as
-dicarboxylic acid, -tricarboxylic acid, etc.). In these cases, the carbon in the carboxyl group does not count as
being part of the main alkane chain. The same is true for the prefix form, "carboxyl-". Citric acid is one example;
it is named 2-hydroxypropane- 1,2,3-tricarboxylic acid, rather than 2-carboxy, 2-hydroxypentanedioic acid.
[edit]Ethers
Ethers (R-O-R) consist of an oxygen atom between the two attached carbon chains. The shorter of the two
chains becomes the first part of the name with the -ane suffix changed to -oxy, and the longer alkane chain
become the suffix of the name of the ether. Thus CH 3OCH3 is methoxymethane, and
CH3OCH2CH3 is methoxyethane (notethoxymethane). If the oxygen is not attached to the end of the main
alkane chain, then the whole shorter alkyl-plus-ether group is treated as a side-chain and prefixed with its
bonding position on the main chain. Thus CH3OCH(CH3)2 is 2-methoxypropane.
[edit]Esters
Main article: Esters
Esters (R-CO-O-R') are named as alkyl derivatives of carboxylic acids. The alkyl (R') group is named first. The
R-CO-O part is then named as a separate word based on the carboxylic acid name, with the ending changed
from -oic acid to -oate. For example, CH3CH2CH2CH2COOCH3 is methyl pentanoate, and
(CH3)2CHCH2CH2COOCH2CH3 is ethyl 4-methylpentanoate. For esters such as ethyl
acetate (CH3COOCH2CH3),ethyl formate (HCOOCH2CH3) or dimethyl phthalate that are based on common
acids, IUPAC recommends use of these established names, called retained names. The -oate changes to -ate.
Some simple examples, named both ways, are shown in the figure above.
If the alkyl group is not attached at the end of the chain, the bond position to the ester group is infixed before "-
yl": CH3CH2CH(CH3)OOCCH2CH3 may be called but-2-yl propanoate or but-2-yl propionate.
For secondary amines (of the form R-NH-R), the longest carbon chain attached to the nitrogen atom becomes
the primary name of the amine; the other chain is prefixed as an alkyl group with location prefix given as an
italic N: CH3NHCH2CH3is N-methylethanamine. Tertiary amines (R-NR-R) are treated similarly:
CH3CH2N(CH3)CH2CH2CH3 is N-ethyl-N-methylpropanamine. Again, the substituent groups are ordered
alphabetically.
Amides (R-CO-NH2) take the suffix "-amide". There is no prefix form, and no location number is required since
they always terminate a carbon chain, e.g. CH3CONH2 (acetamide) is named ethanamide.
Secondary and tertiary amides are treated similarly to the case of amines: alkane chains bonded to the
nitrogen atom are treated as substituents with the location prefix N: HCON(CH3)2 is N,N-dimethylmethanamide.
[edit]Cyclic compounds
Cycloalkanes and aromatic compounds can be treated as the main parent chain of the compound, in which
case the position of substituents are numbered around the ring structure. For example, the three isomers
of xylene CH3C6H4CH3, commonly the ortho-, meta-, and para- forms, are 1,2-dimethylbenzene, 1,3-
dimethylbenzene, and 1,4-dimethylbenzene. The cyclic structures can also be treated as functional groups
themselves, in which case they take the prefix "cycloalkyl-" (e.g. "cyclohexyl-") or for benzene, "phenyl-".
The IUPAC nomenclature scheme becomes rapidly more elaborate for more complex cyclic structures, with
notation for compounds containing conjoined rings, and many common names such as phenol, furan, indole,
etc. being accepted as base names for compounds derived from them.
When compounds contain more than one functional group, the order of precedence determines which groups
are named with prefix or suffix forms. The highest precedence group takes the suffix, with all others taking the
prefix form. However, double and triple bonds only take suffix form (-en and -yn) and are used with other
suffixes.
Prefixed substituents are ordered alphabetically (excluding any modifiers such as di-, tri-, etc.), e.g.
chlorofluoromethane, not fluorochloromethane. If there are multiple functional groups of the same type, either
prefixed or suffixed, the position numbers are ordered numerically (thus ethane-1,2-diol, not ethane-2,1-diol.)
The N position indicator for amines and amides comes before "1", e.g. CH 3CH(CH3)CH2NH(CH3) is N,2-
dimethylpropanamine.
*Note: These suffixes, in which the carbon atom is counted as part of the preceding chain, are the most commonly used. See individual
Number of Prefix as in new Common name for Common name for Common name for
carbons system alcohol aldehyde acid
11 Undec
[edit]Ketones
Common names for ketones can be derived by naming the two alkyl or aryl groups bonded to the carbonyl
group as separate words followed by the word ketone.
Acetone
Acetophenone
Benzophenone
Diethyl ketone
The first three of the names shown above are still considered to be acceptable IUPAC names.
[edit]Aldehydes
The common name for an aldehyde is derived from the common name of the corresponding carboxylic acid by
dropping the word acid and changing the suffix from -ic or -oic to -aldehyde.
Formaldehyde
Acetaldehyde
[edit]Ions
The IUPAC nomenclature also provides rules for naming ions.
[edit]Hydron
Hydron is a generic term for hydrogen cation; protons, deuterons and tritons are all hydrons.
If the cationic center of the hydride is not a halogen, chalcogen or nitrogen-family element then the suffix "-ium"
is added to the name of the neutral hydride after dropping any final 'e'. H 5C+ is methanium, HO-(O+)-H2 is
dioxidanium (HO-OH is dioxidane), and H2N-(N+)-H3 is diazanium (H2N-NH2 is diazane).
The name of each substitution is prefixed to the hydride cation name. If many substitutions by the same
functional group occur, then the number is indicated by prefixing with "di-", "tri-" as with halogenation.
(CH3)3O+ is trimethyloxonium. CH3F3N+ is trifluoromethylammonium.
[edit]See also
[edit]External links
[edit]References
[hide]
v • d • e
Concepts in organic chemistry
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