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For ordinary communication, to spare a tedious description, the ocial IUPAC naming recommendations are
not always followed in practice, except when it is necessary to give an unambiguous and absolute denition to
a compound, or when the IUPAC name is simpler (e.g.
ethanol instead of ethyl alcohol). Otherwise the common or trivial name may be used, often derived from the
source of the compound (see below). In addition, very
long names may be less concise than structural formulae.
Basic principles
(a) It should have the maximum number of substituents of the sux functional group. By
sux, it is meant that the parent functional
group should have a sux, unlike halogen substituents. If more than one functional group
is present, the one with highest precedence
should be used.
(c) It should have the maximum number of single table ( di - 2 tri - 3 tetra - 4 then as for the number of
carbons below with 'a' added)
bonds.
The numbers for that type of side chain will be grouped
(d) It should have the maximum length.
in ascending order and written before the name of the
2. Identication of the parent functional group, if any, side-chain. If there are two side-chains with the same
with the highest order of precedence.
alpha carbon, the number will be written twice. Exam3. Identication of the side-chains. Side chains are the ple: 2,2,3-trimethyl- . If there are both double bonds and
carbon chains that are not in the parent chain, but triple bonds, en (double bond) is written before yne
(triple bond). When the main functional group is a termiare branched o from it.
nal functional group (A group which can only exist at the
4. Identication of the remaining functional groups, if end of a chain, like formyl and carboxyl groups), there is
any, and naming them by the their ion names (such no need to number it.
1
BASIC PRINCIPLES
The nal name is (6E,13E)18-bromo-12-butyl-112. The functional groups with the highest precedence chloro-4,8-diethyl-5-hydroxy-15-methoxytricosaare the two ketone groups.
6,13-dien-19-yne-3,9-dione.
Alkanes
2,2-dimethylpropane
(neopentane)
Cyclic alkanes are simply prexed with cyclo-": for exmas or hyphens: . The longest possible main alkane
ample, C4 H8 is cyclobutane (not to be confused with
chain is used; therefore 3-ethyl-4-methylhexane instead
butene) and C6 H12 is cyclohexane (not to be confused
of 2,3-diethylpentane, even though these describe equivwith hexene).
alent structures. The di-, tri- etc. prexes are ignored
for the purpose of alphabetical ordering of side chains
propane chain
(e.g. 3-ethyl-2,4-dimethylpentane, not 2,4-dimethyl-3ethylpentane).
3
1
methyl
group
2-methylpropane
(isobutane)
2-methylbutane
(correct numbering)
3-methylbutane
( incorrect numbering (
4 FUNCTIONAL GROUPS
OH
3
OH
O
2-hydroxypropanoic acid
ethyne
propyne
(acetylene)
Cl
(methylacetylene)
Cl
Alkynes are named using the same system, with the sufx "-yne" indicating a triple bond: ethyne (acetylene),
propyne (methylacetylene).
F 1
Cl
trichloromethane
(chloroform)
F
2 Cl
Br
2-bromo-2-chloro-1,1,1,-trifluoroethane
(halothane)
4.3 Ketones
4.1
Alcohols
OH
ethanol
(ethyl alcohol)
OH
1
propan-1-ol
(n-propyl alcohol)
HO
OH
2
ethane-1,2-diol
(ethylene glycol)
2
3
1
propan-2-one
(acetone)
3
1
4
2
3-oxohexanal
merical bonding position: CH3 CH2 CH2 OH is propan-1ol. The suxes -diol, -triol, -tetraol, etc., are used for (pronounced own, not won) with an inx position nummultiple -OH groups: Ethylene glycol CH2 OHCH2 OH ber: CH3 CH2 CH2 COCH3 is pentan-2-one. If a higher
precedence sux is in use, the prex oxo-" is used:
is ethane-1,2-diol.
CH3 CH2 CH2 COCH2 CHO is 3-oxohexanal.
If higher precedence functional groups are present (see
order of precedence, below), the prex hydroxy is
used with the bonding position: CH3 CHOHCOOH is 2- 4.4 Aldehydes
hydroxypropanoic acid.
Main article: Aldehydes
Aldehydes (R-CHO) take the sux "-al". If other func4.2 Halogens (alkyl halides)
tional groups are present, the chain is numbered such that
the aldehyde carbon is in the 1 position, unless funcMain article: Halogens
Halogen functional groups are prexed with the bond- tional groups of higher precedence are present.
ing position and take the form uoro-, chloro-, bromo-, If a prex form is required, oxo-" is used (as for ketones),
4.6
Ethers
O
H
methanal
(formaldehyde)
OH
2
3-oxopropanoic acid
cyclohexanecarbaldehyde
4.6 Ethers
Main article: Ethers
Ethers (R-O-R) consist of an oxygen atom between the
O
O
methoxymethane
(dimethyl ether)
methoxyethane
1
2-methoxypropane
4.5
Carboxylic acids
OH
4.7 Esters
O
ethanoic acid
(acetic acid)
O
O
methyl methanoate
(formate)
O
O
methyl ethanoate
(acetate)
O
ethyl methanoate
(ethyl formate)
NH2
(acetamide)
O
N,N-dimethylmethanamide
Amides that have additional substituents on the nitrogen are treated similarly to the case of amines: they
are ordered alphabetically with the location prex N:
HCON(CH3 )2 is N,N-dimethylmethanamide.
but-2-yl propanoate
If the alkyl group is not attached at the end of the chain,
the bond position to the ester group is inxed before "-yl":
CH3 CH2 CH(CH3 )OOCCH2 CH3 may be called but-2-yl
propanoate or but-2-yl propionate.
4.8
ethanamide
methanamine
(methylamine)
NH2
propan-1-amine
(n-propyl amine)
NH
N-methylethanamine
propan-2-amine
(isopropyl amine)
N
N-ethyl-N-methylpropanamine
Amides (R-CO-NH2 ) take the sux "-amide, or "carboxamide if the carbon in the amide group cannot Prexed substituents are ordered alphabetically (excludbe included in the main chain. The prex form is both ing any modiers such as di-, tri-, etc.), e.g. chlorouoromethane, not uorochloromethane. If there are
carbamoyl-" and amido-".
7.1
Hydron
7.1 Hydron
Hydron is a generic term for hydrogen cation; protons,
deuterons and tritons are all hydrons. The Hydrons are
not found in heavier isotopes, however.
6.2
Aldehydes
Ions
8 See also
Preferred IUPAC name
IUPAC nomenclature of inorganic chemistry
International Union of Biochemistry and Molecular
Biology
CahnIngoldPrelog priority rules
Organic nomenclature in Chinese
Nucleic acid notation
Phanes
10
References
[1] The Commission on the Nomenclature of Organic Chemistry (1971 (3rd edition combined)) [1958 (A: Hydrocarbons, and B: Fundamental Heterocyclic Systems), 1965
(C: Characteristic Groups)]. Nomenclature of Organic
Chemistry (3 ed.). London: Butterworths. ISBN 0-40870144-7. Check date values in: |date= (help)
10
External links
EXTERNAL LINKS
11
11.1
11.2
Images
File:IUPAC-alcohol-1.svg Source: http://upload.wikimedia.org/wikipedia/commons/3/3b/IUPAC-alcohol-1.svg License: CC-BY-SA3.0 Contributors: Vector version of Image:Iupac-alcohol-1.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:07, 8 January
2008 (UTC). Original image by DrBob (talk contribs).
File:IUPAC-alcohol-2.svg Source: http://upload.wikimedia.org/wikipedia/commons/4/43/IUPAC-alcohol-2.svg License: CC-BY-SA3.0 Contributors: Vector version of Image:Iupac-alcohol-2.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:07, 8 January
2008 (UTC). Original image by DrBob (talk contribs).
File:IUPAC-aldehyde.svg Source: http://upload.wikimedia.org/wikipedia/commons/0/00/IUPAC-aldehyde.svg License: CC-BY-SA3.0 Contributors: Vector version of Image:Iupac-aldehyde.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:13, 8 January
2008 (UTC). Original image by DrBob (talk contribs).
File:IUPAC-alkane-1.svg Source: http://upload.wikimedia.org/wikipedia/commons/d/d3/IUPAC-alkane-1.svg License: CC-BY-SA3.0 Contributors: Vector version of Image:Iupac-alkane-1.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:04, 8 January
2008 (UTC). Original image by DrBob (talk contribs).
File:IUPAC-alkane-2.svg Source: http://upload.wikimedia.org/wikipedia/commons/0/0b/IUPAC-alkane-2.svg License: CC-BY-SA3.0 Contributors: Vector version of Image:Iupac-alkane-2.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:05, 8 January
2008 (UTC). Original image by DrBob (talk contribs).
File:IUPAC-alkane-3.svg Source: http://upload.wikimedia.org/wikipedia/commons/a/a2/IUPAC-alkane-3.svg License: CC-BY-SA-3.0
Contributors: Vector version of Image:Iupac-alkane-3.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:05, 8 January 2008
(UTC). Original image by DrBob (talk contribs).
File:IUPAC-alkane-4.svg Source: http://upload.wikimedia.org/wikipedia/commons/3/3a/IUPAC-alkane-4.svg License: CC-BY-SA-3.0
Contributors: Vector version of Image:Iupac-alkane-4.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:06, 8 January 2008
(UTC). Original image by DrBob (talk contribs).
File:IUPAC-alkane-5.svg Source: http://upload.wikimedia.org/wikipedia/commons/2/2b/IUPAC-alkane-5.svg License: CC-BY-SA3.0 Contributors: Vector version of Image:Iupac-alkane-5.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:06, 8 January
2008 (UTC). Original image by DrBob (talk contribs).
File:IUPAC-alkene.svg Source: http://upload.wikimedia.org/wikipedia/commons/d/d3/IUPAC-alkene.svg License: CC-BY-SA-3.0
Contributors: Vector version of Image:Iupac-alkene.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:06, 8 January 2008
(UTC). Original image by DrBob (talk contribs).
File:IUPAC-alkyne.svg Source: http://upload.wikimedia.org/wikipedia/commons/a/ae/IUPAC-alkyne.svg License: CC-BY-SA-3.0
Contributors: Vector version of en:Image:Iupac-alkyne.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:06, 8 January
2008 (UTC). Original image by DrBob (talk contribs).
File:IUPAC-amide.svg Source: http://upload.wikimedia.org/wikipedia/commons/8/89/IUPAC-amide.svg License: CC-BY-SA-3.0 Contributors: Vector version of Image:Iupac-amide.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:17, 8 January 2008 (UTC).
Original image by DrBob (talk contribs).
File:IUPAC-amine.svg Source: http://upload.wikimedia.org/wikipedia/commons/f/f4/IUPAC-amine.svg License: CC-BY-SA-3.0 Contributors: Vector version of Image:Iupac-amine.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:17, 8 January 2008 (UTC).
Original image by DrBob (talk contribs).
File:IUPAC-carboxylic_acid.svg Source: http://upload.wikimedia.org/wikipedia/commons/a/a6/IUPAC-carboxylic_acid.svg License:
CC-BY-SA-3.0 Contributors: Vector version of Image:Iupac-carboxyl.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:14,
8 January 2008 (UTC). Original image by DrBob (talk contribs).
File:IUPAC-cyclic.svg Source: http://upload.wikimedia.org/wikipedia/commons/b/b3/IUPAC-cyclic.svg License: CC-BY-SA-3.0 Contributors: Vector version of Image:Iupac-cyclic.png by DrBob (talk contribs). Original artist: Fvasconcellos 20:19, 8 January 2008 (UTC).
Original image by DrBob (talk contribs).
10
11
11.3
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