Chemical Nomenclature

Chemical nomenclature is the term given to the naming of compounds.

Chemists use specific rules and "conventions" to name different
compounds. This section is designed to help you review some of those
rules and conventions.

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Basic Concepts • Naming Compounds
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Nomenclatur
e(REQUIRE Oxidation and Reduction
D FOR When forming compounds, it is important to know something about the
CREDIT!) way atoms will react with each other. One of the most important manners
• Atomic in which atoms and/or molecules react with each other is the
Structure oxidation/reduction reaction. Oxidation/Reduction reactions are the
processes of losing and gaining electrons respectively. Just remember,
• Periodic "LEO the lion says GER:" Lose Electrons Oxidation, Gain Electrons
Table Reduction. Oxidation numbers are assigned to atoms and compounds as a
• Lewis way to tell scientists where the electrons are in a reaction. It is often
Structure referred to as the "charge" on the atom or compound. The oxidation
• Chemical number is assigned according to a standard set of rules. They are as
Reactions follows:
• Stoichiometr 1. An atom of a pure element has an oxidation number of zero.
y 2. For single atoms in an ion, their oxidation number is equal to their
• Acid-Base charge.
Chemistry 3. Fluorine is always -1 in compounds.
Advanced Concepts 4. Cl, Br, and I are always -1 in compounds except when they are
combined with O or F.
Section Tests
Pre-test 5. H is normally +1 and O is normally -2.
Post-test 6. The oxidation number of a compound is equal to the sum of the
oxidation numbers for each atom in the compound.
Useful Materials Forming Ionic Compounds
Glossary
Knowing the oxidation number of a compound is very important when
discussing ionic compounds. Ionic compounds are combinations of
Online Calculators positive and negative ions. They are generally formed when nonmetals
Redox Calculator and metals bond. To determine which substance is formed, we must use
Kinetics Arrhenius the charges of the ions involved. To make a neutral molecule, the positive
Calculator charge of the cation (positively-charged ion) must equal the negative
charge of the anion (negatively-charged ion). In order to create a neutral
Thermodynamics charged molecule, you must combine the atoms in certain proportions.
Calculator Scientists use subscripts to identify how many of each atom makes up the
Nuclear Decay molecule. For example, when combining magnesium and nitrogen we
Calculator know that the magnesium ion has a "+2" charge and the nitrogen ion has a
"-3" charge. To cancel these charges, we must have three magnesium
Linear Least
atoms for every two nitrogen atoms:
Squares Regression
3Mg2+ + 2N3- --> Mg3N2
Newton's Method
Equation Solver Knowledge of the charges of ions is crucial to knowing the formulas of
the compounds formed.
Compressibility
Calculator • alkalis (1st column elements) form "+1" ions such as Na+ and Li+
Units Conversion • alkaline earth metals (2nd column elements) form "2+" ions such as
Calculator Mg2+ and Ba2+
Nomenclature • halogens (7th column elements) form "-1" ions such as Cl- and I-
Calculator
Other common ions are listed in the table below:
Related Positive ions (cations) Negative ions (anions)
Information Links 1+ 1-
Texas Instruments ammonium (NH4 ) +
acetate (C2H3O2-)
Calculators copper(I) (Cu+) azide (N3-)
+
Casio Calculators hydrogen (H ) chlorate (ClO3-)
Sharp Calculators silver (Ag+) cyanide (CN-)
dihydrogen phosphate (H2PO4-)
Hewlett Packard
Calculators 2+ hydride (H-)
cadmium (Cd2+) bicarbonate (HCO3-)
Credits cobalt(II) (Co2+) hydroxide (OH-)
2+
copper(II) (Cu ) nitrate (NO3-)
Contact Webmaster
iron (Fe2+) nitrite (NO2-)
lead (Pb2+) perchlorate (ClO4-)
manganese(II) (Mn2+) permanganate (MnO4-)
mercury(I) (Hg22+) thiocyanate(SCN-)
mercury(II) (Hg2+)
nickel (Ni2+) 2-
tin (Sn2+) carbonate (CO32-)
zinc (Zn2+) chromate (CrO42-)
dichromate (Cr2O72-)
3+ hydrogen phosphate (HPO42-)
aluminum (Al3+) oxide (O2-)
 chromium(III) (Cr3+) peroxide (O22-)
iron(III) (Fe3+) sulfate (SO42-)
sulfide (S2-)
sulfite (SO32-)
3-
nitride (N3-)
phosphate (PO43-)
phosphide (P3-)

Naming Ionic Compounds

The outline below provides the rules for naming ionic compounds:
Positive Ions
1. Monatomic cations (a single atom with a positive charge) take the
name of the element plus the word "ion"

Examples:
○ Na+ = sodium ion
○ Zn+2 = zinc ion

2. If an element can form more than one (1) positive ion, the charge
is indicated by the Roman numeral in parentheses followed by the
word "ion"

Examples:
○ Fe2+ = iron(II) ion
○ Fe3+ = iron (III) ion
Negative Ions
1. Monatomic anions (a single atom with a negative charge) change
their ending to "-ide"

Examples:
○ O2- = oxide ion
○ Cl- = chloride ion

2. Oxoanions (negatively charged polyatomic ions which contain O)

end in "-ate". However, if there is more than one oxyanion for a
specific element then the endings are:

Two less oxygen One less THE MOST One more oxygen tha
than the most oxygen than the COMMON common starts with "
 common starts
most common OXOANION ENDS
with "hypo-" and ends with "-ate"
ends with "-ite" WITH "-ATE"
ends with "-ite"
○ CMost common Most common
l oxyanions with four oxyanions
O oxygens three oxygens
-
2 ○ SO42-
= =
sulfa
c te
h ○ PO43-
l
=
o
phos
r
phat
i
e
t
e ○ CrO4
2-
=
○ N
chro
O
- mate
2
=
ClO- =
n ClO4- =
hypochlorite
i
t
r
i
t
e
○ S
O
3
2-

s
u
l
f
i
t
e

3.
4. Polyatomic anions (a negatively charged ion containing more than
one type of element) often add a hydrogen atom; in this case, the
 anion's name either adds "hydrogen-" or "bi-" to the beginning

Example:
CO32- becomes HCO3-
"Carbonate" becomes either "Hydrogen Carbonate" or
"Bicarbonate"

5. When combining cations and anions into an ionic compound, you

always put the cation name first and then the anion name (the
molecular formulas are also written in this order as well.)

Examples:
○ Na+ + Cl- --> NaCl
sodium + chloride --> sodium chloride
○ Cu2+ + SO42- -->CuSO4
copper(II) + sulfate --> copper(II) sulfate
○ Al3+ + 3NO3- --> Al(NO3)3
aluminum + nitrate --> aluminum nitrate
Arrangement of Atoms
In naming ions, it is important to consider "isomers." Isomers are
compounds with the same molecular formula, but different arrangements
of atoms. Thus, it is important to include some signal within the name of
the ion that identifies which arrangement you are talking about. There are
three main types of classification, geometric, optical and structural
isomers.
1. Geometric isomers refers to which side of the ion atoms lie. The
prefixes used to distinguish geometric isomers are cis meaning
substituents lie on the same side of the ion and trans meaning they
lie on opposite sides. Below is a diagram to help you remember.

2. Optical isomers differ in the arrangement of four groups around a

chiral carbon. These two isomers are differentiated as L and D.

3. Structural isomers differentiate between the placement of two

chlorine atoms around a hexagonal carbon ring. These three
isomers are identified as o, m, and p. Once again we have given
you a few clues to help your memory.
A pop-up nomenclature calculator is available for help when naming
compounds and for practice problems.
Naming Binary Molecular Compounds
Molecular compounds are formed from the covalent bonding between
non-metallic elements. The nomenclature for these compounds is
described in the following set of rules.
1. The more positive atom is written first (the atom which is the
furthest to the left and to the bottom of the periodic table)
2. The more negative second atom has an "-ide" ending.
3. Each prefix indicates the number of each atom present in the
compound.
Pre Number
Number of Atoms Prefix
fix of Atoms
mo
1 6 hexa
no
2 di 7 hepta
3 tri 8 octa
tetr
4 9 nona
a
pent
5 10 deca
a
4.
Examples:
CO2 = carbon dioxide
P4S10 = tetraphosphorus decasulfide
Naming Inorganic Acids
1. Binary acids (H plus a nonmetal element) are acids that dissociate
into hydrogen atoms and anions in water. Acids that only release
one hydrogen atom are known as monoprotic. Those acids that
release more than one hydrogen atom are called polyproticacids.
When naming these binary acids, you merely add "hydro-"
(denoting the presence of a hydrogen atom) to the beginning and
"-ic acid" to the end of the anion name.

Examples:
HCl = hydrochloric acid
HBr = hydrobromic acid
2. Ternary acids (also called oxoacids, are formed by hydrogen plus
another element plus oxygen) are based on the name of the anion.
In this case, the -ate, and -ite suffixes for the anion are replaced
with -ic and -ous respectively. The new anion name is then
followed by the word "acid." The chart below depicts the changes
 in nomenclature.

Anion name Acid name

hypo___ite hypo___ous acid
___ite ___ous acid
___ate ___ic acid
per___ate per___ic acid
3.
Example:
ClO4- to HClO4 => perchlorate to perchloric acid
ClO- to HClO => hypochlorite to hypochlorous acid
Naming Compounds
A detailed treatise on naming organic compounds is beyond the scope of
these materials, but some basics are presented. The wise chemistry student
should consider memorizing the prefixes of the first ten organic
compounds:
Number of Carbons Prefix
1 meth-
2 eth-
3 prop-
4 but-
5 pent-
6 hex-
7 hept-
8 oct-
9 non-
10 dec-
There are four basic types of organic hydrocarbons, those chemicals with
only carbon and hydrogen:
1. Single bonds (alkane): suffix is "ane", formula CnH2n+2
2. Double bonds (alkene): suffix is "ene", formula CnH2n
3. Triple bonds (alkyne): suffix is "yne", formula CnH2n-2
4. Cyclic compounds: use prefix "cyclo"
So, for example, an organic compound with the formula "C6H14"
would be recognized as an alkane with six carbons, so its name is
"hexane".

Examples:
N2O4 = dinitrogen tetraoxide
S2F10 = disulfur decafluoride
Practice Problems
Find the formulas of the following molecules:
8
1. aluminum fluoride ammonium dichromate
.
carbon 9
2. magnesium acetate
tetrachloride .
1
3. strontium nitrate 0 zinc hydroxide
.
1
4. sodium bisulfate 1 nitric acid
.
1
5. iron(III) oxide 2 hypochlorous acid
.
1
6. mercury(II) nitrate 3 phosphoric acid
.
1
7. sodium sulfite 4 aluminum nitrate
.
A solution set is available for viewing.
Write the names of the following molecules:
8
1. CaCO3 Mg3(PO4)2
.
9
2. SCl2 Ba(NO2)2
.
1
3. Li2CrO4 0 Hg2Cl2
.
1
4. NaSCN 1 NaHCO3
.
1
5. KClO3 2 H2S
.
1
Ca(C2H3O2)
6. 3 H2SO3
2
.
1
7. K2Cr2O7 4 SO3
.

A solution set is available for viewing.

 [Basic Index] [Chemical Nomenclature] [Atomic Structure]
[Periodic Table]
[Lewis Structure] [Chemical Reactions] [Stoichiometry] [Acid-
Base Chemistry]

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The University of North Carolina at Chapel Hill
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IUPAC nomenclature of organic chemistry

From Wikipedia, the free encyclopedia
Jump to: navigation, search

The IUPAC nomenclature of organic chemistry is a systematic method of naming organic

chemical compounds as recommended[1] by the International Union of Pure and Applied
Chemistry (IUPAC). Ideally, every organic compound should have a name from which an
unambiguous structural formula can be drawn. There is also an IUPAC nomenclature of
inorganic chemistry. See also phanes nomenclature of highly complex cyclic molecules.
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
• 3 Alkenes and Alkynes
• 4 Functional Groups
○ 4.1 Table of Functional groups
○ 4.2 Alcohols
○ 4.3 Halogens (Alkyl Halides)
○ 4.4 Ketones
○ 4.5 Aldehydes
○ 4.6 Carboxylic acids
○ 4.7 Ethers
○ 4.8 Esters
○ 4.9 Amines and Amides
○ 4.10 Cyclic compounds
• 5 Order of precedence of groups
• 6 Common nomenclature - trivial names
○ 6.1 Ketones
○ 6.2 Aldehydes
• 7 Ions
○ 7.1 Hydron
○ 7.2 Parent hydride cations
○ 7.3 Cations and substitution
• 8 See also
• 9 References
 • 10 External links

[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.
The steps to naming an organic compound are:
1. Identify the parent hydrocarbon chain (The longest continuous chain of
carbon atoms)
2. Identify the functional group, if any (If more than one, use the one with
highest precedence as shown here)
1. Identify the position of the functional group in the chain.
2. Number the carbon atoms in the parent chain. The functional group
should end up the least number possible (as there are two ways of
numbering—right to left and left to right). The number (in Arabic
numerals, i.e. 1, 2, 3....) is written before the name of the functional
group suffix (such as -ol, -one, -al, etc.). If the group is a group that can
only exist at the end of any given chain (such as the carboxylic acid
and aldehyde groups), it need not be numbered.
NOTE: If there are no functional groups, number in both directions,
find the numbers of the side-chains (the carbon chains that are not in
the parent chain) in both directions. The end result should be such that
the first number should be the least possible. In the event of the first
numbers being the same for two methods of numbering, the sum of
the numbers of the side chains should be made the least possible; for
example, 2,2,5-trimethylhexane (2 + 2 + 5 = 9) is preferred over
2,5,5-trimethylhexane (2 + 5 + 5 = 12), as they both start with '2', but
the sum of the numbers of the former is less.
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 "hydroxy" and
the "m" in "dimethyl" alphabetically. The "di" is not considered in both cases.)
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.
6. Arrange everything like this: Group of side chains and secondary
functional groups with numbers made in step 3 + prefix of parent
hydrocarbon chain (eth, meth) + double/triple bonds with numbers
(or "ane") + primary functional group suffix with numbers.
Wherever it says "with numbers", it is understood that between the
word and the numbers, you use the prefix(di-, tri-)
7. Add punctuation:
1. Put commas between numbers (2 5 5 becomes 2,5,5)
2. Put a hyphen between a number and a letter (2 5 5 trimethylhexane
becomes 2,5,5-trimethylhexane)
3. Successive words are merged into one word (trimethyl hexane
becomes trimethylhexane)
NOTE: IUPAC uses one-word names throughout. This is why all parts
are connected.
The finalized name should look like this:
#,#-di<side chain>-#-<secondary functional group>-#-<side chain>-#,#,#-tri<secondary
functional group><parent chain suffix><If all bonds are single bonds, use "ane">-#,#-
di<double bonds>-#-<triple bonds>-#-<primary functional group>
NOTE: # is used for a number. The group secondary functional groups and side chains may not
look the same as shown here, as the side chains and secondary functional groups are arranged
alphabetically. The di- and tri- have been used just to show their usage. (di- after #,#, tri- after
#,#,# , etc.)
Example:
Here is a sample molecule with the parent carbons numbered:
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:
Now, we go by the steps:
1. The parent hydrocarbon chain has 23 carbons. It is called tricos-.
2. The functional groups with the highest precedence are the two ketone
groups.
1. The groups are on carbon atoms 3 & 9. As there are two, we write 3,9-
dione.
2. The numbering of the molecule is based on the ketone groups. when
numbering from left to right, the ketone groups get numbered 3 and
9.when numbering from right to left, the ketone groups get numbered
15 and 21. The sum of 3 & 9 (12) is less than the sum of 15 & 21 (36).
Therefore, the numbering is done left to right, and the ketones are
numbered 3 & 9.
 3. The side chains are: an ethyl- at carbon 4, an ethyl- at carbon 8, and a butyl-
at carbon 12.
NOTE:The -O-CH3 at carbon atom 15 is not a side chain, but it is a methoxy
functional group
○ There are two ethyl- groups, so they are combined to create, 4,8-
diethyl.
○ The side chains shall be grouped like this: 12-butyl-4,8-diethyl. (But
this is not the final grouping, as functional groups may be added in
between.)
2. The secondary functional groups are: a hydroxy- at carbon 5, a chloro- at
carbon 11, a methoxy- at carbon 15, and a bromo- at carbon 18. Grouped
with the side chains, we get 18-bromo-12-butyl-11-chloro-4,8-diethyl-5-
hydroxy-15-methoxy
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
4. The arrangement(with punctuation) is: 18-bromo-12-butyl-11-chloro-4,8-
diethyl-5-hydroxy-15-methoxytricos-6,13-dien-19-yne-3,9-dione
The final name is 18-bromo-12-butyl-11-chloro-4,8-diethyl-5-hydroxy-15-methoxytricos-
6,13-dien-19-yne-3,9-dione.

[edit] Alkanes
Main article: Alkane

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:

Num
ber
of 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 20 30
carb
ons

Prefi Met Et Pro B Pe H He O No D Und Dod Trid Tetra Penta Eic Triac
x h h p ut nt ex pt ct n ec ec ec ec dec dec os ont

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 C4H8 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 possible
occur on any of the other cabon 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(CH3)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).
[edit] Alkenes and Alkynes
Main articles: Alkenes and Alkynes

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": CH2=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

[edit] Table of Functional groups
Alk is the prefix of the group (Meth, Eth, Prop, etc.)

IUPAC IUPAC nomenclature for cyclic Common

Struct
Family nomenclatu parent chains (if different from nomenclatu
ure
re straight chains) re
 Alkyl
R— Alkyl - Alkyl
groups

R—
Halogen
haloge Halo'alkane - Alkyl halide
s
n

Alkyl
Alcohols R—OH Alkanol -
alcohol

Amines R—NH2 Alkanamine - Alkyl amine

(Alk +
Carboxyl
1)anoic Cycloalkanecarboxylic acid -
ic acids
acid

Aldehyd
Alkanal Cycloalkanecarboxaldehyde -
es

Alk(1)yl
Ketones Alkanone - Alk(2)yl
ketone

Thiols R—SH Alkanethiol - -

(Alk +
Amides Cycloalkanecarboxamide -
1)anamide

R1—O— alkoxyalka Alk(1)yl

Ethers -
R2 ne Alk(2)yl ether
 Alk(1)yl Alk(1)yl (Alk
Alk(1)yl
Esters Alk(2)aneoat + 1)
Cycloalk(2)anecarboxylate
e (2)anoate

[edit] Alcohols
Main article: Alcohols

Alcohols (R-OH) take the suffix "-ol" with an infix numerical bonding position: CH3CH2CH2OH
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.

[edit] Halogens (Alkyl Halides)

Main article: Halogens

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
Main article: 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
Main article: 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.
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
Main article: 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 CH3OCH3 is
methoxymethane, and CH3OCH2CH3 is methoxyethane (not ethoxymethane). 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.

[edit] Amines and Amides

Main articles: Amine and Amide
Amines (R-NH2) are named for the attached alkane chain with the suffix "-amine" (e.g. CH3NH2
methanamine). If necessary, the bonding position is infixed: CH3CH2CH2NH2 propan-1-amine,
CH3CHNH2CH3 propan-2-amine. The prefix form is "amino-".
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: CH3NHCH2CH3 is 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.

[edit] Order of precedence of groups

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. CH3CH(CH3)CH2NH(CH3) is N,2-dimethylpropanamine.

Priori
Functional group Formula Prefix Suffix
ty

1 Cations -onio- -onium

 e.g. Ammonium –NH4+ ammonio- -ammonium

-oic acid*
Carboxylic acids carboxy- -thioic acid*
Thiocarboxylic –COOH thiocarboxy -selenoic
acids –COSH - acid*
Selenocarboxylic –COSeH selenocarbo -sulfonic
2
acids –SO3H xy- acid
Sulfonic acids –SO2H sulfo- -sulfinic
Sulfinic acids –SOH sulfino- acid
Sulfenic acids sulfeno- -sulfenic
acid

Carboxylic acid –COOR R-

derivatives –COX oxycarbonyl
-R-oate
Esters –CONH2 -
-oyl halide*
3 Acyl halides – halidealcan
-amide*
Amides CON=C< oyl-
-imide*
Imides – carbamoyl-
-amidine*
Amidines C(=NH)N -imido-
H2 amidino-

Nitriles –CN cyano- -nitrile*

4
Isocyanides –NC isocyano- isocyanide

Aldehydes –CHO formyl- -al*

5
Thioaldehydes –CHS thioformyl- -thial*

Ketones >CO oxo- -one

6
Thioketones >CS thiono- -thione

Alcohols –OH hydroxy- -ol

Thiols –SH sulfanyl- -thiol
7
Selenols –SeH selanyl- -selenol
Tellurols –TeH tellanyl- -tellurol
 -
hydroperox
8 Hydroperoxides –OOH hydroperoxi
y-
de

Amines –NH2 amino- -amine

9 Imines =NH imino- -imine
Hydrazines –NHNH2 hydrazino- -hydrazine

Ethers –O– -oxy-

10 Thioethers –S– -thio-
Selenoethers –Se– -seleno-

Peroxides –OO– -peroxy-

11
Disulfides –SS– -disulfanyl-

*Note: These suffixes, in which the carbon atom is counted as part of the preceding chain, are the most commonly
used. See individual functional group articles for more details.

[edit] Common nomenclature - trivial names

Common nomenclature is an older system of naming organic compounds. Instead of using the
prefixes for the carbon skeleton above, another system is used. The pattern can be seen below.

Number of Prefix as in Common name Common name Common

carbons new system for alcohol for aldehyde name for acid

Methyl alcohol
1 Meth Formaldehyde Formic acid
(wood alcohol)

Ethyl alcohol
2 Eth Acetaldehyde Acetic acid
(grain alcohol)

3 Prop Propyl alcohol Propionaldehyde Propionic acid

4 But Butyl alcohol Butyraldehyde Butyric acid

5 Pent Amyl alcohol Valeraldehyde Valeric acid

6 Hex - Caproaldehyde Caproic acid

Enanthoic
7 Hept Enanthyl alcohol Enanthaldehyde
acid

8 Oct Capryl alcohol Caprylaldehyde Caprylic acid

Pelargonic
9 Non - Pelargonaldehyde
acid

10 Dec Capric alcohol Capraldehyde Capric acid

12 Dodec Lauryl alcohol Lauraldehyde Lauric acid

14 Tetradec - Myristaldehyde Myristic acid

16 Hexadec Cetyl alcohol Palmitaldehyde Palmitic acid

17 Heptadec - - Margaric acid

18 Octadec Stearyl alcohol Stearaldehyde Stearic acid

20 Icos Arachidyl alcohol - Arachidic acid

22 Docos Behenyl alcohol - Behenic acid

Lignoceryl Lignoceric
24 Tetracos -
alcohol acid
26 Hexacos Cerotinyl alcohol - Cerotinic acid

Mountainyl Mountainic
28 Octacos -
alcohol acid

30 Triacont Melissyl alcohol - Melissic acid

[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
• Ethyl isopropyl ketone
• 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.
[edit] Parent hydride cations
Simple cations formed by adding a hydron to a hydride of a halogen, chalcogen or nitrogen-
family element are named by adding the suffix "-onium" to the element's root: H4N+ is
ammonium, H3O+ is oxonium, and H2F+ is fluoronium. Ammonium was adopted instead of
nitronium, which commonly refers to NO2+.
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'. H5C+ is
methanium, HO-O+H2 is dioxidanium (HO-OH is dioxidane), and H2N-N+H3 is diazanium (H2N-
NH2 is diazane).
[edit] Cations and substitution
The above cations except for methanium are not, strictly speaking, organic, since they do not
contain carbon. However, many organic cations are obtained by substituting another element or
some functional group for a hydrogen.
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
• IUPAC nomenclature of inorganic chemistry
• International Union of Biochemistry and Molecular Biology
• Cahn Ingold Prelog priority rules
• Organic nomenclature in Chinese

[edit] References
1. ^ Nomenclature of Organic Chemistry (3 ed.). London: Butterworths. 1971
(3rd edition combined) [1958 (A: Hydrocarbons, and B: Fundamental
Heterocyclic Systems), 1965 (C: Characteristic Groups)]. ISBN 0408701447.
1. ^ Nomenclature of Organic Chemistry, Oxford: Pergamon Press, 1979; A
Guide to IUPAC Nomenclature of Organic Compounds, Recommendations
1993, Oxford: Blackwell Scientific Publications, 1993.

[edit] External links

• IUPAC Nomenclature of Organic Chemistry (online version of the "Blue Book")
• IUPAC Recommendations on Organic & Biochemical Nomenclature, Symbols,
Terminology, etc. (includes IUBMB Recommendations for biochemistry)
• Bibliography of IUPAC Recommendations on Organic Nomenclature (last
updated 2003-04-11)
• ACD/Name Software for generating systematic nomenclature
• G. A. Eller, Improving the Quality of Published Chemical Names with
Nomenclature Software. Molecules 2006, 9, 915-928 (online article)