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IUPAC nomenclature of organic chemistry

 

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IUPAC nomenclature of organic chemistry



 
 
The IUPAC nomenclature of organic chemistry is a systematic
Systematic name

There are millions of possible objects that can be described in science, too many to create common names for every one. As a response, a number of systems of systematic names have been created....
 method of naming organic chemical compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s as recommended by the International Union of Pure and Applied Chemistry
International Union of Pure and Applied Chemistry

The International Union of Pure and Applied Chemistry is a non-governmental organization established in 1919 for the advancing of chemistry. Its members are national chemistry societies....
 (IUPAC). Ideally, every organic compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
 should have a name from which an unambiguous structural formula
Structural formula

The structural formula of a chemical compound is a graphical representation of the molecular structure showing how the atoms are arranged. The chemical bonding within the molecule is also shown, either explicitly or implicitly....
 can be drawn. There is also an IUPAC nomenclature of inorganic chemistry
IUPAC nomenclature of inorganic chemistry

The IUPAC nomenclature of inorganic chemistry is a systematic name method of naming inorganic chemical compounds as recommended by the International Union of Pure and Applied Chemistry ....
. See also phanes
Phanes (organic chemistry)

Phanes are sub-structures of highly complex organic molecules introduced for simplification of the naming of these highly complex molecules.Systematic nomenclature of organic chemistry consists of building a name for the structure of an organic compound by a collection of names of its composite parts but describing also its relative positio...
 nomenclature of highly complex cyclic molecules.

The main idea of IUPAC nomenclature is that every coumpound has one and only one name, and every name corresponds to only one structure of molecules (i.e.






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Encyclopedia


The IUPAC nomenclature of organic chemistry is a systematic
Systematic name

There are millions of possible objects that can be described in science, too many to create common names for every one. As a response, a number of systems of systematic names have been created....
 method of naming organic chemical compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s as recommended by the International Union of Pure and Applied Chemistry
International Union of Pure and Applied Chemistry

The International Union of Pure and Applied Chemistry is a non-governmental organization established in 1919 for the advancing of chemistry. Its members are national chemistry societies....
 (IUPAC). Ideally, every organic compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
 should have a name from which an unambiguous structural formula
Structural formula

The structural formula of a chemical compound is a graphical representation of the molecular structure showing how the atoms are arranged. The chemical bonding within the molecule is also shown, either explicitly or implicitly....
 can be drawn. There is also an IUPAC nomenclature of inorganic chemistry
IUPAC nomenclature of inorganic chemistry

The IUPAC nomenclature of inorganic chemistry is a systematic name method of naming inorganic chemical compounds as recommended by the International Union of Pure and Applied Chemistry ....
. See also phanes
Phanes (organic chemistry)

Phanes are sub-structures of highly complex organic molecules introduced for simplification of the naming of these highly complex molecules.Systematic nomenclature of organic chemistry consists of building a name for the structure of an organic compound by a collection of names of its composite parts but describing also its relative positio...
 nomenclature of highly complex cyclic molecules.

The main idea of IUPAC nomenclature is that every coumpound 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
Trivial name

In chemistry and zoology, a trivial name is a non-systematic name or non-scientific name. That is, the name is not recognised according to the rules of any formal system of nomenclature....
 may be used, often derived from the source of the compound (See Sec 14. below)

Basic principles


In biochemistry, a number of prefixes, suffixes
Affix

An affix is a morpheme that is attached to a word stem to form a new word. Affixes may be derivation , like English -ness and pre-, or inflectional, like English plural -s and past tense -ed....
 and infix
Infix

An infix is an affix inserted inside a stem . It contrasts with adfix, a rare term for an affix attached to the outside of a stem, such as a prefix or suffix....
es are used to describe the type and position of functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
s 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
    Functional group

    In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
    , 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
      Arabic numerals

      The 'arabic numerals', or 'Hindu numerals' are the ten digits , which?along with Decimal Number System by which a sequence was read as a number?were originally defined by Indian mathematics, later modified and transferred to North African Islamic mathematics and transmitted to Europe in the Middle Ages, whence they spread around the wo...
      , 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 more.
  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
    Alpha carbon

    The alpha carbon in organic chemistry refers to the first carbon that attaches to a functional group . By extension, the second carbon is the beta carbon, and so on....
    , 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 s 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.)
  4. 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
  5. 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
  6. The arrangement(with punctuation) is: 18-bromo-12-butyl-11-chloro-4,8-diethyl-5-hydroxy-15-methoxytricos-6,13-diene-19-yne-3,9-dione


The final name is 18-bromo-12-butyl-11-chloro-4,8-diethyl-5-hydroxy-15-methoxytricos-6,13-diene-19-yne-3,9-dione.

THIS IS THE OLDER EXAMPLE
NH2CH2CH2OH


would render the name as 2-aminoethanol, which is preferred. However, the name 2-hydroxyethanamine unambiguously refers to the same compound.

How the name was constructed:

  1. There are two carbons in the main chain; this gives the root name "eth".
  2. Since the carbons are singly-bonded, the suffix begins with "an".
  3. The two functional groups are an alcohol (OH) and an amine (NH2). The alcohol has the higher atomic number
    Atomic number

    In chemistry and physics, the atomic number is the number of protons found in the atomic nucleus of an atom. It is conventionally represented by the symbol Z....
    , and takes priority over the amine. The suffix for an alcohol ends in "ol", so that the suffix is "anol".
  4. The amine group is not on the carbon with the OH (the #1 carbon), but one carbon over (the #2 carbon); therefore we indicate its presence with the prefix "2-amino".
  5. Putting together the prefix, the root and the suffix, we get "2-aminoethanol".


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:

Number of carbons1234567891011121314152030
PrefixMethEthPropButPentHexHeptOctNonDecUndecDodecTridecTetradecPentadecEicosTriacont


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
Back-formation

In etymology, back-formation refers to the process of creating a new lexeme by removing actual or supposed affixes. The resulting neologism is called a back-formation, a term coined by James Murray in 1897....
 from methanol
Methanol

Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a chemical compound with chemical formula carbonhydrogen3oxygenhydrogen ....
, ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
, propionic acid
Propionic acid

Propionic acid is a naturally-occurring carboxylic acid with chemical formula CarbonHydrogen3CH2COxygenOH. In the pure state, it is a colorless liquid with a pungent odor....
 and butyric acid
Butyric acid

Butyric acid , also known under the systematic name butanoic acid, is a carboxylic acid with the structural formula carbonhydrogen3CH2CH2-carboxyl group....
, respectively. The rest are named with a Greek
Greek language

Greek is an Indo-European languages native to the southern Balkan peninsula, the language of the Greek people. It forms an independent branch within Indo-European....
 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
Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
 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 chain
Side chain

A side chain in organic chemistry and biochemistry is a part of a molecule that is attached to a core structure. The placeholder R is often used as a generic placeholder for side chains, the R historically being derived from radical or rest....
s (e.g. 3-ethyl-2,4-dimethylpentane, not 2,4-dimethyl-3-ethylpentane).

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
CIS

CIS usually refers to the Commonwealth of Independent States, a modern political entity consisting of nine former Soviet Union republics.CIS may also refer to:...
 and trans
Trans

Trans is a Latin noun or prefix, meaning "across", "beyond" or "on the opposite side".Trans may refer to:...
 isomers
Geometric isomerism

In chemistry, cis-trans isomerism or geometric isomerism or configuration isomerism or E-Z isomerism is a form of stereoisomerism describing the orientation of functional groups within a molecule....
 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
Acetylene

Acetylene is the chemical compound with the symbol carbonhydrogen. It is the simplest alkyne.As an alkyne, acetylene is Saturation because its two carbon atoms are Chemical bond together in a triple bond....
), propyne (methylacetylene
Methylacetylene

Methylacetylene is an alkyne with the chemical formula Hydrogen3C=CH. It is a component of MAPP gas along with its isomer 1,2-propadiene , which is commonly used in gas welding....
).

Functional Groups


Table of Functional groups


Alk is the prefix of the group (Meth, Eth, Prop, etc.)

Family Structure IUPAC nomenclature IUPAC nomenclature for cyclic parent chains (if different from straight chains) Common nomenclature
Alkyl groups R— Alkyl - Alkyl
Halogens R—halogen Halo'alkane - Alkyl halide
Alcohols R—OH Alkanol - Alkyl alcohol
Amines R—NH2 Alkanamine - Alkyl amine
Carboxylic acids (Alk + 1)anoic acid Cycloalkanecarboxylic acid -
Aldehydes Alkanal Cycloalkanecarboxaldehyde -
Ketones Alkanone - Alk(1)yl Alk(2)yl ketone
Thiols R—SH Alkanethiol - -
Amides (Alk + 1)anamide Cycloalkanecarboxamide -
Ethers R1—O—R2 alkoxyalkane - Alk(1)yl Alk(2)yl ether
Esters
Ester General
Alk(1)yl Alk(2)aneoate Alk(1)yl Cycloalk(2)anecarboxylate Alk(1)yl (Alk + 1)(2)anoate


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
Ethylene glycol

Ethylene glycol is an alcohol with two -OH groups , a chemical compound widely used as an automobile antifreeze. In its pure form, it is an odorless, colorless, syrupy, sweet tasting, toxic liquid....
 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.


Halogens (Alkyl Halides)

Halogen
Halogen

|}The halogens or halogen elements are a chemical series of nonmetal chemical element from Periodic table group International Union of Pure and Applied Chemistry of the periodic table, comprising fluorine, F; chlorine, Cl; bromine, Br; iodine, I; and astatine, At....
 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
Chloroform

Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with chemical formula CarbonHydrogenChlorine3....
) is trichloromethane. The anesthetic Halothane
Halothane

Halothane vapour is an inhalational general anaesthetic. Its IUPAC name is 2-bromo-2-chloro-1,1,1-trifluoroethane. It is the only inhalational anaesthetic agent containing a bromine atom; there are several other halogenated anesthesia agents which lack the bromine atom and do contain the fluorine and chlorine atoms present in halothane....
 (CF3CHBrCl) is 2-bromo-2-chloro-1,1,1-trifluoroethane.


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.


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.


Carboxylic acids

In general carboxylic acids are named with the suffix -oic acid (etymologically a back-formation
Back-formation

In etymology, back-formation refers to the process of creating a new lexeme by removing actual or supposed affixes. The resulting neologism is called a back-formation, a term coined by James Murray in 1897....
 from benzoic acid
Benzoic acid

Benzoic acid, C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for 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
Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
 are in such widespread use they are considered , 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
Citric acid

Citric acid is a weak organic chemistry acid, and it is a natural preservative and is also used to add an acidic, or sour, taste to foods and soft drinks....
 is one example; it is named 2-hydroxypropane- 1,2,3-tricarboxylic acid, rather than 2-carboxy, 2-hydroxypentanedioic acid.


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
Methoxyethane

Methoxyethane, also known as methyl ethyl ether, is a colorless gaseous ether with a medicine-like odor. It is extremely flammable, and its inhalation may cause asphyxiation or dizzyness....
 (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.


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
Ethyl acetate

Ethyl acetate is the organic compound with the formula CH3COOCH2CH3. This colorless liquid has a characteristic sweet smell like certain glues or nail polish removers, in which it is used....
 (CH3COOCH2CH3), ethyl formate
Ethyl formate

Ethyl formate is an ester formed when ethanol reacts with formic acid. It is also known as ethyl methanoate because ethanol and methanoic acid are used to form it....
 (HCOOCH2CH3) or dimethyl phthalate that are based on common acids, IUPAC recommends use of these established names, called . 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.


Amines and Amides

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
Acetamide

Acetamide , CH3CONH2, the amide of acetic acid, is a white crystalline solid in pure form. It is produced by dehydration reaction ammonium acetate:...
) 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.


Cyclic compounds

Cycloalkane
Cycloalkane

Cycloalkanes are types of alkanes which have one or more rings of carbon atoms in the chemical structure of their molecules. Alkanes are types of Organic compound hydrocarbon Chemical compound which have only single chemical bonds in their chemical structure....
s 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
Xylene

The term xylene or xylol refers to a mixture of three aromatic hydrocarbon isomers which is used as a solvent in the printing, rubber, and leather industries....
 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
Phenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
, furan
Furan

Furan, also known as furane and furfuran, is a Heterocyclic compound organic compound. It is typically derived by the thermal decomposition of pentose-containing materials, cellulosic solids especially pine-wood....
, indole
Indole

Indole is an aromatic Heterocyclic compound organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring....
, etc. being accepted as base names for compounds derived from them.


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.

Priority Functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
Formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
Prefix Suffix
1 Cations
   e.g. Ammonium
Ammonium

The ammonium cation is a positively electric charge polyatomic ion of the chemical formula NH4+. It has a formula weight of 18.05 and is formed by protonation of ammonia ....
 
–NH4+
-onio-
ammonio-
-onium
-ammonium
2 Carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s
   Thiocarboxylic acids
   Selenocarboxylic acids
   Sulfonic acid
Sulfonic acid

Sulfonic acid usually refers to a member of the class of organic acids with the general formula R-S2-OH, where R is usually a hydrocarbon side chain....
s
   Sulfinic acids
   Sulfenic acid
Sulfenic acid

A sulfenic acid is an organosulfur chemical compound and oxoacid with the general formula substituentsulfuroxygenhydrogen, where R ? H. Sulfenic acids are generally unstable....
s
–COOH
–COSH
–COSeH
–SO3H
–SO2H
–SOH
carboxy-
thiocarboxy-
selenocarboxy-
sulfo-
sulfino-
sulfeno-
-oic acid*
-thioic acid*
-selenoic acid*
-sulfonic acid
-sulfinic acid
-sulfenic acid
3 Carboxylic acid derivatives
   Ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
s
   Acyl halides
   Amide
Amide

In chemistry, an amide is one of three kinds of compounds:* the organic chemistry functional group characterized by a carbonyl group linked to a nitrogen atom , or a compound that contains this functional group ; or...
s
   Imide
Imide

Organic chemistryIn organic chemistry, imide is a functional group consisting of two carbonyl groups bound to nitrogen. Imides are generally prepared directly from ammonia or a primary amine, and either carboxylic acid or acid anhydrides....
s
   Amidine
Amidine

Amidines are a class of oxoacid derivative .The oxoacid from which an amidine is derived must be of the form RnEOH, where R is a substituent....
s
 
–COOR
–COX
–CONH2
–CON=C<
–C(=NH)NH2
 
R-oxycarbonyl-
halidealcanoyl-
carbamoyl-
-imido-
amidino-
 
-R-oate
-oyl halide*
-amide*
-imide*
-amidine*
4 Nitrile
Nitrile

A nitrile is any organic compound which has a -Carbon=Nitrogen functional group. The -C=N functional group is called a nitrile group....
s
   Isocyanide
Isocyanide

An isocyanide is an organic compound with the functional group R-N=C. The CN functionality is connected to the organic fragment via the nitrogen atom, not via carbon as is found in the isomeric nitriles, which have the connectivity R-C=N....
s
–CN
–NC
cyano-
isocyano-
-nitrile*
isocyanide
5 Aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
s
   Thioaldehydes
–CHO
–CHS
formyl-
thioformyl-
-al*
-thial*
6 Ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
s
   Thioketone
Thioketone

Thioketones are organic compounds related to conventional ketones. Instead of the formula R2C=O, thioketones, or thiones as they are also called, have the formula R2C=S....
s
>CO
>CS
oxo-
thiono-
-one
-thione
7 Alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s
   Thiol
Thiol

In organic chemistry, a thiol is a compound that contains the functional group composed of a sulfur atom and a hydrogen atom . Being the sulfur analogue of an alcohol group , this functional group is referred to either as a thiol group or a sulfhydryl group....
s
   Selenol
Selenol

In organic chemistry, a selenol is a chemical compound that contains the functional group composed of a selenium atom bonded to a hydrogen atom ....
s
   Tellurols
–OH
–SH
–SeH
–TeH
hydroxy-
sulfanyl-
selanyl-
tellanyl-
-ol
-thiol
-selenol
-tellurol
8 Hydroperoxides –OOH hydroperoxy- -hydroperoxide
9 Amine
Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
s
   Imine
Imine

An imine is a functional group or chemical compound containing a carbon?nitrogen double bond . Due to their diverse reactivity, imines are common substrates in a wide variety of transformations....
s
   Hydrazine
Hydrazine

Hydrazine is a chemical compound with the chemical formula N2H4. It is a colourless liquid with an ammonia-like odor and is derived from the same industrial chemistry processes that manufacture ammonia....
s
–NH2
=NH
–NHNH2
amino-
imino-
hydrazino-
-amine
-imine
-hydrazine
10 Ether
Ether

Ether is a class of organic compounds which contain an ether functional group ? an oxygen atom connected to two alkyl or aryl groups ? of general formula R?O?R....
s
   Thioether
Thioether

A thioether is a functional group in organic chemistry that has the structure R1-S-R2 as shown on right. Like many other sulfur-containing compounds, Volatile organic compound thioethers characteristically have foul odors....
s
   Selenoethers
–O–
–S–
–Se–
-oxy-
-thio-
-seleno-
 
11 Peroxide
Peroxide

A peroxide is a compound containing an oxygen-oxygen chemical bond. The simplest stable peroxide is hydrogen peroxide. Superoxides, dioxygenyls, ozones and ozonides compound are considered separately....
s
   Disulfide
Disulfide

In chemistry, a disulfide usually refers to the structural unit composed of a linked pair of sulfur atoms. The disulfide anion is S22-....
s
–OO–
–SS–
-peroxy-
-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.

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 carbonsPrefix as in new systemCommon name for alcoholCommon name for aldehydeCommon name for acid
1MethMethyl alcohol (wood alcohol)FormaldehydeFormic acid
2EthEthyl alcohol (grain alcohol)AcetaldehydeAcetic acid
3PropPropyl alcoholPropionaldehydePropionic acid
4ButButyl alcoholButyraldehydeButyric acid
5PentAmyl alcoholValeraldehydeValeric acid
6Hex
CaproaldehydeCaproic acid
7HeptEnanthyl alcoholEnanthaldehydeEnanthoic acid
8OctCapryl alcoholCaprylaldehydeCaprylic acid
9Non
PelargonaldehydePelargonic acid
10DecCapric alcoholCapraldehydeCapric acid
11Undec
12DodecLauryl alcoholLauraldehydeLauric acid
13Tridec
14Tetradec
MyristaldehydeMyristic acid
15Pentadec
16HexadecCetyl alcoholPalmitaldehydePalmitic acid
17Heptadec
Margaric acid
18OctadecStearyl alcoholStearaldehydeStearic acid
19Nonadec
20EicosArachidyl alcohol
Arachidic acid
21Heneicos
22DocosBehenyl alcohol
Behenic acid
23Tricos
24TetracosLignoceryl alcohol
Lignoceric acid
26HexacosCerotinyl alcohol
Cerotinic acid
28OctacosMontanyl alcohol
Montanic acid
30TriacontMelissyl alcohol
Melissic acid


Ketones

Common names for ketones can be derived by naming the two alkyl
Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
 or aryl
Aryl

In the context of organic molecules, aryl refers to any functional group or substituent derived from a simple aromatic ring, may it be phenyl, thiophene, indole, etc ....
 groups bonded to the carbonyl group as separate words followed by the word ketone.

  • Acetone
    Acetone

    Acetone is the organic compound with the chemical formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones....
  • Acetophenone
    Acetophenone

    Acetophenone is the organic compound with the chemical formula C6H5CCH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances....
  • Benzophenone
    Benzophenone

    Benzophenone is the organic compound with the formula 2Coxygen, generally abbreviated phenyl2CO. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone....
  • Ethyl isopropyl ketone
    Ethyl isopropyl ketone

    Ethyl isopropyl ketone, or 2-methyl-3-pentanone, is an aliphatic ketone with used as a reagent in organic chemistry and as a solvent.Its fully fluorocarbon analog is known as Novec 1230 and is used in gaseous fire suppression....
  • Diethyl ketone


The first three of the names shown above are still considered to be .

Aldehydes

The common name for an aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
 is derived from the common name of the corresponding carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
 by dropping the word acid and changing the suffix from -ic or -oic to -aldehyde.

  • Formaldehyde
    Formaldehyde

    Formaldehyde is a chemical compound with the chemical formula H2CO. It is the simplest aldehyde. Formaldehyde exists in several forms aside from H2CO: the cyclic trimer trioxane and the polymer Polyoxymethylene....
  • Acetaldehyde
    Acetaldehyde

    Acetaldehyde is an organic compound with the chemical formula CarbonHydrogen3CHOxygen or MeCHO. It is a flammable liquid with a fruity smell....


Ions

The IUPAC nomenclature also provides rules for naming ion
Ion

An ion is an atom or molecule which has lost or gained one or more electrons, giving it a positive or negative electrical charge. According to the Bohr_model this will be from or in the outer shield 'n'....
s.

Hydron

Hydron
Hydron (chemistry)

In chemistry, hydron is the general name for the positive hydrogen H+ cation.Hydron is the name for positive hydrogen ions without regard to nuclear mass, or positive ions formed from natural hydrogen ....
 is a generic term for hydrogen cation; protons, deuterons and tritons are all hydrons.

Parent hydride cations

Simple cations formed by adding a hydron to a hydride of a halogen, chalcogen
Chalcogen

The chalcogens are the Chemical element in periodic table group 16 of the periodic table. It is sometimes known as the oxygen family. It consists of the chemical element oxygen , sulfur , selenium , tellurium , the radioactive element polonium , and the synthetic element ununhexium ....
 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).

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.

See also

  • IUPAC nomenclature of inorganic chemistry
    IUPAC nomenclature of inorganic chemistry

    The IUPAC nomenclature of inorganic chemistry is a systematic name method of naming inorganic chemical compounds as recommended by the International Union of Pure and Applied Chemistry ....
  • Cahn Ingold Prelog priority rules


External links

  • (online version of the "Blue Book")
  • (includes IUBMB Recommendations for biochemistry)
  • (last updated 2003-04-11)
  • Software for generating systematic nomenclature
  • G. A. Eller, Improving the Quality of Published Chemical Names with Nomenclature Software. Molecules
    Molecules (journal)

    Molecules is a journal of organic synthesis and Molecular biology. It started publication in 1996 and is an open access publication.The journal is published by the international organization Molecular Diversity Preservation International ....
     2006, 9, 915-928