Nomenclature of Organic Compounds alcohol -ol ester -oate

-caboxylate
Monofunctional and Simple Organic Compounds phenol -ol acid halide -oyl halide
-carbonyl halide
IUPAC (International Union of Pure and Applied Chemistry) Name thiol -thiol amide -amide
-caboxamide
The IUPAC Name has three parts aldehyde -al nitrile -nitrile
-carbalaldehyde -carbonitrile
Prefix- position , number and name of substituents

Stem- number of carbon atoms in the longest chain (parent chain) Prefix: indicates position number and types of substituents.

Suffix- class/family/functionality Table 3. Names of common alkyl groups.

Stem: Indicates the number of carbon atoms in the longest continuous chain structure name structure name
(parent chain) of carbon atoms. H3C methyl CH3CH2CH sec-butyl

Table1. Stems for the first 20 straight chains of carbon atoms. CH3
CH3
CH3CH2 ethyl tert-butyl
Carbon Stem Carbon Stem Carbon Stem Carbon Stem
chain Chain chain chain CH3C
C1 meth C6 hex C11 undec C16 hexadec
CH3
C2 eth C7 hept C12 dodec C17 heptadec
CH3CH2CH2 propyl CH3CH2CH2CH2CH2 pentyl
C3 Prop C8 oct C13 tridec C18 octadec
C4 but C9 non C14 teradec C19 nonadec
CH3 isopropy CH3 isopentyl
C5 pent C10 dec C15 pentadec C20 icos
l

CH3CH CH3CHCH2CH2
Suffix: Indentifies the family or class to which the compound belongs. CH3
CH3CH2CH2CH2 butyl neopenty
l
Table2. Suffixes used for the different classes of organic compounds. CH3CCH2

Compound class suffix compound class suffix CH3

alkane -ane ketone -one CH3 isobutyl
alkene -ene carboxylic acid -oic acid
-carboxylic acid
alkyne -yne acid anhydride -oic anhydride
CH3CHCH2
-carboxylic
anhydride

IUPAC Nomenclature of Organic Compounds Jonas Del Rosario Vedad UPMSUMMER2011


Steps in Assigning IUPAC Names
All classes of organic compounds are named using a common set of IUPAC rules.
The steps outlined below are for alkanes.
Step one: Locate the parent chain.
a. Find the longest continuous chain of carbon atoms present in the
molecule and use the corresponding stem name with suffix –ane as
the parent name.
b. If two different chains of equal lengths are present, choose the one
with the larger number of substituents (groups attached to the
parent chain)
Step two: Number the carbon atoms in the parent chain so that the substituents
are given the lowest position number.
Step three: Identify the substituents and the position of the carbon atoms to which
these are attached. If there are two substituents on the same carbon atom, both
are assigned the same number.
Step four: Write the compound name as a simple word, using hyphens to separate
the different prefixes and using commas to separate position numbers.
a. If there are two or more substituents, arrange them in alphabetical
order.
b. If two or more identical substituents are present, use the
corresponding numerical prefix (di-, tri-, tetra-, etc.) appended to
the same substituent. These numerical prefixes are not considered
in alphabetizing substituents.
Additional Rules
1. Cyclic analogs are named by using the prefix cyclo- before the parent
name.
IUPAC Nomenclature of Organic Compounds Jonas Del Rosario Vedad UPMSUMMER2011
2. Hyphenated prefixes such as sec- and tert- are not considered for
alphabetizing purposes. Non-hyphenated prefixes such as cyclo-, iso- and
neo- are considered in alphabetizing.
3. A complex alkyl substituent is named by applying the four steps above
then naming it as an alkyl group by changing the –ane ending to –yl.
Naming Other Classes of Compounds
Alkenes
1. The longest continuous chain containing the C=C is considered the parent
chain, the parent chain is named using the appropriate stem name with
the suffix –ene.
2. The carbon atoms in the chain are numbered from the end closer to the
C=C.
3. If more than one C=C is present, each double bond position is indicated
by the lower numbered C of the C=C, di-, tri-, etc are inserted between
stem name and suffix –ene to denote the presence of the multiple C=C.
4. Cycloalkenes are named in the same manner, numbering of the ring
carbons is done clockwise or counterclockwise such that the double bond
carbons are assigned as C1 and C2 and the first substituent has the lower
number possible.
Alkynes
1. Same as for alkenes, using suffix –yne for the parent chain.
Alkyl halides
1. Named as halogen substituted alkanes.
2. In the numbering of parent chain, no priority is given to the halogen
substituent, the carbon atoms of the parent chain are numbered from
the end closer to the first substituent.
3. If the chain can be numbered from either end, numbering begins from
the end closer to the substituent that comes alphabetically.
 NH2 H
Aromatic hydrocarbons and benzene derivatives aniline N CH3 acetanilide
Arenes
1. Named as alkyl benzene, if the alkyl group has more than six carbons as
O
it is named as phenyl substituted alkene.
Monosubstituted benzene COOH H
1. Named by giving name of substituent followed by parent name benzene. benzoic acid C CH2 styrene
2. IUPAC recognizes the common names of some monosubstituted
benzenes (Table 4)
Disubstituted benzene
CN CH3
1. Named using prefixes ortho-, meta-, para- to denote relative positions of benzonitrile cumene
the two substituents. CH
CH3
a. Ortho- two substituents on C1 and 2 of the benzene ring
b. Meta- two substituents on C1 and 3 of the benzene ring
c. Para- two substituents on C1 and 2 of the benzene ring CHO OCH3
2. If the structure with a special name (Table 4) is present, this is used as a benzaldehyde anisole
parent structure.
Benzene with more than one substitutents
1. Named by citing the position of each substituent using the lowest
possible numbers.
Alcohols
Table 4. Common names for some monosubstituted benzenes
1. The longest continuous chain containing the hydroxyl group is considered
Structure Name Structure Name the parent chain, the parent chain is derived b y replacing the –e ending
CH3 O of the corresponding alkane with –ol.
toluene acetophenone
2. The lowest possible position numbers is assigned to the carbon bearing –
CH3 OH.

Thiols
OH O
phenol benzophenone
1. Named by the same system used for alcohols with suffix –thiol appended
to the corresponding alkane name.
2. When the –SH group is named as a substituent it is called mercapto.

Aldehydes

1. The longest continuous chain containing the –CHO group is considered

the parent chain, the parent name is derived by replacing the –e ending
of the corresponding alkane name with -al.
IUPAC Nomenclature of Organic Compounds Jonas Del Rosario Vedad UPMSUMMER2011
 2. The carbonyl carbon is numbered C1.
3. For complex aldehydes in which the CHO group is attached to a ring, the
suffix –carbadehyde is used after the name of the ring.
Ketones
1. The longest continuous chain containing the carbonyl group is considered
the parent chain, the parent name is derived by replacing the –e ending
of the corresponding alkane name with –one.
2. The carbons in the parent chain are numbered such that the carbonyl
carbon is assigned the lowest possible number.
1. Amides with NH2 group are named by replacing the -oic acid of the
corresponding carboxylic acid with –amide.
2. For amides with substituents on N, the substituent is named by preceding
with the letter N- and then the parent amide is named as above.
Esters
1. The alkyl group attached to oxygen is named first, followed by the
carboxylic acid name with the ending changed from from –ic acid to –ate.
Nitriles

Ethers 1. For simple open-chain nitriles, append the suffix –nitrile to the
hydrocarbon name, the C of the CN group is assigned as C1.
1. Two systems of naming are allowed by IUPAC rules.
2. Simple ethers with no other functional groups are named by giving the Amines
names of the alkyl groups attached to the O and adding the word ether.
3. If other functional groups are present, the ether is considered as an 1. For simple amines, the suffix –amine is added to the name of the alkyl
alkoxy substituent. substituent(s) or the suffix –amine can be used in place of the final –e in
the name of the parent compound.
Carboxylic acids 2. When named as a substituent, the NH2 group is called amino.

1. Two systems of naming are allowed by IUPAC rules Bicyclic compounds

2. Open chain carboxylic acids are systematically named by replacing the –e
ending of the corresponding alkane with –oic acid. 1. Consists of two rings sharing two carbon atoms called the bridgehead
3. Compounds that have a –COOH group bonded to a ring are named using carbons.
the suffix carboxylic acid. 2. Name begins with prefix bicyclo-, ring sizes are then indicated by citing
the number of C atoms in between the bridgehead carbons in decreasing
Functional derivatives of carboxylic acids order (separated by periods) and enclosing in brackets, this is followed by
Acid halides the parent name derived from the hydrocarbon containing the same
number of carbon atoms as in the bicyclic ring system.
1. Changing the –ic acid of the corresponding carboxylic acid with –yl halide. 3. Name appears as: bicyclo[#.#.#]alkane
4. Numbering of the ring carbons begins at one bridgehead carbon and
Acid anhydride proceeds along the longest bridge, to the second bridgehead carbon,
then along the second longest bridge back to the starting point and so on
1. Replace the word acid of the corresponding carboxylic acid with until all the atoms has been numbered.
anhydride.
Spiro compounds
Amides
1. Consists of two rings sharing only one carbon atom, the shared carbon
atom is called the spiro carbon.
IUPAC Nomenclature of Organic Compounds Jonas Del Rosario Vedad UPMSUMMER2011
 2. Parent name is the name of the alkane having the same number of Table 5. Prefixes for the different functional groups in order of decreasing
atoms. priority.
3. Ring sizes are indicated by the numbers corresponding to the number of Compound class Prefix Compound Class Prefix
carbon atoms linked to the spiro carbon and placing those numbers in Carboxylic acid carboxy alcohol hydroxyl
increasing order inside brackets, this is then followed by the parent acid anhydride phenol hydroxyl
name. ester alkoxycarbonyl thiol mercapto
4. Name appears as: spiro[#.#]alkane acid halide halocarbonyl amine amino
5. Numbering begins from the carbon attached to the spiro carbon in the amide amido imine imino
smaller ring, then along the carbons in the larger ring passing through the nitrile cyano alkene alkenyl
spiro carbon. aldehyde oxo alkyne alkynyl
ketone oxo alkane alkyl
Polyfunctional compounds
Subordinate
Gorups
1. Named with the same components: prefix-stem-suffix
Ethers alkoxy nitro nitro
sulfides alkylthio azide azido
Suffix
halides halo diazo diazo
1. Functional groups are divided into principal and subordinate groups
(Table 2). Principal groups may be cited using prefixes or suffixes while
subordinate groups are cited as prefixes only.
2. Proper suffix for a given compound is determined by the principal Writing the name
functional group of highest priority.
3. Only one suffix is used except in the case of an alkane or alkyne parent 1. Prefixes are written with substituents listed in alphabetical order.
chain. 2. When the principal functional groups is in itself an element or specific
compound the name is a single word, if it is not the compound is written
Stem as a separate word.
1. The longest continuous chain containing the largest number of principal 3. Parenthesis are used when complex substituents are present to prevent
groups is chosen as the parent chain. ambiguity.
2. In case where there is an open chain and cyclic structure, the compound
is named after whichever contains the highest priority principal
functional groups.
Organic chemistry is enough
enough to drive one mad. It
Suffix
1. Identifies the position, number and types of substituents, lowest position
appears as a primeval forest of the tropics, full of the
number is assigned to the highest priority functional groups. most remarkable things, a monstrous and boundless
2. The highest priority group of a polyfunctional compound dictates what
suffix to use in naming. thicket, with no escape, into which one may dread to
venture.
-Wohler, 1835

IUPAC Nomenclature of Organic Compounds Jonas Del Rosario Vedad UPMSUMMER2011