Naming Organic Compounds

The increasingly large number of organic compounds identified with each passing day, together with the fact
that many of these compounds are isomers of other compounds, requires that a systematic nomenclature system
be developed. Just as each distinct compound has a unique molecular structure which can be designated by a
structural formula, each compound must be given a characteristic and unique name.

As organic chemistry grew and developed, many compounds were given trivial names, which are now
commonly used and recognized. Some examples are:

Name Methane Butane Acetone Toluene Acetylene Ethyl Alcohol

Formula CH4 C4H10 CH3COCH3 CH3C6H5 C2H2 C2H5OH

Such common names often have their origin in the history of the science and the natural sources of specific
compounds, but the relationship of these names to each other is arbitrary, and no rational or systematic
principles underly their assignments.

The IUPAC Systematic Approach to Nomenclature

A rational nomenclature system should do at least two things. First, it should indicate how the carbon atoms of a
given compound are bonded together in a characteristic lattice of chains and rings. Second, it should identify
and locate any functional groups present in the compound. Since hydrogen is such a common component of
organic compounds, its amount and locations can be assumed from the tetravalency of carbon, and need not be
specified in most cases.

The IUPAC nomenclature system is a set of logical rules devised and used by organic chemists to circumvent
problems caused by arbitrary nomenclature. Knowing these rules and given a structural formula, one should be
able to write a unique name for every distinct compound. Likewise, given an IUPAC name, one should be able
to write a structural formula. In general, an IUPAC name will have three essential features:

• A root or base indicating a major chain or ring of carbon atoms found in the molecular structure.
• A suffix or other element(s) designating functional groups that may be present in the compound.
• Names of substituent groups, other than hydrogen, that complete the molecular structure.

As an introduction to the IUPAC nomenclature system, we shall first consider compounds that have no specific
functional groups. Such compounds are composed only of carbon and hydrogen atoms bonded together by
sigma bonds (all carbons are sp3 hybridized).

Alkanes
Hydrocarbons having no double or triple bond functional groups are classified as alkanes or cycloalkanes,
depending on whether the carbon atoms of the molecule are arranged only in chains or also in rings. Although
these hydrocarbons have no functional groups, they constitute the framework on which functional groups are
located in other classes of compounds, and provide an ideal starting point for studying and naming organic
compounds. The alkanes and cycloalkanes are also members of a larger class of compounds referred to
as aliphatic. Simply put, aliphatic compounds are compounds that do not incorporate any aromatic rings in their
molecular structure.
1
 The following table lists the IUPAC names assigned to simple continuous-chain alkanes from C-1 to C-10. A
common "ane" suffix identifies these compounds as alkanes. Longer chain alkanes are well known, and their
names may be found in many reference and text books. The names methane through decane should be
memorized, since they constitute the root of many IUPAC names. Fortunately, common numerical prefixes are
used in naming chains of five or more carbon atoms.

Examples of Simple Unbranched Alkanes

Molecular Structural Molecular Structural
Name Isomers Name Isomers
Formula Formula Formula Formula

methane CH4 CH4 1 hexane C6H14 CH3(CH2)4CH3 5

ethane C2H6 CH3CH3 1 heptane C7H16 CH3(CH2)5CH3 9

propane C3H8 CH3CH2CH3 1 octane C8H18 CH3(CH2)6CH3 18

butane C4H10 CH3CH2CH2CH3 2 nonane C9H20 CH3(CH2)7CH3 35

pentane C5H12 CH3(CH2)3CH3 3 decane C10H22 CH3(CH2)8CH3 75

Some important behavior trends and terminologies:

(i) The formulas and structures of these alkanes increase uniformly by a CH2 incr ement.
(ii) A uniform variation of this kind in a series of compounds is called homologous.
(iii) These formulas all fit the CnH2n+2 rule. This is also the highest possible H/C ratio for a stable
hydrocarbon.
(iv) Since the H/C ratio in these compounds is at a maximum, we call them saturated (with hydrogen).

The IUPAC system requires first that we have names for simple unbranched chains, as noted above, and second
that we have names for simple alkyl groups that may be attached to the chains. Examples of some
common alkyl groups are given in the following table. Note that the "ane" suffix is replaced by "yl" in naming
groups. The symbol R is used to designate a generic (unspecified) alkyl group.

C2H5 CH3CH2 (CH3)2CH CH3CH2CH2 (CH3)2CHCH CH3CH2CH(C (CH3)3C–

Group CH3– R–
– CH2– – CH2– 2– H3)–

Methyl Ethyl Alkyl

Name Propyl Isopropyl Butyl Isobutyl sec-Butyl tert-Butyl

2
 IUPAC Rules for Alkane Nomenclature

1. Find and name the longest continuous carbon chain.

2. Identify and name groups attached to this chain.
3. Number the chain consecutively, starting at the end nearest a substituent group.
4. Designate the location of each substituent group by an appropriate number and name.
5. Assemble the name, listing groups in alphabetical order using the full name (e.g. cyclopropyl before
isobutyl).
The prefixes di, tri, tetra etc., used to designate several groups of the same kind, are not considered when
alphabetizing.

Halogen substituents are easily accommodated, using the names: fluoro (F-), chloro (Cl-), bromo (Br-)
and iodo (I-). For example, (CH3)2CHCH2CH2Br would be named 1-bromo-3-methylbutane. If the halogen is
bonded to a simple alkyl group an alternative "alkyl halide" name may be used. Thus, C 2H5Cl may be named
chloroethane (no locator number is needed for a two carbon chain) or ethyl chloride. Halogenated alkyl
substituents such as bromomethyl, BrCH2–, and trichloromethyl, CCl3–, may be listed and are alphabetized
according to their full names.

Examples:

3
Cycloalkanes
Cycloalkanes have one or more rings of carbon atoms. The simplest examples of this class consist of a
single, unsubstituted carbon ring, and these form a homologous series similar to the unbranched alkanes. The
IUPAC names of the first five members of this series are given in the following table. The last (yellow shaded)
column gives the general formula for a cycloalkane of any size. If a simple unbranched alkane is converted to a
cycloalkane two hydrogen atoms, one from each end of the chain must be lost. Hence the general formula for a
cycloalkane composed of n carbons is CnH2n. Although a cycloalkane has two fewer hydrogen than the
equivalent alkane, each carbon is bonded to four other atoms so such compounds are still considered to
be saturated with hydrogen.

Examples of Simple Cycloalkanes

Name Cyclopropane Cyclobutane Cyclopentane Cyclohexane Cycloheptane Cycloalkane

Molecular
C3H6 C4H8 C5H10 C6H12 C7H14 CnH2n
Formula

4
 Structural
(CH2)n
Formula

Line
Formula

Substituted cycloalkanes are named in a fashion very similar to that used for naming branched alkanes.
The chief difference in the rules and procedures occurs in the numbering system. Since all the carbons of a ring
are equivalent (a ring has no ends like a chain does), the numbering starts at a substituted ring atom.

IUPAC Rules for Cycloalkane Nomenclature

1. For a monosubstituted cycloalkane the ring supplies the root name (table above) and the substituent group is
named as usual. A location number is unnecessary.
2. If the alkyl substituent is large and/or complex, the ring may be named as a substituent group on an alkane.
3. If two different substituents are present on the ring, they are listed in alphabetical order, and the first cited
substituent is assigned to carbon #1. The numbering of ring carbons then continues in a direction (clockwise or
counter-clockwise) that affords the second substituent the lower possible location number.
4. If several substituents are present on the ring, they are listed in alphabetical order. Location numbers are
assigned to the substituents so that one of them is at carbon #1 and the other locations have the lowest possible
numbers, counting in either a clockwise or counter-clockwise direction.
5. The name is assembled, listing groups in alphabetical order and giving each group (if there are two or more) a
location number. The prefixes di, tri, tetra etc., used to designate several groups of the same kind, are not
considered when alphabetizing.

For examples of how these rules are used in naming substituted cycloalkanes .

Small rings, such as three and four membered rings, have significant angle strain resulting from the distortion of
the sp3 carbon bond angles from the ideal 109.5º to 60º and 90º respectively. This angle strain often enhances
the chemical reactivity of such compounds, leading to ring cleavage products. It is also important to recognize
that, with the exception of cyclopropane, cycloalkyl rings are not planar (flat).

Hydrocarbons having more than one ring are common, and are referred to as bicyclic (two
rings), tricyclic (three rings) and in general, polycyclic compounds. The molecular formulas of such
compounds have H/C ratios that decrease with the number of rings. In general, for a hydrocarbon composed
of n carbon atoms associated with m rings the formula is: CnH(2n + 2 - 2m). The structural relationship of rings in
a polycyclic compound can vary. They may be separate and independent, or they may share one or two common
atoms. Some examples of these possible arrangements are shown in the following table.

Examples of Isomeric C8H14 Bicycloalkanes

Isolated Rings Spiro Rings Fused Rings Bridged Rings

5
 No common atoms One common atom One common bond Two common atoms

Haloalkanes
Haloalkanes are chemical compounds in which one or more of the hydrogen atoms in an alkane have
been replaced by halogen atoms (usually one or more of fluorine, chlorine, bromine or iodine). As also applies
to alkanes, haloalkanes are saturated organic compounds, meaning that all of the chemical bonds attaching the
atoms within the molecule are single bonds. Each carbon atom forms 4 bonds (either with other carbon atoms or
with hydrogen or halogen atoms). Each hydrogen and halogen atom is connected to a single carbon atom.
Haloalkanes are also known as halogenalkanes and (less commonly) as alkyl halides.Haloalkanes are similar to
alkanes but one or more of the hydrogen atoms in the corresponding alkane is replaced by a halogen atom(s) in
the haloalkane.

Halogens - elements in Group 7 (Group VII) of the periodic table, specifically: Fluorine (F), Chlorine (Cl),
Bromine (Br), Iodine (I) and Astatine (At). The halogens most commonly found in, and of greatest importance
in organic chemistry, are fluorine, chlorine, bromine and iodine.

GENERAL FORM: CnH2n+1X

EXAMPLES:

Name of Halomethane Four different ways to represent exactly the same molecular structure:

fluoromethane

CH3F

chloromethane

CH3Cl

6
bromomethane

CH3Br

iodomethane

CH3I

Alkenes
IUPAC Rules for Alkene and Cycloalkene Nomenclature
1. The ene suffix (ending) indicates an alkene or cycloalkene.
2. The longest chain chosen for the root name must include both carbon atoms of the
double bond.
3. The root chain must be numbered from the end nearest a double bond carbon atom. If the
double bond is in the center of the chain, the nearest substituent rule is used to determine
the end where numbering starts.
4. The smaller of the two numbers designating the carbon atoms of the double bond is used
as the double bond locator. If more than one double bond is present the compound is
named as a diene, triene or equivalent prefix indicating the number of double bonds, and
each double bond is assigned a locator number.
5. In cycloalkenes the double bond carbons are assigned ring locations #1 and #2. Which of
the two is #1 may be determined by the nearest substituent rule.
6. Substituent groups containing double bonds are:

H2C=CH- Vinylgroup
H2C=CH–CH2– Allyl group

Example:

butene: C4H8 (CH2=CHCH2CH3)

If the double bond is not terminal (if it is on a carbon somewhere in the center of the
chain) then the carbons should be numbered in such a way as to give the first of the two double-
bonded carbons the lowest possible number, and that number should precede the "ene" suffix
with a dash, as shown below.

pent-2-ene (CH3CH=CHCH2CH3)
7
 If there is more than one double bond in an alkene, all of the bonds should be numbered
in the name of the molecule - even terminal double bonds. The numbers should go from lowest
to highest, and be separated from one another by a comma. The IUPAC numerical prefixes are
used to indicate the number of double bonds.

octa-2,4-diene: CH3CH=CHCH=CHCH2CH2CH3
deca-1,5-diene: CH2=CHCH2CH2CH=CHCH2CH2CH2CH3

cis Isomers

.The two largest groups are on the same side of the double bond.

trans Isomers

...The two largest groups are on opposite sides of the double bond.

E/Z nomenclature

E = entgegan ("trans") Z = zusamen ("cis")

Priority of groups is based on the atomic mass of attached atoms (not the size of the group). An
atom attached by a multiple bond is counted once for each bond.

fluorine atom > isopropyl group > n-hexyl group>deuterium atom > hydrogen atom

-CH2-CH=CH2 > -CH2CH2CH3l

8
Alkynes

Rule 1

Find the longest carbon chain that includes both carbons of the triple bond.

Rule 2

Number the longest chain starting at the end closest to the triple bond. A 1-alkyne is referred to
as a terminal alkyne and alkynes at any other position are called internal alkynes. For example:

4-chloro-6-diiodo-7-methyl-2-nonyne

Rule 3

After numbering the longest chain with the lowest number assigned to the alkyne, label each of
the substituents at its corresponding carbon. While writing out the name of the molecule,
arrange the substituents in alphabetical order. If there are more than one of the same substituent
use the prefixes di, tri, and tetra for two, three, and four substituents respectively. These
prefixes are not taken into account in the alphabetical order. For example:

2,2,10-triiodo-5-methyl-3-decyne

If there is an alcohol present in the molecule, number the longest chain starting at the end
closest to it, and follow the same rules. However, the suffix would be –ynol, because the
alcohol group takes priority over the triple bond.

9
 5- methyl-7-octyn-3-ol

When there are two triple bonds in the molecule, find the longest carbon chain including both
the triple bonds. Number the longest chain starting at the end closest to the triple bond that
appears first. The suffix that would be used to name this molecule would be –diyne. For
example:

4-methyl-1,5-octadiyne

Rule 4

Substituents containing a triple bond are called alkynyl. For example:

1-chloro-1-ethynyl-4-bromocyclohexane

Benzene Derivatives
The nomenclature of substituted benzene ring compounds is less systematic than that of the alkanes, alkenes
and alkynes. A few mono-substituted compounds are named by using a group name as a prefix to "benzene", as
10
shown by the combined names listed below. A majority of these compounds, however, are referred to by
singular names that are unique. There is no simple alternative to memorization in mastering these names.

Two commonly encountered substituent groups that incorporate a benzene ring are phenyl, abbreviated Ph-,
and benzyl, abbreviated Bn-. These are shown here with examples of their use. Be careful not to confuse a
phenyl (pronounced fenyl) group with the compound phenol (pronounced feenol). A general and useful generic
notation that complements the use of R- for an alkyl group is Ar- for an aryl group (any aromatic ring).

When more than one substituent is present on a benzene ring, the relative locations of the substituents must be
designated by numbering the ring carbons or by some other notation. In the case of disubstituted benzenes, the
prefixes ortho, meta & para are commonly used to indicate a 1,2- or 1,3- or 1,4- relationship respectively. In the
following examples, the first row of compounds shows this usage in red. Some disubstituted toluenes have
singular names (e.g. xylene, cresol & toluidine) and their isomers are normally designated by the ortho, meta
or para prefix. A few disubstituted benzenes have singular names given to specific isomers (e.g. salicylic acid &
resorcinol). Finally, if there are three or more substituent groups, the ring is numbered in such a way as to
assign the substituents the lowest possible numbers, as illustrated by the last row of examples. The substituents
are listed alphabetically in the final name. If the substitution is symmetrical (third example from the left) the
numbering corresponds to the alphabetical order.

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Alcohol
Rules for naming the alcohols
1. Find the longest chain containing the hydroxy group (OH). If there is a chain with more carbons than the
one containing the OH group it will be named as a substituent.
2. Place the OH on the lowest possible number for the chain. With the exception of carbonyl groups such
as ketones and aldehydes, the alcohol or hydroxy groups have first priority for naming.
3. When naming a cyclic structure, the -OH is assumed to be on the first carbon unless the carbonyl group
is present, in which case the later will get priority at the first carbon.
4. When multiple -OH groups are on the cyclic structure, number the carbons on which the -OH groups
reside.
5. Remove the final e from the parent alkane chain and add -ol. When multiple alcohols are present use di,
tri, before the ol, after the parent name. ex. 2,3-hexandiol. If a carbonyl group is present, the -OH group
is named with the prefix "hydroxy," with the carbonyl group attached to the parent chain name so that it
ends with -al or -one.
Examples:

Ethane: CH3CH3 ----->Ethanol: (the alcohol found in beer, wine and other consumed sprits)

Secondary alcohol: 2-propanol

12
Other functional groups on an alcohol: 3-bromo-2-pentanol

Cyclic alcohol (two -OH groups): cyclohexan-1,4-diol

Other functional group on the cyclic structure: 3-hexeneol (the alkene is in bold and indicated by
numbering the carbon closest to the alcohol)

A complex alcohol: 4-ethyl-3hexanol

Nomenclature of Ethers
Ethers are organic chemical compounds whose structure has the general form:

Where the symbols "R1" and "R2" represent organic radicals, usually carbon chains.

When working-out the name of ether given its molecular structure, the first steps are:

Recognize that the molecule is ether because it has the general form:

1. Identify the parts labelled "R1" and "R2".

2. To do this recall the standard system of labelling carbon chains as used for alkanes.
3. Note that "R1" and "R2" might be linear carbon chains (which are simpler to name) or they might be
branched, or might even have other functional groups (e.g. halogens,) attached as well.

According to the standard system for naming ethers, the shorter of the two chains "R1" and "R2" becomes
the first part of the name with the "-ane" suffix that applies to the corresponding alkane changed to -oxy, and the
name of the longer alkane chain forming the suffix of the name of the ether.

Another system for naming ethers works by citing the names of the groups R1 and R2 in alphabetical order,
followed by the class name "ether". So, for example "methoxy ethane" = "ethyl methyl ether"

13
EXAMPLES:

1 methoxy methane
(C2H6O)

2 methoxy ethane
(C3H8O)

3 ethoxy propane
(C5H12O)

4 ethoxy butane
(C6H14O)

5 propoxy pentane
(C8H18O)

Amines
In the IUPAC system of nomenclature, functional groups are normally designated in one of two ways.
The presence of the function may be indicated by a characteristic suffix and a location number. This is common
for the carbon-carbon double and triple bonds which have the respective suffixes ene and yne. Halogens, on the
other hand, do not have a suffix and are named as substituents, for example: (CH3)2C=CHCHClCH3 is 4-
chloro-2-methyl-2-pentene.

Amines are derivatives of ammonia in which one or more of the hydrogens has been replaced by an alkyl or aryl
group. The nomenclature of amines is complicated by the fact that several different nomenclature systems exist,
and there is no clear preference for one over the others. Furthermore, the terms primary (1º), secondary (2º) &
tertiary (3º) are used to classify amines in a completely different manner than they were used for alcohols or
alkyl halides. When applied to amines these terms refer to the number of alkyl (or aryl) substituents bonded to
the nitrogen atom, whereas in other cases they refer to the nature of an alkyl group. The four compounds shown
in the top row of the following diagram are all C4H11N isomers. The first two are classified as 1º-amines, since
only one alkyl group is bonded to the nitrogen; however, the alkyl group is primary in the first example and
tertiary in the second. The third and fourth compounds in the row are 2º and 3º-amines respectively. A nitrogen
bonded to four alkyl groups will necessarily be positively charged, and is called a 4º-ammonium cation. For
example, (CH3)4N(+) Br(–) is tetramethylammonium bromide.

14
 The IUPAC names are listed first and colored blue. This system names amine functions as substituents
on the largest alkyl group. The simple -NH substituent found in 1º-amines is called an amino group. For 2º and
3º-amines a compound prefix (e.g. dimethylamino in the fourth example) includes the names of all but the root
alkyl group.

Nomenclature of Carboxylic Acids

The IUPAC system of nomenclature assigns a characteristic suffix to these classes. The –e ending is
removed from the name of the parent chain and is replaced -anoic acid. Since a carboxylic acid group must
always lie at the end of a carbon chain, it is always is given the #1 location position in numbering and it is not
necessary to include it in the name.

Many carboxylic acids are called by the common names. These names were chosen by chemists to
usually describe a source of where the compound is found. In common names of aldehydes, carbon atoms near
the carboxyl group are often designated by Greek letters. The atom adjacent to the carbonyl function is alpha,
the next removed is beta and so on.

Example: (Common Names are in red)

15
 Naming carboxyl groups added to a ring
When a carboxyl group is added to a ring the suffix -carboxylic acid is added to the name of the cyclic
compound. The ring carbon attached to the carboxyl group is given the #1 location number.

Naming carboxylic acids which contain other functional groups

Carboxylic acids are given the highest nomenclature priority by the IUPAC system. This means that the
carboxyl group is given the lowest possible location number and the appropriate nomenclature suffix is
included. In the case of molecules containing carboxylic acid and alcohol functional groups the OH is named as
a hydroxyl substituent. However, the l in hydroxyl is generally removed.

In the case of molecules containing a carboxylic acid and aldehydes and/or ketones functional groups
the carbonyl is named as a "Oxo" substituent.

16
 In the case of molecules containing a carboxylic acid an amine functional group the amine is named as
an "amino" substituent.

When carboxylic acids are included with an alkene the following order is followed:

(Location number of the alkene)-(Prefix name for the longest carbon chain minus the -ane ending)-(an –enoic
acid ending to indicate the presence of an alkene and carboxylic acid)

Remember that the carboxylic acid has priority so it should get the lowest possible location number. Also,
remember that cis/tran or E/Z nomenclature for the alkene needs to be included if necessary.

Remember that the carboxylic acid has priority so it should get the lowest possible location number. Also,
remember that cis/tran or E/Z nomenclature for the alkene needs to be included if necessary.

Nomenclature of Esters
Esters are organic chemical compounds whose structure has the general form:

where the symbols "R1" and "R2" represent organic radicals, usually carbon chains.

The standard system for naming esters uses the suffix -oate to indicate that a molecule is an ester.
The two organic radicals (which are often carbon chains) labeled "R1" and "R2" in the diagram at the top of this
page are also identified in the name of the compound, or molecule drawn-out to represent the compound.

When working-out the name of an ester given its molecular structure, the first steps are:
17
 Recognize that the molecule is an ester because it has the general form:

1. Identify the parts labeled "R1" and "R2".

2. To do this recall the standard system of labeling carbon chains as used for alkanes.
3. Also take care to distinguish "R1" and "R2" by noticing which "R" the oxygen atom is attached to by a
double bond.
4. Note that "R1" and "R2" may be linear carbon chains (which are simpler to name) or they may be branched,
and they may even have other functional groups (e.g. halogens) attached as well.

EXAMPLES:

methyl ethanoate
1
(C3H6O2)

methyl propanoate
2
(C4H8O2)

methyl butanoate
3
(C7H10O2)

methyl pentanoate
4
(C6H12O2)

methyl hexanoate
5
(C7H14O2)

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Nomenclature of Amides
The amide functional group has an nitrogen atom attached to a carbonyl carbon atom. If the two
remaining bonds on the nitrogen atom are attached to hydrogen atoms, the compound is a simple amide. If one
or both of the two remaining bonds on the atom are attached to alkyl or aryl groups, the compound is a
substituted amide.

The carbonyl carbon-to-nitrogen bond is called an amide linkage. This bond is quite stable and is found
in the repeating units of protein molecules, where it is called a peptide linkage.

Simple amides are named as derivatives of carboxylic acids. The -ic ending of the common name or the
-oic ending of the International Union of Pure and Applied Chemistry (IUPAC) name of the carboxylic acid is
replaced with the suffix -amide.

Nomenclature of Anhydrides
The acid anhydride functional group results when two carboxylic acids combine and lose water
(anhydride = without water). Symmetrical acid anhydrides are named like carboxylic acids except the ending -
acid is replaced with -anhydride. This is true for both the IUPAC and Common nomenclature.

Symmetrical Anhydrides

Unsymmetrical acid anhydrides

19
Unsymmetrical acid anhydrides are named by first naming each component carboxylic acid alphabetically
arranged (without the word acid) followed by spaces and then the word anhydride.

Nomenclature of Aldehydes & Ketones

Aldehydes and ketones contain the carbonyl group. Aldehydes are considered the most important
functional group. They are often called the formyl or methanoyl group. Aldehydes derive their name from
the dehydration of alcohols. Aldehydes contain the carbonyl group bonded to at least one hydrogen atom.
Ketones contain the carbonyl group bonded to two carbon atoms.

Aldehydes and ketones are organic compounds which incorporate a carbonyl functional group, C=O.
The carbon atom of this group has two remaining bonds that may be occupied by hydrogen, alkyl or aryl
substituents. If at least one of these substituents is hydrogen, the compound is an aldehyde. If neither is
hydrogen, the compound is a ketone.

Benzene Aldehydes
The IUPAC system of nomenclature assigns a characteristic suffix -al to aldehydes. For example,
H2C=O is methanal, more commonly called formaldehyde. Since an aldehyde carbonyl group must always lie at
the end of a carbon chain, it is always is given the #1 location position in numbering and it is not necessary to
include it in the name. There are several simple carbonyl containing compounds which have common names
which are retained by IUPAC.

Also, there is a common method for naming aldehydes and ketones. For aldehydes common parent chain
names, similar to those used for carboxylic acids, are used and the suffix –aldehyde is added to the end. In
common names of aldehydes, carbon atoms near the carbonyl group are often designated by Greek letters. The
atom adjacent to the carbonyl function is alpha, the next removed is beta and so on.

If the aldehyde moiety (-CHO) is attached to a ring the suffix –carbaldehyde is added to the name of
the ring. The carbon attached to this moiety will get the #1 location number in naming the ring.
20
ALDEHYDE NOMENCLATURE RULES

1. Aldehydes take their name from their parent alkane chains. The -e is removed from the end and is
replaced with -al.
2. The aldehyde functional group is given the #1 numbering location and this number is not included in the
name.
3. For the common name of aldehydes start with the common parent chain name and add the suffix -
aldehyde. Substituent positions are shown with Greek letters.
4. When the -CHO functional group is attached to a ring the suffix -carbaldehyde is added, and the carbon
attached to that group is C1.

The IUPAC system names are given on top while the common name is given on the bottom in parentheses.

Ketones
The IUPAC system of nomenclature assigns a characteristic suffix of -one to ketones. A ketone carbonyl
function may be located anywhere within a chain or ring, and its position is usually given by a location number.
Chain numbering normally starts from the end nearest the carbonyl group. Very simple ketones, such as
propanone and phenylethanone do not require a locator number, since there is only one possible site for a
ketone carbonyl function.

The common names for ketones are formed by naming both alkyl groups attached to the carbonyl then
adding the suffix -ketone. The attached alkyl groups are arranged in the name alphabetically.

KETONE NOMENCLATURE RULES

1. Ketones take their name from their parent alkane chains. The ending -e is removed and replaced with -
one.
2. The common name for ketones is simply the substituent groups listed alphabetically + ketone.
3. Some common ketones are known by their generic names. Such as the fact that propanone is commonly
referred to as acetone.

21
The IUPAC system names are given on top while the common name is given on the bottom in parentheses.

Naming Aldehydes and Ketones in the Same Molecule

As with many molecules with two or more functional groups, one is given priority while the other is named as a
substituent. Because aldehydes have a higher priority than ketones, molecules which contain both functional
groups are named as aldehydes and the ketone is named as an "oxo" substituent. It is not necessary to give the
aldehyde functional group a location number; however, it is usually necessary to give a location number to the
ketone.

Naming Dialdehydes and Diketones

For dialdehydes the location numbers for both carbonyls are omitted because the aldehyde functional groups are
expected to occupy the ends of the parent chain. The ending –dial is added to the end of the parent chain name.

For diketones both carbonyls require a location number. The ending -dione or -dial is added to the end
of the parent chain.

Naming Cyclic Ketones and Diketones

In cyclic ketones the carbonyl group is assigned location position #1, and this number is not included in
the name, unless more than one carbonyl group is present. The rest of the ring is numbered to give substituents
the lowest possible location numbers. Remember the prefix cyclo is included before the parent chain name to
indicate that it is in a ring. As with other ketones the –e ending is replaced with the –one to indicate the
presence of a ketone.

With cycloalkanes which contain two ketones both carbonyls need to be given a location numbers. Also, an –
e is not removed from the end, but the suffix –dione is added.

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Naming Carbonyls and Hydroxyls in the Same Molecule
When aldehyde or ketone is present in a molecule which also contains an alcohol functional group the carbonyl
is given nomenclature priority by the IUPAC system. This means that the carbonyl is given the lowest possible
location number and the appropriate nomenclature suffix is included. In the case of alcohols the OH is named
as a hydroxyl substituent. However, the l in hydroxyl is generally removed.

Naming Carbonyls and Alkenes in the Same Molecule

When and aldehyde or ketone is present in a molecule which also contains an alkene functional group
the carbonyl is given nomenclature priority by the IUPAC system. This means that the carbonyl is given the
lowest possible location number and the appropriate nomenclature suffix is included. When carbonyls are
included with an alkene the following order is followed:

(Location number of the alkene)-(Prefix name for the longest carbon chain minus the -ane ending)-(an -
en ending to indicate the presence of an alkene)-(the location number of the carbonyl if a ketone is present)-
(either an –one or and -anal ending).
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Remember that the carbonyl has priority so it should get the lowest possible location number. Also, remember
that cis/tran or E/Z nomenclature for the alkene needs to be included if necessary.

Aldehydes and Ketones as Fragments

 Alkanoyl is the common name of the fragment, though the older naming, acyl, is still widely
used.

 Formyl is the common name of the fragment.

 Acety is the common name of the CH3-C=O- fragment.

Nomenclature of Nitriles
Name the parent alkane (include the carbon atom of the nitrile as part of the parent) followed with the
word -nitrile. The carbon in the nitrile is given the #1 location position. It is not necessary to include the
location number in the name because it is assumed that the functional group will be on the end of the parent
chain.

Cycloalkanes are followed by the word -carbonitrile. The substituent name is cyano.

1-butanenitrile or 1-cyanopropane

Nomenclature of Sulfur Compounds

1. Nomenclature of Mercaptans

a. Mercaptans can be named by naming the parent compound immediately followed by the word thiol.
The -SH group can also be named as a substituent using the group name, sulfhydryl. Mercaptans can
also be named by naming the carbon group as a separate word followed by the word mercaptan.

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Example:

CH3SH – methanethiol/ methyl mercaptan

2,2-dimethyl-1-propanethiol/ 2,2-dimethyl-1-propyl mercaptan

- Thiophenol

Nomenclature of Sulfides
Sulfides can be named most readily by naming each of the two carbon groups as a separate
word followed by a space and the word sulfide.

CH3-CH2-S-CH3 - ethyl methyl sulfide

- 2-butyl methyl sulfide

-cyclopentyl ethyl sulfide

Nomenclature of Disulfides
Disulfides can be named most readily by naming each of the two carbon groups as a separate
word followed by a space and the word disulfide.

CH3CH2-S-S-CH2CH2CH3 - ethyl 1-propyl disulfide

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 - cyclobutyl 2-propyl disulfide

Nomenclature of Sulfoxides
Sulfoxides can be named most readily by naming each of the two carbon groups as a separate
word followed by a space and the word sulfoxide.

- ethyl methyl sulfoxide

Nomenclature of Sulfoxides

Sulfoxides can be named most readily by naming each of the two carbon groups as a separate
word followed by a space and the word sulfoxide.

- ethyl methyl sulfoxide

- ethyl phenyl sulfoxide

Nomenclature of Sulfonic Acids

Sulfonic acids can be named most readily by naming the carbon group as a separate word
followed by the words sulfonic acid.

- phenyl sulfonic acid

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o - 4-decylphenylsulfonic acid

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