A.

Halogen and Nitro- Substituted Aromatics 24

NOMENCLATURE IN ORGANIC CHEMISTRY B. Carboxylic Acids and Derivatives 24
C. Phenols and Thiophenols 25
Contents D. Aldehydes and Ketones 26
1. INTRODUCTION 3 E. Sulfonic acids and Sulfonic Acid Derivatives 27
2. HYDROCARBONS 3 F. Aromatic Amines 28
(i) Alkanes 3 G. Diazonium Salts 29
A. Unbranched Chains 3 6. RADICOFUNCTIONAL NAMING 29
B. Unbranched chains 4 A. Alkyl Halides 29
(ii) Alkenes 5 B. Alcohols 29
A. One double bond 5 C. Ketones 30
B. More than one double bond 5 D. Nitriles (or Cyanides) 30
C. E/Z Isomers in Alkenes 6 E. Grignard Reagents 30
(iii) Alkynes 8
(iv) Combined Alkenes and Alkynes 8
(v) Cyclic Hydrocarbons 9
3. COMPOUNDS CONTAINING HALOGENS AND NITRO GROUPS 10
4. COMPOUNDS WITH FUNCTIONAL GROUPS NAMED AS SUFFIXES 12
(i) General Naming Scheme 12
A. Choosing the Principal Chain 13
B. Naming the Principal Chain 13
C. Numbering the Principal Chain 13
(ii) Naming Various Classes of Organic Compounds 14
A. Ethers and Thioethers 14
B. Alcohols and Thiols 14
C. Acids, Salts of Acids and Acid Anhydrides 15
D. Esters 17
E. Acid Halides 18
F. Amides 18
G. Nitriles 19
H. Aldehydes 19
I. Ketones 21
J. Amines and Ammonium Salts 22 Revised and updated
5. AROMATIC COMPOUNDS 23 Professor L D Field
(i) General Notes 23 May 2004
(ii) Aromatic Hydrocarbons 23
(iii) Substituted Aromatic Hydrocarbons 24

1 2
 B. Branched Chains
NOMENCLATURE IN ORGANIC CHEMISTRY The following steps are taken in naming an alkane with a branched chain:
(a) Find the longest continuous carbon chain and select the appropriate alkane name
1. INTRODUCTION from Table 1. (Side chains are not included in the carbon count.)
It is important that organic compounds are corrrectly and unambiguously named so that there (b) Name all of the side chains (carbon chains attached to the longest chain) and list
can be absolutely no confusion about what compounds are actually being reported or them in alphabetical order. Ignore multiplicative prefixes such as “di-“ (2), “tri-“
described. There have been many conventions for naming organic compounds - some have (3), "tetra-" (4) etc. Also ignore "sec-" and "tert-" but not "iso".
had limit scope or become embedded in common usage and some have persisted over time
(c) Number the longest chain so that substituents have the lowest possible numbers
The International Union of Pure and Applied Chemistry (I.U.P.A.C.) periodically reviews and insert location numbers before each of the side chain names.
naming practice, attempting to standardise nomenclature. The following guidelines for
organic nomenclature are based on the definitive rules published by I.U.P.A.C.1 (the Special Note: The following groups have the special names indicated:
International Union of Pure and Applied Chemistry).
CH 3 CH3
2. HYDROCARBONS isopropyl isobutyl
CH CH CH2
(i) The Alkanes (CnH2n+2)
CH3 CH3
A. Unbranched Chains
The first four (n=1-4) unbranched chain saturated hydrocarbons are called methane, ethane, CH 3 secondary-butyl CH3 tertiary-butyl
propane and butane. After this, there is a numerical term (of Greek origin) followed by the sec-butyl tert-butyl
ending "-ane". The first twelve members are given in Table 1. CH CH3 C
s-butyl t-butyl
Table 1. The names of the first 12 linear alkanes CH 3 CH3
n Name Molecular formula Constitutional formula
CH3
1 methane CH4 CH4
2 ethane C2H6 CH3CH3
3 propane C3H8 CH3CH2CH3 Examples

4 butane C4H10 CH3CH2CH2CH3 CH3 CH2 CH CH2 CH3 3-methylpentane

5 pentane C5H12 CH3CH2CH2CH2CH3 CH3

6 hexane C6H14 CH3CH2CH2CH2CH2CH3
CH3 CH CH2 CH CH CH2 CH3 2,4,5-trimethylheptane
7 heptane C7H16 CH3CH2CH2CH2CH2CH2CH3
(not 3,4,6-)
8 octane C8H18 CH3CH2CH2CH2CH2CH2CH2CH3 CH3 CH3 CH3

9 nonane C9H20 CH3CH2CH2CH2CH2CH2CH2CH2CH3 CH3

10 decane C10H22 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 4-isopropyl-2,2-dimethyloctane
CH3 CH2 CH2 CH CH2 CH CH3
11 undecane C11H24 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
CH CH3
12 dodecane C12H26 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3 CH3 CH3

CH3 CH2 4-ethyl-5-methyloctane

The group derived from one of these alkanes by removal of a terminal (end) hydrogen is
(not 5-ethyl-4-methyloctane)
called an alkyl group. The group name is found by removing "ane" from the alkane name CH3 CH2 CH2 CH CH CH2 CH2 CH3
and adding "yl".
CH3
Example: CH3-CH2-CH2-CH3 butane
becomes CH3-CH2-CH2-CH2- butyl
Note: The free valence must be on the terminal carbon.

1
I.U.P.A.C. Nomenclature for Organic Chemistry, Sections A, B and C (combined edition),
Butterworths Scientific Publications, London, 1971.

3 4
The following compounds have special names: CH3 CH CH2 propene
CH3 CH CH3
CH3 CH CH CH3 2-butene
CH3 isobutane

CH3
CH3 CH CH2CH3
CH3 C CH CH 4,4-dimethyl-2-pentene
isopentane CH3
CH3
CH3
CH3
neopentane Special Note
CH3 C CH3
CH2 CH2 has the special name “ethylene”.
CH3

B. More than one double bond

Branched side chains are named by renumbering the alkyl group giving the carbon with the
(a) Find and name the longest carbon chain containing the maximum number of
free valence (i.e. point of attachment to the main chain) the number 1 and giving substituents
double bonds.
the appropriate number in the usual way.
(b) Change the "ane" of the alkane name to:
Examples
"adiene" 2 double bonds
CH3CH2 CH CH2
"atriene" 3 double bonds
CH3 2-methylbutyl group
"atetraene" 4 double bonds etc.
(c) Number the chain so as to give the double bonds the lowest possible numbers.
CH3 CH CH CH2 CH CH3 1,3,4-trimethylpentyl group (d) Name the alkyl side chains in the usual way.
CH3 CH3

Examples (note position of numbers and punctuation)

The following example gives the name of an alkane having a branched side chain: CH2 CH CH CH2 1,3-butadiene

CH3
CH3 CH CH C CH CH CH2
CH2 CH CH2 CH3 4-butyl-2-methyl-1,3,5-heptatriene
CH3 CH2 CH2 CH2 CH3
CH3 CH2 CH2 CH CH2 CH CH2 CH2 CH2 CH2
CH3 CH2 CH3
Special Note
4-ethyl-6-(2-methylbutyl)undecane has the special name “allene”.
CH2 C CH2

(ii) The Alkenes (CnH2n)

A. One double bond C. E/Z Isomers in Alkenes

(a) Find and name the longest carbon chain containing the double bond. In the past, the terms cis and trans have been used to differentiate the isomers; cis to
indicate the isomer in which the substituents are on the same side of the double bond, trans
(b) Change the “ane" of the alkane name to “ene". when they are on opposite sides. This nomenclature is still used in some older texts,
(c) Number the carbon chain giving the double bond the lowest possible location however, the approved nomenclature for alkene stereoisomers involves the prefixes Z- or E-.
number. There are two substituents attached to each of the carbon atoms which form a C=C. The
(d) Name side chains in the usual way. carbon atoms at either end of the C=C are considered separately and at each end, the two
attached substituents are ranked according to a simple set of priority rules (or sequence
rules). The priority of the two groups attached to each carbon atom of the C=C is based
Examples (note position of numbers and punctuation) initially on the atomic number of the atom at the point of attachment. For example, a chlorine

5 6
substituent would have a higher priority than a CH3- which in turn would have a higher priority CH3 CH3 E-3-methyl-2-pentene
than a H-.
C C (note that –CH2CH3 has greater priority than – CH3)
When the C=C is considered as a whole, if the groups with the highest priorities are on the H CH2CH3
same side of the double bond then the name of the alkene is prefixed with a Z (from the
German 'zusammen' meaning 'together'). If they are on opposite sides then the prefix is E Cl CH3 E-3-chloro-2-methyl-2-penten-1-ol
(from 'entgegen' meaning 'opposite'). C C (note that –Cl has higher priority than –CH3 and
high priority high priority high priority low priority
CH3 CH2OH -CH2OH has higher priority than -CH3)
A X A X
priority A > B C C priority X > Y priority A > B C C priority X < Y
B Y B Y (iii) The Alkynes (CnH2n-2)
low priority low priority low priority high priority
These are named in identical fashion to alkenes except that "ene" in the alkene name is
replaced by:
Z- alkene E- alkene
"yne" 1 triple bond
Priority Rules "adiyne" 2 triple bonds
Each of the atoms attached directly to the C atom of a C=C is assigned a priority based on its "atriyne" 3 triple bonds etc.
atomic number: the higher the atomic number, the higher the priority. In terms of priority, if Example (note position of numbers and punctuation)
there is a hydrogen attached to one carbon of the C=C, it must always have the lowest
priority. Groups which have an oxygen atom attached directly to the C=C (eg. -OH, -OCH3) CH3 C C CH2 CH3 2-pentyne
have higher priority than groups which have a nitrogen atom attached directly to the C=C
atom (eg. –NH2, -N(CH3)2) and so on. Special Note
-I > -Br > -Cl > -OH > -NH2 > -CH3 > -H H C C H has the special name “acetylene”.
If two of the groups attached to the same carbon of a C=C begin with the same element
(eg. –CH3, -CH2CH3), then look to the next atoms away from the C=C. If the groups at this Salts of Alkynes
point are still the same, then move further from the C=C until the point of difference is found The salts of hydrocarbon anions are named by adding the ending "-ide" together with a
(there must be a point of difference somewhere). The group priority is then assigned based location number.
on the atomic numbers of the atoms at the point of difference.
Examples
So for example –CH2Cl has a higher priority than –CH2OH.
C
- + lithium 1-propyn-1-ide (from propyne)
-CH2Br > -CH2Cl > -CH(CH3)2 > -CH2CH3 > -CH3 CH3 C Li
For the purposes of assigning group priorities, double bonds or multiple bonds are expanded
to be an equivalent number of atoms attached by single bonds. So a -CH=CH2 group is H3C C
- + sodium 1-butyn-1-ide (from 1-butyne)
CH2 C Na
considered as equivalent to -CH(-CH2)2.
Examples Special Note:

CH3 CH3 - + + -C - + are called monosoium acetylide and

H C C Na Na C Na disodium acetylide respectively
C C Z-2-butene
H H
(iv) Combined Alkenes and Alkynes
H CH3
C C E-2-butene If a compound has double and triple bonds then the longest chain is selected so as to
contain the maximum number of double and triple bonds and is named by replacing the
CH3 H
"ane" of the corresponding alkane by "en(e)", "adien(e)" etc. followed by "yne", "diyne" etc.
Z-2-chloro-2-butene The "e" is omitted before a vowel or a "y".
Cl CH3
C C (note –Cl has higher priority than -CH3) The chain is numbered so as to give the lowest numbers to the double bonds, then triple
bonds.
CH3 H

7 8
Examples (note positions of numbers and punctuation) H Cl
CH2 CH C CH 1-buten-3-yne 4-chloro-3-methyl-1-cyclohexene
CH2 C
H
CH2 CH C C C CH CH3 5-methyl-1,5-heptadien-3-yne H2C C
CH3
CH3 CH CH

H C C C C CH CH CH3 2-hepten-4,6-diyne CH2 CH2

1-cyclohexylheptane
CH3 (CH2)6 HC CH2
(note that the carbon chain has more
Groups derived from alkenes, alkynes or combined hydrocarbons are named by dropping the CH2 CH2 carbons than the ring)
final "e" and replacing it by "yl". The chain is renumbered to give the carbon with the free
valence the number 1 position:
Examples (note positions of numbers and punctuation)

H C C CH CH CH2 2-penten-4-ynyl group

H C C CH2 2-propynyl group

CH3 CH CH CH2 2-butenyl group

H C C ethynyl group

Special Note: The following have special names:

CH2 CH vinyl group

CH2 CH CH2 allyl group

H C C CH2 propargyl group

(v) Cyclic Hydrocarbons

Compounds with hydrocarbon rings are named by the insertion of "cyclo"- before the name
of the hydrocarbon corresponding to the open chain compound containing the same number
of carbons.
Examples

CH2
Cyclopropane
H2C CH2

CH2 CH2
Cyclohexane
H2C CH2
CH2 CH2

9 10
3. COMPOUNDS CONTAINING HALOGENS AND NITRO GROUPS 3 COMPOUNDS WITH FUNCTIONAL GROUPS NAMED AS SUFFIXES
The halogens (F, Cl, Br, I) and the nitro group (-NO2) are always named as prefixes in the (i) General Naming Scheme
same way as side chains on hydrocarbons. The prefixes are as follows:
The name of every organic molecule containing a functional group whose name appears as
Group Prefix a suffix may be thought of as made up of four parts:
F- fluoro
Numbers Prefixes Stem Suffix
Cl- chloro
Locates the Substituents in The name of the Identifes the
Br- bromo substituents in alphabetical order pricipal (longest) principal
I- iodo the molecule chain functional group

NO2- nitro
The Principal Functional Group (PFG) whose suffix name is used is selected from Table 2
The list is in order of decreasing priority.
Examples
Table 2. Table of Functional Groups (descending order of priority)
CH3 I Iodomethane
Class Formula Prefix Suffix

CH3 CH CH3 Cation -NR3+ ammonio- -ammonium

2-chloropropane Carboxylic acid -COOH carboxy- -oic acid
Cl
Sulfonic acid -SO2OH sulfo- -sulfonic acid
CH3 Salt of Carboxylic Acid -COO- M+ carboxylato- cation name ..-oate
2-bromo-2-methylpropane Ester -COOR R-oxycarbonyl- R-…-oate
CH3 C CH3
Acid Halide C X haloformyl- -oyl halide
Br O

CH3 CH2 Amide C NH2 carbamoyl- -amide

3-ethyl-1-fluoropentane O
CH3 CH2 CH CH2 CH2 F
Nitrile C N cyano- -nitrile
CH3 CH2 NO2 nitroethane
Aldehyde C H formyl- -al
O
CH2 CH2 CH2 1-bromo-3-chloropropane
Ketone C oxo- -one
Cl Br
O

CH2 CH CH2 CH2 Cl 4-chloro-1-butene Alcohol -OH hydroxy- -ol

Thiol -SH mercapto- -thiol

Special Note: The following have special names: Amine -NH2 amino- -amine

F3C H fluoroform Imine =NH imino- -imine

Ether -OR R-oxy- -
Cl3C H chloroform
Thioether -SR R-thio- -
Br3C H bromoform

I3C H iodoform Wherever "R" appears in the prefix or suffix table then the group name (i.e. alkyl, alkenyl,
carbon tetrachloride etc.) for the R group is used.
CCl4

CBr4 carbon tetrabromide

11 12
A. Choosing the Principal Chain (ii) Naming Various Classes of Organic Compounds
The Principal Chain is chosen according to the following rules, applied in order: A. Ethers and Thioethers
(a) The chain must contain the (maximum number of) principal functional group(s); In the naming of ethers as alkyloxy derivatives of alkanes, it is general practice to shorten
then the names of compounds containing four or less carbons to alkoxy derivatives (i.e., omit the
(b) it must contain the maximum number of double and triple bonds; then syllable "-yl-°'), e.g., methyloxy becomes methoxy, ethyloxy becomes ethoxy, but pentyloxy
(for CH3CH2CH2CH2CH2O-) is correct.
(c) it must be the longest possible carbon chain (the carbons of the -CO2H, -CΞN,
-C(=O)H etc. groups are counted when they form part of the principal chain). An alternative system for naming ethers (or thioethers) is to name the alkyl groups on oxygen
(sulfur) and list them in alphabetical order as separate words before the name "ether" (or
B. Naming the Principal Chain sulfide).
The principal chain is named after the alkane having the same number of carbon atoms, and Examples
is modified when unsaturated by the replacement of “ane" by "en(e)", "enyn(e)", "adiene",
etc. The final “e” of the name is omitted before "y" or a vowel (e.g. methaneol becomes CH3 CH2 O CH2 CH3 diethyl ether or ethoxyethane
methanol).
C. Numbering the Principal Chain CH3
CH3 CH CH3 isopropyl methyl ether or 2-methoxypropane
The principal chain is numbered according to the following rules, taken in order: O
(a) the PFG.'s must be given the lowest possible numbers; then ethyl propyl sulfide or 1-ethylthiopropane
CH3 CH2 CH2 S CH2 CH3
(b) the double and triple bonds must be given the lowest possible numbers; then
(c) the remaining functional groups and substituents must be given the lowest
possible numbers. B. Alcohols and Thiols
(a) -OH or -SH as the principle functional group
The following example illustrates the basic approach to naming: Examples

CH3 OH methanol
HO CH2 CH CH C C CH3
CH3 Cl O CH3 SH methanethiol

Principal group C -one

CH3
O 2-propanol
CH3 CH OH
Principal chain C C C C C C hexane
CH2 CH2 CH2 CH2
Principal chain name plus 1,4-butanediol
C C C C C C OH OH
principal group
2-hexanone
O CH2 CH2 CH2
1,3-propanedithiol
SH SH
Modified name ("ane" 6 5 4 3 2 1 3-hexen-2-one
becomes "en") C C C C C C CH3 CH CH CH2
2-buten-1-ol
O OH

Prefixes (alphabetical with 3-chloro cyclohexanethiol

Cl SH
location number)
OH 6-hydroxy
CH3 5-methyl

Complete name: 3-chloro-6-hydroxy-5-methyl-3-hexen-2-one

13 14
(b) -OH or -SH as other than the principle functional group Table 3 lists the carboxylic acids that have have special (trivial) names which are preferred to
the formal (systematic) names.
Examples
Table 3. Special Names of Common Carboxylic Acids
CH2 CH2 CH2 CH2 C H
5-hydroxypentanal Formula Trivial Name Systematic Name
OH O
H C OH formic acid methanoic acid

CH3 CH2 CH CH CH C OH O
4-hydroxy-2-hexenoic acid
OH O acetic acid ethanoic acid
CH3 C OH
CH2 CH2 CH2 O
3-mercapto-1-propanol
OH SH
CH3 CH2 C OH propionic acid propanoic acid

O
Alcohol and Thiol Salts
The salts of alcohols and thiols are most simply named by adding "-ate" after the "-ol" of the CH3 CH2 CH2 C OH butyric acid butanoic acid
name. Alternatively, the alcoholates may be named as alkyloxides (dropping the "yl" syllable
for the first four members as in ether naming). O
Examples HO C C OH oxalic acid ethanedioc acid
sodium methoxide or sodium methanolate
CH3 O- Na+ O O
potassium pentyloxide or potassium pentanolate malonic acid propanedioic acid
CH3 CH2 CH2 CH2 CH2 O- K+ HO C CH2 C OH
O O
C. Acids, Salts of Acids and Acid Anhydrides succinic acid butanedioic acid
HO C CH2 CH2 C OH
Carboxylic acids are named by identifying the longest carbon chain containing the carboxylic
acid functional group and using this carbon chain as the stem for the carboxylic acid name. O O
The ending "-anoic acid" is added to the stem to indicate that the compound is a carboxylic
acid. COOH fumaric acid E-butenedioic acid
H
Examples
HOOC H
CH3 CH2 CH2 CH2 CH2 C OH
hexanoic acid H H maleic acid Z-butenedioic acid
O

CH3 CH2 CH CH C OH HOOC COOH

2-bromo-3-methylpentanoic acid
CH3 Br O CH3 CH C OH lactic acid 2-hydroxypropionic acid

OH O
CH2 CH CH CH2 CH3
2-ethyl-3-butenoic acid
COOH
The stem name formed by removal of "-ic" from the trivial name is also used in naming other
acid derivatives and aldehydes.

15 16
Acid anhydrides are named when symmetrical by replacement of the word "acid" by E. Acid Halides
anhydride. When unsymmetrical, the two acid groups are named as separate words in
Acid halides are maned by replacing the "-ic acid" ending of the parent carboxylic acid with
alphabetical order and the word anhydride is added.
"-yl halide”.
Examples
Examples
CH3 C O C CH3 acetic anhydride
CH3 C Cl acetyl chloride
O O
O
CH3 CH2 CH2 C O C CH3 acetic butyric anhydride
CH3 CH2 C Br propionyl bromide
O O
O

CH3
Acid salts are named by replacicing the “ic” ending of the acid name with “ate”. 2-methylpentanoyl bromide
CH3 CH2 CH2 CH C Br
Examples
O
sodium butyrate
CH3 CH2 CH2 C O- Na+
O
F. Amides
- ammonium acetate Primary amides are named by identifying the carboxylic acid from which the amide is derived
CH3 C O NH4+
and replacing the "-ic acid" or "-oic acid" ending of the parent carboxylic acid name with the
O ending "-amide".

CH3 When there are substituents on the N atom, these are named using N-alkyl or N,N-dialkyl as
prefixes (note N or N,N are italicised) immediately before the main chain name.
- + potassium 5,5-dimethylhexanoate
CH3 C CH2 CH2 CH2 C O K
Examples
CH O
3
CH3 C NH2 acetamide

2+ calcium formate (or calcium diformate) O

Ca (HCO 2-)2
CH3 CH2 CH2 CH2 CH2 CH2 C NH2 heptanamide

D. Esters
O

The alkyl (alkenyl etc.) group on oxygen is named as a separate word and is followed by the CH3 CH2 CH2 C NH N-methylbutyramide
acid salt name ("-ic acid" becomes "-ate").
O CH3
Examples

CH3 CH2 C O CH2 CH3 ethyl propionate CH3 N,N-dimethylformamide

O H C N
propyl formate O CH3
H C O CH2 CH2 CH3
O 6-methyl-N-ethyl-N-
CH3 CH CH2 CH2 CH2 CH2 C N CH2CH3
propylheptanamide
CH3 CH CH C O CH2 CH2 CH3 propyl 2-butenoate CH3 O CH2CH2CH3
O

CH3
CH3 CH2 CH2 C O CH CH3 isopropyl butyrate
O

17 18
G. Nitriles Cl
The nitriles formed from acids with trivial names are named by replacing the “ic acid” ending 5-chlorohexanal
of the parent carboxylic acid with "-onitrile". Otherwise, "-nitrile" is used as a suffix to the CH3 CH CH2 CH2 CH2 C H
stem name of the parent alkane. O
Examples
CH3 CH2 CH2 CH2 CH2 CH CH CH2 C H 3-nonenal
CH3 CN acetonitrile
O
CH3 CH2 CH2 CH2 CH2 CH2 CN heptanenitrile

Special Note: the compound

CH3
2-hydroxy-2-methylpropanenitrile H C C H has the special name glyoxal
CH3 C CN
O O
OH

Cl
2-chloropentanenitrile Special Note: The prefix "formyl" is only used when a functional group of higher priority is
CH3 CH2 CH2 CH CN present.
hydrogen cyanide (not formonitrile) H C CH2 CH2 CH2 CH2 C OH 5-formylpentanoic acid
H CN
O O

Special Note: The prefix "cyano" is only used when a functional group of higher priority is + (4-formylbutyl)trimethylammonium
present. H C CH2 CH2 CH2 CH2 N(CH3)3 Br- bromide
CH3CH2 CH CH2 COOH 3-cyanopentanoic acid O
CN
methyl cyanoacetate Derivatives of aldehydes and ketones, e.g. oximes or hydrazones are named simply by
NC CH2 C OCH3
adding the word oxime etc. after the aldehyde or ketone name.
O
Examples

CH3 CH2 CH2 C H butyraldehyde oxime

H. Aldehydes
N OH
Aldehydes formally derived from acids having a trivial name are named by adding
"-aldehyde" to the trivial stem (see Section 3), otherwise the suffix “-al” is used. acetone oxime
CH3 C CH3
Examples
N OH
H C H formaldehyde
cyclohexanone hydrazone
O NHNH2

CH3 C H acetaldehyde
CH3CH2 C CH2CH3 3-pentanone oxime
O
NOH
CH3 CH2 CH2 C H butyraldehyde (or butanal)

19 20
I. Ketones J. Amines and Ammonium Salts
Ketones are named by adding the suffix "-one" to the stem of the parent carbon chain. The systematic method of naming amines, whereby "-amine" is added to the principal chain
name is, in practice, only rarely used and an older method is in common (I.U.P.A.C.
Examples
accepted) use. Amines are named as derivatives of ammonia. The longest chain attached
CH3 C CH2 CH3 butanone to the nitrogen atom is named in the usual way for an alkyl group (the carbon attached to the
nitrogen is carbon 1). Any other N-substituents are named as N-alkyl, or N,N-dialkyl
O substituents. The alkyl name for the longest stem is then added to the suffix "amine".

3-pentanone Examples The following examples show this common naming in practice (together with
CH3 CH2 C CH2 CH3 the formal, systematic names in parenthesis):
O methylamine (methanamine)
CH3 NH2
cyclopentanone
O CH3 NH dimethylamine (N-methylmethanamine)

CH3
CH3 CH CH2 C CH2 CH3 5-methyl-3-hexanone

CH3 O CH3
dimethylamine (N,N-dimethylmethanamine)
CH3 NH
CH3 C CH2 CH2 CH2 C CH3 2,6-heptanedione
CH3
O O
CH2CH3
H 4-ethylcyclohexanone
O N-ethyl-N-methylpentylamine (N-ethyl-N-methyl-
CH3CH2CH2CH2CH2 N
CH3CH2 1-pentanamine)
CH3

Special Note: the following compounds have special names: CH2CH3

1-ethyl-N-methylbutylamine
CH3 C CH3 acetone CH3CH2CH2CH NH
(N-methyl-3-hexanamine)
O CH3

CH3 C C CH3 biacetyl

Imines are best named systematically
O O
Examples
CH3CH NH ethanimine
Special Note: The prefix "oxo" is used when the ketone is not the principal functional group.
Examples CH3CH2CH2CH NCH2CH3 N-ethyl-1-butanimine

CH3 C CH2 CH2 C H 4-oxopentanal

O O
CH3CH2 C CH2CH2COOH
O
Ammonium Salts are named as alkyl derivatives of inorganic ammonium salts. Note that
the N- system is not used and the four alkyl groups attaached to N are listed alphabetically.
4-oxohexanoic acid
Examples
(CH3)4N+ I- tetramethylammonium iodide

CH2CH3
+ - diethylhexylmethylammonium chloride
CH3CH2CH2CH2CH2CH2 N CH3 Cl
CH2CH3

21 22
5 AROMATIC COMPOUNDS (iii) Substituted Aromatic Compounds
(i) General Notes A. Halogen and Nitro- Substituted Aromatics
The use of numbers to indicate the position of substituents on aromatic rings is These are named using halo- or nitro- prefixes before the name of the aromatic
supplemented in the case of disubstituted derivatives of benzene by the terms: hydrocarbon in the usual way.
ortho- abbreviated o- indicating 1,2-disubstitution Examples
meta- abbreviated m- indicating 1,3-disubstitution Cl NO2
para- abbreviated p- indicating 1,4-disubstitution chlorobenzene nitrobenzene
Examples
Br
NO2 NO2 1-chloro-2,4-
benzene Cl o-bromochlorobenzene
dinitrobenzene
p-dinitrobenzene
O2N Cl
NO2
I Cl
m-iodonitrobenzene p-chloronitobenzene
B. Carboxylic Acids and Derivatives
NO2 The following list gives the trivial (usually accepted) names for some of the common aromatic
NO2 acids and derivatives.
COOH COOH
benzoic acid CH3 o-toluic acid
(ii) Aromatic Hydrocarbons
The following aromatic compounds have the special name and derived group names shown
below:
1 phenyl group COOH COOH
6 2 m-anisic acid phthalic acid
benzene (abbreviated –Ph)
COOH
5 3
OCH3
4

CH3 CH3 tolyl group COOH Br COOH

toluene (o-tolyl shown) m-nitrobenzoic 3,5-
acid dibrombenzoic
acid
anisyl group NO2 Br
OCH3 OCH3
anisole (o-anisyl shown) NO2 COOH
COOH 2,4,6- 2-naphthoic acid
CH2CH3 CH2 benzyl group trinitrobenzoic
acid
ethylbenzene (abbreviated -Bz) O2N NO2

1
NO2 COOH
8 naphthyl group
2
COOH 6-nitro-o-toluic 6-bromo-2-
7 naphthalene (2-naphthyl shown) acid Br naphthoic acid
6 3
CH3
5 4

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Carboxylic acid Derivatives When the -OH group is not the principal functional group, "hydroxy" is used in the usual way.
Acid derivatives, esters, anhydrides, amides and nitriles are named in the usual way, Example
replacing "-oic" or "-ic" of the acid name with the appropriate endings.
OH OH
Examples
p-hydroxybenzoic acid p-hydroxybenzonitrile
COO Na
- + COCl
sodium benzoate m-anisoyl chloride
(from m-anisic acid) COOH CN
OCH3

CN CONH2 D. Aldehydes and Ketones

benzonitrile Cl o-chlorobenzamide Aldehydes are named by replacing the "-ic" or "-oic" of the acid name by "aldehyde”.
Examples
O O
O benzaldehyde o-tolualdehyde
C C
O propyl benzoate C methyl o-toluate H H
CH3CH2CH2 C OCH3
O CH3
CH3
O O
O
C o-nitrobenzaldehyde C salicylaldehyde
O p-chlorophenyl C phthalic anhydride H H
C benzoate
O NO2 OH
Cl O C
O O
C p-hydroxybenzaldehyde
H
C. Phenols and Thiophenols
HO
Phenols have an –OH group attached directly to an aromatic ring.

OH OH Aromatic ketones are named by changing the "ic" or "oic" ending of the acid name
phenol 2-naphthol corresponding to the acyl group attached to the benzene ring to "-ophenone"
Examples
O O
OH OH acetophenone propiophenone
C C
m-cresol 3,4-dibromophenol CH3 CH2CH3

CH3 Br
O
Br
C m-nitrobutyrophenone
CH2CH2CH3
SH
thiophenol (or
benzenethiol)
NO2

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Aldehydes and ketones in which the carbonyl group is not directly attached to the aromatic F. Aromatic Amines
ring are named using the corresponding group name for the aromatic system as a prefix.
Special Names
Examples
NH2 NH2
CH2CHO aniline m-toluidine
phenylacetaldehyde
CH3
O
CH2 C CH2CH3 1-(m-nitrophenyl)-2-butanone NH2 NH2
p-anisidine o-phenylene
CH3O NH2 diamine

NO2
The remaining aromatic amines are named as derivatives of these or (in the presence of
E. Sulfonic Acids and Sulfonic Acid Derivatives more important functional groups) as "amino-" derivatives, or as "phenylamines".
Sulfonic acids are named by adding the suffix "-sulfonic acid". Examples
Examples NH2 2,4,6-tribromoaniline

SO3H Br Br
benzenesulfonic acid

SO3H o-hydroxybenzenesulfonic acid Br

OH diphenylamine
p-toluenesulfonic acid N
SO3H
H
CH3 NHCH3
NO2 2,4-dinitro–N-methylaniline
Sulfonic Acid Derivatives. Derivatives of sulfonic acids (esters, amides and sulfonic acid
chlorides) are named by analogy with carboxylic acids.
Examples NO2
SO2OCH3
methyl o-toluenesulfonate Ammonium Salts
CH3 These are named by changing the "-e" of the special names to “-ium".
SO2NH2 Examples
benzenesulfonamide + -
NH3 Cl
anilinium chloride
SO2Cl
m-nitrobenzenesulfonyl chloride
+ - 3-nitro-N,N-dimethylanilium
(CH3)2NH Br
bromide.
NO2

NO2

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Acyl Derivatives (Amides) C. Ketones
Simple acyl derivatives are named by adding the trivial acid name stem to "-anilide" etc. CH3 CH3 CH3CH2 CH3 ethyl methyl
C C ketone
Example dimethyl ketone
O O
H
acetanilide O O methyl vinyl
N CH3 ketone
C C methyl phenyl ketone CH2 CH C CH3
O CH3

G. Diazonium Ions (ArN2+)

These are named in an analogous fashion to sulfonic acids; the syllable "-diazonium" is D. Nitriles (Cyanides)
added to the aromatic name. methyl cyanide
CH3CN CH2CN
Examples benzyl cyanide
+
N2
benzenediazonium ion
E. Grignard Reagents
+ -
N2 HSO4 CH3CH2MgBr ethyl magnesium MgCl phenyl
p-bromobenzenediazonium bromide magnesium
hydrogen sulfate chloride
Br

6. RADICOFUNCTIONAL NAMING
An alternate system of naming, which is still very common in many textbooks, consists of
naming the alkyl or aryl groups attached to a certain functional group as separate words
followed by the functional group name. The alternative naming of ethers and amines is a
remnant of this system. The following examples suffice to illustrate the system.
A. Alkyl Halides
CH3 I methyl iodide (CH3)2CHBr isopropyl
bromide
(CH3)3CCl tert-butyl chloride CH2Cl
benzyl chloride

B. Alcohols
CH3OH methyl alcohol (CH3)3COH tert-butyl alcohol

CH2OH
benzyl alcohol Revised and updated
Professor L D Field
May 2004

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