CHEMICAL NOMENCLATURE FOR USE IN MATRICULATION

EXAMINATIONS

October 2003

MATRICULATION AND SECONDARY EDUCATION CERTIFICATE

EXAMINATIONS BOARD
 Foreword

This document is intended as a guide for teachers, examiners and students preparing for
the Advanced (mainly) and Intermediate Matriculation Examinations in Chemistry of the
University of Malta. It deals with the nomenclature of those inorganic and organic
compounds likely to be relevant to the syllabus matter of these examinations. The
document is inspired especially by information contained in the publications listed in the
reference section: these books contain significantly longer “Lists of recommended
names” than found here.

The statements in this document must not be construed as extending, in any way, the
examinable material described in the Syllabus for Intermediate and Advanced Chemistry
of the Matriculation and Secondary Education Certificate Examinations Board.

The Syllabus Panel working on the review of the Advanced and Intermediate Chemistry
Syllabus for 2005-7 has approved this document.

Alfred J. Vella
Department of Chemistry
October 2003 University of Malta

© Matriculation and Secondary Education Certificate Examinations Board, 2003

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 CHEMICAL NOMENCLATURE FOR USE IN MATRICULATION
EXAMINATIONS

1. Chemical nomenclature in Matriculation examination papers

It is proposed that the following principles are followed in setting examination questions
for Matriculation Chemistry.

(a) In general, recommended names derived from rules of nomenclature as outlined

in this publication are used for all compounds.
(b) In the case of carbon compounds and their derivatives, recommended names are
used except that common names may be used additionally for certain well-known
compounds, especially those containing one or two carbon atoms, mono-
substituted benzene derivatives and natural products.

In answers to examination questions, candidates may use any name or symbol, which is
generally accepted for a compound or a group, unless the question is specifically on some
aspect of nomenclature that falls within the syllabus.

2. Inorganic Nomenclature

This section describes briefly some aspects of nomenclature as it pertains to those

inorganic compounds as may be encountered in the syllabus material for Matriculation
Chemistry; parts of this discussion are not applicable to Intermediate Chemistry.

Names for inorganic compounds can be trivial or systematic and the choice of name is
dictated by the context; e.g. the substance known trivially as Glauber’s salt can be named
systematically as sodium sulfate-10-water. Trivial names are generally sufficient to
identify what is in a bottle and, if for no other reason than this, will probably remain
indefinitely as part of school chemical knowledge.

2.1 Binary compounds

Binary compounds have names ending in ‘-ide’ with the more electropositive element
named first, e.g. ZnO is zinc oxide, OF2 is oxygen difluoride. For historical reasons,
hydroxides and cyanides break this rule. Other chief exceptions are water, ammonia
(which may, in future, be renamed ‘azane’), methane and other non-metal hydrides. A
Roman numeral in parenthesis indicates the oxidation number of the less electronegative
constituent after the name of that element unless the compound consists of simple
molecules whose composition is revealed by the name itself. For example, copper(I)
oxide, phosphorus(V) oxide but sulfur dioxide for SO2 and phosphorus trichloride for
PCl3.

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Notice the spelling ‘sulfur’ for the element S (rather than ‘sulphur’) and this accords with
IUPAC rules, although phosphorus retains its traditional spelling.

In ionic or polymeric solids, the oxidation state of the electropositive element is given
unless there can be no doubt about what it is, e.g. sodium chloride not sodium(I) chloride
but copper(II) bromide; for Ag+, the oxidation state may be omitted (even though a few
silver(II) compounds exist since these will almost certainly not be encountered in school
chemistry).

2.2 Simple salts

Simple salts are named as shown in the following illustrative examples: Al(NO3)3:
aluminium nitrate(V); KHCO3: potassium hydrogencarbonate; CuSO4: copper(II)
sulfate(VI); PbCO3: lead(II) carbonate; AgNO3: silver nitrate(V).

2.3 Double salts, basic salts and double oxides

In double salts there are two cations that are independent of each other, though each
might be hydrated, e.g. the alums; less commonly there may be more than one anion.

The order of naming is that cations precede anions and within each category the ions are
listed in alphabetical order of their names. In writing chemical formulae, however, the
sequence within each class should be in alphabetical order of the symbols except that
hydrogen is always cited last, before the anion.

Basic salts are named as double salts with oxide or hydroxide anions whenever the
structure is known and the same procedure is used for double oxides.

Examples:

aluminium potassium sulfate(VI)-12-water AlK(SO4)2.12H2O

ammonium chromium(III) sulfate(VI)-12-water CrNH4(SO4)2.12H2O
bismuth(III) chloride oxide BiClO
sodium hydrogensulfate(IV) NaHSO3
dilead(II) lead(IV) oxide Pb 3O4 or (PbII)2PbIVO4
oxovanadium(IV) sulfate(VI) VOSO4

2.4 Coordination compounds

Coordination compounds are treated as consisting of a central metal ion to which ligands
(ions or molecules) are attached to form a complex. As in simple ionic salts, for ionic
coordination compounds, the cation is named first and then the anion. The name of the
complex is formed by placing the names of the ligands in alphabetical order, ignoring
numerical prefixes, before the name of the central atom. The oxidation number of the
central atom is placed after the metal name for a complex cation and after the metal name
and the suffix ‘-ate’ for a complex anion. For some metals, the Latin version of the name

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is used in anionic complexes, the more important cases being ferrate for Fe, argentate for
Ag, stannate for Sn and plumbate for Pb. For the purposes of the Matriculation
Examination, in writing formulae of complexes containing more than one type of ligand,
the metal ion should always appear first but the ligands may be shown in any order.

Examples:

tetraamminecopper(II) [Cu(NH3)4] 2+
tetracarbonylnickel(0) Ni(CO)4
pentacyanonitrosylferrate(II) [Fe(CN)5(NO)]2-
hexaaquaaluminium(III) [Al(H2O)6]3+
tetraamminechloronitrocobalt(III) nitrate(V) [Co(NH3)4(NO2)Cl]NO3

There is no hyphen between the numerical prefixes and the names of the ligands (e.g.
between ‘hexa’ and ‘ammine’ or ‘aqua’). Anionic ligands have names ending in ‘o’
derived by adding the letter to the stem name of the group, e.g. chloro for Cl-, cyano for
CN-, OH- hydroxo. For neutral ligands, the name of the free molecule is used as such but
special names are given to some common ligands, of which the more important are aqua
(H2O), ammine (NH3), carbonyl (CO) and nitrosyl (NO).

2.5 Hydrates

The number of water molecules of hydration are shown by an Arabic number after the
name of the anhydrous substance as shown by this example: copper(II) sulfate(VI)-5-
water. The formula is written thus: CuSO4.5H2O. If the context warrants, this salt may
also be described as tetraaquacopper(II) sulfate(VI)-1-water. When the extent of
hydration is unknown, or the context warrants it, the word “hydrated” may be placed
before the name of the anhydrous material.

2.6 Oxoacids

Oxoacids and their salts are named as ‘-ic acid’ and ‘-ate’, respectively, giving the
oxidation number of the central atom. The number of oxygen atoms need not be
indicated. Thus, although the name of the species SO42- is formally tetraoxosulfate(VI),
the species can also be named sulfate(VI) and the latter form will be used in examination
papers. In the traditional system, the use of the terms ‘sulfate’ and ‘sulfite’ distinguished
between the two oxoanions of sulfur, i.e. sulfate(VI) and sulfate(IV), and similarly the
use of the terms ‘nitrate’ and ‘nitrite’. Use of these names, and of the corresponding
acids (sulfuric, sulfurous, nitric and nitrous) will be allowed in the examination, but not
in answers to questions dealing specifically with nomenclature when students are
expected to give systematic names. The ion S2O32- will be named ‘thiosulfate’ without
reference to oxidation number (which raises problems).

Phosphorus oxoacids require special mention. The distinction between simple and
condensed acids and their salts is made by using names such as phosphate(V) for PO43-,
diphosphate(V) for P2O72-, (cf dichromate(VI)), implying presence of P-O-P link and

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polytrioxophosphate(V) for (PO3)nn-. Those acids containing P-H bonds are named as
follows:

HOPH2O phosphinic acid (previously hypophosphorous acid)

(HO)2PHO phosphonic acid (previously phosphorous acid)

and the corresponding salts are phosphinate (PH2O2-) and phosphonate (PHO32-). The
terms hypophosphite and phosphite should not be used.
Although the free acid (HO)3P , or trioxophosphoric(III) acid is not known, esters
regarded as derived from it exist and are named as phosphate(III), e.g. (C2H5O)3P is
triethyl phosphate(III). These organophosphorus compounds, however, are not included
in the current Advanced Chemistry syllabus.

2.7 List of recommended names of typical inorganic species (with traditional names)

The following list, which is not comprehensive, is intended to illustrate further the
application of the rules of nomenclature as described in this document.

Recommended Name (and formula, where Traditional Name

appropriate)
aluminate ion, regarded as AlO2- or Al(OH)4- aluminate ion
ammonium dihydrogenphosphate(V) ammonium dihydrogenorthophosphate
ammonium iron(II) sulfate(VI)-6-water ferrous ammonium sulphate
ammonium peroxodisulfate(VI) ammonium persulphate
ammonium polytrioxovanadate(V), ammonium vanadate
NH4VO3
aqueous ammonia, NH3(aq) ammonium hydroxide
aqueous calcium hydroxide limewater
bromate(I), BrO- hypobromite
bromic(V) acid, HBrO3 bromic acid
carbon (diamond) diamond
carbon (fullerene) buckminsterfullerene
chlorate(III), ClO2- chlorite
chlorate(VII), ClO4- perchlorate
dichlorine oxide chlorine monoxide
chromium(III) chromic
hexacyanoferrate(II) ferrocyanide
disulfate(IV), S2O52- metabisulphite
hydrazinium chloride hydrazine hydrochloride
tetrahydridoaluminate aluminohydride
hydrogendifluoride ion, HF2- hydrogen fluoride ion
iron(II) disulfide iron pyrites
dilead(II) lead(IV) oxide triplumbic tetraoxide, red lead
manganate(VII) permanganate
nitric(III) acid nitrous acid

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Recommended Name (and formula, where Traditional Name
appropriate)
nitryl cation, NO2+ nitronium ion
oxoacids oxyacids
ozonolysis ozonolysis
trioxygen (in discussing allotropy) ozone
oxygen or dioxygen (in discussing oxygen
allotropy)
phosphorus(III) oxide phosphorus trioxide
phosphorus trichloride oxide phosphorus oxychloride
phosphorus pentachloride, PCl5 (as gas, the phosphorus pentachloride
solid is, strictly, tetrachlorophosphonium(V)
hexachlorophosphate(V))
silicon(IV) oxide silicon dioxide, silica
disulfur dichloride sulphur monochloride
sulfur dichloride dioxide, SCl2O2 sulphuryl chloride
sulfur dichloride oxide, SCl2O thionyl chloride
tetrahydridoaluminate ion, AlH4- aluminohydride ion
vanadium(IV) oxide sulfate, VOSO4 vanadyl sulphate
zincate ion (tetrahydroxozincate(II) and zincate ion
trihydroxozincate(II) may exist in aqueous solution
while molten sodium zincate may contain
dioxozincate(II) ions. Other solid zincates should be
named as double oxides.

3. Organic Nomenclature

3.1 General Principles

The IUPAC nomenclature is used: every name consists of a root, one suffix and as many
prefixes as necessary. For the purposes of the Advanced Chemistry syllabus, the root is
an aliphatic hydrocarbon or a single ring homocyclic system: multicyclic and
heterocyclic compounds are not in the syllabus.

Compounds are regarded as derived from hydrocarbons by replacement of hydrogen

atoms by alkyl or other groups and by introduction or saturation of multiple bonds. The
systematic name is formed by attaching a suffix and prefixes to denote this substitution of
hydrogen. While only one suffix may be used, as many prefixes as are needed may be
included. The following list of functional groups defines the priority order for the
principal group to be chosen as the suffix: the group nearest the top of the list has the
higher priority.

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Formula Name as Suffix Name as Prefix Name as Suffix
(if the functional group
carbon is not counted in
C-chain forming the root)

-COOH -oic acid -carboxylic acid

-COO- -oate (ion) -carboxylate (ion)
-COOR alkyl…-oate alkyl…-carboxylate
-COCl -oyl halide -carbonyl halide
-CONH2 -amide -carboxamide
-CN -nitrile cyano- -carbonitrile
-CHO -al oxo- -carbaldehyde
-CO -one oxo-
-OH -ol hydroxy-
-NH2 -amine amino-

In the carbon-containing functional groups given in the list, the carbon atom of the
functional group is counted in the carbon chain which forms the root. Any other group
present in a structure, including those not in the above list such as –Cl, and -NO2, is
named by a prefix. If more than one prefix is needed they are placed in alphabetical
order. Multiplying prefixes, such as di- or tri- do not affect alphabetical order. The
syllables ‘ane’, ‘ene’ and ‘yne’ for denoting alkane, alkene and alkyne functionality
respectively are regarded to form part of the root and not as suffixes. When ‘ene’ and
‘yne’ appear together in a name, they are included in alphabetical order.

For certain structures, it may be required to include carbon-containing functional groups

in the name of the compound by using a prefix (e.g. “chlorocarbonyl” for -COCl ):
questions involving the naming of such structural formulae will not be set in the
Matriculation Examination.

The carbon atoms in the parent hydrocarbon (the root) are numbered consecutively and
the appropriate number (locant) precedes the name of the prefix or suffix indicating the
group attached to that carbon atom. The numbering is arranged to give, first, the lowest
possible number to the group cited by a suffix and then the lowest possible individual
numbers (not sum!) to those groups cited as prefixes, observing that when series of
locants containing the same number of terms are compared term by term, that series is
“lowest” which contains the lowest number on the occasion of the first difference. This
principle is applied irrespective of the nature of the substituents. The lowest possible
locant is assigned to a C=C double bond when present.

Numbers are omitted when the structure can be deduced without them, especially the
locant ‘1’, e.g. butanone not butan-2-one.

An italicised atomic symbol is used in appropriate circumstances to indicate the atom to

which the substituent is attached, e.g. N-phenylpropanamide.

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Other illustrative examples:
ClCH2CH2Br 1-bromo-2-chloroethane
HOCH2CH2CH2CHO 4-hydroxybutanal
CH3OC(CH3)3 2-methoxy-2-methylpropane
HOCH2CH2NH2 2-aminoethan-1-ol or 2-aminoethanol
CH3CH2CH(CH3)CH(CH3)(CH2)4CH(CH3)2 2,7,8-trimethyldecane
HC C CH2CH CHCH3 hex-2-ene-5-yne
CH3CH=CHCH(CH3)2 4-methylpent-2-ene

3.2 Aromatic compounds

A Kekulé structure or a hexagon/circle symbol may be used for benzene. The benzene
ring is numbered from the carbon atom to which the principal group is attached. Students
are expected to be familiar with the nomenclature for disubstituted benzene rings which
in place of numeral locants uses the prefixes ortho-, meta- and para- (abbreviated o-, m-,
p-) e.g. p-nitrophenol for 4- nitrophenol; or o-dichlorobenzene for 1,2-dichlorobenzene.

Homologues of benzene are named as alkylbenzenes, e.g. ethylbenzene for C6H5CH2CH3.

When a side-chain contains a functional group it would be possible either to name the
compound as a derivative of benzene or to name it as a phenyl-substituted aliphatic
compound. The guiding principle is to use a name that places emphasis on the functional
group that dominates the chemistry being taught at school level. Thus while
C6H5CH=CH2 can either be named ethenylbenzene or phenylethene, it is recommended
to adopt the second name since at Advanced Matriculation Level, the substance is studied
as a substituted alkene. However, either name derived as explained earlier will be
acceptable to the examiners.

To name benzene rings substituted by carboxylic acids or derivatives, etc. the use of
suffixes -carboxylic acid, -carbaldehyde etc. is recommended, e.g. benzene-1,2-
dicarboxylic acid; benzenecarboxamide (C6H5CONH2); benzenecarbonyl chloride
(C6H5COCl). However, semi-systematic names for these compounds will also be
acceptable, e.g. benzamide for benzenecarboxamide, benzoyl chloride for
benzenecarbonyl chloride, 2-nitrobenzaldehyde for 2-nitrobenzenecarbaldehyde.
The names phenol and phenyl, derived from “phene”, an unsuccessful replacement name
for benzene, continue to be used but polyhydroxy-compounds of benzene should be
named systematically, e.g. benzene-1,4-diol but 4-nitrophenol and not 4-nitrohydroxy-
benzene.

3.3 Amines

At present amines are generally named as methylamine, phenylamine, diethylamine,

methylethylamine etc. However, for primary amines, alternatives derived from the name
of the alkane rather than the alkyl group, e.g. methanamine for methylamine, are also
acceptable and may be encountered in the examination paper. (N.B. Other examining
boards may not be happy with such names and prefer alkylamines.) When an amine
group is not bonded to the first carbon atom of an alkyl chain or when more than one

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amine group is present, a substitutive name such as propan-2-amine or ethane-1,2-
diamine, analogous to benzene-1,3-diamine, can be used.

Amine salts should be named as alkylammonium compounds, e.g. ethylammonium

chloride for C2H5NH3Cl; use of names such as “ethylamine hydrochloride” should be
avoided.

Use of the systematic name for ethylenediaminetetraacetic acid, which is 1,2-

bis[bis(carboxymethyl)amino]ethane is not recommended and will not be tested; rather
this compound should be referred to as “H4edta” since “edta” is the commonly used term
for the ligand formed from the parent acid by loss of protons. Similarly, use of the
abbreviation “en” for ethane-1,2-diamine in formulae showing this substance reacting as
a ligand is acceptable.

3.4 Terms and generic names

The following list contains some of the terms and generic names which continue to be
useful and may be encountered in examination questions.

Acetal; acetylide; alcohol; aldehyde; aliphatic; alkoxide; alkyl; amide; amine; amino acid;
anhydride; aromatic; aryl; carbohydrate; carbonyl; carboxyl; cyanohydrin; epoxide; ester;
ether; glycol; hemiacetal; hydroxy acid; ketone; monosaccharide; nitrile; peptide; phenol;
polymer; polysaccharide; protein; sugar; sulfonic acid.

The terms ‘primary, secondary, tertiary’ as applied to classes of alcohols and amines
remain useful; however prefixes such as n-, iso-, sec-, tert- etc are not recommended.
Thus iso-propyl becomes 1-methylethyl.

3.5 Polymers

Polymers are named according to one of two systems: either one that is based on the
source (monomer) or process from which the polymer is made or one based on the
structure of the polymer itself. Most addition polymers are named according to the
monomer or source from which they were formed while most condensation polymers are
described by the types of linkages involved in their structures.

The source-based naming of addition polymers leads to poly(alkene) descriptions, e.g.

poly(propene), poly(methyl 2-methylpropenoate) (for acrylic, Perspex or polymethyl
methacrylate). The structure based name for poly(tetrafluoroethene) would be
poly(difluoromethylene). It is recommended to use the source-based system of naming
for addition polymers.

Names for condensation polymers are difficult to construct and will not be tested. These
polymers should be described by simple block diagrams such as

…–NHCO-‫ٱ‬-CONH-X-NHCO-‫ٱ‬-CONH-X-NHCO-…

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The latter structure could represent a polyamide such as, e.g., Nylon-6,6 derived from
condensation of a six-carbon diamine (hexane-1,6-diamine) and a six-carbon diacid
(hexanedioic acid).

3.6 Policy on dual naming

Much chemical information is currently available in sources using many trivial or semi-
systematic names and this situation will probably continue long into the future. It is thus
felt that the commoner of the traditional names should be taught alongside the systematic
names and these names should include formic, acetic, benzoic and their related names,
ethylene, acetylene and phenol. This knowledge, however, will not be examined unless
in a manner that does not raise any doubt; moreover, the use of these names in student
answers will be permitted unless given in response to questions on nomenclature, when
systematic or, for aromatic compounds, semi-systematic names will be expected. Thus 2-
nitrobenzenecarboxylic acid and 2-nitrobenzoic acid are equally acceptable names and
both may be employed in the examination paper. In biochemistry, trivial names and
approved abbreviations (e.g. Ala, Gly) for amino acids should continue to be employed
when the structure of the entity is not being considered. It is strongly recommended that
optical activity in molecules be represented by the symbols + and – and use of the letters
d and l be discontinued.

3.7 List of recommended names of typical organic species (with traditional names)

The following list, which is not comprehensive, is intended to illustrate further the
application of the rules of nomenclature as described in this document.

Recommended Name Traditional Name

alkanes paraffins
alkanoic acids fatty acids
alkenes olefins
alkyl alkyl
alkylmagnesium halide alkyl magnesium halide (Grignard reagent)
alkynes acetylenes
aminoethanoic acid glycine
arenes aromatic hydrocarbons
aryl aryl
benzenecarbaldehyde or benzaldehyde
benzaldehyde
benzenecarbaldehyde oxime or benzaldoxime
benzaldehyde oxime
benzenecarbonitrile or benzonitrile
benzonitrile
benzenecarbonyl chloride or benzoyl chloride
benzoyl chloride

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 Recommended Name Traditional Name
benzenediazonium ion benzenediazonium or phenyldiazonium ion
benzenesulfonic acid benzenesulphonic acid
but-1-ene butylenes
cis-butenedioic acid maleic acid
trans-butenedioic acid fumaric acid
calcium ethynediide or calcium carbide or calcium acetylide
calcium dicarbide
carbamide or urea urea
1,2,3,4,5,6-hexachlorocyclohexane benzene hexachloride
trichloromethane chloroform
(chloromethyl)benzene benzyl chloride
chloro-2-methylbenzene o-chlorotoluene
(trichloromethyl)benzene benzotrichloride
dicopper(I) ethynediide cuprous acetylide
ethanenitrile acetonitrile
ethanal oxime acetaldoxime or acetaldehyde oxime
ethanal tetramer metaldehyde
ethanal trimer paraldehyde
ethane-1,2-diol ethylene glycol
ethanoic anhydride acetic anhydride
ethanoic methanoic anhydride acetic formic anhydride
ethenyl ethanoate vinyl acetate
ethoxyethane ether or diethyl ether
ethyl benzenecarboxylate or ethyl benzoate ethyl benzoate
cyclohexene cyclohexene
4-hydroxy-4-methylpentan-2-one diacetone alcohol
2-hydroxy-2-methylpropanenitrile acetone cyanohydrin
2-hydroxypropane-1,2,3-tricarboxylic acid citric acid
litmus litmus
methyl orange methyl orange
2-methylbenzenecarboxylic acid or o-toluic acid
2-methylbenzoic acid
3-methylbutyl- isoamyl-
1,1-dimethylethyl- tert-butyl-
2-methyl-1,3,5-trinitrobenzene trinitrotoluene
N-methylphenylamine N-methylaniline
4-nitrophenylamine p-nitroaniline
3-oxobutanoic acid acetoacetic acid (keto form)
pentyl- n-amyl
benzeneperoxycarboxylic acid or perbenzoic acid
peroxybenzoic acid
phenol phenol
phenylamine aniline
4-(phenylazo)phenol p-hydroxyazobenzene

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 Recommended Name Traditional Name
phenylmethanol benzyl alcohol
(phenylmethyl)amine benzyl amine
diphenylmethanone benzophenone
poly(tetrafluoroethene) poly(tetrafluoroethylene) or ptfe
propane-1,2,3-triol glycerol or glycerine
propane-1,2,3-triyl trinitrate(V) glyceryl trinitrate or nitroglycerine
sodium ethoxide sodium ethoxide or sodium ethylate
sodium phenoxide sodium phenoxide or sodium phenate

4. References

Chemical nomenclature, symbols and terminology for use in school science, 3rd Edition,
The Association for Science Education, 1985.

Swinfen, T.C., Signs, symbols and systematics, The ASE companion to 16-19 science,
The Association for Science Education, 2000.

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