Cycloalkanes
Number the parent carbon chain
1) Count the number of carbons in the ring and
name the parent cyclic chain (just like an alkane)
2) Add the prefix cyclo to the IUPAC name of the
unbranched alkane, e.g., cyclopentane
3) Name any alkyl groups on the ring in the
usual way
4) If there is just one ring substituent, it is not
necessary to locate it by number.
5) When 2 ring substituents are present, the
carbon atoms in the ring are numbered
beginning with the substituent of higher
alphabetical priority and proceeding in the
direction (clockwise or counterclockwise) that
gives the other substituent the lower number.
6) When 3 or more ring substituents are present,
ring numbering begins at the substituent that
leads to the lowest set of location numbers.
7) When 2 or more equivalent numbering sets
exist, alphabetical priority among substituents
determines the set used.
Halogenated Alkanes
1) Halogen atoms are treated as substituents on
a carbon chain: fluoro-, chloro-, bromo-, and
iodo-
2) The chain is numbered from the end closer to
a substituent, whether it be a halo- or an alkyl
group
3) Alkyl and halogen substituents have the same
ranking
4) If 2 or more different substituents are present,
the alphabetical order determines their priority
Alkenes
Rule 1. Replace the alkane suffix -ane with the
suffix -ene, which is used to indicate the
presence of a carbon–carbon double bond
Rule 2. Select as the parent carbon chain the
longest continuous chain of carbon atoms that
contains both carbon atoms of the double bond
> Carbon–carbon double bonds take precedence
over alkyl groups and halogen atoms in
determining the direction in which the parent
carbon chain is numbered
Rule 3.
beginning at the end nearest the double bond.
> If the double bond is equidistant from both
ends of the parent chain, begin numbering from
the end closer to a substituent
>> A number is not needed to specify double
bond position in ethene and propene because
there is only one way of positioning the double
bond in these molecules
Rule 4. Give the position of the double bond in
the chain as a single number, which is the lower-
numbered carbon atom participating in the
double bond. This number is placed immediately
before the name of the parent carbon chain
> In 1993, IUPAC rules were revised relative to
the positioning of numbers used in names.
> Instead of placing the number immediately in
front of the base name (2-pentene) IUPAC
recommended that the number be placed
immediately before the part of the name that the
number serves as a locator for (pent-2-ene).
Rule 5. Use the suffixes -diene, -triene, -tetrene,
and so on when more than one double bond is
present in the molecule. A separate number
must be used to locate each double bond.
Rule 6. Do not use a number to locate the
double bond in unsubstituted cycloalkenes with
only one double bond because that bond is
assumed to be between carbons 1 and 2.
Rule 7. In substituted cycloalkenes with only one
double bond, the double-bonded carbon atoms
are numbered 1 and 2 in the direction (clockwise
or counterclockwise) that gives the fi rst-
encountered substituent the lower number.
Again, no number is used in the name to locate
the double bond.
Rule 8. In cycloalkenes with more than one
double bond within the ring, assign one double
bond the numbers 1 and 2 and the other double
bonds the lowest numbers possible.
Alkynes removed from each other (on opposite sides of
The rules for naming alkynes are identical to the ring))
those used to name alkenes except the ending - NOTE: The use of ortho-, meta-, and para- in
yne is used instead of –ene place of position numbers is reserved for
disubstituted benzenes. The system is never
Benzene Derivatives with One Substituent
used with cyclohexanes or other ring systems.
1) Name the substituent followed by the name
benzene
2) When one of the two substituents in a
2) Monosubstituted benzene structures are often
disubstituted benzene imparts a special name to
drawn with the substituent at the “12 o’clock”
the compound (as, for example, toluene), the
position
compound is named as a derivative of that
3) No need to indicate position if there is only
parent molecule. The special substituent is
one substituent
assumed to be at ring position 1.
4) A few monosubstituted benzenes have names
wherein the substituent and the benzene ring
3) When neither substituent group imparts a
taken together constitute a new parent name.
special name, the substituents are cited in
5) For monosubstituted benzene rings that have
alphabetical order before the ending –benzene.
a group attached that is not easily named as a
The carbon of the benzene ring bearing the
substituent, the benzene ring is often treated as
substituent with alphabetical priority becomes
a group attached to this substituent
carbon 1.
> The benzene ring attachment is called a
phenyl group
4) Benzene ring bearing 2 methyl groups is a
> The compound is named according to the rules
situation that generates a new special base
for naming alkanes, alkenes, and alkynes
name called xylenes
Benzene Derivatives with Two Substituents
Benzene Derivatives with Three Substituents
1) When two substituents, either the same or
1) When parent names such as toluene and
different, are attached to a benzene ring, three
xylene are used, additional substituents present
isomeric structures are possible. To distinguish
cannot be the same as those included in the
among these three isomers, we must specify the
parent name. If such is the case, name the
positions of the substituents relative to one
compound as a substituted benzene.
another. This can be done in either of two ways:
a) by using numbers
2) When more than 2 groups are present on the
> 1,2 disubstitution (the substituents are on
benzene ring, their positions are indicated with
adjacent carbon atoms)
numbers
> 1,3 disubstitution (the substituents are one
The ring is numbered in such a way as to obtain
carbon removed from each other)
the lowest possible numbers for the carbon
> 1,4 disubstitution (the substituents are two
atoms that have substituents. If there is a choice
carbons removed from each other (on opposite
of numbering systems (two systems give the
sides of the ring))
same lowest set), then the group that comes first
b) by using nonnumerical prefixes
alphabetically is given the lower number.
> Ortho- (the substituents are on adjacent
carbon atoms)
> Meta- (the substituents are one carbon
removed from each other)
> Para- (the substituents are two carbons