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ALKANES

IUPAC Rule 1. Find the longest chain in the


molecule and name it.
TWO OR MORE CHAINS OF EQUAL LENGTH

Chain with largest number of


substituents is the base stem chain

the carbon number to which it is attached


and a hyphen)
2. Add name of stem.
Should a molecule contain more
than one of a particular substituent, its
name is preceded by prefix di, tri, tetra,
penta, etc.
These prefixes, as well as sec- and
tert-,
are
not
considered
in
the
alphabetical ordering, except when they
are part of a complex substituent name.

IUPAC Rule 2. Name all groups attached to the


longest chain as alkyl substituents.
If the substituent chain is branched, same IUPAC
rules apply to such complex substituents:

Find longest chain in the substituent


Name all its substituents

In the chain of a complex


substituent:
CARBON NUMBERED ONE (C1)
IS ALWAYS THE CARBON ATOM
DIRECTLY ATTACHED TO STEM
CHAIN.

IUPAC Rule 3. Number carbons of longest


chain beginning with the end that is closest to
TWO SUBSTITUENTS AT EQUAL DISTANCE
FROM THE TWO ENDS OF THE CHAIN

Use alphabet to decide how to


number.

The substituent to come first in


alphabetical order is attached to
carbon with lower number.

a substituent.

Five common group names permitted by


IUPAC:

Substituent groups are numbered outward


from the main chain, with C1 of the group being
the carbon attached to the main stem.
IUPAC Rule 4. Write the name of the alkane.
1. Arrange
all
substituents
in
alphabetical order (each preceded by
THREE OR MORE SUBSTITUENTS
First Point of Difference Principle

Number chain in direction that


gives lower number at the first
difference between two possible
numbering schemes.

CYCLOALKANES
Rule 1.
*SINGLE SUBSTITUENT ON A RING
No need to number its position on
the ring
Rule 2.

RING HAS TWO DIFFERENT SUBSTITUENTS

Cite in alphabetical order


The number 1 position is given to
the substituent cited first.

Rule 3.
Systematic name of a complex substituent
should be enclosed in parentheses to avoid
possible ambiguities.
COMPLEX SUBSTITUENT PRESENT MORE THAN
ONCE

Special set of prefixes is placed in


front of parenthesis: bis, tris,
tetrakis, pentakis, and so on, for 2,
3, 4, 5, etc.

To name haloalkanes, we treat the halogen


as a substituent to the alkane framework.
Four rules should be applied in sequence when
naming a branched alkane:
(1) Find longest chain;
(2) find the names of all alkyl groups attached to
stem;
(3) number chain;
(4) name alkane, with substituent names in
alphabetical order and preceded bynumbers to
indicate their locations.
Haloalkanes are named in accord with the rules
that apply to naming the alkanes, the halo
substituent being treated the same as alkyl
groups.

MORE THAN TWO SUBSTITUENTS ON


RING

Cite in alphabetical order.


Substituent given t number 1 position
is the one that results in a second
substituent getting as low a number as

ALKENES
2 SUBSTITUENTS HAVE SAME LOW
NUMBER
Ring is numberedeither clockwise or
counterclockwisein the direction that gives
the third substituent lowest possible number.
Rule 1.
NAME THE STEM
Find longest chain that includes both
carbons making up the double bond.
NOTE: Molecule may have longer carbon
chains, but ignore them.
Rule 2.

If RING HAS MORE CARBONS THAN THE


ATTACHED ALKYL SUBSTITUENT:

LOCATION OF DOUBLE BOND

Ring is the parent hydrocarbon.

Indicate location of double bond in the


main chain by number.

If ALKYL SUBSTITIUENT HAS MORE


CARBONS THAN THE RING:
Substituent is the parent hydrocarbon and
the ring is named as a substituent.

NOTE: Start at end closer to double bond.

Rule 3. Add substituents and their positions


to alkene name as prefixes.
ALKENE SYSTEM IS SYMMETRIC
Begin from end that gives first substituent
along the chain the lowest possible
number.
Rule 4. Identify any stereoisomers.
Rule 5. For molecules with three or four
different substituents attached to the
double-bond carbons, the E,Z system is
used in naming.

Rule 7. YOU ALWAYS FORGET MISS!


SUBSTITUENTS CONTAINING A
DOUBLE BOND ARE NAMED
ALKENYL

Numbering of a substituent chain begins at


the point of attachment to the basic stem.

ALKYNES
Rule 1. IUPAC rules for alkenes also apply to
alkynes, the ending -yne replacing -ene.
Rule 6.
NAMING ALKENOLS
The stem incorporating both functions is
numbered to give the carbon bearing the OH
group the lowest possible assignment.
Note: last e in alkene is dropped in
naming of alkenols

A number indicates the position of triple


bond in main chain.
Rule 2.
SUBSTITUENTS BEARING TRIPLE BOND
Substituents are named as alkynyl
groups.
Ex. Substituent
is named ethynyl

Rule 3.

ALKENYNES
hydrocarbons containing both double and triple bonds

Number chain starting from end closest


to either of functional groups.

When double bond and a triple bond at


equidistant
positions
from
either
terminus, double bond is given the lower
number.

Rule 4.

ALKYNOLS
Alkynes incorporating hydroxy function are
named alkynols. OH group takes precedence
over both double and triple bonds in the
numbering of a chain
Note: omission of the final e of -ene in
-enyne and of -yne in -ynol.

NOTE:
Alkenes and alkynes rank below amines in order
of precedence. But, when a carbon carbon
double or triple bond is part of the parent chain or
ring of a molecule:
Insert -en(e)- or -yn(e)- just before the
suffix for the highest-ranking functional
group.

CARBOXYLIC
ACIDS
Rule 1. Replace ending e in
by -oic acid.

alkane

Rule 2. Number alkanoic acid stem


assigning number 1 to carboxy carbon.

by

Rule 3. Label any substituents along the


longest chain incorporating the CO2H group
accordingly.
Rule 4. In multiply functionalized carboxylic
acids, main chain is chosen to include other
functional groups as much as possible.
CYCLOALKANECARBOXYLIC ACIDS
Name saturated cyclic acids as cycloalkanecarboxylic
acids.

BENZOIC ACIDS

Aromatic counterpart of cycloalkanecarboxylic acids

DICARBOXYLIC SYSTEMS
Dicarboxylic systems are labeled alkanedioic
acids.

ALDEHYDES
Rule 1. Replace ending -e of alkane by -al. An
alkane thus becomes an alkanal.

Number substituent chain beginning with the


carbonyl carbon.

Rule 2.
For historical reasons, simpler aldehydes often
retain their common names. These names are
derived from the common name of the
corresponding carboxylic acid, with the ending
ic or -oic acid replaced by -aldehyde,

Rule 3. Systematic nomenclature accepts


both alkanoyl and acyl as names for the
fragment
Acyl is more widely used.
Prefix for aldehyde:
formyl
Prefix for ketone:
oxo

ALCOHOLS

Rule 3.
CARBALDEHYDES

CHO group is attached to a ring

carbon atom bearing the CHO group is C1.

NOTE:
Instead
of
benzenecarbaldehyde,
benzaldehyde is more widely used.

Rule 1.
Replace ending -e of the alkane is replaced by
-ol.
Rule 2.
In more complicated branched systems, name of
alcohol is based on longest chain containing the
OH substituent not necessarily the longest
chain in the molecule.
Rule 3. To locate positions along the chain,
number each carbon atom beginning from end
closest to the OH group.

KETONES

Rule 4. When there is more than one hydroxyl


substituent along the alkane stem, the molecule
is called a diol, triol, and so on.

Rule 1. Ketones are called alkanones, the


ending -e of the alkane replaced with -one.
Rule 2. CYCLOALKANONES
Assign number 1 to carbonyl carbon when it is in
a ring.

Rule 5.
CYCLOALKANOLS
cyclic alcohols
Carbon carrying the functional group automatically
receives number 1.

Rule 6. When named as a substituent, the


OH group is called hydroxy.

AMINES

MONOSUBSTITUTED BENZENES
Rule 1. Some monosubstituted benzenes are named

Rule 1. To name aliphatic amines, used method


by
Chemical
Abstracts

that
is,
as
alkanamines.
The name of the alkane stem is modified by
replacing the ending -e by -amine. The position
of the functional group is indicated by a prefix
designating the carbon atom to which it is
attached, as in the alcohols.

simply by stating the name of the substituent, followed


by the word benzene.

Rule 2. Some monosubstituted benzenes have names

that incorporate the name of the substituent. Such


names have to be memorized.

Rule 2. BENZENAMINES
The aromatic amines, or anilines, are
called benzenamines.
For secondary and tertiary amines, the
largest alkyl substituent on nitrogen is chosen as
the alkanamine stem, and the other groups are
named by using the letter N-, followed by the
name of the additional substituent(s).

Rule 3. An alternative way to name amines


treats the functional group, called amino-, as a
substituent of the alkane stem.

Rule 3. With the exception of toluene, benzene rings with

an alkyl substituent are named as alkyl-substituted


benzenes or as phenyl-substituted alkanes.

Rule 4. PHENYL vs BENZYL


Phenyl Group
- When a benzene ring is a substituent
Benzyl Group
- A benzene ring with a methylene group

Rule 5. An aryl group (Ar) is the general term for either a


phenyl group or a substituted phenyl group, just as an

alkyl group (R) is the general term for a group derived


from an alkane.

AVECC