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How to name organic compounds using the IUPAC rules

In order to name organic compounds you must first memorize a few basic
names. These names are listed within the discussion of naming alkanes. In
general, the base part of the name reflects the number of carbons in what
you have assigned to be the parent chain. The suffix of the name reflects
the type(s) of functional group(s) present on (or within) the parent chain. Other
groups which are attached to the parent chain are called substituents.

Alkanes - saturated hydrocarbons

The names of the straight chain saturated hydrocarbons for up to a 12
carbon chain are shown below. The names of the substituents formed
by the removal of one hydrogen from the end of the chain is obtained by
changing the suffix -ane to -yl.

Number of Carbons Name

1 methane
2 ethane
3 propane
4 butane
5 pentane
6 hexane
7 heptane
8 octane
9 nonane
10 decane
11 undecane
12 dodecane

There are a few common branched substituents which you should

memorize. These are shown below.

Here is a simple list of rules to follow. Some examples are given at the
end of the list.

1. Identify the longest carbon chain. This chain is called the parent
chain.

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2. Identify all of the substituents (groups appending from the parent

chain).

3. Number the carbons of the parent chain from the end that gives
the substituents the lowest numbers. When compairing a series of
numbers, the series that is the "lowest" is the one which contains
the lowest number at the occasion of the first difference. If two or
more side chains are in equivalent positions, assign the lowest
number to the one which will come first in the name.

4. If the same substituent occurs more than once, the location of

each point on which the substituent occurs is given. In addition,
the number of times the substituent group occurs is indicated by a
prefix (di, tri, tetra, etc.).

5. If there are two or more different substituents they are listed in

alphabetical order using the base name (ignore the prefixes). The
only prefix which is used when putting the substituents in
alphabetical order is iso as in isopropyl or isobutyl. The prefixes
sec- and tert- are not used in determining alphabetical order
except when compared with each other.

6. If chains of equal length are competing for selection as the parent

chain, then the choice goes in series to:
a) the chain which has the greatest number of side chains.
b) the chain whose substituents have the lowest- numbers.
c) the chain having the greatest number of carbon atoms in the
smaller side chain.
d)the chain having the least branched side chains.

7. A cyclic (ring) hydrocarbon is designated by the prefix cyclo-

which appears directly in front of the base name.

In summary, the name of the compound is written out with the

substituents in alphabetical order followed by the base name (derived
from the number of carbons in the parent chain). Commas are used
between numbers and dashes are used between letters and numbers.
There are no spaces in the name.

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Here are some examples:

Alkyl halides
The halogen is treated as a substituent on an alkane chain. The halo-
substituent is considered of equal rank with an alkyl substituent in the
numbering of the parent chain. The halogens are represented as
follows:

F fluoro-
Cl chloro-
Br bromo-
I iodo-

Here are some examples:

Alkenes and Alkynes - unsaturated hydrocarbons

Double bonds in hydrocarbons are indicated by replacing the suffix -ane
with -ene. If there is more than one double bond, the suffix is expanded
to include a prefix that indicates the number of double bonds present (-
adiene, -atriene, etc.). Triple bonds are named in a similar way using
the suffix -yne. The position of the multiple bond(s) within the parent
chain is(are) indicated by placing the number(s) of the first carbon of the
multiple bond(s) directly in front of the base name.

Here is an important list of rules to follow:

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1. The parent chain is numbered so that the multiple bonds have the
lowest numbers (double and triple bonds have priority over alkyl
and halo substituents).

2. When both double and triple bonds are present, numbers as low
as possible are given to double and triple bonds even though this
may at times give "-yne" a lower number than "-ene". When there
is a choice in numbering, the double bonds are given the lowest
numbers.

3. When both double and triple bonds are present, the -en suffix
follows the parent chain directly and the -yne suffix follows the -en
suffix (notice that the e is left off, -en instead of -ene). The location
of the double bond(s) is(are) indicated before the parent name as
before, and the location of the triple bond(s) is(are) indicated
between the -en and -yne suffixes. See below for examples.

4. For a branched unsaturated acyclic hydrocarbon, the parent chain

is the longest carbon chain that contains the maximum number of
double and triple bonds. If there are two or more chains
competing for selection as the parent chain (chain with the most
multiple bonds), the choice goes to (1) the chain with the greatest
number of carbon atoms, (2) the # of carbon atoms being equal,
the chain containing the maximum number of double bonds.

5. If there is a choice in numbering not previously covered, the parent

chain is numbered to give the substituents the lowest number at
the first point of difference.

Here are some examples:

Alcohols
Alcohols are named by replacing the suffix -ane with -anol. If there is
more than one hydroxyl group (-OH), the suffix is expanded to include a
prefix that indicates the number of hydroxyl groups present (-anediol, -
anetriol, etc.). The position of the hydroxyl group(s) on the parent chain
is(are) indicated by placing the number(s) corresponding to the

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location(s) on the parent chain directly in front of the base name (same
as alkenes).

Here is an important list of rules to follow:

1. The hydroxyl group takes precedence over alkyl groups and

halogen substituents, as well as double bonds, in the numbering of
the parent chain.

2. When both double bonds and hydroxyl groups are present, the -en
suffix follows the parent chain directly and the -ol suffix follows the
-en suffix (notice that the e is left off, -en instead of -ene). The
location of the double bond(s) is(are) indicated before the parent
name as before, and the location of the hydroxyl group(s) is(are)
indicated between the -en and -ol suffixes. See below for
examples. Again, the hydroxyl gets priority in the numbering of the
parent chain.

3. If there is a choice in numbering not previously covered, the parent

chain is numbered to give the substituents the lowest number at
the first point of difference.

Here are some examples:

Ethers
You are only expected to know how to name ethers by their commmon
names. The two alkyl groups attached to the oxygen are put in
alphabetical order with spaces between the names and they are
followed by the word ether. The prefix di- is used if both alkyl groups are
the same.

Here are some examples:

Aldehydes
Aldehydes are named by replacing the suffix -ane with -anal. If there is
more than one -CHO group, the suffix is expanded to include a prefix
that indicates the number of -CHO groups present (-anedial - there
should not be more than 2 of these groups on the parent chain as they
must occur at the ends). It is not necessary to indicate the position of the
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-CHO group because this group will be at the end of the parent chain
and its carbon is automatically assigned as C-1.

Here is an important list of rules to follow:

1. The carbonyl group takes precedence over alkyl groups and

halogen substituents, as well as double bonds, in the numbering of
the parent chain.

2. When both double bonds and carbonyl groups are present, the -en
suffix follows the parent chain directly and the -al suffix follows the
-en suffix (notice that the e is left off, -en instead of -ene). The
location of the double bond(s) is(are) indicated before the parent
name as before, and the -al suffix follows the -en suffix directly.
Remember it is not necessary to specify the location of the
carbonyl group because it will automatically be carbon #1. See
below for examples. Again, the carbonyl gets priority in the
numbering of the parent chain.

3. There are a couple of common names which are acceptable as

IUPAC names. They are shown in the examples at the end of this
list but at this point these names will not be accepted by the
computer. Eventually they will be accepted.

4. If there is a choice in numbering not previously covered, the parent

chain is numbered to give the substituents the lowest number at
the first point of difference.

Here are some examples:

Ketones
Ketones are named by replacing the suffix -ane with -anone. If there is
more than one carbonyl group (C=O), the suffix is expanded to include a
prefix that indicates the number of carbonyl groups present (-anedione,
-anetrione, etc.). The position of the carbonyl group(s) on the parent
chain is(are) indicated by placing the number(s) corresponding to the
location(s) on the parent chain directly in front of the base name (same
as alkenes).
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Here is an important list of rules to follow:

1. The carbonyl group takes precedence over alkyl groups and

halogen substituents, as well as double bonds, in the numbering of
the parent chain.

2. When both double bonds and carbonyl groups are present, the -en
suffix follows the parent chain directly and the -one suffix follows
the -en suffix (notice that the e is left off, -en instead of -ene). The
location of the double bond(s) is(are) indicated before the parent
name as before, and the location of the carbonyl group(s) is(are)
indicated between the -en and -one suffixes. See below for
examples. Again, the carbonyl gets priority in the numbering of the
parent chain.

3. If there is a choice in numbering not previously covered, the parent

chain is numbered to give the substituents the lowest number at
the first point of difference.

Here are some examples:

Carboxylic Acids
Carboxylic acids are named by counting the number of carbons in the
longest continuous chain including the carboxyl group and by replacing
the suffix -ane of the corresponding alkane with -anoic acid. If there are
two -COOH groups, the suffix is expanded to include a prefix that
indicates the number of -COOH groups present (-anedioic acid - there
should not be more than 2 of these groups on the parent chain as they
must occur at the ends). It is not necessary to indicate the position of the
-COOH group because this group will be at the end of the parent chain
and its carbon is automatically assigned as C-1.

Here is an important list of rules to follow:

1. The carboxyl group takes precedence over alkyl groups and

halogen substituents, as well as double bonds, in the numbering of
the parent chain.

2. If the carboxyl group is attached to a ring the parent ring is named

and the suffix -carboxylic acid is added.

3. When both double bonds and carboxyl groups are present, the -en
suffix follows the parent chain directly and the -oic acid suffix
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follows the -en suffix (notice that the e is left off, -en instead of -
ene). The location of the double bond(s) is(are) indicated before
the parent name as before, and the -oic acid suffix follows the -en
suffix directly. Remember it is not necessary to specify the location
of the carboxyl group because it will automatically be carbon #1.
See below for examples. Again, the carboxyl gets priority in the
numbering of the parent chain.

4. There are several common names which are acceptable as IUPAC

names. They are shown in the examples at the end of this list but
at this point these names will not be accepted by the computer.
Eventually they will be accepted.

5. If there is a choice in numbering not previously covered, the parent

chain is numbered to give the substituents the lowest number at
the first point of difference.

Here are some examples:

Esters
Systematic names of esters are based on the name of the
corresponding carboxylic acid. Remember esters look like this:

The alkyl group is named like a substituent using the -yl ending. This is
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followed by a space. The acyl portion of the name (what is left over) is
named by replacing the -ic acid suffix of the corresponding carboxylic
acid with -ate.

Here are some examples:

Amines
You are only expected to know how to name amines by their common
names . They are named like ethers, the alkyl (R) groups attached to the
nitrogen are put in alphabetical order with no spaces between the
names and these are followed by the word amine. The prefixes di- and
tri- are used if two or three of the alkyl groups are the same.
NOTE: Some books put spaces between the parts of the name, but we
will not. Follow the examples.

Here are some examples:

Summary of functional groups

Functional group Prefix Suffix

carboxylic acids none -oic acid
aldehydes none -al
ketones none -one
alchols hydroxy- -ol
amines amino- -amine
ethers alkoxy- -ether
fluorine fluoro- none
chlorine chloro- none
bromine bromo- none
iodine iodo- none

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