Nomenclature of Organic Compounds

Identification of Functional Groups

Hydrocarbons
Alkanes - also known as saturated hydrocarbons or the paraffin series because all bond sites between
carbon atoms and between carbon and hydrogen are single bonds.
In naming the alkanes, the stem is based on the number of carbon atoms in the longest continuous chain.
Be careful because the chain may be twisted in several directions. Groups that are attached to the chain of
hydrocarbons are called substituted or alkyl groups. The ending for an alkane is -ane.
Prefixes that represent the different number of carbon atoms are as follows:
# carbons
1
2
3

prefix
methethprop-

# carbons
4
5
6

prefix
butpenthex-

# carbons
7
8
9

prefix
heptoctnona-

# carbons prefix
10
dec11
unidec12
dodec-

Ex. CH3CH2CH2CH3 is called butane, also known as n-butane because this is the normal isomer of
butane.
If the substituted group contains hydrocarbons, the name of the substituted group uses the above prefixes.
All substituted groups, including halogens and alkyl groups, are listed in alphabetical order. Numbers
are used to designate the location of the substituted group on the parent chain. Prefixes such as di- and
tri- are not considered in determining alphabetical order.
Ex. CH3CH2CHCH2CHCH2CH2CH3
|
|
CH2CH3
CH3

is called 5-ethyl-3-methyloctane

If two of the same type of alkyl groups are attached to a single carbon in the parent chain, the number is
repeated.
CH3
|
Ex. CH3CH2CH2CH2CCH2CHCH2CH3
|
|
is called 3-ethyl-5,5-dimethylnonane
CH3 CH2CH3
When trying to draw a structural formula from a condensed formula, alkyl groups are put in parentheses
and follow the carbon to which they are bonded. If a saturated hydrocarbon has (CH2)- in the condensed
formula, that is part of the parent chain.
Ex. CH3CH(CH3)(CH2)4CH(CH2CH3)CH2CH2CH3
would have the following skeletal formula:
and would be named 7-ethyl-2-methyldecane

C
C-C
|
|
C-C-C-C-C-C-C-C-C-C

Problem: name the following: CH3(CH2)3C(CH3)2C(CH2CH3)2C(CH3)3

-2(Answer to previous problem: 3,3-diethyl-2,2,4,4-tetramethyloctane)

Alkenes also known as olefins; contains at least one double bond
In naming the alkenes, the stem is based on the number of carbon atoms in the longest continuous chain
that contains the double bond. Be careful because the chain may be twisted in several directions and
this chain may not be the longest chain in the molecule. The ending for alkenes is -ene.
C-C=C-C-C would be named 2-pentene.
This particular molecule actually has two geometric isomers a cis- and a trans- form.
C
C-C
H
C-C
\
/
\
/
C=C
C=C
/
\
/
\
H
H
C
H
cis-2-pentene

trans-2-pentene

If more than one double bond is contained in the molecule, prefixes are used to indicate the number of
bonds.
Ex.
C-C=C-C-C=C-C
|
|
would be named 2,4-dimethyl-2,5-heptadiene
C
C
Alkynes contains at least one triple bond; also called acetylenes which is also the common name for
the simplest of the alkynes.
In naming the alkynes, the stem is based on the number of carbon atoms in the longest continuous chain
that contains the triple bond. Be careful because the chain may be twisted in several directions. The
ending for alkynes is -yne.
Ex.

CH3CH2CCCH2CH(CH3)CH2CH3 is named 6-methyl-3-octyne

Note that the triple bond takes higher priority in the numbering
system.

Aromatics based on the benzene ring

If a methyl group is attached to the benzene ring, the compound is named methylbenzene or toluene.
If a hydroxyl group is attached to the benzene ring, the compound is named phenol.
Important note: If the benzene ring serves as a substituted group, the name for this substituted
group is phenyl. The structure below is named 1,2-diethylbenzene.

CH2CH3
CH2CH3

-3Functional Groups the active site of organic compounds

Substituted Hydrocarbons
1. Alkyl Halides
If the halogens are the substituted groups on a hydrocarbon, they become the reactive site, or the
functional group. If the compound is given a common name that focuses on the reactive halide, then
the second word in the name describes the halide. For example, C-C-Br would be named ethyl
bromide. Based on the IUPAC system, the halide would be considered a substituted group, and the
same compound would be named bromoethane.
C
C-C-C
\
|
also written as
C-F would be named isopropyl fluoride or 2-fluoropropane
F
/
C
Give the common and the IUPAC name for the following: CH3CH(CH3)CH2CH2Br
[isopentyl bromide and 1-bromo-3-methylbutane]
2. Alcohols contain the hydroxyl group (-OH)
Alcohols are classified as primary (1o), secondary (2o), or tertiary (3o), based on how many carbons
are bonded to the carbon that holds the hydroxyl group.
Formula
Ex. CH3CH2CH2OH
C-C-C
|
OH

also written as

Common Name

IUPAC Name

propyl alcohol

propanol

(primary alcohol)

C
\
C-OH would be named isopropyl alcohol or 2-propanol.
/
C
Another familiar name is rubbing alcohol.

Because the hydroxyl group is bonded to a secondary carbon, another name for this alcohol is s-propyl
or sec-propyl alcohol. s- or sec- indicates a secondary carbon and should be underlined.
An example of a tertiary alcohol would be tert-butyl or t-butyl alcohol, which may be written as:
C
|
C-C-OH A condensed formula for this would be: (CH3)3COH
|
C
The IUPAC name would be 2-methyl-2-propanol.

Ex. CH3CH2C(OH)(CH3)CH2CH3 would be named 3-methyl-3pentanol

Ex. CH3CH(OH)CH2CH(OH)CH2CH3 would be named 2,4-hexanediol

-4-

Groups containing the carboxylate group -COO- (one oxygen is double bonded to the carbon)

3. Carboxylic acids contain the COOH group; also written as -CO2H or

-C-O-H
||
O

First five organic acids actually go by their common name rather than the IUPAC name.
Formula

Common Name

IUPAC Name

HCOOH
CH3COOH
CH3CH2COOH
CH3(CH2)2COOH
CH3(CH2)3COOH

formic acid
acetic acid
propionic acid
butyric acid
valeric acid

methanoic acid
ethanoic acid
propanoic acid
butanoic acid
pentanoic acid

CH3(CH2)4COOH
CH3(CH2)5COOH

hexanoic acid
heptanoic acid

In naming, the carbon of the carboxylate group (COOH) is always the #1 carbon. This carbon is
counted as part of the main chain, and must be part of the longest chain
Ex. CH3(CH2)4CH(C2H5)COOH would be named 2-ethylheptanoic acid.
What is the common and IUPAC name for the following acid: CH3CH(CH3)CH2COOH

4. Esters when an organic base (an alcohol) reacts with an organic acid, the products of the
neutralization reaction still produces a salt and water. The term for an organic salt is called an
ester.
The general formula for an ester is R-COO-R. The R is derived from the acid while the R is derived
from the base (the alcohol).
For inorganic salts, the stem of the name is based on the acid.
Thus, when sodium hydroxide is reacted with chloric acid, the salt formed is named sodium chlorate.
When ethyl alcohol is reacted with formic acid, the resulting salt is named ethyl formate.
Ex. CH3(CH2)4COOCH(CH3)2 would be named isopropyl n-hexanoate.
What is the IUPAC name for the following acid: CH3CH2COOCH3

-5-

Groups containing the carbonyl group -CO- (oxygen is double bonded to the carbon)
Also written as R-CO-R

5. Aldehydes - If the carbon of the carbonyl group is a terminal carbon (which would make R a
hydrogen), the group is called an aldehyde
ex. CH3CHO
also written as

common name is acetaldehyde, IUPAC name is ethanal

H O
| ||
H-C-C-H
|
H

HCHO is known as formaldehye. When dissolved in water, a substance known as formalin is

produced. Formalin is used as an embalming agent something used to preserve dead specimens.
For the simple aldehydes (those with less than six carbons) the common name is often based on the
name of the acid from which it was formed.
Ex. CH3CH2CH2CH2CHO is named valeraldehyde (common) or pentanal (IUPAC)
What is the common and the IUPAC name for the following:

CH3C(CH3)2CH2CHO

6. Ketones - If the carbon of the carbonyl group is a carbon other than a terminal carbon, the group is
called a ketone. The R and R may be the same or different substituted groups. In the common
naming system, the name is based on the two substituted groups attached to the carbonyl group.
Ex. CH3CH2CH2C-CH2CH2CH2CH3
||
is called n-butyl propyl ketone
O
In the IUPAC system, this same compound is called 4-octanone.
If R and R are the same, the prefix di may be dropped.
Ex. CH3COCH3 is known as dimethyl ketone or simply methyl ketone.
This particular ketone is also known as acetone.
Give the common and IUPAC name for the following: CH3CH(CH3)CO(CH2)4CH3

-67. Amines derives from the ammonia molecule. May be primary, secondary, or tertiary, depending on
how many substituted groups are used to replace the hydrogens.
Ex. CH3NH2 is named methylamine
(a primary amine)

CH3NH is named ethylmethylamine

|
(a secondary amine)
CH2CH3

CH3
|
CH3CH2CH2NCH2CH3 is named ethylmethylpropylamine (a tertiary amine)
Ex. CH3CH(CH3)NH(CH2)3CH3 would be named n-butylisopropylamine
Give the name for the following: CH3CH(CH3)N(C2H5)(CH2)3CH3

8. Ethers generally, these compounds are not very reactive because the active site is an oxygen atom
that is bonded directly into the parent chain. Some of the ethers with small molecular masses were
used as anesthetics. Takes the general formula of R-O-R

Ex. CH3CH2OCH2CH3 is named diethyl ether or simply ethyl ether. (Like the ketones, if R and R
are the same alkyl group, then the prefix di is dropped.)

Ex. CH3(CH2)3OC(CH3)3 is named n-butyl t-butyl ether

Give the name for the following: CH3C(CH3)2CH2O(CH2)7CH3