Organic nomenclature and

formula writing
Science department
INDEX
1. Introduction
2. Hydrocarbons
a. Alkanes
b. Alkenes
c. Alkynes
d. Halogenated hydrocarbons
e. Unbranched and branched chains
3. Hydroxyl group
4. Ethers
5. Carbonyl group
6. Carboxyl group
7. Esters
1. Introduction
Any compound containing carbon atom(s) is classified as an organic compound. Some common organic
compounds are proteins, carbohydrates, fats, plastics, and fuels.
Facts about organic compounds:
• All contain carbon atoms.
• Almost all contain hydrogen atoms.
• Many common ones have oxygen, nitrogen, or sulfur atoms.
• Most are molecular, few are ionic.
• Most carbon-containing compounds are organic compounds. Ex: CH4, H2CO3
 2. Hydrocarbons
Alkanes
Organic compounds consisting only of carbon and hydrogen atoms Nº of C Prefix (single bonds)
are called hydrocarbons.
1 Meth- Methane
➔ Alkanes are structurally the simplest type of hydrocarbon,
consisting of only a single bond between carbon atoms. 2 Eth- Ethane
They are denoted by the suffix -ane. The prefix varies, 3 Prop- Propane
dependent on the number of carbons within the compound
4 But- Butane
5 Pent- Pentane
6 Hex- Hexane
7 Hept- Heptane
8 Oct- Octane
9 Non- Nonane
10 Dec- Decane
➔ Alkenes are hydrocarbons consisting of one or more double bonds.
The rules to naming alkenes are the same as that of alkanes, except
that alkenes are given the suffix –ene. Alkenes
Also, it is necessary to state the position of the double bond. Nº of C Prefix (double bonds)
The carbon which is given the number 1 is the one closest to the
double bond. 1 Meth- -

2 Eth- Ethene

3 Prop- Propene

4 But- Butene

5 Pent- Pentene

6 Hex- Hexene

7 Hept- Heptene

8 Oct- Octene

9 Non- Nonene

10 Dec- Decene
 Alkynes
➔ Alkynes are hydrocarbons consisting of one or more triple Nº of C Prefix (triple bonds)
bonds.
The rules to naming alkynes are the same as that of alkenes, 1 Meth- -
except that alkynes are given the suffix –yne.
2 Eth- Ethyne

3 Prop- Propyne

4 But- Butyne

5 Pent- Pentyne

6 Hex- Hexyne

7 Hept- Heptyne

8 Oct- Octyne

9 Non- Nonyne

10 Dec- Decyne
 ➔ Halogenated hydrocarbons
The hydrogen atoms in the chain can be replaced by other atoms or group or atoms to form a whole different
compound.

In this formula, two hydrogen atoms are replaced by one chlorine atom and one bromine atom. The name of
the compounds depends on the location of the replaced atom.
In this case, the chlorine is at the end of the carbon chain, therefore, it is given the systematic name 1-chloro
for the reason that it is attached to the first carbon from one end of the carbon chain. Bromine is attached to
the third carbon atom, so the second part of the name is 3-bromo.
With four carbon atoms and solely single bonds in this compound, the full name is 3-bromo-1-chlorobutane.
➔ Unbranched and branched chains
● Unbranched alkanes: all carbon atoms lie in a continuous chain.

● Branched alkanes: all of the carbon atoms do not lie in a continuous chain.
1. The principal chain has to be identified.
The principal chain will be the one that incorporates more carbons. Be careful! The principal
chain will not necessarily be obvious at first glance.
The principal chain (7 C atoms).

2. If two or more chains within a structure have the same length, choose as the principal chain the one
with the greater number of branches. In the molecule shown below, there are two chains containing 7 C
atoms. The structure on the left has 1 branch, while the structure on the right has 2 branches. The
principal chain is thus identified correctly in the structure on the right.
3. Number the carbon atoms of the principal chain consecutively from one end to the other in the direction that
gives the lower number to the first branch. In the example below, the two possible numbering schemes are
indicated. The scheme with the underlined numbers is correct, because the first branch occurs at C2 rather than
C5.

4. Name each branch and identify the carbon number of the principal chain at which it occurs. Note: Groups
which are not part of the principal chain are called substituent groups. To name them, you need to
be able to name alkyl groups. An alkyl group is derived from an alkane by removing a hydrogen atom, and
using the “hanging bond” left behind as the point of attachment to a larger molecule. The names of unbranched
alkyl groups are derived by replacing the “-ane” ending of the alkane name with “-yl”, as demonstrated below
for “methyl” and “ethyl.”
5. In writing the name, the substitutent groups are listed first. The name of each substituent is preceded by its
position along the principal chain. Numbers are separated from letters by hyphens, and from other numbers by
commas.
The substituent groups are cited in alphabetical order regardless of their location in the principal chain.
The name of the alkane corresponding to the principal chain is given after all of the substituent groups are listed.
(a) If there are identical substitutents, the prefixes di-, tri-, tetra-, etc., are used to indicate the number.
(b) When there are multiple substituent groups on the principal chain, each substituent receives its own
number, even if there are substituents located on the same carbon.
(c) The numerical prefixes di-, tri-, tetra-, etc., are ignored in alphabetizing.
6. When the numbering of different groups is not resolved by any of the other rules, the first-cited group
receives the lower number.
Exercises
Exercises
Write the name of each of the hydrocarbon molecules shown below:

1. .
5.

.
2. . 6.

3. 7.

4.
 11.
8.

12.

9.

13.

10.
14.
Exercises
For each, draw a structural diagram (line, condensed or complete)
1. 2-methylpent-1-ene 14. 3-ethyl-4-methylpent-1-yne
2. 3-heptyne 15. 4-butyl-2-ethyloct-2-ene
3. 4-methylpent-2-yne 16. 3,5-dimethyl-4-propyl-oct-1,6-diene
4. 3,4,6-triethyl-5,7-dimethylnon-1-yne 17. 3-propyl-2,4-dimethylhexane
5. 2-butene 18. 3,3-dipropyldec-1,5.7-triene
6. 3-ethylpent-2-ene 19. trichlorometane
7. 3-ethyl-3-methylhex-1-ene 20. hept-1,3-dien-5-yne
8. 4-octyne 21. 1-chlorohept-1-en-3,6-diyne
9. 3-ethylpent-2-ene
10. 3-ethyl-2,4-dimethylhexane
11. 2,4-dimethylpent-1-ene
12. 3-ethyl-2-methylheptane
13. 5-ethyl-2,4,6-trimethyloct-3-ene
3. Hydroxyl group
Compounds that contain the functional group –OH are generally known as alcohols and are given the suffix
–ol.
The simplest alcohol is methanol, CH3OH, in which one of the hydrogen atoms is replaced by an –OH group.
The systematic name methanol comes from methane with the –e replaced by the designated suffix –ol.
However, more complicated compounds require more indication of the position of the functional group.

metanol 1-propanol
Exercises
● 2-methylpropan-1-ol

1)

● non-3-en-1-ol
2) CH3-CH2-CHOH-CH2OH

3) CH3-C(OH)2-CH2OH

● butan-2,3-diol

4)

● methanotriol

5)
4. Ethers
Exercises
5. Carbonyl group
Exercises
6. Carboxyl group
Compounds containing the carboxyl group are called carboxylic acids. The first alkane-based carboxylic
acid is methanoic acid. In the systematic name, the methan- indicates one carbon atom and single bonds, and
the –oic ending indicates a carboxylic acid

Methanoic acid Butanoic acid

Exercises
7.Esters
Exercises