Nomenclature of Organic Compounds CHM131.

2-Organic Chem Lab Manual

Activity No. 1
Nomenclature of Organic Compounds

The objective of this exercise is for the students to learn how to name an organic compound
from the given structure and to derive the structure of the compound from the name. Although some
compounds are known by their common names, it is best to adapt and practice the IUPAC (International
Union of Pure and Applied Chemistry) system of nomenclature.

I. Fundamental Principle
IUPAC nomenclature is based on naming a molecule’s longest chain of carbons connected
by single bonds, whether in a continuous chain or in a ring. All deviations, either multiple bonds or
atoms other than carbon and hydrogen, are indicated by prefixes or suffixes according to a specific
set of priorities.

II. Alkanes and Cycloalkanes

Alkanes are the family of saturated hydrocarbons, that is, molecules containing carbon and
hydrogen connected by single bonds only. These molecules can be in continuous chains (called
linear or acyclic), or in rings (called cyclic or alicyclic).
❖ The names of alkanes and cycloalkanes are the root names of organic compounds. Beginning
with the five-carbon alkane, the number of carbons in the chain is indicated by the Greek or
Latin prefix.
❖ Rings are designated by the prefix “cyclo”. (In the geometrical symbols for rings, each apex
represents a carbon with the number of hydrogens required to fill its valence.)

CH4 Methane CH3(CH2)10CH3 dodecane

CH3CH3 Ethane CH3(CH2)11CH3 tridecane
CH3CH2CH3 Propane CH3(CH2)12CH3 tetradecane
CH3(CH2)2CH3 butane CH3(CH2)18CH3 icosane
CH3(CH2)3CH3 pentane CH3(CH2)19CH3 henicosane
CH3(CH2)4CH3 Hexane CH3(CH2)20CH3 docosane
CH3(CH2)5CH3 heptane CH3(CH2)21CH3 tricosane
CH3(CH2)6CH3 Octane CH3(CH2)28CH3 triacontane
CH3(CH2)7CH3 Nonane CH3(CH2)29CH3 hentriacontane
CH3(CH2)8CH3 Decane CH3(CH2)38CH3 tetracontane
CH3(CH2)9CH3 undecane CH3(CH2)48CH3 pentacontane

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cyclopropane cyclobutane cyclopentane

cyclohexane cycloheptane cyclooctane

III. Molecules Containing Substituents and Functional Groups

A. Priorities of Substituents and Functional Groups

LISTED HERE FROM HIGHEST TO LOWEST PRIORITY, except that the substituents within
Group C have equivalent priority.
Group A - Functional Groups Indicated by Prefix or Suffix
Family of Compound Structure Prefix Suffix
- oic acid
1. Carboxylic Acid carboxy - - carboxylic acid*
- oate
2. Ester ------- - carboxylate*
- amide
3. Amide -------- - carboxamide*
cyano- - nitrile
4. Nitrile - carbonitrile*
oxo – - al
5. Aldehyde (formyl) - carbaldehyde*

6. Ketone oxo - - one

7. Alcohol hydroxyl - - ol

8. Amine amino - - amine

9. Ether –OR

*If the functional group is attached to a ring

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Group B - Functional Groups Indicated by Suffix Only

Family of Compound Structure Prefix Suffix
Alkene ----- - ene

Alkyne ----- - yne

Group C - Functional Groups Indicated by Prefix Only

Family of Compound Structure Prefix Suffix
Alkyl (see list below) R– alkyl- -----
Alkoxy RO– alkoxy- -----
Halogen F– fluoro- -----
Cl– chloro- -----
Br– bromo- -----
I– iodo- -----

Group C (cont.)– Common alkyl groups

Replace “ane” ending of alkane name with “yl”. Alternate names for complex substituents are
given in parenthesis.

methyl

isopropl sec-butyl
ethyl (1-methylethyl) (1-methylpropyl)

propyl (n-propyl)

isobutyl tert-butyl or t-butyl

(2-methylpropyl) (1,1-dimethylethyl)
butyl (n-butyl)

Miscellaneous Substituents and their Prefixes

nitro vinyl allyl phenyl

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B. Naming Substituted Alkanes and Cycloalkanes – Group C Substituents Only

Organic compounds containing substituents from Group C are named following this
sequence of steps, as indicated on the examples below:

Step 1. Find the longest continuous carbon chain. Determine the root name for this parent chain.
In cyclic compounds, the ring is usually considered the parent chain, unless it is attached
to a longer chain of carbons; indicate a ring with the prefix “cyclo” before the root name.
(When there are two longest chains of equal length, use the chain with the greater number
of substituents.)

Step 2. Number the chain in the direction such that the position number of the first substituent is
the smaller number. If the first substituents from either end have the same number, then
number so that the second substituent has the smaller number, etc.

Step 3. Determine the name and position number of each substituent. (A substituent on a nitrogen
is designated with an “N” instead of a number; see Section III.D.1. below.)

Step 4. Indicate the number of identical groups by the prefixes di, tri, tetra, etc.

Step 5. Place the position numbers and names of the substituent groups, in alphabetical order,
before the root name. In alphabetizing, ignore prefixes like sec-, tert-, di, tri, etc., but
include iso and cyclo. Always include a position number for each substituent, regardless
of redundancies.

Examples:

3-bromo-2-chloro-5-ethyl-4,4-dimethyloctane 3-fluro-4-isopropyl-2-methylheptane

1-sec-butyl-3-nitrocyclohexane
(numbering determined by the
alphabetical order of substituents)

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C. Naming Molecules Containing Functional Groups from Group B – Suffix Only

1. Alkenes—Follow the same steps as for alkanes, except:

a. Number the chain of carbons that includes the C=C so that the C =C has the lower position
number, since it has a higher priority than any substituents;
b. Change “ane” to “ene” and assign a position number to the first carbon of the C=C;
c. Designate geometrical isomers with a cis, trans or E, Z prefix.

4,4-difluoro-3-methylbut-1-ene 1,1-difluoro-2-methyl-buta- 5-methylcyclopenta-

1,3-diene 1,3-diene

Special case: When the chain cannot include the C=C, a substituent name is used.

3-vinylcyclohex-1-ene

2. Alkynes – follow the same steps as for alkanes, except:

a. Number the chain of carbons that includes the C≡C so that functional group has the lower
position number;
b. Change “ane” to “yne” and assigned a position number to the first carbon of C≡C
Note: The Group B functional groups (alkene and alkyne) are considered to have equal priority:
in a molecule with both a double and a triple bond, whichever is closer to the end of
the chain determines the direction of numbering. In the case where each would have
the same position number, the double bond takes the lower number. In the name,
“ene” comes before “yne” because of alphabetization.

Examples:

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Notes:
1. An “e” is dropped if the letter following it is a vowel: “pent-3-en-1-yne” , not “3-pent-3-ene-1-yne”.
2. An “a” is added if inclusion of di, tri, etc., would put two consonants consecutively: “buta-1,3-
diene”, not “but-1,3-diene”.)

D. Naming Molecules Containing Functional Groups from Group A – Prefix or Suffix

In naming molecules containing one or more of the functional groups in Group A, the group of
highest priority is indicated by suffix; the others are indicated by prefix, with priority equivalent to
any other substituents. The table in Section III.A. defines the priorities; they are discussed below
in order of increasing priority. Now that the functional groups and substituents from Groups A, B,
and C have been described, a modified set of steps for naming organic compounds can be applied
to all simple structures:
Step 1. Find the highest priority functional group. Determine and name the longest continuous
carbon chain that includes this parent functional group.
Step 2. Number the chain so that the highest priority functional group is assigned the lower
number.
Step 3. If the carbon chain includes multiple bonds (Group B), replace “ane” with “ene” for an
alkene or “yne” for an alkyne. Designate the position of the multiple bond with the
number of the first carbon of the multiple bond.
Step 4. If the molecule includes Group A functional groups, replace the last “e” with the suffix of
the highest priority functional group, and include its position number.
Step 5. Indicate all Group C substituents, and Group A functional groups of lower priority, with a
prefix. Place the prefixes, with appropriate position numbers, in alphabetical order before
the root name.

1. Amines: prefix: amino-; suffix: -amine—substituents on nitrogen denoted by “N”

propan-1-amine 3-methoxycyclohexan-1-amine N,N-diethylbut-3-en-2-amine

("1" is optional in this case)

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2. Alcohols: prefix: hydroxy-; suffix: -ol

ethanol but-3-en-2-ol 2-aminocyclobutan-1-ol

("1" is optional in this case)
3. Ketones: prefix: oxo-; suffix: -one

3-hydroxybutan-2-one cyclohex-3-en-1-one 4-(N,N-dimethylamino)pent-4-en-2-one

("1" is optional in this case)

4. Aldehydes: prefix: oxo-, or formyl- (O=CH-); suffix: -al (abbreviation: —CHO).

An aldehyde can only be on carbon 1, so the “1” is generally omitted from the name.

methanal; ethanal; 4-hydroxybut-2-enal 4-oxopentanal

formaldehyde acetaldehyde

Special case: When the chain cannot include the carbon of the CHO, the suffix
“carbaldehyde” is used:

cyclohexanecarbaldehyde

5. Carboxylic Acids: prefix: carboxy-; suffix: -oic acid (abbreviation: —COOH).

A carboxylic acid can only be on carbon 1, so the “1” is generally omitted from the name.

methanoic acid; ethanoic acid; 2-amino-3-phenylpropanoic acid 2,2-dimethyl-3,4-

formic acid acetic acid dioxobutanoic acid

(Note: Chemists traditionally use, and IUPAC accepts, the names “formic acid” and “acetic acid” in
place of “methanoic acid” and “ethanoic acid”.)

Special case: When the chain numbering cannot include the carbon of the COOH, the suffix
“carboxylic acid” is used.

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Example:
2-formyl-4-oxocyclohexanecarboxylic acid
("formyl" is used to indicate an aldehyde as
a substituent when its carbon cannot be in
the chain numbering)

E. Naming Carboxylic Acid Derivatives

The six common groups derived from carboxylic acids are salts, anhydrides, esters, acyl halides,
amides, and nitriles. Salts and esters are most important.
1. Salts of Carboxylic Acids. Salts are named with cation first, followed by the anion name of
the carboxylic acid, where “ic acid” is replaced by “ate” :
acetic acid becomes acetate
butanoic acid becomes butanoate
cyclohexanecarboxylic acid becomes cyclohexanecarboxylate

2. Esters. Esters are named as “organic salts” that is, the alkyl name comes first, followed by the
name of the carboxylate anion. (common abbreviation: —COOR)

IV. Nomenclature of Aromatic Compounds

“Aromatic” compounds are those derived from benzene and similar ring systems. As with aliphatic
nomenclature described above, the process is: determining the root name of the parent ring;
determining priority, name, and position number of substituents; and assembling the name in
alphabetical order. Functional group priorities are the same in aliphatic and aromatic
nomenclature.

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A. Common Parent Ring Systems

benzene naphthalene anthracene

B. Monosubstituted Benzenes
1. Most substituents keep their designation, followed by the word “benzene”:

chlorobenzene nitrobenzene ethylbenzene

2. Some common substituents change the root name of the ring. IUPAC accepts these as root
names, listed here in decreasing priority:

benzoic acid benzene sulfonic acid benzaldehyde phenol

anisole toluene aniline

C. Disubstituted Benzenes
1. Designation of substitution—only three possibilities:

common: ortho- meta- para-

IUPAC: 1,2- 1,3- 1,4-

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2. Naming disubstituted benzenes—Priorities determine root name and substituents

1,4-dibromobenzene 3-aminobenzoic acid 2-methoxybenzaldehyde 3-methylphenol

D. Polysubstituted Benzenes

3,4-dichloro-N-methylaniline 2,4,6-trinitrotoluene ethyl 4-amino-3-hydroxybenzoate

E. Aromatic Ketones
A special group of aromatic compounds are ketones where the carbonyl is attached to at least one
benzene ring. Such compounds are named as “phenones”, the prefix depending on the size and
nature of the group on the other side of the carbonyl. These are the common examples:

acetophenone butyrophenone

propiophenone benzophenone

REFERENCES:
Klein, D. (2012). Organic Chemistry. USA: John Wiley & Sons, Inc.
McMurry, J. (2010). Foundations of Organic Chemistry. Singapore: Learning Cengage Asia PTE, Ltd.
Fabre, H. & Powell, W. Nomenclature of Organic Chemistry. IUPAC Nomenclature and Preferred Names
2013. IUPAC. Royal Society of Chemistry 2014.
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Courtesy of Dr. Jan Simek, California Polytechnic State University at San Luis Obispo

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