Chemistry 33 Laboratory

NOMENCLATURE OF
ORGANIC COMPOUNDS
by Marc Ralph M. Solomon
Instructor III
Department of Physical Sciences and Mathematics
University of the Philippines Manila

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Ways of Representing Molecules
1. Molecular Formula
2. Condensed Structures
3. Partially Condensed Structures
4. Lewis Structures
5. Bond-line Structures

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Lewis Structures
• Shows all connections in the molecule
• Still cumbersome for larger molecules

H
O
H H
H C C C H
H H H

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Bond-line Structures
• Most efficient way to draw organic compounds
• Each vertex is a carbon atom and hydrogens connected to carbon are
hidden.

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Bond-line Structures
Interpreting Bond-line Structures
• Each vertex is a carbon atom.
• A line represents a bond between atoms.
• Hydrogens connected to carbon are assumed
(assumes enough hydrogens to fill the octet).
• Heteroatoms (non-carbon and hydrogen atoms)
are written as usual.
• Hydrogens connected to heteroatoms are still
written.
• Carbon chains are drawn as zigzags to mimic the
tetrahedral geometry of carbon.

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Common Names

Camphor Salicylic Acid Cysteine

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 IUPAC Naming
• International Union of Pure and Applied Chemistry
• Has set a systematic way of naming organic compounds
• Systematic Name or IUPAC Name

1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 2-hydroxybenzoic acid

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Organic Compounds
Organic Compounds

HYDROCARBONS HYDROCARBONS DERIVATIVES

Saturated Alkanes

Aliphatic Alkenes
Unsaturated
Alkynes

Aromatic

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Alkanes
• Saturated hydrocarbons
• Also called paraffins
• General chemical formula: 𝐶𝑛 𝐻2𝑛+2 (linear and branched)
• Suffix: -ane
• Tetrahedral geometry (sp3 carbon)

linear branched cyclic

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 Acyclic/Linear Alkanes
No. of No. of
Name (Prefix + ane) Structure Name (Prefix + ane) Structure
C’s C’s

1 Methane 7 Heptane
H H
2 Ethane H C C H 8 Octane
H H
H H H
3 Propane H C C C H 9 Nonane
H H H

4 Butane 10 Decane

5 Pentane 11 Undecane

6 Hexane 12 Dodecane

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Acyclic/Linear Alkanes

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Cyclic Alkanes
• Cycloalkanes
• carbon atoms arranged in a ring
• General chemical formula: 𝐶𝑛 𝐻2𝑛
• Prefix: cyclo-

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Branched Alkanes
• With alkyl substituents

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 NOTE:
Exercise Parent chain should be the longest chain
and with the most number of substituents.
• Determine the parent chain

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Branched Alkanes
• Naming alkyl substituents
• Suffix: -yl

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Naming using IUPAC System
Step [1]
Find the parent carbon chain and add the suffix.

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Naming using IUPAC System
Step [1]
Find the parent carbon chain and add the suffix.

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Naming using IUPAC System
Step [2]
Number the atoms in the carbon chain.

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Naming using IUPAC System
Step [2]
Number the atoms in the carbon chain.

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Naming using IUPAC System
Step [2]
Number the atoms in the carbon chain.

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Naming using IUPAC System
Step [2]
Number the atoms in the carbon chain.

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Naming using IUPAC System
Step [3]
Name and number the substituents.

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Naming using IUPAC System
Step [4]
Combine the substituent names and numbers + parent + suffix.

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Naming using IUPAC System
Step [4]
Combine the substituent names and numbers + parent + suffix.

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Exercise

1-methyl-2- 2-cyclohexyl-4-ethyl-5,6- 3-ethyl-2,5-dimethyl-4-

propylcyclohexane dimethyloctane propylheptane

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Exercise

Complex Alkyl Substituent

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Carbon Classification

• A primary carbon (1° carbon) is bonded to one other C atom.

• A secondary carbon (2° carbon) is bonded to two other C atoms.
• A tertiary carbon (3° carbon) is bonded to three other C atoms.
• A quaternary carbon (4° carbon) is bonded to four other C atoms.
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Carbon Classification

• A primary carbon (1° carbon) is bonded to one other C atom.

• A secondary carbon (2° carbon) is bonded to two other C atoms.
• A tertiary carbon (3° carbon) is bonded to three other C atoms.
• A quaternary carbon (4° carbon) is bonded to four other C atoms.
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Hydrogen Classification

• A primary hydrogen (1° H) is on a C bonded to one other C atom.

• A secondary hydrogen (2° H) is on a C bonded to two other C atoms.
• A tertiary hydrogen (3° H) is on a C bonded to three other C atoms.

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Hydrogen Classification

• A primary hydrogen (1° H) is on a C bonded to one other C atom.

• A secondary hydrogen (2° H) is on a C bonded to two other C atoms.
• A tertiary hydrogen (3° H) is on a C bonded to three other C atoms.

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Complex Alkyl Substituents

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Complex Alkyl Substituents

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Complex Alkyl Substituents

Note:
If a prefix such as “di” is part of a branch name, it is included in the alphabetization.
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Exercise

4-tert-butyl-3,3,5-
trimethylheptane
3,3,5-trimethyl-4-(1,1-
dimethylethyl)heptane
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Cyclic Alkanes

1-methyl-2- 1-cyclopropyl-2-
propylcyclohexane methylpentane

isopropylcyclopentane 1,2-dicyclopentylethane

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Assignment

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Bicyclic Alkanes
• contain two fused rings are called bicyclic compounds, and they can be
drawn in different ways:

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Bicyclic Alkanes
• Naming bicyclic alkanes
1 carbon
[STEPS]
1. Determine the number of carbon atoms.
2. Name the parent by adding the prefix bicyclo-
to the parent name.
3. Identify the bridgehead. From the bridgehead, 2 carbons
there are three paths to take. For each path, 2 carbons
count the number of carbon atoms between
bridgeheads.
4. Arrange the numbers from largest to smallest
and construct the name: Bicyclo[2.2.1]heptane
bicyclo + [<no1>.<no2>.<no3>] + parent alkane

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Bicyclic Alkanes
• Naming substituted bicyclic alkanes
[STEPS]
1. start at one of the bridgeheads
2. start numbering at the bridgehead that
gives the substituent the lowest
possible number
3. begin numbering along the longest
path, then go to the second longest
path, and finally go along the shortest
path

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 Exercise

3-sec-butyl-2-
2,7,7- methylbicyclo[3.1.0]hexane
trimethylbicyclo[4.2.2]decane
2-methyl-3-(1-
methylpropyl)bicyclo[3.1.0]hexane
2,2,5,7-
tetramethylbicyclo[4.2.0]
octane
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Alkenes
• Unsaturated hydrocarbons
• Also called olefins
• General chemical formula: 𝐶𝑛 𝐻2𝑛 (one double bond)
• Suffix: -ene
• Can be linear, branched or cyclic
• Trigonal planar geometry (sp2 carbon) R R
• As a substituent: alkenyl C C
R R
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Naming Alkenes
Step [1]
Determine the parent chain containing the carbons of the double bond.

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Naming Alkenes
Step [2]
Number the carbon chain to give the double bond the lower number,
and apply all the rules of nomenclature.

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Naming Alkenes
Multiple double bonds
• Put multiplier prefixes (di-, tri-). Report all locants where double bonds
occur. Add an –a– to help make the name pronounceable.

Cyclohexa-1,3-diene

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Naming Alkenes
Common Names recognized by IUPAC

Ethylene Propylene Styrene

a ripening agent a precursor to a wide monomer unit of
variety of compounds polystyrene plastic

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Naming Alkenes
Some Alkenyl Substituent

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 Exercise

2-ethyl-4-methyl-1-pentene 5-tert-butyl-1-
2-ethyl-4-methylpent-1-ene methylcyclohexa-1-ene

3,4-dimethylcyclopent-1-ene

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Exercise

2-ethylbut-1,3-diene
or
3-methenylpent-1-ene

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Stereoisomerism in Alkenes
• Cis trans
• E or Z (based on the Cahn-Ingold-Prelog Priority Rules)

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Alkynes
• Unsaturated hydrocarbons
• General chemical formula: 𝐶𝑛 𝐻2𝑛−2 (one triple bond)
• Suffix: -yne
• Linear geometry (sp carbon)
• As a substituent: alkynyl

R C C R

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Naming Alkynes
• In the IUPAC system, change the -ane ending of the parent alkane to
the suffix -yne.
• Choose the longest carbon chain that contains both atoms of the
triple bond and number the chain to give the triple bond the lower
number.
• Compounds with two triple bonds are named as diynes, those with
three are named as triynes, and so forth.
• Compounds with both a double and a triple bond are named as
enynes. The chain is numbered to give the first site of unsaturation
(either C=C or C≡C) the lower number.

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Naming Alkynes

4-isopropyl-2-heptyne 2,4-hexadiyne
4-isopropylhepta-2-yne hexa-2,4-diyne

Penta-3-en-1-yne Hexa-2-en-4-yne

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Acetylene (Common Name)

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Alkyne Substituents

R R R
ethynyl propynyl
propargyl

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Exercise

5-ethyl-7,7-dimethyldeca-3-yne 1,1,1-trichloro-8-ethyl-4,4-dimethyldeca-2-
yne

ethynylcyclohexane

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Exercise

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References
Bruice, P. Y. (2014). Organic chemistry (7th ed.). Upper Saddle River, NJ:
Pearson/Prentice Hall.
Klein, D. R. (2017). Organic chemistry (3rd ed.). Hoboken, NJ: Wiley.
Smith, J. G. (2011). Organic chemistry (3rd edition.). New York, NY:
McGraw-Hill.
Favre, H. A., Powell, W. H., & International Union of Pure and Applied
Chemistry. (2014). Nomenclature of Organic Chemistry: IUPAC
Recommendations and Preferred Names 2013. Cambridge,
England: Royal Society of Chemistry.

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