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Nomenclature - Carbon Bonding
Nomenclature - Carbon Bonding
Nomenclature - Carbon Bonding
Exercise
In this lab we will learn the basic
rules for drawing and naming
organic structures.
Functional Groups:
Alkanes Hydrocarbons that have only single
bonds between all of the atoms.
Alkenes Hydrocarbons with AT LEAST one
double bond.
Alkynes Hydrocarbons with AT LEAST one
triple bond.
Cyclic Carbon compounds that form a circle.
Compounds
4-ethylnonane
3-ethylheptane
Single bonds end in “ane”,
1 or more double bonds end in “ene”,
triple bonds end in “yne”.
hexan 3- 2-butyne
e hexene
2,4-
heptadiene
Carbon branches are named by their length and position on
the main chain. The branch is named by using the parent
name with the suffix “yl”.
3,4-dimethyl
octane 4,5-diethyl
octane
Carbon chains are numbered from left to right or right to left.
You may not change direction once started. (This rule is
used to allow you to describe where changes are occurring.)
The numbering always starts from the direction that will
allow the branch numbers to be the lowest.
4-propylnonane….NOT 6-propylnonane
Names of the substituent groups (any atom or group of
atoms that substitutes for a hydrogen atom in an organic
molecule) are placed in alphabetical order before the name of
the parent chain regardless of their position number.
4-ethyl-2-
methylnonane
Multiple branches are named in order of where the branches
occur, by the number of branches of that type, and given a
name for the size of the branch.
4,7-diethyl-5,6-dimethyldecane
Hyphens (“-”) are always used to separate numbers from
names and commas (“,”) are used to separate numbers from
themselves. The last alkyl group is prefixed to the name of
the parent compound to form one word.
4,7-diethyl-5,6-dimethyldecane
Halogen substitutions (Fluorine, Chlorine, Bromine, and
Iodine) of hydrogen are named in the same manner as
hydrocarbon branches. The prefixes are shown below.
F Cl
Br
3-bromo-6-chloro-4-fluorononane
Carbons that form rings start with the prefix “cyclo-”.
cyclopropa
cyclobutane
ne cyclohexane
cyclopropene cyclopentadiene
When there are substituents, numbers are required and are
assigned so that the carbons bearing the substituents have the
lowest numbers listed in alphabetical order. Remember that
multiple bonds in the parent chain get the lowest number
before substituents.
Br
Br
2-bromo-4-ethyl-1-methylcyclohexane
3-bromo-1-ethyl-4-methylcyclohexene
Benzenes – are a special type of cyclic compound because
the alternating single and double bonds make it a very stable
molecule.
If the benzene ring is the parent compound, the molecule’s
name will have the suffix “benzene”. If the benzene ring is
the substituent it is given the prefix “phenyl-”.
ethylbenzene 2-phenylnonane
Benzene rings are numbered in such a way that the substituents are
given the lowest possible numbers alphabetically. For di-
substituted benzene rings a special designation is used. If the
substituents are in the 1,2 position it is know as “ortho” or “o”. If
they’re in the 1,3 position it is known as “meta” or “m”, and if
they’re in the 1,4 position it is “para” or “p”.
o- m-dimethylbenzene
dimethylbenzene
p-dimethylbenzene
Alcohols (carbons with an “-OH” group) end with the suffix
“-ol”. In other regards, they use the same rules as for
branches.
OH
OH
IUPAC
butanol 2-propanol name
Commo
butyl isopropyl n name
alcohol alcohol
Common
name propylene glycerin or
glycol glycerol
Aldehydes (carbons ending with an “=O” (carbonyl) group) end
with the suffix “-al”. In other regards, they use the same rules as
for branches.
O Cl
Cl
3-methylhexanal 4,5-dicholor-3-
methylheptanal
Ketones (carbons with a “=O” group in the middle) end with
the suffix “-one”. In other regards, they use the same rules as
for branches. (Remember Aldehydes at the end, Ketones in
the middle!)
O O O
4-heptanone 3,5-heptadione
Functional groups:
Carboxylic Acids These compounds contain a special H O
combination of both a carbonyl group H C C OH
and a hydroxyl group attached to the
H
same end carbon.
Ethers Have two carbons attached directly to
the same oxygen atom. O
O O
Anhydrides Are like esters but both carbons
attached to either side of the oxygen are O
also carbonyl groups.
More functional groups:
Amines Compounds in which nitrogen
is bonded to carbon. N
replaced by nitrogen.
OH H
O
Structure O
O O
O O
ethyl hexanoate
dimethylbutanamine ne
dimethylbutylamine propylami Common name
ne
If more than one amine group is present, specify the
position of each group, use the prefix di, and retain the
final –e of the hydrocarbon chain.
NH2
H2N 1,3-propanediamine
Amides are the nitrogen replacements of –OH groups in carboxylic acids.
The nitrogen does not need to be terminal. These compounds are named
as derivatives of carboxylic acids.
In other words, they’re named as if they were carboxylic acids, except the
“-oic acid” ending is replaced with “-amide”.
The group attachment to a nitrogen is indicated by the capital letter N-
O
3 O
1
4 2
N
H
NH2
N-methylbutanamide Butanami
de
Hierarchy of naming
H
O
3 Ketone -one Oxo-
H N OH
H
5—amino-5-hydroxy-4-methylpentanoic
acid O
OH O
H2N OH
H
N H
O H
3-amino-2-oxopropanoic 7-amino-5-
acid hydroxyheptanal