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Nomenclature Lab

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

Alcohols Compounds that contain hydroxyl


OH
(OH) groups.
Aldehydes Compounds that contain a carbonyl O

group (an oxygen double bonded to a


carbon) bonded to an end carbon. H

Ketones Are like aldehydes except their O

carbonyl group is in the middle of the


molecule.
Hydrocarbons are named according to the longest continuous chain of
carbons in the molecule (rather than the total # of carbon atoms). The
longest chain is called the parent compound.

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

Alcohols are classified as primary (1°), secondary


(2°), or tertiary (3°), depending on the number of
carbon groups bonded to the carbon bearing the
–OH group.
An alcohol in which two hydroxyl groups are present is named
with the suffix -diol, one containing three hydroxyl groups is
named with suffix- triol, etc.
In these names, the final –e of the parent alkane name is retained
for pronunciation reasons.
OH OH OH OH
│ │ │ │
CH3-CH-CH2-OH CH2-CH-CH2

IUPAC 1,2- 1,2,3-


name propanediol propanetriol

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

Esters Are like ethers but one of the carbons O

attached directly to the ether carbon is


also a carbonyl group. 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

Amides Are like carboxylic acids but


the hydroxyl group is N O

replaced by nitrogen.

Thiols These compounds are just


like alcohols, but instead of SH
oxygen, they have sulfur.
Carboxylic Acids ( carbons with a “-OOH” group) end with
the suffix “-oic acid”.
• Notice the structure: they must occur at the end of a chain.
• The hydrogen attached to the oxygen is the proton source for the acid.
• The C=O group is generally known as a “carbonyl” group. You will see the
carbonyl group again as part of other functional groups in the following
sections.
• Main chain numbering always starts at the carboxylic acid functional group
end!
O
O

OH H

hexanoic acid 5-ethyl-3-methyloctanoic


acid
Ethers (Carbons with an “-O-”group in the middle, as in C-O-C’), are named
for their two parts.
- It begins with the core of the smaller hydrocarbon, then “oxy”, then the full
name of the larger hydrocarbon.
- An acceptable alternate (common name) has the smaller, then the larger
hydrocarbon group cores, each followed by the suffix “-yl”, followed by the
word “ether”.
- In other regards, they use the same rules as for branches.

O
Structure O

IUPAC name ethoxybutane isopropoxypentane

Common name ethyl butyl ether isopropyl pentyl


ether
Esters are named for their two parts. The core of the first part has
the suffix “-yl” and with the second part (with the double bonded
O) having the suffix “-oate”. In other regards, they use the same
rules as for branches.

O O

O O

ethyl hexanoate

“Parent acid” “Parent”


alcohol
Amines are hydrocarbons containing an ammonia group (-NH2)
and are named as branches coming off nitrogen, followed by the
suffix “amine”.
Amines can be primary, secondary, and tertiary
In secondary and tertiary amines, the prefix N- is used for each
substituent of the nitrogen atom NH
2
N

N,N- propanami IUPAC name

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

Not all chemical compounds have only one type of functional


group. For those compounds with mixed groups, for
example, a molecule that is both an amine as well as a
carboxylic acid, a system of priorities must be established.
These priorities and names associated with them are found in
the following table.
Hierarchy of Naming Table

Priorit Classification Functional Suffix if the Prefix if a


y Group highest Lower Priority
priority.
1 Carboxylic O -oic acid -
Acid
OH

2 Aldehyde O -al Oxo-

H
O
3 Ketone -one Oxo-

4 Alcohol -OH -ol Hydroxy-

5 Amine -NH2 -amine Amino-


Hierarchy examples:
OH O

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