CHM 004 (ORGANIC CHEMISTRY)

LECTURE NOTE 2:
CLASSES AND NOMENCLATURE
(Naming an Organic Compound)

DEPARTMENT OF CHEMISTRY, U
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NIVERSITY OF LAGOS
 Outline
0 Representing organic compounds
0 Classes of organic compounds
0 Nomenclature of organic compounds

DEPARTMENT OF CHEMISTRY, UNIVERSITY OF LAGOS 2

 Learning outcome
0 Understand the different ways of representing organic
compounds.

0 Identify the different functional groups in organic compounds

and classes.

0 Apply the basic rule to naming organic compounds

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REPRESENTATION OF ORGANIC COMPOUNDS

Organic compounds are represented using:

❖ Open structure

❖ Condensed structure

❖ Line/Stick structure

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 EXAMPLES
S/N
Compound Molecular Lewis Structure Condensed Stick/Line
Formula Structure Formula
1.
Ethane C2H6 CH3CH3

2
Isobutane C4H10 (CH3)3CH

3 Cyclohex-3- C6H10
ene

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 ACTIVITY 1
❖ Represent the organic compounds with the following structural formula using the
open structure, condensed structure and line formula

a. C6H6 b. C2H5OH

c. C3H6

❖ Convert the following line formula to open structures and condensed structures

a. b. c.

d.

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DEPARTMENT OF CHEMISTRY, UNIVERSITY OF LAGOS
 CLASSES OF ORGANIC COMPOUNDS

❖Organic compounds are compounds of carbon.

❖Have structural features called functional groups

used in classifying them into families called
homologous series.

❖Functional group is an atom or group of atoms within

a larger molecule or multiple bond between carbon
atoms that has characteristic chemical behaviour.
DEPARTMENT OF CHEMISTRY, UNIVERSITY OF LAGOS 7
 CLASSES OF ORGANIC COMPOUNDS

❖Organic compounds are compounds of carbon.

❖Have structural features called functional groups

used in classifying them into families called
homologous series.

❖Functional group is an atom or group of atoms within

a larger molecule or multiple bond between carbon
atoms that has characteristic chemical behaviour.
DEPARTMENT OF CHEMISTRY, UNIVERSITY OF LAGOS 8
 CLASSES OF ORGANIC COMPOUNDS CONT’D.
❖Homologous series is a family of organic compounds
which follows a regular structural pattern such that
each successive member differs from the preceding one
by a -CH2 group.
❖ Characteristics
➢ same functional group
➢similar chemical properties
➢gradually changing physical properties
DEPARTMENT OF CHEMISTRY, UNIVERSITY OF LAGOS 9
COMMON FUNCTIONAL GROUPS AND CLASSES
ALKANE CARBOXYLIC ACID
ALKENE

ALKYNE
ESTER
HALOALKANE

ACYL CHLORIDE
AMINE

NITRILE
AMIDE
ALCOHOL

ETHER
NITRO

ALDEHYDE

SULPHONIC ACID
KETONE

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 ACTIVITY 2
❖ Mention the classes of the following functional groups

a.
d.

b. e.

c. f.

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General - Nomenclature

The name of every organic molecule has 3 parts:

1. The parent name indicates the number of carbons in t
he longest continuous chain.
2. The suffix indicates what functional group is present.
3. The prefix tells us the identity, location, and number o
f substituents attached to the carbon chain.

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General - Nomenclature
To name any given organic molecule:
1. Identify the number of carbons in the longest continu
ous chain.
2. Identify the functional group(s) and assign coordinate
s such that it/they is/are given the lowest coordinate(s
) possible
3. Identify the substituent(s) if present and assign coordi
nates such that it/they is/are given the lowest coordin
ate(s) possible secondary to the identified functional
group(s)
4. Name the compound starting with the prefix (the ident
ity, location, and number of substituents), then the par
ent name (derived from the longest carbon chain) and
the suffix (the functional group) 13
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 Alkanes - Nomenclature
Parent – Longest straight carbon chain

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Alkanes - Nomenclature
Suffix – Our first functional group is alkane, so the suffix is –ane
For later functional groups we will drop the –ane root suffix for others
Alkane chain # Carbons Name
CH4 1 methane
CH3CH3 2 ethane
CH3CH2CH3 3 propane
CH3CH2CH2CH3 4 butane
CH3CH2CH2CH2CH3 5 pentane
CH3CH2CH2CH2CH2CH3 6 hexane
CH3CH2CH2CH2CH2CH2CH3 7 heptane
CH3CH2CH2CH2CH2CH2CH2CH3 8 octane
CH3CH2CH2CH2CH2CH2CH2CH2CH3 9 nonane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 10 decane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3 11 undecane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3 12 dodecane

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 FUNCTIONAL GROUPS
Organic chemistry is a vast subject so it is easier to split it into small sections for study
. This is done by studying compounds which behave in a similar way because they hav
e a particular atom, or group of atoms, FUNCTIONAL GROUP, in their structure.

Functional groups can consist of one atom, a group of atoms or multiple bonds betwee
n carbon atoms.

Each functional group has its own distinctive properties which means that the propertie
s of a compound are governed by the functional group(s) in it.

H H H H H H H H H H
H C C C C C NH2 H C C C C C OH
H H H H H H H H H H
Carbon Functional Carbon Functional
skeleton Group = AMINE skeleton Group = ALCOHOL

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 COMMON FUNCTIONAL GROUPS

GROUP ENDING GENERAL FORMULA EXAMPLE

ALKANE - ane RH C2H6 ethane

ALKENE - ene C2H4 ethene
ALKYNE - yne C2H2 ethyne
HALOALKANE halo - RX C2H5Cl chloroethane
ALCOHOL - ol ROH C2H5OH ethanol
ALDEHYDE -al RCHO CH3CHO ethanal
KETONE - one RCOR CH3COCH3 propanone
CARBOXYLIC ACID - oic acid RCOOH CH3COOH ethanoic acid
ACYL CHLORIDE - oyl chloride RCOCl CH3COCl ethanoyl chloride
AMIDE - amide RCONH2 CH3CONH2 ethanamide
ESTER - yl - oate RCOOR CH3COOCH3 methyl ethanoate
NITRILE - nitrile RCN CH3CN ethanenitrile
AMINE - amine RNH2 CH3NH2 methylamine
NITRO nitro- RNO2 CH3NO2 nitromethane
SULPHONIC ACID - sulphonic acid RSO3H C6H5SO3H benzene sulphonic acid
ETHER - oxy - ane ROR C2H5OC2H5 ethoxyethane

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 Alkanes - Nomenclature
Prefix – Our substituents will be branches in the alkane structure
A branch is another alkane minus one hydrogen – an alkyl group
Example – if CH3- is a branch on a longer chain:

CH3- is CH4 minus 1 hydrogen

Since it is a side chain it will replace the –ane suffix with –yl

CH3- is a methyl group

We can also abbreviate this group as Me-

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 Alkanes - Nomenclature

Prefixes -
Alkyl group Structure IUPAC name Abbreviation

CH3- CH3- methyl Me-

CH3CH2- ethyl Et-

CH3CH2CH2- n-propyl n-Pr

CH3CHCH3 isopropyl or i-propyl i-Pr

CH3CH2CH2CH2- n-butyl n-Bu

CH3CH2CHCH3 sec-butyl s-Bu

(CH3)2CHCH2- isobutyl or i-butyl i-Bu

(CH3)3C- tert-butyl or t-butyl t-Bu

C6H5- phenyl Ph
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 Alkanes - Nomenclature

1. Find the parent carbon chain and add the suffix.

Note that it does not matter if the chain is straight or it bends.

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DEPARTMENT OF CHEMISTRY, UNIVERSITY OF LAGOS
Alkanes - Nomenclature

Also note that if there are two chains of equal length, pick the
chain with more substituents. In the following example, two dif
ferent chains in the same alkane have seven C atoms. We circl
e the longest continuous chain as shown in the diagram on th
e left, since this results in the greater number of substituents.

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Alkanes - Nomenclature

2. Number the atoms in the carbon chain to give the first subst
ituent the lowest number.

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Alkanes - Nomenclature

If the first substituent is the same distance from both ends, nu

mber the chain to give the second substituent the lower numb
er.

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DEPARTMENT OF CHEMISTRY, UNIVERSITY OF LAGOS
Alkanes - Nomenclature

When numbering a carbon chain results in the same numbers

from either end of the chain, assign the lower number alphabe
tically to the first substituent.

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DEPARTMENT OF CHEMISTRY, UNIVERSITY OF LAGOS
Alkanes - Nomenclature
3. Name and number the substituents.

• Name the substituents as alkyl groups.

• Every carbon belongs to either the longest chain or a substit
uent, not both.
• Each substituent needs its own number
• If two or more identical substituents are bonded to the longe
st chain, use prefixes to indicate how many: di- for two group
s, tri- for three groups, tetra- for four groups, and so forth.

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DEPARTMENT OF CHEMISTRY, UNIVERSITY OF LAGOS
Alkanes - Nomenclature
4. Combine substituent names and numbers + parent and suffix.
• Precede the name of the parent by the names of the substituents.
• Alphabetize the names of the substituents, ignoring all prefixes exc
ept iso, as in isopropyl and isobutyl.
• Precede the name of each substituent by the number that indicates
its location.
• Separate numbers by commas and separate numbers from letters b
y hyphens. The name of an alkane is a single word, with no spaces
after hyphens and commas.

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Other Functional Groups - Nomenclature
The IUPAC rules for all other functional groups will differ only by the followi
ng:
1.Suffix will change to reflect functional group
2.Some functional groups have priority over others

For now: Alcohol > Alkyne > Alkene > alkane=alkyl halide
3.The longest chain must contain the suffix functional group – even if not th
e longest chain overall
4.Numbering gives this functional group the lowest number – even if there
are other groups that would be lower
5.If an alkene has stereochemistry, it must be specified in the prefix

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Alkyl Halides - Nomenclature

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Alcohols - Nomenclature

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 Alcohols - Nomenclature
• When an OH group is bonded to a ring, the ring is numbered begin
ning with the OH group.
• Because the functional group is at C1, the 1 is usually omitted fro
m the name.
• The ring is then numbered in a clockwise or counterclockwise fashi
on to give the next substituent the lowest number.

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Alcohols - Nomenclature

• Compounds with two hydroxyl groups are called diols or glyc

ols.
• Compounds with three hydroxyl groups are called triols.

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Alkenes - Nomenclature

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 Alkenes - Nomenclature

• Compounds that contain both a double bond and a hydroxy group are na
med as alkenols and the chain (or ring) is numbered to give the OH group
the lower number.

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DEPARTMENT OF CHEMISTRY, UNIVERSITY OF LAGOS
Alkenes - Nomenclature
Disubstituted Alkenes - Stereochemistry:

There is no free rotation about the p-bond

cis- vs. trans-

▪cis: two identical or substantial groups on the same side of C=C

▪trans: two identical or substantial groups on the opposite side of

C=C

Cl

ClCl Cl
c
is -
1,
2-
Di
chl
oro
e
th
en
e t
r
ans -
1,
2-
Di
chl
oro
e
th
en
e
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Alkenes - Nomenclature

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Alkynes - Nomenclature

• Alkynes are named in the same general way that alkenes are
named.

• In the IUPAC system, change the –ane ending of the parent al

kane name to the suffix –yne.

• Choose the longest continuous chain that contains both atoms

of the triple bond and number the chain to give the triple bond
the lower number.

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Alkynes - Nomenclature

• 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 triple bond are named as e
nynes.
• The chain is numbered to give the first site of unsaturation (eith
er C=C or CC) the lower number.

DEPARTMENT OF CHEMISTRY, UNIVERSITY OF LAGOS

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Nomenclature – Drawing Structure from a Given Name
• Draw the longest carbon chain.
• Assign coordinates to the carbon chains and draw the functional
group(s) at the appropriate coordinate(s).
• Indicate the substituents at the appropriate coordinate(s) and en
sure every carbon atom has four bonds around it and balance up
with hydrogen.
• Example:
2,2 dimethyl heptane

The longest chain is 7

Assign coordinates to the longest chain

1 3 5 7

2 4 6

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Nomenclature – Drawing Structure from a Given Name

• Indicating the substituents – methyl (CH3) at the appropriate co

ordinate C-2
CH3

CH3

• Since the functional group here is alkane, that is the structure

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 ACTIVITY 3
❖ Name the following compounds

a. b. c.

d.

❖ Convert the following names to structure

1. 2-bromo-3-methylpentane
2. 4-ethyl-5-methyl-4-hexen-1-yne

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