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Module 5
IUPAC Nomenclature Classification of
Organic Compounds
(Functional Groups, Aliphatic and
Aromatic Compounds)
Functional Group
 Is a special group of atoms acting as a single atom, these functional groups differentiate a
substance from another substance.

 It confers characteristic chemical and physical properties on a family of organic compounds.

 Example hydroxyl, carboxyl, carbonyl, amines, esthers, ethers, aldehydes and ketones.
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Chemical Formula and Structure of the Hydroxyl Group

 A hydroxyl group is composed of one hydrogen atom bonded to one oxygen atom. Its
chemical formula is written as either -OH or HO-. The ‘ - ' represents the carbon to which the
hydroxyl group is bonded.

The general formula of alcohol is:

R – OH

where: R – is the alkyl group

OH – is the functional group

The general formula for R is CnH2n +1

 The R in the structural formula stands for the carbon backbone of the organic molecule to
which the hydroxyl attaches.

Classification of Alcohols
Alcohols are classified according to the number of hydroxyl groups (-OH) present in the chain.

1. Monohydric (one – OH group)

ethyl alcohol or ethanol (is a type of alcohol) with the hydroxyl group on the far right.

2. Dihydric ( 2 – OH groups) or diol

CH₂OH

CH₂OH

Ethylene glycol is used as an antifreeze and as solvent.

CH₃

H₃C C OH

CH₃

Isobutyl alcohol is used as a solvent; also found in paint removers and cleansers.

3. Trihydric or triol (3 – OH groups in the structure)

CH₂OH

CHOH

CH₂OH

Glycerol is a by-product of soap making.

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Alcohols are further classified as:

1. Primary Alcohols – The OH group is attached to a primary carbon (terminal carbon) and has the type
formula. R – OH
H
H C OH
H
Methanol or methyl alcohol
Methanol boils at 64.7 ⁰ C and melts at -97.8 ⁰ C

2. Secondary Alcohol – has the – OH attached to a secondary carbon atom (carbon is attached to 2 other
carbon atoms). It has the type formula.

R₂ - CHOH

H₃C C CH₃

OH

Isopropyl alcohol or 2 – propanol

3. Tertiary Alcohol – has the – OH attached to a tertiary carbon atom ( carbon attached to 3 other carbon
atoms) with the type formula.

R₃C – OH

CH₃

H₃C C CH₃

OH

2 – methyl- 2 – propanol or tert – butyl alcohol

Nomenclature of Alcohol

Rule 1 Common names consist of the alkyl group followed by the word alcohol.

Number of Complete name

Root Sufix
carbon Alcohol of alcohol
word -yl
atoms
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Example: alcohol with 5 Carbon atoms

5 pent -yl Alcohol pentyl alcohol

Rule 2 IUPAC name of alcohols are derived from the parent alkane

Number of Name of to
Change Complete name
carbon parent Suffix
“e” of alcohol
atoms alkane “ol”

Example: alcohol with two carbon atoms

2 Ethane - ethan + ol ethanol

CYCLIC OR AROMATIC ALCOHOLS

1. Aromatic alcohols have their –OH attached to a side chain.

Example: CH₂OH - benzanol or benzyl alcohol

Aromatic alcohols have fragrant odor, are colorless liquids and used in soaps, cosmetics and
perfumes.

2. Phenols are alcohols with their –OH attached directly to the ring

Example: OH - phenol

Phenols have strong aromatic odors, are corrosive, antiseptic, and are used in the manufacture of
plastics, dyes and explosives.
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Introduction to Carbonyl Compounds

Aldehydes and Ketones

The functional group on aldehydes and ketones is a carbonyl group (double bond oxygen
to a carbon). In aldehydes, the carbonyl group is on the "end" of a carbon chain, while in
ketones, it is in the "middle" of a carbon chain.

Nomenclature of Aldehydes and Ketones

Aldehyde -al propanal

-one propanone
or
Ketone acetone (common
name)

The names of aldehydes and ketones are simply derived by dropping "-e" from the root and
adding "-al" or "-one" respectively. A position number is needed for ketones since the carbonyl
group may be on any number of several carbons in the "middle" of a chain. The carbonyl on the
aldehyde is always on the number one carbon so no position number is needed.
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Rules in Naming Aldehydes

1. In Aldehydes, determine the longest carbon chain attached to the formyl group, change the “e”
ending of the parent alkane to the prefix “al” from aldehyde.

Rule 1:

Number of Parent Change Suffix Complete

carbon atoms to “al” Name
Alkane “e”

6
hexane hexan al hexanal

Preparation of Aldehydes
Oxidation of Primary Alcohol
 Aldehydes are formed by controlled oxidation of primary alcohols.
H O
H C O H + O H C + H₂O
H H
H Oxidation
Methanol + oxygen methanol + water
Aldehydes are named from the acids they form on oxidation.
Benzaldehyde is an aldehyde used as a flavoring material
Other Aldehydes
H C=O H C=O

OCH₃
OH
benzaldehyde vanillin
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ALDEHYDE (-al)

Pentanal

KETONES
 Ketones like steroids, camphor, some fragrances and sugars are
reactive compounds with the general formula, R – CO – R’, where
R and R’ are alkyl groups.
Nomenclature of KETONES
Ketones are better known by their common names. These are the alkyl
or aryl names followed by the word, ketone. The IUPAC names of
ketones are derived from the parent alkane; but the “e” ending is
changed to –one, the suffix of ketone.
Rule 1:

Number of Name of Suffix Complete

Change toto
carbon atoms Parent “al” Name of
4 “e” one ketone
Alkane
butan butanone
butane

Rule 2: ( for substituted Ketones)

Parent chain is numbered by giving the lowest number to the carbonyl ( C=O ).

Example: C₂H₅ O

1. C C C C

CH ₃

3 – ethyl – 3 – methyl – 2 - butanone

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2.

O Cl

CH₃ C CH ₂ CH CH ₂ CH ₂

C₃H₇

4 – chloro - 4 – propyl - 2 – hexanone

Propanone, commonly called acetone is the simplest ketone. It is the product of the metabolism of
fats. It is used as a solvent, a cleaning or drying agent.

O O

CH ₃C CH ₃ CH ₃ CH ₂ CH ₂ C CH ₂CH ₃

dimethyl ketone ethyl – n – propyl ketone

or or

Propanone or acetone 3 – propanone

Just like the aldehydes, ketones also undergo oxidation reactions to form carbon dioxide and water.

KETONE (-one)

What's a Carboxyl Group?

 A carboxyl group is defined as having a carbonyl and hydroxyl group both linked to a carbon
atom.

 The general formula for a carboxyl group is R-COOH.

Where R – is the hydrocarbon group

COOH – is the functional group called carboxyl

 When you hang out with carboxyl, as an organic compound, you receive the benefit of joining
the club of acidity. Carboxyl groups will make organic compounds acidic because of their own
ionizing property.
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Carboxylic acids may contain 1 or more carboxyl groups within its structure. Straight – chain carboxylic
acids are called fatty acids.

Most carboxylic acids ….

 are weak acids;

 have high boiling temperature;

 have strong, unpleasant odor ( when in the free state)

like the acid responsible for goat’s body odor – caproic,

capric or caprylic.

The common names of the carboxylic acids are based from the properties and the materials where
these were extracted.

Rule 1:

Number of Name of Change Suffix Word,

carbon Parent “e” to “oic” Acid
atoms Alkane
=
Pentan
oic acid
pentanoic acid
5 pentane pentan

Some Common Carboxylic Acids

1. Formic or methanoic Acid; HCOOH

The structure of Formic Acid O

H C

OH

The swelling, itchiness and redness of the skin after an ant’s bite is due to formic acid.

2. Acetic acid or ethanoic acid, CH₃COOH - this is the most important carboxylic acid produced by the
oxidation of an aldehyde – acetaldehyde.
 O O 10

CH₃―C + O₂ 2 CH₃ ― C
OH OH
Acetaldehyde Oxygen Acetic Acid
Acetic acid, CH₃COOH

 Vinegar, a 5% acetic acid and water, is used to flavor foods.

 Glacial Acetic acid (100% acetic acid) is toxic.

 Acetic acid is used in the manufacture of drugs, dyes and photographic chemicals.

3. Butanoic Acid ( C₃H₇ COOH) is the acid behind the odor of rancid butter. It is used in the manufacture
of pharmaceuticals and disinfectants.

4. Benzoic Acid ( C₆ H₅ COOH) is used in the manufacture of dentrifices, polymers and medicines. When
combines with sodium, it may be used as food additive.

COOH

Structure of benzoic acid

CARBOXYLIC ACID (-oic acid)

Some Foods which contain carboxylic

O acids are:
H₂―C― C 1. Citrus Fruits – Citric Acid,
H
HOC (CH₂COOH)₂ COOH
O 2. Tomatoes – ascorbic Acid,
HO―C ―C C₆ H₈ O₆
OH 3. Tea – tannic Acid,
O C₇₆ H₅₂ O₄₆
H₂― C ― C 4. Green apples contain malic acid,
OH HOOCCH = CHCOOH
Structure of Acetic Acid
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Esters
 These organic compounds have the general formula R –COO- R¹
or R - CO₂ - R¹;
 Where R and R¹ are the hydrocarbon groups, -COO or -CO₂ is the
functional group – the carboxylate.
 Esters are formed from the reaction between a carboxylic acid
and an alcohol, called esterification as shown in this equation:

O O
CH₃ C + CH₃CH₂O H CH₃ C + H₂O
H OCH₂CH₃
ethanoic acid ethanol ethyl ethanoate water

Nomenclature of Esters
Esters are named after the alcohol and acid from which they are
produced. The name of the alcohol is given first, the suffix change to –
yl; followed by the carboxylic acids with the suffix change to -oate.
Example:
An acid from propyl alcohol and formic acid will be named propyl
formate.
Esters have distinctive fruity odor and have low boiling
temperature.
Esters are the compounds formed from the reaction of an acid
and a base. This process is called saponification
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⁄⁄
C₁₇ H₃₅ ― C
COOCH₂ CH₂ OH
ǀ \ O ǀ
OH ⁄⁄ + 3NaOH
C₁₇ H₃₅ COOCH₂ 3C₁₇ H₃₅ COONa + CHOH
―O―C ǀ
CH₂ OH
\
C₁₇ H₃₅ COOCH₂
CH₃
Carboxylic acid Sodium Hydroxide Soap Glycerol
Structure of Aspirin
ESTER (-oate)

COMMON ESTERS IN FRUITS

SOURCE ESTER FORMULA

Orange Octyl acetate CH₃ COO (CH₂ )₇ CH₃

Banana Pentyl acetate CH₃ COO (CH₂ ) -CH₃

Amyl butyrate C₃ H₇ COO C₅ H₁₁

Pineapple Butyl butyrate C₃ H₇ COO C₄ H₉

Methyl butyrate C₃ H₇ COO CH₃

apple Amyl valerate C₄ H₉ COO C₅ H₁₁

Amines and Amides
Amines and Amides are organic compounds containing O the amino group,
A very important esters is aspirin, which
-NH₂. ―C
⁄⁄

is used
[Link]
relieve is
minor pains, reduce
an organic compound containing
\ O
OH ⁄⁄ an amino
fever (antipyretic)
group, -NH₂,and act as anti-
attached to the hydrocarbon ― O ―chain.
C
\
The general formula
inflammatory agent of simple amines is R -NH₂; CH₃ secondary
Structure of Aspirin
amines is R – NH; and for tertiary amines,
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 Naming Amines
Amines are named by adding the suffix, -amine to the root name of the hydrocarbon.
Example:
CH₃ CH₂ NH₂ - is ethylamine because the hydrocarbon is ethane.
The common name for amines is derived from the name of the hydrocarbon chain taken as a
branch chain, then adding the suffix – amine
USES OF AMINES
• They are responsible for some odors. Cadaverine is the amine produced by bacteria on decaying
organisms.
• The ptomaines are amines formed by bacteria on meat and fish. This can cause food poisoning.
 Several other compounds containing the amino group are proteins, nucleic acids, vitamins, and
some addictive compounds (nicotine, cocaine and amphetamines).

AMINE (-amine)

B. Amides

 Amide is an organic compound containing an amino group attached to the carbon atom of a carbonyl group.
NAMING AMIDES
Amides are named by adding the suffix – amide to the root name of the hydrocarbon (this depends upon the
carboxylic acid from which the amide is derived).
The amide from pentanoic acid (C₅ H₁₁ COOH) is pentanamide; octanoic acid, octanamide; decanoic acid,
decanamide, and so forth.
USES OFEthers
AMIDES
Amides have various uses. These organic compounds link amino acids to form proteins. Its amino group is found
in polyamide fibers (nylon).
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 Ethers is an organic compound containing an oxygen atom that is

bonded to two carbon atoms.
 Ethers are very important organic compounds, usually referred to
as the functional isomers of their corresponding alcohols.
 The general formula of the ethers is R – O - R¹, where R and R¹ are
the hydrocarbon chains attached to the central oxygen atom.
1. The common name is derived by naming the hydrocarbon chains on
either sides of the oxygen atom and then adding the word, ether.
Example: CH₃ (CH₂)₂ O (CH₂)₄ CH₃ - propyl pentyl ether
ETHER (-ether)

2. IUPAC system
The IUPAC names of ethers are derived by naming the smaller hydrocarbon
chain bonded to the central oxygen atom, changing its suffix to –oxy, and naming the
remaining parts just as hydrocarbons are named.
Example: CH₃ CH₂ O CH₂ CH₃ - ethoxy ethane
Ethers do not form hydrogen bonds, they have varied solubility in water (small
ethers are more soluble in H₂O than the larger ether molecules).
Ethers such as diethyl ether are used as solvent for organic compounds. Some
HALIDES
ethers(depends
are used as
onanaesthetic,
the halogenand one is used in gasoline to improve engine’s
group)
efficiency.
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 Flourine (-flouro) -F
 Bromine (-bromo) -Br
 Chlorine (-chloro) - Cl
 Iodine (-iodo) -I
QUIZ: WHAT IS THE SPECIFIC NAME OR THE IUPAC NAME OF
A AND B.
Identify the functional
group (name and General
formula) of the ff.:
c. Alcohol
d. Ether
e. Aldehyde
f. Ketone
g. Carboxylic acid
h. Ester
i. Amine
j. Amide
Identify the following:
1. an alcohol with 6 carbon atoms
2. the general formula of amines and amides
3. an acid and a carboxylic acid which relieves minor pain
4. which substance is used in gasoline to improve the engines efficiency
5. the reaction between a carboxylic acid and an alcohol.
6. These are amines formed by bacteria on meat and fish that can cause
food poisoning.
7. The acid found in green apple.
8. Is used in the manufacture of dentrifices, polymers and medicines.
When combines with sodium, it may be used as food additive.
9. The swelling, itchiness and redness of the skin after an ant’s bite is
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due to________.
10. _______have strong aromatic odors, are corrosive, antiseptic, and
are used in the manufacture of plastics, dyes and explosives
ENUMERATION:
1-2 What are the two general classifications of alcohols.
3-5 Name the 3 classes of alcohol based on the first classification.
6-8 Another 3 classes of alcohol based on the second classification.
9. Define what is functional group.
10. Give an example of functional group.