FUNCTIONAL GROUP

FUNCTIONAL GROUP

 Isa special group of atoms acting as a single atom,

these functional groups differentiate a substance from
another substance.
 Itconfers characteristic chemical and physical
properties on a family of organic compounds.
 Example hydroxyl, carboxyl, carbonyl, amines,
esthers, ethers, aldehydes and ketones.
 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.

 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

H
H ₃C 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

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

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
 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

propanal
Aldehyde -al
Ketone -one propanone
or
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.
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 Alkane “e” to “al” Name

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 Oxidation
H
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
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 ”
Change Suffix Complete
carbon atoms to “one” Name of
Parent “e”
Alkane ketone

4 butane
butan one butanone
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
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.
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 atoms Parent “e” to “oic” Acid
Alkane =
Pentan
5 acid oic acid
pentane pentan pentanoic
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.
O O
2. Acetic
CH₃―Cacid or ethanoic
+ O₂ acid, CH₃COOH
2 CH₃ ― -Cthis is the most important carboxylic
acid produced by OHthe oxidation of an aldehyde –OH acetaldehyde.

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)
 O
Some Foods which contain carboxylic
H₂―C― C acids are:
H

O
1. Citrus Fruits – Citric Acid,
HOC (CH₂COOH)₂ COOH
HO―C ―C 2. Tomatoes – ascorbic Acid,
OH
C₆ H₈ O₆
3. Tea – tannic Acid,
O
H₂― C ― C C₇₆ H₅₂ O₄₆
OH 4. Green apples contain malic
Structure of Acetic Acid acid,
HOOCCH = CHCOOH
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

C₁₇ H₃₅ COOCH₂ CH₂ OH

ǀ ǀ
C₁₇ H₃₅ COOCH₂ + 3NaOH 3C₁₇ H₃₅ COONa + CHOH
ǀ
CH₂ OH
C₁₇ H₃₅ COOCH₂
Carboxylic acid Sodium Hydroxide Soap Glycerol
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

A very important esters is O

⁄⁄
aspirin, which is used to ―C
relieve minor pains, \ O
OH ⁄⁄
reduce fever (antipyretic)
―O―C
and act as anti- \
inflammatory agent CH₃

Structure of Aspirin
Amines and Amides
Amines and Amides are organic
compounds containing the amino group, -NH₂.

A. Amine is an organic compound containing

an amino group, -NH₂, attached to the
hydrocarbon chain.

The general formula of simple amines is R -

NH₂; secondary amines is R – NH; and for
tertiary amines,
the formula is R - NR¹ R¹¹ .
 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 OF AMIDES
Amides have various uses. These organic compounds link
amino acids to form proteins. Its amino group is found in polyamide
fibers (nylon).
 ETHERS

 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 ethers are used as anaesthetic,
and one is used in gasoline to improve engine’s efficiency.
 HALIDES
(DEPENDS ON THE HALOGEN GROUP)

 Flourine (-flouro) -F
 Bromine (-bromo) -Br
 Chlorine (-chloro) - Cl
 Iodine (-iodo) -I
QUIZ: WHAT IS THE Identify the functional
SPECIFIC NAME OR THE
IUPAC NAME OF A AND B. 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 atom
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 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.
KUDOS