Week: 4 Date: 3rd October, 2022

Topic: Organic Chemistry

Content:
 Alkanoic acids /Carboxylic acids
 Alkanoates/Esters
 Fats/oils
Alkanoic Acids
Alkanoic acids are organic compounds containing –COOH functional group. They are also known as
carboxylic acids or organic acids. They form a set of homologous series represented by the general
molecular formula CnH2n+1COOH where n is an integer and the value n starts from 0. The acids are
named by removing the last letter –e ending of the names of corresponding alkanes and replacing it
with the suffix oic acid. The higher members of the series with unbranched carbon chains are
obtained from naturally occurring fats, they are generally referred to as fatty acids. Below is a list of
few members of the acids
Value of n Formula of acid Name of acid Source
0 HCOOH Methanoic acid Ant
1 CH3COOH Ethanoic acid Vinegar
2 C2H5COOH Propanoic acid Fat
3 C3H7COOH Butanoic acid Butter
15 C15H31COOH Hexadecanoic acid Palm oil
17 C17H35COOH Octadecanoic acid Tallow

There are aliphatic organic acids containing more than one carboxylic –COOH functional group. The
most common are those containing two carboxylic acid –COOH functional group and are called
dicarboxylic acids. These are usually found in plants and fruit juice.
Examples
1. 2.
Ehandioc acid
(found in grapes and potatoes)
(found in unripe apple)

There are also aromatic organic acids containing benzene nucleus. Examples
Physical Properties of Alkanoic Acids
The lower members of alkanoic acids are liquids miscible with water, this is as a result of hydrogen
bonding between the –OH group of the acid and the –OH group of the water molecules. They also
have relatively high boiling points, this is attributed to the association between the acid molecules
through hydrogen bonding. The higher members are waxy solids; the solubility of the alkanoic acids
decreases with increasing chain length.
Chemical Properties of Alkanoic Acid
1. Acidic Properties: As a weak monobasic acid, ethanoic acid shows all the usual acidic properties.
Thus, it
i. Librates carbon (iv) oxide form trioxocarbonate (iv) and hydrogen trioxocarbonate (iv).
ii. It attacks strongly electropositive metals. E.g. magnesium and calcium and.
iii. Neutralizes bases and alkalis to form salts known as ethanoates and water.
2. Ester formation: Ethanoic acid reacts reversibly with alkanols to form esters. For example, it
reacts with ethanol when heated to produce ethyl ethanoate, CH3CODC2H5. The reaction is
catalysed by tetraoxosulphate (vi) acid.
Test for Carboxylic Group
Different tests are carried out in order to identify the carboxylic functional group. These include
sodium bicarbonate test, ester test and litmus test.
Sodium bicarbonate test: when carboxylic acid reacts with sodium bicarbonate solution, carbon
dioxide is formed with a brisk effervescence as well as sodium acetate is formed. This experiment is
conducted to differentiate carboxylic acid from phenol. The chemical reaction for the same is as
follows.
RCOOH +NaHCO3 → RCOONa + H2O + CO2 ↑ (Brisk effervescence)
Ester test: A reaction of carboxylic acid takes place with alcohol in the presence of concentrated
tetraoxosulphate(vi) acid creating a pleasant smelling ester. This reaction is also called esterification
RCOOH + R’-OH + H2SO4→ RCOOR’(Ester) + H2O
The formation of a sweet smelling compound defines the presence of a carboxylic group in the
organic compound.
Uses of Ethanoic Acid
Ethanoic acid is used in making compound like:
 Ethyl ethanoate which is used in vinykl resins
 Ethanoic anhydride which is used aspirin
 Propanone (acetone) and
 Various dyes.
Alkanoates/Esters

All esters are similar chemically although they may vary in degree of reactivity. Ethyl ethanoate is
one of the simple esters. Its molecular formula is CH3COOC2H5.

Preparation of Alkanoates

Ethyl ethanoate is prepared by the esterification between ethanol and glacial ethanoic acid at 150 oC
in the presence of concentrated tetraoxosulphate (vi) acid.
H2SO4
C2H5OH(aq) + CH3COOH(l) ⇌ CH3COOC2H5(l) + H2O(l)

Physical Properties of Alkanoates

1. Physical state. Esters are colourless, volatile and oily liquids with a characteristic fruity smell.
The smell of the most of the flowers and fruits is due to esters present in them. The
characteristic tastes and smells of different esters find applications in the manufacture of
artificial flavouring and perfuming agents. The flavours of some of the esters are given below:

Ester Flavour Ester Flavour

n-Pentyl ethanoate Banana Amyl but)’rate Apricot

Octyl ethanoate Orange Isobutyl Raspberry

Ethyl butanoate Pineapple Benzyl ethanoate Jasmine

2. Solubility. Esters are sparingly soluble in water but are quite miscible in organic solvents like
alcohols and ethers. In fact, most of the esters are themselves very good solvents for plastics
and nitrocellulose.

3. Boiling points. The boiling points of esters are always less than the corresponding carboxylic
acids because esters do not form hydrogen bonds.

Chemical Properties

Hydrolysis. Esters are hydrolysed slowly by water at boiling temperature. The reaction is
catalysed by small amount of acid or base. The basic hydrolysis is also known as saponification. It
is because of the fact that the esters with high molecular mass acids (C12-C17) give soap on
hydrolysis with a base. Soaps are sodium or potassium salts of carboxylic acids with high
molecular mass (C12-C17). Ethyl ethanoate can be hydrolyzed by water into its component acid and
alkanol again. The reaction is catalyzed by hydrogen or hydroxide ions i.e dilute acid or alkali
CH3COOC2H5(l) + H2O(l) → C2H5OH(aq) + CH3COOH(l)

1. Reduction. Esters are reduced to alcohols by the reducing agents like (sodium/ethanol) or
(lithium aluminium hydride).
Uses of Esters

Esters are used

 In perfumes and cosmetics

 In artificial flavouring for foods

 as solvents for lacquers, paints, and varnishes;

 to make surfactants E.g. soap, detergents

Home work

State 3 differences between esterification reaction and neutralization reaction

Fats and Oils

Fats and oils are called lipids. They occur abundantly in nature in plants and animals. Fats are
mainly from animals and oils are mainly from plants. Both fats and oils are esters of trihydric
alkanol, propane – 1,2,3 – triol (glycerol).

The alkyl groups R, R’ and R’’ may be the same or different.

The fatty acids found in lipids are long chain containing 10 to 18 carbon atoms. The terminal
carboxylic group, -COOH is polar, making them soluble in water. Fatty acids are weak acids. They
are able to ionize in water to produce carboxylate ion and hydrogen ion.

Properties of Fats and Oils

Fats cannot be represented by a single formula because they contain complex mixtures of esters. Fats
are solid at 25oC while oils are liquid at the same temperature. The level of unsaturation in oils is
higher than it is in fats.
Saponification

When fats and oil are hydrolysed with caustic soda or caustic potash, they produce sodium or
potassium salts of the corresponding fatty acids and glycerol. This reaction is called saponification.
Saponification is the alkaline hydrolysis of fatty acids to produce soap and glycerol. This reaction is
widely applied in industries to produce soap. The glycerol is produced as a by-product.

Fat or oil + NaOH or KOH → Soap and propane-1,2,3-triol.

The reaction is a complex one but can be represented as below.

Hydrogenation of Oils

Oil hardened by hydrogenation to produce margarine. Hydrogen is bubble into oil heated to about
200° C at a pressure of about 5 atm. finely divided nickel is used as catalyst. The hydrogen adds
along double bond of the carbons of the unsaturated compounds in the oil.

Fat & Oils - Uses & Tests

Uses of Fat and Oil

1. Humans consume fats and oils. Palm oil, cotton seed oil, and groundnut oils are used for cooking.

2. Fats and oils are solvent for water insoluble vitamins in the body.

3. Lipids also provide energy for animals and insulate our organs in our bodies.

4. Coconut oil and palm oil are used in making soap.

Tests for Fat and Oil

Sudan III test: Add about 3cm3 vegetable oil, about 4cm3 of water in a boiling tube, and shake.
Then add 3 or 4 drops of Sudan (III) stain. A red stain is formed.

Paper test: Add a few drops of vegetable oil on a piece of white paper or filter paper. Translucent
spot is observed on the paper.