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Nadir Educational Centre

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hC 2021
According to
Syllabus
Dr. Nadir I. Ghobrial
B.Sc Pharmacy-Alexandria

Organic Chemistry
(Part Two)
 Alkanols (alcohols)
*These are organic compounds which are characterised by the presence of
a hydroxyl group (OH)
*They have the general formula: CnH OH
2n+1
*The first members of this homologous series are:

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a
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b
CH3OH C H OH C H OH

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2 5 3 7
(Toxic) (Least toxic) (Toxic)

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Production of ethanol:
(1) Fermentation: in which yeast is added to a solution of a sugar eg. glucose
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where the yeast produces an enzyme that causes the decomposition of glucose
d

into ethanol and carbon dioxide:

a

Glucose ethanol + carbon dioxide

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CH O 2C H OH + 2 CO2
6 12 6 2 5
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 Note about the reaction:

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(a) Two observations during fermentation are:

* Bubbles of colourless gas f carbon dioxide.
* The temperature of the mixture increases (as the reaction is exothermic)
(b) The rate of the reaction starts slow first then increases as the temperature
increasesuntil 40oC (where the particles get more energetic and the enzyme,
catalyst, becomes more active) then starts to decrease as the temperature
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increases above 40 C (where the catalyst starts to destroy).( see the graph)
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 rate of fermentatin

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a
time
(c) The reaction is carried out in absence of air (no oxygen is allowed) to avoid

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the oxidation of the ethanol into acid (ethanoic acid). This is done by fitting

b
of an air lock that allows the escape of the carbon dioxide and prevents

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the entrance of air.

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d
a
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(d) Ethanol is obtained from the fermentation mixture by fractional distillation

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where the distillate at 78 C contains ethanol.
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(2) Catalytic hydration of ethene: in which ethene is allowed to react

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steam by passing this mixture over phosphoric acid catalyst at 330 C and
60 atm. pressure.
ethene + steam ethanol

CH + HO C H OH
2 4 2 2 5
2
Physical properties of alcohols:
(1) They are colourless having characteristic alcoholic smell.
(2) The first members are liquids, higher members are solids.
(3) They are miscible with water.
Chemical properties of alcohols:
(1) Oxidation of alcohols:

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In general, oxidation of alcohols produces carboxylic acids.

a
Alcohol + oxygen carboxylic acid + water

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e.g. ethanol + oxygen ethanoic acid + water

b
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C H OH + O CH COOH + H O
2 5 2 3 2
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The common oxidising agents used are:

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 In the laboratory is acidified potassium manganate (VII)

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 In industry is oxygen in presence of a catalyst.

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(2) Dehydration of alcohols:

In general, dehydration of alcohols produces alkenes.
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Alcohol alkene + water

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eg. propanol propene + water

C H OH CH + HO
3 7 3 6 2
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The common dehydrating agent used is conc. sulphuric acid(at180 C) or
very hot aluminium oxide as a catalyst.
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(3) Esterification: ( Ester formation):
In general, alcohols react with carboxylic acids to produce esters and water.
Carboxylic acid + alcohol ester + water

eg. ethanoic acid + ethanol ethyl ethanoate + water

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b
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CH COOH + C H OH CH COOC H
3 2 5 3 2 5

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Conditions of reaction: concentrated sulphuric acid at 50 oC
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The esters are compounds which contain the functional group:
This group is called ester linkage
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d

Naming of esters:
a

Esters are named as (alkyl alkanoate ) Where:

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* the alkyl name is derived from the alcohol ....and

*the alkanoate name is derived from the aicd.
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Examples:
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ethanol + propanoic acid ethyl propanoate + water

methanol + ethanoic acid methyl ethanoate + water
methanoic acid + propanol propyl methanoate + water

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How to draw the structure of an ester:
This is done by:
 drawing first the alkanoate part as if it is the carboxylic acid but without the
acidic hydrogen,
 then drawing the alkyl group attached to the oxygen of the alkanoate part.
Examples:

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b
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d
a
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Physical properties of esters:

(1) Esters are colourless having fragrant smell
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(2) Esters are immiscible with water.

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chemical properties of esters:

Hydrolysis of esters:
Hydrolysis: it is the break down of a compound by the addition of water.
(a) Hydrolysis of esters in acidic or neutral solution:
Esters are hydrolysed in acidic or neutral solutions to give an alcohol and a
carboxylic acid.
Ester + water alcohol + carboxylic acid
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e.g. methyl etanoate + water methanol + ethanoic acid

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a
(b) Hydrolysis of esters in alkaline solutions:

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Esters are hydrolysed in alkaline medium to produce an alchol and the salt of

b
carboxylic acid (which is commonly called soap)

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Ester + alkali alcohol + salt of carboxylic acid

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eg methyl ethanoate + sodium hydroxide methanol +sodium ethanoate
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d
a
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N.B. The hydrolysis of esters in alkaline medium is commonly called

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saponification because it is the same method by which soap is made by the

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hydrolysis of fats ( natural esters) using sodium hydroxide.

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Specific test for alcohols / carboxylic acids:

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Uses of ethanol:
(1) Most of the ethanol is used in alcoholic drinks.
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(2) Ethanol and other alcohols are used as a fuel (e.g. in Brazil it is mixed
d

with gasoline and the mixture is used as a fuel for cars)

a

(3) Ethanol is used as a universal solvent (e.g. in perfumes, where it dissolves

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water soluble substances and oily substances)

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 Alkanoic acids
(Carboxylic acids)
* Alkanoic acids are compounds which contain the carboxylic functional
group Which is written as -COOH or -CO. H 2

CnH2n+1*COOH

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* They have the general formula:

a
* The first members of carboxylic acids are:

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b
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HCOOH CH 3COOH CH 3CH2COOH
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Production of carboxylic acids:

d

Carboxylic acids are produced by the oxidation of alcohols, where the

a

common oxidising agent used:

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 In the lab is acidified pot. manganate (VII)

 In industry is oxygen in presence of a catalyst.
r.

eg. propanol + oxygen propanoic acid + water

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Physical properties of carboxylic acids:

(1) They are colourless having vinegary smell.
(2) The first members are liquids while the higher members are solids.
(3) They are soluble / miscible in water.
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Chemical properties of carboxylic acids:
(A) As acids: (proton doner) ( similar to mineral acids)
(1) They turn litmus paper into red and universal indicator into orange or
yellow.
(2) They react with metals to produce salts and hydrogen gas.
ethanoic acid + magnesium magnesium + hydrogen
ethanoate

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a
2 CH3COOH + Mg (CH3COO)2 Mg + H2

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(3) They react with bases to produce salts and water.

b
ethanoic acid + potassium hydroxide pot. ethanoate + water

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CH3COOH + KOH CH3COOK + H2O

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(4) They react with metal carbonates to produce salts, carbon dioxide and
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water
ethanoic acid + calcium calcium + carbon + water
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carbonate ethanoate dioxide

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2 CH3COOH + Ca CO 3 (CH 3COO) 2Ca + CO2 + H 2O

a
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(b) As Carboxylic acids: (unlike the mineral acids)

Carboxylic acids under go esterificaton reactions,
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carboxylic acid + alcohol ester + water

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ethanoic acid + propanol propyl ethanoate + water

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 Polymers & polymerisation
Polymers are classified into two types based on the type of polymerisation:
Addition polymers Condensation polymers
 Made by addition type of  Made by condensation type of
polymerisation polymerisation
 Involve one type of monomer  Mostly involve two types of

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a
which is an alkene. monomers which are not alkenes

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(see addition polymers in alkenes)

b
Condensation reaction: it is the type of reaction in which two molecules are

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joined together by elimination of water, e..g. the esterification reaction in

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which water molecule is elimenated and the alcohol and the acid are joined
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to form the ester
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d
a
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Condensation polymerisation: it is the joining up of simple molecules

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(monomers) –by elimination of water molecules – to form a macromolecule

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called polymer
Condensation polymers are classified into two types:
Natural macromolecules Synthetic condensation polymers
(man made fibres)
These are macromolecules found These are man made fibres which are
naturally in living organisms, they synthesised from simple chemicals.
are: Proteins, Fats Carbohydrates they include: Nylon and Polyester.
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(a) Natural macromolecules;
(1) Proteins:
The proteins are macromolecules made by the condensation polymerisation
of the simple molecules amino acids, the basic structure of the aminoacid is:

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The diagram below shows how a protein is formed from amino acids by

b
condensation polymerisation:

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a
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Important notes about the structure of proteins:

(1) Proteins contain amide linkages.
(2) The amide linkages are found in a regular sequenced pattern.

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Analysis of a protein:
Proteins are analysed in two steps:
Step 1: the protein is hydrolysed into amino acids by the addition of water.
( hydrochloric acid or sodium hydroxide are used as catalysts)
Step 2: the amino acids are separated and identified using chromatgraphy
technique. Water is used as a solvent, known amino acids are used as

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standards and a suitablehe locating agent to visualise the colourless spots

a
of the amino acids.. (See the diagam below)

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(2) Fats:
Fats are natural macromolecules which contain ester linkages. They are the
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triester of glycerol and fatty acids (see the structure of fat molecule below:
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structure of fat molecule

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(3) Carbohydrates:
Carbohydrates are compounds which consist of carbon, hydrogen and oxygen
where the ratio of hydrogen to oxygen is 2:1.
The simple most common carbohydrate is glucose, which canbe represented

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Glucose is made in plants by a process called photosynthesis which is a is

a
a chemical reaction between carbon dioxide and water to produce glucose

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and oxygen. The reaction occurs inpresence of light as a source of energy

b
and chlorophyll as a catalyst.

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6 CO2 + 6 H 2O C 6H12O 6 + 6 O2

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Starch is a macromolecule formed by the condensation polymerisation of
glucose. (Glycogen and cellulose are other macromolecules of glucose made
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the same way)

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The diagram below shows how starch is made from glucose by condensation
a

polymerisation:
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Analysis of starch:
Starch is analysed in two steps:
Step 1: the starch is hydrolysed into the monomer, glucose by the addition
of water. (N.B.: complete hydrolysis is checked by the addition of drops of
iodine solution to a drop of the solution, there should be no blue black colour.
Step 2: the hydrolysis mixture is then investigated using chromatography

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technique. Water is used as a solvent, and a suitable locating agent is used

a
to visualise the colourless spots of glucose. (One spot appears at the same

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level as that of the standard glucose)

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a
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(b) Synthetic condensation polymers: (Man made fibres):

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(1) Nylon:
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Nylon is made of two monomers .these are:

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Through condensation polymerisation these two monomers are joined to
form nylon as shown in the diagram below:

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b
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Note the following about the structure of nylon
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(1) It contains amide linkages.

d

(2) The amide linkages are mirror images to each other.

a
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(2) Polyester (Terylene

Polyester is a man made fibre which is made of two monomers, these are:
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Through condensation polymerisation, these two types of monomers are
joined to form the polymer polyester as shown in the diagram below:

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b
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Advantages of plastics and man made fibres:
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(1) They have low densities (i.e. they have light weights)
d

(2) They do not corrode (no rusting or quick wearing out)

a

(3) They are cheaper than natural materials.

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Disadvantages of plastics and man made fibres:

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(1) They are non biodegradable (i.e. they cannot be broken down by natural
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decomposers of bacteria and fungi)

(2) They are flammable (can catch fire easily)
(3) When burn they produce toxic (poisonous) gases like carbon monoxide
and sulphur dioxide.

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