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ALCOHOLS AND

CARBOXYLIC ACIDS
 ALCOHOLS
 Recap of alkanes and alkenes
 Hydroxyl Group (-OH) as functional group
 First few members of alcohols
 Physical properties of alcohols
 Reaction of alcohols (chemical properties)
• Combustion
• Oxidation
 Manufacture of ethanol
• Hydration of ethene
• Fermentation of glucose
 Uses of ethanol
Homologous series

• A homologous series is a series of compounds that


have similar properties and the same general formula.
• Lets revise the formula of the homologous series of
alkanes and alkenes:
• Alkanes
• These compounds only contain hydrogen and carbon and
possess single bond. They are saturated (by having only
carbon single bonds, they have bonded with the maximum
number of atoms). Their general formula is CnH2n+2
Homologous series (cont.)
NAME MOLECULAR CONDENSED FORMULA
FORMULA
Methane CH4  

Ethane C 2H 6 CH3─CH­3

Propane C 3H 8 CH3─CH­2─CH3

Butane C4H10 CH3─CH­2─CH2─ CH3

Pentane C5H12 CH3─CH­2─CH2─ CH2─ CH3


PHYSICAL PROPERTIES OF ALKANES
• As alkanes increase in chain length (with an increase in the number of carbon
atoms), their boiling points increase. First four members of alkane series are
colorless and odorless gases. The alkanes consisting of C5 to C10 are colorless and
odorless liquids while higher members of the series are solids which are also
colorless and odorless.
• Alkane molecules are non-polar so they are insoluble in water but soluble in non-
polar solvents. They are less dense than water and are insoluble in it.
• iii. The density of alkanes increases gradually with the increase of molecular size.
• iv. Alkanes are unreactive towards most ionic compounds. This lack of reactivity
makes them useful solvents e.g. hexane is used to extract vegetable oils from
Corn, Soya beans, Cotton seed etc.
• v. As the molecular size of alkanes increases their burning becomes difficult.
• vi. Their melting and boiling points increase with the increase in molecular size.
This is due to the increase of attractive forces between the molecules of alkanes.
Alkenes
These compounds also only contain hydrogen and
carbon but do possess one or more double bonds. They
are unsaturated Their general formula is CnH2n.
Homologous series(cont.)
NAME MOLECULAR CONDENSED FORMULA
FORMULA
Ethene C2H 4 CH2 = CH2
Propene C3H 6 CH2 = CH─CH3
Butene C4H 8 CH2 = CH─CH2─CH3
Pentene C5H10 CH2 = CH─CH2─CH2─CH3
Hexene C6H12 CH2 = CH─CH2─CH2─CH2 ─CH3
PHYSICAL PROPERTIES OF ALKENES
i. Alkenes are unsaturated hydrocarbons.
First three members i.e. ethene, propene
and butene are gases while C5-C15members
are liquids and the higher members are
solids.
ii. They are insoluble in water but soluble in
organic solvents such as alcohol etc.
iii. They have a characteristic smell.
iv. They burn with luminous (glowing)
flame.
WHAT ARE ALCOHOLS?
WHAT IS THEIR FUNCTIONAL
GROUP
General Formula of Alcohol
ELEMENTS PRESENT IN
ALCOHOLS
There are three elements present in
alcohols
Carbon
Hydrogen
 oxygen
FIRST MEMBER OF ALCOHOL
SERIES

Structural formula

CH3OH
Methanol (molecular Formula)
NAMING ALCOHOLS
NAMING ALCOHOLS (cont.)
NAMING ALCOHOLS (cont.)
PHYSICAL PROPERTIES OF
ALCOHOLS
• Alcohols are soluble in water, but their solubility decreases as the
molecular size increases.
• Alcohols with lower molecular masses are colorless, toxic liquids.
• They have characteristic smell which diminishes then disappears on
ascending the series.
• The boiling point of alcohols increases as the number of carbon atom
increases.
• Their melting and boiling points are much higher than corresponding
alkanes.
• Higher alcohols are waxy solids, insoluble in water. This is due to
insoluble alkyl potion.
• Alcohols have hydrogen bonding.
THINK ABOUT IT…..
• The alkanes CH4 to C4H10 and the alkenes C2H4 are
gases at room temperature and pressure. Why are
alkanes and alkenes gases, when alcohols are volatile
liquids at room temperature and pressure?
Methane and ethane only contain C-C and C-H
bonds but no O-H bonds and there cannot be H
bonding between Hydrogen and Carbon atoms. In
alcohols hydrogen bond is present which keeps the
molecules of alcohol together. Hence we can say
that the forces of attraction between methane and
ethane molecules are much weaker than those in
methanol and ethanol. 
CHEMICAL PROPERTIES OF
ALCOHOLS
• POINTS TO REMEMBER

• Although alcohols contain the –OH group but


they are not alkalis. In fact, they are neutral.
Any how under certain condition they it can
behave like an acid or a base.
• Alcohols are more reactive than alkanes and
alkenes. This is due o the presence of O–H and
and C–O bonds. In alkanes and in alkenes the
bond is present between C – C and C–H.
• All alcohols show similar chemical properties.
REACTIONS OF ALCOHOLS
• Alcohols show various types of reactions.
Here we will talk about

Combustion and
oxidation reactions
only.
COMBUSTION OF ALCOHOLS
SIGNIFICANCE OF COMBUSTION OF
ALCOHOL
OXIDATION OF ALCOHOLS

They can also be oxidized by the oxygen in the air.

(an oxidizing agent)


OXIDATION OF ALCOHOLS (cont.)

K2Cr2O7

dil. H2SO4
OXIDATION OF ALCOHOLS (cont.)
POINTS TO REMEMBER

• During oxidation of ethanol color of potassium


dichromate (VI) changes form orange to green.
• During the reaction ethanol acts as a reducing
agent while acidified potassium dichromate (VI)
acts as an oxidizing agent.
• Ethanol is oxidized to ethanoic acid which is an
example of carboxylic acid.
THINK ABOUT IT…..
On oxidation ethanol
becomes ethanoic acid and
propanol becomes
propanoic acid. What is the
product when methanol is
oxidized?
• Oxidation of methanol gives Methanal or formaldehyde,
which belong to aldehyde functional group.
SIGNIFICANCE OF OXIDATION OF
ALCOHOL
• Breathalyzer is a device used by police for measuring the
amount of alcohol in a driver's breath. It contains acidified
potassium dichromate (VI). If breath of driver contains a
high level of alcohol a color change is registered on the
device. This device is used by police in Singapore.
MANUFACTURING OF ETHANOL
1. MANUFACTURE OF ETHANOL BY
ETHENE
MANUFACTURE OF ETHANOL BY
ETHENE (cont.)

Symbolic Equation
2. MANUFACTURE OF ETHANOL BY
FERMENTATION
What is fermentation?

(Sugar and starch are the examples of carbohydrates).


2. MANUFACTURE OF ETHANOL BY
FERMENTATION (cont.)
2. MANUFACTURE OF ETHANOL BY
FERMENTATION (cont.)
CHEMICAL REACTION TAKING
PLACE DURING FERMENTATION OF
GLUCOSE
yeast
WHAT IS THE PURPOSE OF LIME
WATER WHILE MANUFACTURING
ETHANOL?
• It provides an air-lock. It does not allow the
air enter into the flask. Otherwise, oxidation
of glucose will not allow the fermentation
reaction to proceed further.
• Lime water turns milky when CO2 is passed
through it. So it ensures that reaction is
going on.
WHAT HAPPENS IF ETHANOL IS
EXPOSED TO AIR?
When ethanol is expose to air it will turn sour after a few days.
Bacteria in the air oxidizes ethanol into ethanoic acid.
Word Equation
bacteria
Ethanol + Oxygen form air Ethanoic acid + Water
Symbolic Equation
C2H5OH + O2 bacteria CH3COOH + H2O

wine must be kept in tightly corked bottle. Moreover


fermentation of sugar is also carried out in the absence of
air. otherwise the alcohol will be oxidized to form an acid.
In alcoholic
drinks

USES OF
ETHANOL

As solvent As a Fuel
USES OF ETHANOL
(cont.)
1. IN ALCOHOLIC DRINKS
Large quantities of ethanol is used in alcoholic drinks.
Drink Alcohol content (%)
Beer 3–7
Wine 12 – 15
Whisky 40
Brandy 40

BAD EFFECTS OF ALCOHOL


Alcohol is a drug. Addiction of ethanol can cause serious health
problems such as damage to liver and kidneys, coma or even death.
SCIENCE TIDBIT

Methanol and ethanol have similar


chemical properties, but methanol
is extremely toxic. Drinking
methanol can lead to blindness an
even death
USES OF ETHANOL (cont.)
AS A SOLVENT
Ethanol can dissolve many substances which are insoluble in
water. It evaporates easily. It is used to dissolve;
Paints
Varnish
Deodorants
Perfumes
Colognes
Aftershaves
Lotions
Shellac dissolved in ethanol is used as liquid polish
QUICK CHECK
Name an organic substance that is suitable for
removing
a) Blood stains
b) Ink from a ball point
USES OF ETHANOL AS FUEL (cont.)
AS A FUEL
 Ethanol is the main constituent of methylated spirit.
Methylated spirit contains 85% ethanol, 5% methanol and 10% water. Methanol
is added to make it unsuitable for drinking. This process is called denaturing.
 Methylated spirit is used in spirit lamps in laboratories and burners for
cooking.
 For households use a purple or blue dye is added to Methylated spirit so that
it is not confused with other liquids.
In Brazil, ethanol is mixed with petrol and used as fuel to run motor vehicles.
Uses
CARBOXYLIC ACIDS
CARBOXYLIC ACIDS
Recap of alkanes, alkenes and alcohols
Carboxylic acid Group (-COOH) as functional
group
Naming first few members of carboxylic
acids
Manufacture of ethanoic acid
Physical properties of ethanoic acid
Physical properties of carboxylic acids
Reaction of carboxylic acids (chemical
properties)
Uses of carboxylic acids
CARBOXYLIC ACIDS
WHAT ARE CARBOXYLIC ACIDS
WHAT IS THE GENERAL FORMULA
OF CARBOXYLIC ACIDS?
NAMING CARBOXYLIC ACIDS
NAMING CARBOXYLIC ACIDS(Cont,)
NAMING CARBOXYLIC ACIDS
HOMOLOGOUS SERIES OF
CARBOXYLIC ACIDS
MAKING ETHANOIC ACID
Ethanoic acid can be prepared by following two
methods.
1. By the oxidation of Ethanol
2. By heating a mixture of ethanol and potassium
dichromate (VI)
MAKING ETHANOIC ACID BY THE OXIDATION
OF ETHANOL
MAKING ETHANOIC ACID BY HEATING A
MIXTURE OF ETHANOL AND POTASSIUM
DICHROMATE (VI)
MAKING ETHANOIC ACID BY HEATING A MIXTURE
OF ETHANOL AND POTASSIUM DICHROMATE (VI) cont.
PROPERTIES OF ETHANOIC ACID
• It is a colorless liquid at room temperature
• It has a characteristic sour-ish or vinegar smell.
• Like ethanol, ethanoic acid is completely miscible
with water.
• All aqueous solutions of ethanoic acid are weakly
acidic having pH value equal to 3.
PHYSICAL PROPERTIES OF
CARBOXYLIC ACIDS
• Carboxylic acids:
have relatively high melting and boiling points
are very soluble in water
are weak acids
have a characteristic smell.
• Examples of everyday carboxylic acids include:
citric acid (found in citrus fruits)
lactic acid (found in tired muscles)
malic acid (found in sour and tart foods).
MATCH THE PROPERTIES
BOILING POINTS AND THE
SOLUBILITIES OF SOME
CARBOXYLIC ACIDS

As the number of carbon atoms increases in the carboxylic


acids their m.p. and b.p. also increase.
• A dog can be trained to track people because of its
sensitive nose can recognize the characteristic smell
of human sweat. Each person’s sweat contains a
unique blend of carboxylic acids.
CHEMICAL PROPERTIES OF
CARBOXYLIC ACIDS
• The functional group in carboxylic acid is carboxyl
group.

or more simply ─ COOH. All the chemical reactions take


place in the carboxyl group.
CHEMICAL PROPERTIES OF
CARBOXYLIC ACIDS(cont.)
A carboxyl group
consists of one
carbon atom

A double bond A single bond


with an oxygen with ( - OH)
atom group
CHEMICAL PROPERTIES OF
CARBOXYLIC ACIDS(cont.)
CHEMICAL PROPERTIES OF CARBOXYLIC ACIDS(cont.)
1. IONIZATION OF ETHANOIC ACID IN WATER
Ethanoic acid is weak acid because it ionizes partially in water to
form hydrogen ion.
Word Equation:-
Ethanoic acid Ethanoate ion + hydrogen ion
Symbolic Equation:-
CHEMICAL PROPERTIES OF CARBOXYLIC ACIDS(cont.)
REACTION WITH METALS
• Ethanoic acid reacts with reactive metals like Na, K or Mg etc. to give
salts and hydrogen gas.
• Salts of ethanoic acid are called ethanoates.
CHEMICAL PROPERTIES OF CARBOXYLIC ACIDS(cont.)
REACTION WITH METAL CARBONATES
Ethanoic acid reacts with carbonates to
give a salt, carbon dioxide and water.
CHEMICAL PROPERTIES OF CARBOXYLIC ACIDS(cont.)
REACTION WITH BASES
• Ethanoic acid reacts with bases to give salt and water.
CAN YOU DO THIS??
CHEMICAL PROPERTIES OF
Carboxylic acids are typical CARBOXYLIC
weak acids. ACIDS
What would happen if you added a few cm3 of dilute ethanoic
acid to each of these substances?

 A few drops of universal


indicator.
 3 cm3 sodium hydroxide
solution.
 Half a spatula of sodium
carbonate.
 A piece of magnesium
ribbon.
Reactions of carboxylic acids
QUICK CHECK
Both CH3CH2OH and CH3COOH contain – OH group but only
CH3COOH conducts electricity in aqueous solution. Why?
• Ethanol is also called a covalent compound because it does not
contain ions that are necessary for electricity to be able to flow
through a liquid or a solution. This means that electrical charge
cannot be carried completely through ethanol. Whereas, ethanoic
acid can be ionized into its ions (CH3COO- and H+), which are
responsible for for the conduction of electric current. In sum,
ethanol cannot conduct electricity.
QUICK CHECK
USES OF CARBOXYLIC ACIDS
• Ethanoic acid is the most important organic acid.
• It is used in vinegar as preservative and flavoring.
• Carboxylic acids are also used in making drugs, dyes, paints,
insecticides and plastics.
• Carboxylic acids are used to make esters.
SOURCES OF SOME OTHER ORGANIC
ACIDS
CARBOXYLIC ACIDS: SUMMARY
ESTERS
What are esters?
Esterification
Functional group in
esters
Naming esters
Manufacture of esters
Uses of esters
WHAT ARE ESTERS?

Alcohols and Carboxylic acids react with each other to form esters.
The process of making esters is called “esterification”.
Esters have characteristic smells, and are often used in
flavourings and perfumes.
For example:
 Propyl ethanoate smells of pears
 Butyl butanoate smells of pineapple
 Methyl butanoate smells of apple.
GENERAL FORMULA AND
FUNCTIONAL GROUP IN ESTERS
• Esters have following general formula.

R
R
It can also be written as RCOOR.
NAMING ESTERS
• The name of an ester consists of two parts. Esters are named after
the alcohol and the carboxylic acid from which they are made. The
alcohol gives the first part of the name, and the carboxylic acid gives
the second. Esters always end in “–anoate”.
PRACTISING NAMING ESTERS
PREPARATION OF ESTERS
Conc. H2SO4 is used as catalyst during the reaction.

Conc. H2SO4

Conc. H2SO4

Conc. H2SO4

The process of making esters is called “esterification”.


PREPARATION OF ESTERS (cont.)
PREPARATION OF ESTERS IN
LABORATORY
PREPARATION OF ESTERS IN
LABORATORY (cont.)
What are the stages in making an ester?
NAME OF SOME COMMON ESTERS, TOGETHER WITH
THE ALCOHOL AND CARBOXYLIC ACIDS USED TO
PREPARE THEM
MATCHING CARBOXYLIC ACIDS TO
THEIR ESTERS
PROPERTIES OF ESTERS
USES OF ESTERS
• There are various uses of esters.
• 1. Esters that are have fragrant odors are used as a constituent of
perfumes, essential oils, food flavorings, cosmetics etc.
• 2. Esters are used as an organic solvents for cosmetics and glues.
• 3. They are found in vegetable oils and waxes.
• 4. Naturally occurring fats and oils are fatty acid esters of glycerol
• 5. Phospoesters form the backbone of DNA molecules
• 6. Nitrate esters, such as nitroglycerin, are known for their explosive
properties.
• 7. Polyesters are used to make plastics.
• 8. Esters are used to make surfactants E.g. soap, detergents.
MULTIPLE-CHOICE QUIZ

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