B : NON-HYDROCARBON

11.8
1. 2.

ALCOHOL
Alcohols are organic compounds that contain carbon, hydrogen and oxygen atoms. The general formula for alcohol is :

CnH2n + 1OH
3.

where n = 1, 2, 3, ,

Each member of alcohol series contains hydroxyl as the functional group ( -OH ) which is covalently bonded to the carbon atom.

4.

Naming alcohol using IUPAC nomenclature :

S1 : Determine the number of carbon atoms in the longest carbon chain which contains the hydroxyl group ( OH ) obtain the name of alkane with the same number of carbon atom as alcohol. S2 : Replace the ending e from the name of alkane with ol Example : Methane Ethane Propane Butane Penthane Methanol Ethanol Propanol Butanol Pentanol

S3 : Number the carbon atom in the longest carbon chain which is joined to the hydroxyl group -OH with the smallest number the number is placed in front of the ol to indicate which carbon atom the hydroxyl group is attached to. Example :
4 carbon -OH

Butan-2-ol
-OH at the 2nd C

the -OH is attached at the second carbon atom from the end. The structural formula : H H H H C C H H C H C OH or H H H H C H Isomer Butan-1-ol C H OH Butan-2-ol C4H9OH C C H C H

H H

H OH H

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S4 : For alcohols with branches, write the names of all the branches as prefix. H H H C C H CH3 H C C H C H H

H OH H

Name : 4-methylpentan-2-ol

5.

Isomerism in alcohol :
 Isomers are molecules that have same molecular formula but different structural formula.

Activity 13 :Complete the following table : Name of alcohol Methanol Molecular Formula Condensed structural formula Structural Formula & IUPAC name Number of isomers 0

CH3OH

Ethanol

C2H5OH

CH3CH2OH

Propanol

C3H7OH

Propan-1-ol

Propan-2-ol

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Butanol

 Methanol and ethanol do not have isomers because each molecule only has one structural formula.  Isomerism in alcohol begins with propanol.

6.

Preparation of Ethanol

Two methods of preparation of Ethanol

(i) Preparation of ethanol, C2H5OH in the laboratory ( Fermentation of glucose)  Fermentation is a process in which microorganism such as yeast act on carbohydrates (sugar or starch) to produce ethanol and cabon dioxide.

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 Yeast is added to glucose solution ( or fruit juices such as grape/pineapple juice) and left in a warm place for a three days in the absence of oxygen.  Yeast contains enzyme (zymase) which break down the sugar/starch into glucose (hydrolisis process) and then to ethanol and cabon dioxide.  Fermentation equation :

C6H12O6
Glucose 

2C2H5OH

2CO2

Ethanol The ethanol is purified by fractional distillation. (78 0C)

(ii)

Industrial production of ethanol, C2H5OH ( Hydration of ethene)

y Alkene is reacted with steam (H2O) at temperature; 300 oC and pressure; 60 atm in presence of phosphoric acid (H3PO4) as a catalyst. y Chemical equation of the reaction :

C2H4 +
Ethene

H2O
steam

C2 H5OH
ethanol

7.

Physical properties of alcohol

1 Alcohols with one to eleven carbon atoms exist as liquids.

2 Methanol, ethanol and propanol are miscible in all proportions with water. The solubility of alcohol in water decreases with increasing of their molecular size // number of carbon atom. 3 Physical properties of ethanol, C2H5OH : y y y y 8. colourless liquid mixes with water in all proportions less dense than water boiling point is 78 oC at 1 atm.

Chemical properties of ethanol, C2H5OH

(a) Combustion of ethanol (i) Ethanol burns in air to produce water and carbon dioxide. Ethanol burns readily with a blue flame and without producing soot.

C2H5OH
(ii)

+ 3O2

2CO2 + 3H2O

Combustion of ethanol releases large amount of heat (ethanol is suitable for use as a fuel)

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Activity 13 :Balance the following equations :

2C3H7OH + 9O2 C4H9OH + O2 C5H11OH + O2 C6H13OH + 9O2

6CO2 CO2 CO2

+ + +

8H2O H2O H2O 7H2O

6CO2 +

(b) Oxidation of ethanol (i) Ethanol is oxidised by an oxidising agent such as acidified potassium manganate(VII), KMnO4 or acidified potassium dichromate(VI), K2Cr2O7 solution. (ii) Both these oxidising agents are represented as 2[O] in the chemical equation.

(iii) One oxygen atom joins the ethanol molecule to form C = O and the other oxygen atom is joined to the two hydrogen atoms that are removed from the ethanol to form H2O. (iv) atom. Example : Oxidation of alcohol is the process where an alcohol molecule loses two H atoms and receives one O

From oxidising agent

C2H5OH
Ethanol

+ 2[O]

CH3COOH
Ethanoic acid

H2O
water

or

H H H C C H OH H + 2[O]

H H C H C

O OH + H2O

Activity 14 :Complete the following equations :

C3H7OH
or

+ + 2[O]

2[O]

C2H5 COOH + + 30

H2O H2O

CH3CH2 CH2OH

Propanol or

propanoic acid

H H H C C H H

H C OH .. H +

2[O]

H2O

(v)

Alcohol undergoes oxidation reaction to produce carboxylic acid.

CnH2n+1 + 2[O]


CnH2n+1COOH + H2O

n =n-1

This reaction is used to prepare carboxylic acid.

(c) Dehydration of ethanol (i) (ii) Dehydration of an alcohol involves the removal of water molecule from each of alcohol molecule. Water molecule from the alcohol molecule is removed by a dehydrating agents such as porcelain chips / aluminium oxide (alumina) / concentrated sulphuric acid / concentrated phosphoric acid. There are two ways to carry out the dehydration of ethanol in the laboratory : 1 Hot vapour of ethanol is passed over a heated catalyst such as porcelain chips /aluminium oxide. 2 Ethanol is heated under reflux with excess of concentrated sulphuric acid / concentrated phosphoric acid.

(iii)

Draw a labeled diagram to show the set-up of apparatus to carry out the dehydration of ethanol.

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(iv)

Dehydration of ethanol produces ethene and water.

H H H C C H H H porcelain H C C

Equation for the reaction :

H +

H2O

H OH or

C2H5OH
Ethanol Ethene

C2H4

+ H2O

Activity 15 :Complete the following equations : (a) C3H7OH ..

+ H2O

(b) Butanol

+ H2O

(c)

H2O

(d)

CnH2n+1OH
n = 2, 3, 4..

CnH2n

H2O

Dehydration of alcohol produces .................................

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9.

Uses of alcohol

(a) As a fuel combustion of alcohol produces water and carbon dioxide (clean emission) and releases a lot of heat energy (exothermic). Example :

CH3OH

+ O2

CO2

2H2O

H = - x kJ mol-1

(b) As a solvent to dissolve many organic compound such as paint, varnish, lacquer, and perfume. (c) In medical field as a solvent for the preparation of certain medicines. Ethanol for example is used as an antiseptic and an ingredient in cough mixtures. (d) Production of cosmetics main component in production of cosmetics, creams, lotions, soaps and others.

10. Alcohol Misuse and Abuse

Activity 16 :Complete the following chart : STARCH GLUCOSE Fermentation . Hydration ETHENE PETROLEUM

Combustion in excess oxygen

Oxidation by an oxidising agent

Dehydration by a dehydrating agent

. and

. and .

. and .

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2.9 CARBOXYLIC ACID [ ORGANIC ACID ]

1. An acid that comes from an organic source, either from plants or animals such as ethanoic acid in vinegar, citric acid in lemon and methanoic acid from ants. 2. Consists of elements : carbon, C ; hydrogen, H ; and oxygen, O. 3. The difference compared to alcohol is that carboxylic acids have two oxygen atoms whereas alcohols have only one oxygen atom. 4. Functional group is the carboxyl group : O C OH 5. The general formula of the carboxylic acid is :

CnH2n+1COOH

n = 0,1, 2, 3........

6. For straight chain carboxylic acid molecules, the name ends with oic and acid.

Activity 17 :Complete the following table : Number of carbon atoms Molecular Formula

CnH2n+1COOH HCOOH

Structural Formula O

Name

C OH

methanoic acid

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O 2

CH3COOH

C OH

ethanoic acid

. 7. For branched chain carboxylic acid molecules : y the name and position of the branched group is written as prefix y the smallest number is given to the carbon atom that is joined to the functional carboxyl group. Example : H H H O | | | // HCCCC | | | \ H H CH3 OH 2-methylbutanoic acid

8. Preparation of ethanoic acid :  Laboratory preparation through oxidation of ethanol by acidified KMnO4 / K2Cr2O7 solution H H H O

35

| | H - C - C - OH + 2[O] | | H H ethanol

| // H - C - C | \ H OH ethanoic acid

+ H2O

Activity 18 :Draw the set-up of apparatus for the preparation of ethanoic acid by reflux method. (preparation of ethanoic acid in laboratory)

 Industrial preparation using petroleum and natural gas. 9. Chemical properties of carboxylic acid (i) Reacts as an acid with base, metal carbonates and metals that are more electropositive than hydrogen. (a) Carboxylic acid + electropositive metal (b) Carboxylic acid + base carboxylate salt + hydrogen gas

carboxylate salt + water carboxylate salt + water + carbon dioxide

(c) Carboxylic acid + metal carbonate

Activity 19 :Complete the following equations : (a)

HCOOH

Mg
magnesium

+
+ ........................

.. acid

(b) C2H5COOH

KOH 36

H2O

. ..

water

(c) CH3COOH . acid

Na2CO3

CH3COONa

+ H2O
water

CO2

sodium carbonate Sodium ethanoate +

+ carbon dioxide

(d)

C2H3COOH +

K2CO3

+ CO2

(e)

C2H5COOH

+ NaOH

(f)

C5H11COOH

(ii) React with alcohol to produce ester and water. Carboxylic acid reacts with alcohol to produce ester and water with the presence of concentrated sulphuric acid as a catalyst (Esterification reaction).

Carboxylic acid CnH2n+1COOH

+ Alcohol CnH2n+1OH

Ester

+ Water H2O

CnH2n+1COOCnH2n+1

(a)

C2H5COOH +

C2H5OH

C2H3COOC2H5
ethanol

+ H2O

propanoic acid

ethyl propanoate

(b)

C3H7COOH +

C3H7OH

C2H3COOC2H5
propanol

+ H2O

butanoic acid

propyl butanoate

(c)

HCOOH

C2H5OH

C2H3COOC2H5
ethanol

+ H2O

methanoic acid

ethyl methanoate

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(d)

ethanoic acid +

ethanol

Ethyl ethanoat + water

H O | // H - C - C | \ H OH ethanoic acid

H H | | HO - C - C - H | | H H ethanol

(d)

butanoic acid +

pentanol

+ water

10. Uses of Carboxylic Acid

2.10 ESTERS
1. Esters are non-hydrocarbon organic compounds containing carbon, hydrogen and oxygen. 2. General formula of ester :

38

O || R - C - O - R

or

RCOOR

O || R C - O : Derived from carboxylic acid, name ending with oate. R is alkyl group with general formula CnH2n+1, n = 0, 1, 2, 3,
: Derived from alcohol, name ending with yl. R is alkyl group with general formula CnH2n+1 ; n = 1, 2, 3, .

-R

3. Formation of esters : Esters are produced when carboxylic acid reacts with alcohol in the presence of concentrated sulphuric acid as a catalyst (Esterification reaction) :

O || R - C O-H + H-O-R p carboxylic acid alcohol Example: CH3COOH + C3H7OH ethanoic acid propanol 4. Naming of esters :

O || R - C - O - R ester + H-O-H water

CH3 COOC3H7 prophyl ethanoate

H2O

Name for esters are : first : read from the alcohol component followed by : the carboxylic acid component. Example: CH3COOH + C3H7OH ethanoic acid propanol or H O H C H ethanoic acid H H H || C O-H H-O C H O C C H H H H || H C C O H CH3 COOC3H7 prophyl ethanoate + H2O

C C

H + H-O-H

H H H propanol

H H H

propyl ethanoate

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Activity 20 :Complete the following equations : (i)

H2SO4

HCOOH

+ C2H5OH
ethanol

+
Ethyl methanoate

H2O
water

methanoic acid

(ii)

H2SO4

C3H7OH
Propanol

+ C4H9COOH
pentanoic acid

C4H9COOC3H7

H2O
water

(iii)

H2SO4

C3H7COOH
Butanoic acid (iv) H H H O | | | || H C C - C - C - OH | | | H H H Butanoic acid (v) H H O | | || H C C - C - OH + | | | H H H Propanoic acid

C2H5OH
ethanol .

+ H2O
water

H H H H H | | | | | + HO - C - C - C - C - C - H | | | | | H H H H H pentanol

H H H H | | | | HO - C - C - C - C - H | | | | H H H H butanol ...........

water

5. Physical properties of esters : y y y y y Ester is a neutral compound with a sweet smell / fruity smell. Esters have low density ; less dense than water. Simple esters are colourless liquid at room temperature. Simple esters are very volatile. Insoluble in water.

6. Uses of esters :  Most simple esters are found naturally in fruits and flowers. The fragrance of flowers and fruits is due to the presence of esters. Example:

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Ester

Name

Naturel source Pineapple Apple Banana

CH3COOC5H11 C2H5COOCH3 C3H7COOC5H11

Pentyl ethanoate Methyl propanoate Pentyl butanoate

 Used in the preparation of cosmetics and perfumes.  As artificial flavour in processed of food and drinks  Used in the production of polyester ( synthetic fibers for making textiles)  Natural fats are esters which react with alkalis to produce soap.

Activity 21 :1 Compound J is prepared by the fermentation of glucose. Diagram 1 shows a few reactions that involve compound J with the molecular formula C2H6O. Glucose Fermentation Combustion Compound J C 2H6O Heated Al2O3 Gas M Compound K CHO

Gas N

41 Reflux
Compound J and K

(a)

Name the compound J.

(b) Write the equation for the complete combustion of compound J in air.

(c) (i) Gas M is produced when vapour of compound J is heated strongly and continuously with aluminium oxide. Draw the set-up of the apparatus to carried out this reaction.

(ii)

Name the type of reaction occur.

.. (iii) Write the molecular formula and name the gas M.

.. (iii) If gas M is passed through bromine water, predict your observation.

..

(d) (i)

Compound K is produced when compound J is reacted with oxidising agent. Name an oxidising agent that can be use in this reaction.

.. (ii) Write the chemical equation for the reaction.

..

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(iii)

Draw the structural formula and name the compound K.

(iii)

Compound K can react with calcium carbonate. Write the chemical equation of this reaction..

..

(e)

A mixture of compound J and compound K with concentrated sulphuric acid is heated under reflux to form compound L. Diagram 2 shows the wrong set-up of apparatus for heating under reflux.

DIAGRAM 2 (i) State two mistakes shown in the set-up in Diagram 2.

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.. .. (ii) Name the type of reaction occur.

.. (iii) Draw the structural formula of compound L.

(iv)

Name the compound L in (d) (iii).

..

(v)

State two uses of compound L in our daily lives.

.. .. 2 Describe how the following conversions can be carried out.

[Include the reagents used, suitable conditions and the chemical equations involved] Glucose

(a)

etene

(b)

Propan-1-ol

propane

(c)

Butan-1-ol

butyl propanoate

(d)

Ethanol

sodium ethanoate

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