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Alkanes

1.
General Formula : CnH2n+2 (number of atoms, n = 1,2,3......)
2. They are saturated hydrocarbons;
each carbon atom is bonded to four other atoms by
single covalent bonds.
3. The members of the family, ending with name ane.
Number of carbon
atoms
(n)

Name

Molecular formula
CnH2n+2

Molar
mass
(g mol-1)

Physical state at
room
temperature

Methane

C1H2x1+2 = CH4

16

Gas

Ethane

C2H2x2+2 = C2H6

30

Gas

Propane

C3H2x3+2 = C3H8

44

Gas

Butane

C4H2x4+2 = C4H10

58

Gas

Pentane

C5H2x5+2 = C5H12

72

Liquid

Hexane

C6H2x6+2 = C6H14

86

Liquid

Heptane

C7H2x7+2 = C7H16

100

Liquid

Octane

C8H2x8+2 = C8H18

114

Liquid

Nonane

C9H2x9+2 = C9H20

128

Liquid

10

Decane

C10H2x10+2 = C10H22

142

Liquid

Consecutive members different in molar mass is 14 g mol-1


4.

Structural formulae of alkanes


Name

No. of isomers

Structural formulae and Name

Methane

HCH

CH4

Ethane,
C2H6

Propane,
C3H8

Butane,
C4H10

H H

HCCH

H H
H H H

HCCCH

H H H
H H H H

HCCCCH

H H H H
n-butane

H
H
H

H C C C H

H HCH H

H
2 - methyl propane
Pentane,
C5H12

H H H H H

HCCCCCH

H H H H H
n-pentane
H
H
H H


H C C C C H
1
2
3
4


H HCH H H

H
2-methyl butane

H HCH H

H C C C H

H HCH H

H
2,2-dimetyl propane
Hexane,
C6H14

H H H H H H

HCCCCCCH

H H H H H H
n-hexane
H
H
H H H


H C C C C C H


H HCH H H H

2 - methyl pentane

H H
H
H H


H C C C C C H


H H HCH H H

H
3 - methyl pentane
H

H HCH H H


H C C C C H


H HCH H H

H
2,2 - dimethyl butane
H

H
H H CH
H

H C C C C H

H HCH H
H

H
2,3 - dimethyl butane

Physical Properties
Physical properties of alkanes
i.
cannot conduct electrity
ii.
less dense than water
iii.
dissolve in organic solvents, insoluble in water
iv.
low melting and boiling points
Conclusion:
- molecule held together by weak intermolecular forces
- properties of covalent compound
- gradually steady increase as the number of carbon in alkane
increases

6. Steps to name branched alkanes;


i.
determined and named the long chains
ii.
determined and named the branch chain
CH3
: methyl
C2H5 OR
CH2CH3
: ethyl
C3H7 OR
CH2CH2CH3
: prophyl
iii.
give number to the carbon atoms in long chain, which started from the nearest branched
iv.
The number for carbon atom which branched emerged from, must put before/infront the alkyl
v.
Named the branched first, followed by the named of long chains
The word di, tri is used if the branched chains is more than one

Chemical Properties
Pg 38
Reactivity of alkanes
1.
Not reactive/unreactive because saturated hydrocarbon
2. Did not decolourized purple solution of acidified potassium
manganate(VII)
3. Did not decolourized reddish brown solution of bromin water
4. Neutral.

Combustion of alkanes
1.
In the presence of sufficient oxygen, alkanes burns to form carbon dioxide and water. complete combustion
Chemical equation:
i.

ii.

CH4
+
O2
CO2
CH4 + 2O2 CO2 + 2H2O
C2H6

iii.

iv.

H2O

O2

2CO2

+ 3H2O

C4H10 + 13/2 O2

4CO2

C6H14

Answers
i. CH4
ii. C2H6

2 x C2H6

2C2H6

+ 7/2

+ 19/2 O2

2O2

CO2

7 O2
2

7 O2

2x 2CO2

iii.

C4H10

+ 13/2 O2

iv.

C6H14

+ 19/2 O2

7H2O

+ 2H2O

2CO2

+ 2 x 7 O2
2
+

6CO2

5H2O

3H2O

+ 2x 3H2O

4CO2

6H2O

4CO2

5H2O

6CO2

7H2O

C3H8
C5H12
C7H16
C8H18
C9H20
C10H22

2. If there is insufficient oxygen, carbon monoxide or carbon


may be formed incomplete combustion

i. CH4 + 3/2 O2
2CH4 + 3 O2
ii. CH4 + O2

CO + 2H2O

2CO + 4H2O
C + 2H2O

Halogenation
1.
The reaction is between alkane dan chlorine.
2. Takes place under sunlight/ultra violet light.
3. Carbon-hydrogen bonds broken and new carbon-halogen bonds
are formed. One or more hydrogen atoms in alkanes molecule may be subtituted by halogen.
4. Halogenation is substitution reaction.
Chlorination of methane
First stage;

HCH

Second stage;
H
H

H C Cl
;
Third stage
H
Cl

H C Cl

Fourth stage;
H
Cl

H C Cl

Cl

+Cl-Cl

Cl2

Cl2

Cl2

Overall equation/chemical equation


CH4 + 4Cl2

CCl4
+

4HCl

H
|
H C Cl + HCl
|
H monochloromethane
Cl
|
H C Cl + HCl
|
H dichloromethane
Cl
|
H C Cl + HCl
|
Cl trichloromethane
Cl
|
Cl C Cl + HCl
|
Cl tetrachloromethane

HW: PG41 EP B no. 1-3


Prepared;
Kamal Ariffin Bin Saaim
SMKDBL
Alkenes
1.
General formulae : CnH2n
[ no alkene corresponding to n = 1 as CH2 is not exist]

2.
3.

Alkenes containing at least one carbon-carbon


Alkenes isdouble
unsaturated hydrocarbon
bond because the presence of the double bond.
Name of each members end with ene.

ethenes

No. of
carbon atom

Name

Molecular formulae

Molar mass /
g mol-1

Physical state at room


condition

None

Ethene

C2H4

28

Gas

Propene

C3H6

42

Gas

Butene

C4H8

56

Gas

Pentene

C5H10

70

Liquid

Liquid

Liquid

Liquid

Liquid

10

Liquid

WHEN THE NUMBER OF CARBON IN HYDROCARBON INCREASES/GREATER/HIGHER, THE SIZE OF HC MOLECULE IS


BIGGER.
THUS, THE INTERMOLECULAR FORCES/Van der Waals FORCES IS STRONGER.
THUS, MORE ENERGY IS NEEDED TO OVERCOME THE FORCES.

4.

Structure formula for few members of alkenes


Name
Number of isomer
Ethene
C2H4

Propene
C3H6

Structure formula and name

H H

CC

H H

H
H

CCCH

H H H

Butene,
C4H8

H
H H


CCCCH

H H H H
but -1- ene
H
H

HCCCCH

H H H H
but -2- ene

H
H

C C C H

H HCH H

H
2-methyl propene

Pentene,
C5H10

H
H H H


CCCCCH

H H H H H
pent -1- ene
H H
H

HCCCCCH

H H H H H
pent -2- ene

H
H H


C C C C H


H HCH H H

H
2-methylbut -1- ene
H H
H
H

C C C C H

H
HCH H

H
3-methyl but -1- ene

H
H H


H C C C C H

H HCH
H

H
2-methyl but -2- ene
Hexene,
C6H12

12

H
H H H H


CCCCCCH

H H H H H H

H
H H H


HCCCCCCH

H H H H H H

H H
H H


HCCCCCCH

H H H H H H

H
H H H


C C C C C H


H HCH H H H

H
H
H H


C C C C C H


H H HCH H H

H
H
H
H

C C C C C H

H H H HCH H

H
H H H


H C C C C C H


H HCH
H H

H
H H


H C C C C C H


H H HCH H H

H
H
H

HC C C C C H

H H H HCH H

H
H
H H H


C C C C C H


H HCH H H H

H
HCH H

C C C C H

H
H HCH H
H
H
HCH H
H

C C C C H

H
H HCH H
H
HCH
H
H

H C C C C H

H HCH
H

Can you named the molecules?


Steps to name branched alkenes;
i.
determined and named the long chains that has double covalent bond
ii.
numbered the carbon atom from the nearest end to double covalent bond
iii.
determined and named the branch chain
CH3
: methyl
C2H5 or
CH2CH3
: ethyl
C3H7 or
CH2CH2CH3
: prophyl
vi.
vii.
viii.

give number to branched chain


The number for carbon atom which branched emerged from, must put before/infront the alkyl
The word di, tri is used if the branched chains is more than one

Physical Properties
Physical properties of alkenes (similar to alkanes)
i.
cannot conduct electrity
ii.
less dense than water
iii.
obeys like dissolve like;

dissolve in organic solvents

insoluble in water
v.
low melting and boiling points, gradually steady increase as the number of carbon in alkene increases

Chemical Properties
Reactivity of alkenes
1.
Alkenes is more reactive because the presence of double covalent bond, (unsaturated hydrocarbon)
2. Alkenes decolourized purple solution of acidified potassium
manganate(VII)
3. Alkenes decolourized reddish brown solution of bromin water
4. Neutral.
Combustion of alkenes
.

Addition Reaction
The carbon-carbon double bond is converted into

(5.2)

two single bonds

H
H
H
H


C=C

H H
Alkenes
(Unsaturated)

1.

XY

X CCY

Molecule

H
Alkanes
(Saturated)

Addition of hydrogen

Mixture of alkenes gas/vapour and hydrogen gas, is passed through platinum or nickel at 180 oC. The process is known as
catalytic Hydrogenation.
Catalyst: platinum or nickel

C=

H
Ethene
Chemical equation:

H2

Hydrogen
C2H4 + H2

C2H6

Ni/Pt
H C C H
180oC

Ethane

Example use of this process:


Manufacture of margarine is through hydrogenation

2.

Addition of halogens
The process is known as halogenation

H

C=C

H
Ethenes
(unsaturated)

Br Br

Bromine

Chemical equation: C2H4 + Br2

Br C C Br

1,2-dibromoethanes

C2H4Br2

[HW-notes book]
Q1: Write a chemical equation reaction between but-1-ene with
bromine water. Show the structural formula as well.
[HW-exercises book]
Q2: Halogenation process is best used to differentiate between
alkanes and alkenes. Explain how it can be done?
[notes: refer to SAB]
3.

Addition of hydrogen halides

i. Alkenes reacts with hydrogen halide in room condition.


Hydrogen halide molecules is added to double bond in alkenes,
to produce halogenoalkane.

H
(saturated)

ii. When

hydrogen chloride gas is passed through into ethenes, monochloroethanes is produced.


H H

C=C

H H
Ethenes
(Unsaturated)

HCl

Hydrogen chloride

1.
2.

H C C Cl

Monochloroethanes

H H
(Saturated)

Chemical equation: C2H4 + HCl

4.

C2H5Cl

Addition of acidified potassium manganate(VII)


When alkenes is mixed with acidified potassium manganate(VII), its purple colour is decolourised.
This is because addition process occurred, a group of
hydroxyl (--OH) is added to the molecules of alkenes to form a molecule of diol (type of alcohol) which is saturated and
colourless.

C=C

Alkenes
(Unsaturated)

+ H2O


[fromacidified
KMnO
4]
CC
[O]

OH OH

alkanes-diol compound
(Saturated)

Example;
H

C=

C + H2O + [O]

Ethene
(Unsaturated)

H C C H

OH OH

Ethane-1,2-diol
(Saturated)

Q: Use propene as example.

H
H

H C C = C + H2O + [O]


H
H H

HH

H CC C H


H OH OH

Propene, C3H6

Propane-1,2-diol

C3H6 + H2O + [O] C3H8O2

5. Steam
(Hydration process)
1. Alkenes react with steam to produce equivalent alcohol
at the temperature of 300 oC and in the pressure of 60
atmosphere.
2. Reactions catalyst by concentrated phosphoric acid, H3PO4.
3. This method is one of the industrial preparation to produce
alcohol.
H H

C=C

H H
Ethene

C2H4

+ HOH

H C C H o

Q: Use but-1-ene
C4H8 + H2O C4H9OH / C4H10O

H H

300 C, 60 atm

H PO4 H OH

Steam

H2O

Ethanol

300 oC, 60 atm


H3PO4

C2H5OH @ C2H6O

Polymerization
5.3
Polymer : Large molecules made up from many identical
repeating sub-units called monomers, which joined
together by covalent bond.

Polymerization is a process of repeated linking


when a monomers are joined into chains

Reaction to form a polymer from alkene monomers is called an addition polymerisation

Homologous Series

Characteristic of Homologous Series

Kamal Ariffin Bin Saaim


SMKDBL
http://kemhawk.webs.com
Comparing properties of Alkanes and Alkenes
Similarities:
Properties
Solubility in water
Solubility in organic solvent
Conductivity
Boiling and melting point
Molecular formula
Molecular mass

Alkanes & Alkenes


No
Yes
No
Low
Each member of homologous differs from the next/successive member by a unit
CH2
Each member of homologous differs from the next/successive member of 14 unit

Differences:
Properties

Alkanes

Reaction with oxygen, O2 gas

It burned with less sooty yellow flame

Reaction with bromine, Br2 water


Reaction with acidified potassium
manganate(VII), KMnO4 solution
ESSAY;

The reddish-brown colour of bromine water


remains unchanged
The purple colour of acidified potassium
manganate(VII)
solutions remained unchanged

Alkenes
It burned with a more sooty yellow
flame
The reddish-brown colour of
bromine water decolourised
The purple colour of acidified
potassium manganate(VII)
solutions was decolourised

HOW TO DIFFERENTIATE THE ALKANE and ALKENE IN THE BOTTLES?


Solutions:
i. Procedure
ii. Observations
iii. Inference
[8marks]
Sample answer
Aim: To investigate the liquid in bottle A and B

Dropper

Test tube

Test tube A

Test tube B

Procedure;
1. The apparatus shown above is prepared.
2. 2-5 cm3 bromine water is measured with measuring
cylinder 5ml and poured into a test tube.
3. A few drops of liquid from bottle A is put/added with
dropper into the test tube, and shake.
4. Obsevation is recorded.
5. The experiments is repeated by replace the liquid from
bottle A with bottle B.
Observation:
Test Tube

Observation

Inference

Liquid
in bottle A

The reddish-brown colour of bromine water


remains unchanged

Contains alkane

Liquid
in bottle B

The reddish-brown colour of bromine water


decolourised

Contains alkene

Easylah!

Prepared by;
Kamal Ariffin Bin Saaim
SMKDBL
http://kemhawk.webs.com
ALCOHOL

The Alcohol Family


1.
One of member of homologous series which contain carbon, hydrogen and oxygen.
2.

General formula for alcohol is CnH2n+1OH. [n=1,2,3..]

3.

Alcohol contains the hydroxyl group, -OH as their functional group. [notes: not hydroxide ion, OH - , alcohol not is alkaly ]

4.

Alcohol is neutral compound.

5.

Alcohol are named by replacing -e for alkane with ol.

6.

Structural formula and molecule for few alcohol.

Name

Methanol

Ethanol
very important

Mr

12+3+
16+1
= 32

12x2 + 5 +16
+ 1 = 46

Molekul Formula

CH3OH
@

CH4O

C2H5OH
@
C2H6O

Propan-1-ol

60

C3H7OH

Butan-1-ol

74

C4H9OH

C5H11OH

Pentan-1-ol

88

Hexan-1-ol

102

Q: Give names for this alcohol.


OH

CH3 CH2 CH CH2 CH2 CH3


Formula: C6H13OH
Name

: HEXAN-3-OL

C6H13OH

Structural formula

H
|
H C OH
|
H

H
H
|
|
H C C OH
|
|
H
H

H
H H
|
|
|
H C C C OH
|
|
|
H
H H

Naming Alcohol
1. Find the longest continous carbon chain containing OH.
Number the carbon beginning at the end nearer to the OH, write the number in front of the ending ol.
Locate the alkyl group (branch chain), give number to the carbon and named the alkyl group. Put the number in front of the
group.
CH3
: methyl
C2H5 atau
CH2CH3
: ethyl
C3H7 atau
CH2CH2CH3
: propyl
-

Complete the name for the alcohol

(ii)
OH

CH3 CH2 C CH2 CH2 CH3


|
CH3
Formula: C7H15OH
Name : 3-methyl hexan-3-ol

(iii)
OH

CH3 CH2 CH CH CH2 CH3


|
CH3
Formula
Name

: C7H15OH
: 4-methyl hexan-3-ol

(iii)
OH

CH3 CH CH CH CH2 CH2


|
|
|
CH3
CH3
CH3
Formula : C9H19OH
Name
: 2, 4 dimethyl heptan-3-ol

(iv)
C2H5

OH

CH3 CH2 CH CH2 CH CH2 CH3

Formula : C9H19OH
Name
: 5-ethyl heptan-3-ol

Physical Properties
1. Liquid at room temperature. (pg. 62) [ no gas]
2. Simple alcohol are very soluble in water, infinite solubility.
Methanol, ethanol dan propan-1-ol is miscible in all proportions
(terlarut campur dengan air dalam semua kadaran).
The rest of the alcohol less soluble or insoluble.
Isomerism
Similar to alkenes, isomerism in alcohol results from the branching of the carbon chain and the different location of the hydroxyl
group.
You only have to know the isomerism in propanol dan butanol.
Q : Draw 2 isomers for propanol and 4 isomers for butanol,
and dan named the isomers.

Propanol

Butanol

Propanol

H H H

H C C C OH

H H H

Molecular formula: C3H7OH


Name: Propan-1-ol

H H H

HCCCH

H OH H

Butanol

Molecular formula: C3H7OH


Name: Propan-2-ol

H H H H

H C C C C OH

H H H H
H H H H

HCCCCH

H H OH H

H
H
H

H C C C OH

H HCH H

H
OH
H

H C C C H

H HCH H

Molecular formula: C4H9OH


Name: Butan-1-ol

Molecular formula: C4H9OH


Name: Butan-2-ol

Molecular formula: C4H9OH


Name: 2-methylpropan-1-ol

Molecular formula: C4H9OH


Name: 2-methylpropan-2-ol

ETHANOL
1.
Preparation of ethanol.
i.
Laboratory preparation (fermentation)
ii. Industrial production (hydration process)
Making Ethanol Fermentation
1.
Two stages;
i.
Fermentation
ii.
Purification
- through fractional distillation at 78 oC
( boiling point of ETHANOL)
Fermentation of Glucose
1.
Yeast is added to sugar or starch.
2. Anaerobic process ( takes place in the absence of oxygen).
3.

Yeast releases enzymes. These enzymes break down the sugars/starch into glucose, C 6H12O6.

4. Zymase slowly decomposes the glucose to form ethanol and carbon dioxide.

C6H12O6 (aq)

Zymase @ C2H5OH @ C2H6O

2CH3CH2OH (l) + 2CO2 (g)


30 oC

Delivery tube
Conical flask
Beaker
Glucose + yeast

When the concentration of ethanol reach 15%, the yeast dies.


Q: How to produce pure alcohol?
A: Purified the ethanol through fractional distillation.

Lime water

Purification of Ethanol
1.
Ethanol produced from the fermentation process is impure, because its mix with the glucose solution.
Q : Draw labeled diagram to carry out the purification of ethanol
through fractional distillation process.

Thermometer

Fractioning
collum

Water out

Liebig
condenser

Retort stand
with clamp
Rounded
conical

Water
Product from
fermentation

Wire
gauge

XXXXXXXXXXXXXXX

Porcelain
chips
Bunsen
burner

Q: Why the solution/filtrate in rounded conical must heated at


78oC.
A: The boiling point of ethanol is 78 oC.

Q: Ethanol produced may still contains of some water.


What should be done to be sure that ethanol is 100% pure?
A: Anhydrous calcium oxide or anhydrous calcium chloride is
add/put into the ethanol.

Q: What is the function of;


thermometer
porcelain chips
Liebig condenser
A: thermometer is used to ensure that temperature is always

Water in
Distillate
(Ethanol)

at 78 oC.
B: Porcelain chips is used to avoid the solution jumped/
effervesence (breaking bubbles)
C: To cooled the ethanol vapour to become liquid.
Q: Named the process in Liebig condenser.
A: Condensation
Q: What is the properties of ethanol
A: Properties;
-

colourless
volatile
good organic solvent
miscible with water
highly flammable
antiseptic
chemically reactive

Q: What is the uses of ethanol


A: Uses;
-

As a solvent in perfumes/cosmetics
As a thinner in varnish, ink
As a cleaner for compact disc.
As a fuel for transport
As a raw material for the manufacture of vinegar,
As a raw material to make industrial product such as
antiseptic and cough syrup.

Industrial production of ethanol


Ethene is mix with steam is passed through concentrated
phosphoric acid (catalyst) at 300 oC (temperature) and 60 atmosphere (pressure).

@ C2H4
CH2 = CH2 +

H3PO4
concentrsted
H2O

300 o C, 60 atm

C2H5OH
CH3CH2OH

Chemical Properties
1. Combustion
i.
ii.

Alcohol are very flammable sustances.


Ethanol burns with non-smoky and blue flame and releases
lot of heat. Suitable for use as fuel, described as clean fuel.

C2H5OH
+ 3O2

Ethanol
Oxygen
Q: Write combustion equation for hexanol

2CO2
+
Carbon
dioxide

+ 9O2

Oxygen

6CO2
+
Carbon
dioxide

C6H13OH
hexanol

2. Oxidation
i. Ethanol can be oxidised into ethanoic acid by an oxidising agent.

3H2O
Water
7H2O
Water

[Ethanoic acid is a family of carboxilic acids]

CH3CH2OH + 2[O]
Etanol
Q: Show the structural
formula for the equation above.
H
H
|
|
H C C OH + 2[O]
|
|
H
H

Q: Named 2 solutions are commonly used as oxidising agent.


(i)

Acidified potassium manganate(VII), KMnO 4


(purple to colourless / decolourised)

(ii)
Acidified potassium dichromate(VI), K2Cr2O7
(orange to green)
Q: Draw a labeled diagram for the process.

CH3COOH +
Ethanoic acid

H2O

H
O
|

H C C OH + H2O
|
H

Ethanol +
potassium dikromat(VI) +
dilute sulfuric acid

Heat
Cold
water

Distillate
(ethanoic acid)

Distillate (ethanoic acid)


-

Colourless
Vinegar smell
Blue litmus paper turns red (acidic properties)

3. Dehydration

ALCOHOL

ALKENE

- H2O

1. Converted ethanol into ethene and a molecule of water.


2.

The elimination of water results the formation of a carbon-carbon double bond.

3.

Dehydration occur when


a.
ethanol vapours is passed over a heated catalyst such as.
iPorous pot / porcelain chips
iiPurnice stone / aluminium oxide, Al2O3 /alumina
b.

Ethanol is heated under reflux at 170 oC with excess


concentrated sulphuric acid.

CH3CH2OH
Ethanol

H
H
|
|
HCCH
|
|
H
OH

CH2 = CH2
Ethene

Q : Draw the structural molecule for the process

H2O

H H
|
|
H C C H + H2O

Q : Draw labeled diagram.

Glass wool
soaked with
ethanol

Porcelain
chips
Ethene
gas

Heat

Heat

Delivery
tube

Water

Prepared by;
Kamal Ariffin Bin Saaim
SMKDBL
http://kemhawk.webs.com
CARBOXILIC ACID
General formula CnH2n+1COOH
One hydrogen atom is replaced with functional group COOH

Test
tube

Retort
stand
with
clamp

Formula: HCOOH

Formula: CH3COOH

H C OH

H O
|

H C C OH
|
H

CARBOXYL GROUP

Why families known as carboxylic acid

Carboxyl group plays a vital role to gives acidic properties to carboxilic acid families.

CH3COOH
Ethanoic
acid

H+ + CH3COOHydrogen Ethanoate
ion
ion

Molecular and Structural Formula

Name

Methanoic acid

Molecular formula

C0H2(0)+1COOH

Structural
formula

Mr

H C OH
46

= HCOOH

60

H
O
|

H C C OH
|
H

74

H
H
O
|
|

H C C C OH
|
|
H
H

C1H2(1)+1COOH
1

Ethanoic acid

Propanoic acid

= CH3COOH
[C2H4O2]

C2H2(2)+1COOH
= C2H5COOH

Butanoic acid

Naming carboxilic acids

Carbon number 1

O
C
O

Example 1:

H
H

Longest continuous chains: propanoic acid

H
C

COOH

H
H

C4H8O2 / C3H7COOH

Carboxyl carbon: carbon number 1

C H

Attached alkyl group: 2-methyl

H
Name: 2-methylpropanoic acid
Example 2:

Attached alkyl group: 2-methyl


Longest continuous chains: butanoic acid

H
CH3

COOH
Carboxyl carbon: carbon number 1

C2H5
Name: 2-methylbutanoic acid

Example 3:

H
C2H5

COOH
Name: 2-ethyl pentanoic acid

C3H7
Example 4:

H
C3H7

COOH
Name: 2-ethyl pentanoic acid

C2H5
Ethanoic Asid
Can be prepared through oxidation of an ethanol.
Chemical equation:

CH3CH2OH + 2[O] CH3COOH + H2O


Etanol
ethanoic acid

H H

H C C OH + 2[O]

K2Cr2O7 solutions
+
dilute H2SO4
reflux

H O

H C C OH + H2O

This is carried out by refluxing ethanol with an oxidising agent such as acidified potassium dichromate(VI) or potassium
manganate(VII) solution.

Preparation of ethanoic acid through refluxing

Tissel tube
Water out

Retort
stand

Label the
diagram please

Liebig condenser

Water
in

Rounded bottom flask

Wire
gauge

xxxxxxxxxxxxxx

Absolute ethanol, C2H5OH +


Acidified potassium dichromate(VI),
K2Cr2O7 solution

Heat

Condenser is used to prevent the loss of a volatile liquid by vaporisation.


This method of retaining a volatile liquid during heating is called refluxing.

How to carry out the activity?

Physical Properties
- pH less than 7
- sharp or unpleasant smell
- turn moist blue litmus paper to red
- colourless liquid
Chemical Properties
Acid Properties
- Only hydrogen atom in the carboxyl group,
[-COOH] can ionize in water to produce
hydrogen ions, H+.

CH3COOH
Ethanoic
acid

CH3COO- + H+
CH3COOEthanoate Hydrogen
ion
ion

Ethanoic acid is a weak acid. Why?


- it dissociates in water partially, most of
the molecules remain unchanged.

Reactions with metals


- Dilute ethanoic acid reacts with reactive
metal (Zn, Mg, Al) to produce a salt and
hydrogen gas.

2CH3COOH + Mg Mg(CH3COO)2 + H2
Ethanoic acid
Magnesium ethanoate
2CH3COOH + Zn Zn(CH3COO)2 + H2
Ethanoic acid
Zink ethanoate
6CH3COOH + 2Al 2Al(CH3COO)3 + 3H2
Ethanoic acid
Aluminium ethanoate

Reactions with bases


- Dilute ethanoic acid neutralizes alkalis such
as sodium hydroxide solution to give an
organic salt and water.

CH3COOH + NaOH CH3COONa + H2O


Ethanoic acid
Sodium ethanoate

- Black copper(II) oxide powder dissolves in


dilute ethanoic acid.

2CH3COOH + CuO Cu(CH3COO)2 + H2O


Ethanoic acid
Copper(II) ethanoate

Reactions with carbonates


- Dilute ethanoic acid reacts with metal
carbonates to produce a salt, carbon dioxide
and water.

2CH3COOH + Na2CO3 2CH3COONa + CO2 + H2O


Ethanoic acid
Sodium ethanoate
2CH3COOH + CaCO3 Ca(CH3COO)2 + CO2 + H2O
Ethanoic acid
Calcium ethanoate

Reactions with alcohols [Esterification]


Esterification:

Concentrated
H2SO4
Carboxilic acid + Alcohol Ester +
Carboxilic acid reacts with alcohol to
produce an ester and water.

Water

Concentrated H2SO4 : catalyst


[will discuss more in next chapter]

Uses of carboxilic acid:

i. Ethanoic acid is known as acetic acids use in;


- Food flavoring
- Food preservatives
- To make drugs, dyes, paints insectisides,
plastics
- To make esters for use as slovents
ii.
iii.
iv.
v.

Methanoic acid is used to coagulate latex.


Benzoic acids is used as food preservatives
Fatty acids used in making soaps
Carboxilic acids use in the manufactured of
polyester and polyamids (fibres) in textile

Conclusion on chemical reaction;


Carboxilic acid + reactive metal
carboxylate salt + hydrogen
Carboxilic acid + base
carboxylate salt + water
Carboxylate acid + metal carbonate
carboxylate salt + carbon dioxide +
Water
Carboxilic acid + alcohol
ester + water
1. Learning task 2.9 Summarizing pg 75
[notes book]

2. Effective Practise pg 75
1, 2, 3
[exercise book]

ESTER
General formula CnH2n+1COOCmH2m+1

R
R

: alkyl group in carboxilic acid


: alkyl group in alcohol

CnH2n + 1C OH + CmH2m+1OH

Esterification
- Carboxilic acid reacts with alcohol to produce
ester and water.
- The functional group of ester is carboxilate
group.
- Concetrated sulphuric acid is catalyst.
- Carboxilic acid losses OH and
- Alcohol losses H
- The bond that break up will rejoin again

(carboxilic acid)

(alcohol)

CnH2n + 1C O CmH2m+1 + H2O


(ESTER)

Break up
and rejoin

CnH2n + 1 C
Derived from
carboxilic acid

O
Carboxilate
group, -COO-

CmH2m+1
Derived from
alcohol

Naming Ester
- Name of ester consists of two parts, the name
of alcohol part is given first and followed by
the acid part.
Example: i. Ethanoic acid + methanol
methyl ethanoate + water
Chemical equation:

CH3COOH

+ CH3OH CH3COOCH3 + H2O

H
O
|

H C C OH
|
H
CH3COOH
(Etanoic acid)

H
|
H C OH
|
H
CH3OH
(Methanol)

H
O
H
|

|
H C C O C H + H2O
|
|
H
H
CH3COOCH3
(Methyl ethanoat)

Water

Example: ii. Ethanoic acid + ethanol


ethyl ethanoate + water
Chemical equation:

CH3COOH

+ CH3CH2OH CH3COOCH2CH3 + H2O

H
O
|

H C C OH
|
H
Ethanoic acid

H
H
|
|
H C C OH
|
|
H
H
Ethanol

H
O
H
H
|

|
|
H C C O C C H + H2O
|
|
|
H
H
H
ethyl etanoat
Water

Example: iii. Methanoic acid + Ethanol


ethyl methanoate + water
Chemical equation:

HCOOH

+ CH3CH2OH HCOOCH2CH3 + H2O

H C OH
Methanoic acid

H
H
|
|
H C C OH
|
|
H
H
Ethanol

O
H
H

|
|
H C O C C H + H2O
|
|
H
H
Ethyl metanoat

Q: Draw structural molecule of


i. Methyl metanoate
ii. Pentyl propanoate
iii. Propyl ethanoate
Solutions; i. Methyl metanoate

Air

Methyl methanoate
From carboxilic acid

From alcohol

Methanoic acid

Methanol

H C OH

H
|
H C OH
|
H
Break up and rejoin

O
H

|
H C O C H + H2O
|
H
ii. Pentyl propanoate
Try now

methyl metanoate

Air

Prophyl ethanoate
From carboxilic acid

From alcohol

Ethanoic acid
H O
|
H C C OH
|
H

Propanol
H
H H
|
|
|
H C C C OH
|
|
|
H
H H
Break up and rejoin

H
O
H H
H
|

|
|
|
H C C O C C C H + H2O
|
|
|
|
H
H
H
H
propyl ethanoate

Preparation of ester through reflux

Water

Tissel tube
Water
out
Uniform
heating

Water
bath

Porcelain chip
To prevent
bumping and
ensure smooth
boiling
How to carry out this process?
[Success pg 378]
After boiling, Liebig condenser is rearranged
To carry out the fractional distillation at
74oC 78oC to collect ethyl ethanoate.

Physical properties of ethyl ethanoate


colourless
fragrant smell
insoluble in water
lese dense in water
Natural Sources
- Most simple esters are found in fruits and
flowers.
ex: benzyl ethanoate in Jasmine
ethyl butanoate in pineapple

Liebig
condenser
Water
in

XXXXXXXXXXXXXXX

To cold the
ethanol and
ethanoic acid

Ethanol +
ethanoic acid +
concentrated
sulphuric acid

- Palm oil are liquid ester.


- The higher and complex ester does not
produce pleasant smells

Uses of ester

to make perfume, cosmetics


to make artificial food flavoring
[Text Book: Table 2.8 pg 81]
used as organic solvents
eg. ethyl ethanoate used in sunburn
lotion, polish removers, glues.
to make synthetic polymers/fabrics
to make aspirin (pain reliever)
-

Exercise:
Effective Practise pg 84 no. 1-3
[Ex. Books]

Prepared by;
Kamal Ariffin Bin Saaim
SMKDBL
http://kemhawk.webs.com

PETROLEUM
( Hydrocarbon)

Cracking process

ETHENE
C2H4

Alumina, Al2O3
(heated)

Hydration
process
Concentrated phosphoric acid,
H3PO4 300 oC, 60 atmosphere

GLUCOSE
C6H12O6

Nickel/platinum
180 oC

Dehydration
process
i. Heated porcelain
chips/ porous pot

Oxyge

Com

ii. Concentrated sulphuric


acid, H2SO4 180 oC (reflux)

Fermentation
process

ETHANOL
C2H5OH

Yis (zymase)
30 oC

Oxidation
process
Acidified potassium manganate(VII)/
Acidified potassium dichromate(VI)

HOT SPOT
SPM09

Catalytic
hydrogenation process

ETHANOIC ACID
CH3COOH

FATS
Fats and oils are chemically similar, but differ in physical states.

Oxygen, O2
Combustion
process
Concentrated
sulphuric acid,
H2SO4

Esterification
process

MEM
DIAG
IT W

Fats

: - found in animals
- solid in room temperature
- butter and tallow (types of fat)

Oil
: - fats from plants
- liquid in room temperature
- palm oil, coconut oil, sunflower oil
- Fats and oil are mixtures of different esters.
- Fats are formed from 3 molecules of longchain carboxylic acids called fatty acids
with 1 molecules of alcohol called glycerol.

OH C R1
O

OH C R2
O

OH C R3

H

H C OH

H C OH

H C OH


Formation of a fat molecule

Fatty acids
- R1 , R2 , R3 contains
12 to 18 carbon
atoms per molecule
- R1 , R2 , R3 are three
alkyl groups which
may be the same or
different
- group: carboxilic acid

Glycerol
- propane-1,2,3-triol
- group: alcohol

H C OH

H C OH

H C OH

Break up
and rejoin
+
Break up
and rejoin

Break up
and rejoin

OH C R1
O

OH C R2
O

OH C R3

Importance of fats and oils


energy
nutrients
thermal insulation

H
O

H C O C R1

H C O C R2

H C O C R3

+ 3H2O

protection to internal organ

[Text book: Figure 2.34 pg. 86]


Saturated and unsaturated fats
- Fat or oil molecules is affected by parent fatty
acids.
- Fatty acids can be differentiated in two ways;
i. the length of the carbon chains
(12 to 18 carbon atoms)
ii.
saturated or unsaturated
Saturated fatty acid
- All carbon atoms joined together by
carbon-carbon single covalent bond.
- example:
Lauric acid
(12 carbon atoms)
Palmitic acid
(16 carbon atoms)
Stearic acid
(18 carbon atoms)
Unsaturated fatty acid
- The carbon chain has one or more
carbon-carbon double covalent bond.
Example:
i. Oleic acid: monounsaturated fatty acid
(one carbon-carbon double bond)[no of C = 18, DB = 9&10]
ii. Linoleic acid: polyunsaturated fatty acid
(two carbon-carbon double bond)
[no. of C = 18, DB = 9&10, 12&13]
iii. Linolenic acid: polyunsaturated fatty acid
(three carbon-carbon dauble bond)
[no. of C = 18, DB = 9&10, 12&13,
15&16]

Saturated Fats
Fats contain esters of glycerol and saturated fatty acids.
- Example:
i. Tristearin
( glycerol + stearic acid)
ii. Tripalmitin (glycerol + palmitic acid)
Tristearin

H
O

H C O C (CH2)16 CH3

H C O C (CH2)16 CH3

H C O C (CH2)16 CH3

H
Tripalmitin

H
O

H C O C (CH2)14 CH3

H C O C (CH2)14 CH3

H C O C (CH2)14 CH3

H
- Animal fats have large proportions of
saturated fats.
- They have high melting point and solids at
room temperature.

Unsaturated Fats
- Fats contain esters of glycerol and
unsaturated fatty acids.
Example:
i. Triolein

(glycerol + oleic acid)

H
O

H C O C (CH2)7 CH CH (CH2)7 CH3

H C O C (CH2)7 CH CH (CH2)7 CH3

H C O C (CH2)7 CH CH (CH2)7 CH3

H
- Plant or vegetable oils contain a large
proportions of unsaturated fats.
- They have lower melting points and are
liquids at room tempoerature.

Converted unsaturated fats to saturated fats


Unsaturated fats can be converted into saturated fats by process called catalytic hydrogenation.
The hydrogenation process is carried out by bubbling hydrogen gas through hot, liquid oil in the presence of fine
particles of nickel catalyst.

Effect of fats on health


Saturated fats (animal oil) will raise the level of cholesterol.
Cholesterol causes fatty deposites or the wall of veins or arteries.
Blood circulation is restricted and will raise the blood presure
Arteriosclerosis, can result in heart attack.
Unsaturated fats (plant oil) do not contain cholesterol. Do not cause cardiovascular problems.
Uses of palm oil
Has many advantages.
A cheaper, better and healthier oil.
[Text book: Figure 2.36 pg. 90]

Prepared by;
Kamal Ariffin Bin Saaim
SMKDBL
http://kemhawk.webs.com
Natural Rubber

Natural rubber is a natural polymer.


Natural rubber is obtained from the latex secreted by rubber tree.
Latex is a colloid. It consists of rubber particles dispersed in water.
Natural rubber is poly(isopropene).
Its monomer is 2-metyhlbuta-1,3-diene or isopropene. Each isopropene molecule contains two pairs of double bonds.
The isopropene molecules undergo addition polymerization to produce a long-chain molecule called poly(isopropene)
Each rubber particles is made up of many long-chain rubber molecules, enclosed by a protein-like membrane which is negatively
charged.

Latex

Long chain
rubber
molecules

Negatively-charge
protein membrane

Rubber
particle

Polymerization of Isopropene

Isoprene

Isoprene

Isoprene

H CH3 H H + H CH3 H H
+ H CH3 H H





CCCC
CCCC
CCCC

H
H
H
H
H
H

polymerization
H CH3 H H
H CH3 H H
H CH3 H H



C C C C C C C C C C C C

H
H
H
H
H
H

Repeated unit in polymer

Coagulation process of latex

Rubber particle

Rubber particle has negatively-charged protein


membrane.
The repulsion between the negatively-charged
particles prevents the rubber particles from coming
close to each other.
Latex could not coagulate.

Q: So what causes the latex to coagulate?

+
+

When an acid is added, the hydrogen ions, H+ neutralize the negative charges on the protein membrane.

Q: Can you named the acid that usually used to coagulated


the latex in rubber industry?
A: Ethanoic acid also known as acetic acid.
[notes: all acid solutions can make latex coagulate]

Q: What do you think will happen next?

+
+

The rubber particles now come close together.


This enable them to collide with one another resulting in the breakage of the protein membrane.
The rubber molecules/polymer combine with one another and entangle.
Thus, causing the latex to coagulate.
EASY lah

Q: The coagulation of latex will also occur if latex is exposed


to air. Why?
A: Bacteria from air can enter latex. The growth and spread
of bacteria produce lactic acid that causes the process
above.

Q: Named the substance can be used to preserve latex in


liquid state? Explain.
A: Ammonia, NH3.
NH3 solutions contains hydroxide ions, OH- that
neutralised the acid/hydrogen ions, H+ produced by the
bacteria. The rubber particles remain negatively charged
and the coagulation is prevented.
[notes: all alkaly solutions also can be used]

Properties of natural rubber


Soft
Elasticity decreases over time.
Easily oxidized by air.
Sensitive to heat. When heated, it becomes sticky. When cooled, it becomes hard and brittle.

Vulcanization of rubber
Properties of rubber can be improved through vulcanization.
Vulcanization is a process whereby rubber is reacted with sulphur to improved its properties.

Q: How the vulcanization process is carry out in industry?


A: 1st method: Latex is heated with sulphur, or
2nd method: Rubber products are exposed to disulphur
dichloride, S2Cl2.

Q: Compare and contrast the properties of vulcanised and


unvulcanised rubber.
Similarities
Vulcanised and unvulcanised rubber is elastic, and
heat and electrical insulator
Differences [notes: draw a table]

Elasticity

Properties

Vulcanised rubber
More elastic

Unvulcanised rubber
Less elastic

Hardness

Harder

Softer

Tensile strength

Stronger

Weaker

Resistance to heat

Can withstand higher temperature

Cannot withstand temperature

Resistance to oxidation

Less easily oxidized

Easily oxidized

Effect of organic solvent

Does not become soft and sticky


easily

Become soft and sticky easily

Q: Why?

CC

CC

CC

CC

CC

vulcanisation

CC

CC

S
S

CC

CC

Natural rubber

S
C

S
C

Rubber molecules

S
C

Vulcanised rubber

C
S

S
S

CC

C
S
S
C

Cross-linkage of
sulphur atoms

A: Improved properties of vulcanised rubber is due to the


presence of cross-linkage of sulphur atoms between the
rubber molecules.

Q: How the cross-linkage of sulphur atom improve elasticity


and strength of the vulcanized rubber:
A: When vulcanised rubber is streched and released, the
cross linkage pull the chains back to their original
arrangement.

Q: Why vulcanized rubber more resistant to heat and organic


solvent?
A: The presence of sulphur cross-linkage increases the size
of rubber molecules.

Q: Why vulcanized rubber more resistant to oxidation?


A: Vulcanized rubber has much lesser carbon-carbon double
bond.

Uses of natural rubber

Home Work
Review Questions
i.
ii.
iii.

pg 100 - 102
objective (no. 1-8)
subjective questions (1 and 2)
essay (no. 1c)

SPM Question (2006)


Diagram 2 shows the stretching phases of a vulcanised rubber and an unvulcanized rubber strands.
Stretching phases

Length of vulcanized rubber

Length of unvulcanized rubber

Before

45 mm

45 mm

During

59 mm

60 mm

45 mm

After

Diagram 2
Plan an experiment to compare one characteristic shown in Diagram 2 for both types of rubber.
Your planning should include the following aspects:
(a) Aim of the experiment
(b) All the variables
(c) Statement of the hypothesis
(d) List of substances and apparatus
(e) Procedure of the experiment
(f ) Tabulation of data
[17 marks]

Answer
(i) Problem statement:
Does vulcanized rubber is more elastic than
unvulcanized rubber?
(a) Aim:
To compare the elastic properties between vulcanized
rubber and unvulcanized rubber.
(b)

List of variable:
Manipulated variable = Type of rubber

Responding variable = Elasticity //


length of rubber strip during and
after stretching phase.
Fixed variable

= Original length of rubber strip //


Length/size/mass of rubber
(before stretching phase)

(c) Hypothesis:
Vulcanized rubber is more elastic than unvulcanized
rubber. // sk3

The more elastic of the rubber, the less length of the


rubber during and after stretching phase. // sk2

50 mm

Rubber that is more elastic shows less length when/after


it has been stretched. sk3

(iv) List of materials and apparatus:


Vulcanized rubber, unvulcanized rubber,
Meter ruler, 50 g weight, retort stand and clamp,
clip, thread.

Clip
Rubber strip
Retort stand
with clamp
Thread
Weight 50 g
(vi) Procedure :
1. Clip is used to hung the strip of vulcanized rubber.
2. The original length of the vulcanized rubber is
measured.
3. A weight of 50 g is hung on the strip of vulcanized
rubber.
4. The increased in length of the vulcanized rubber
strip is measured.
5. The weight is removed.
6.
The final length of the vulcanized rubber strip is
measured.
7.
Step 1 to 6 are repeated using unvulcanized rubber.
(vii) Tabulation:

Type of rubber strip

Original
length /mm

Final Length when weight


is hung /mm

Increase in
length /mm

Final length when weight is


removed /mm

Vulcanized rubber

45

59

14

45

unvulcanized rubber

45

60

15

50

HOT SPOT
SPM 2008

Prepared by;
Kamal Ariffin B Saaim
SMKDBL

Manipulated variable:

Action to be taken:

Responding variable:

Action to be taken:

How the variable responds?:

Fixed variable:

Action to be taken:

Alumina,
Alumina,AlAl
2O
2O
3 3
CC
(ce)
(ce)
CC
(g)(g)
9H
9H
20 20
2H
2H
6 (g)
6 (g)+ +CC
7H
7H
14 14
Panas
Panas
Nonana
Nonana
Etana
Etana
Heptena
Heptena