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) 1 2 3 4 5 6 7 8 9 10 Physical Molar state at mass room -1 (g mol ) temperatu re 16 30 44 58 72 86 100 114 128 142 Gas Gas Gas Gas Liquid Liquid Liquid Liquid Liquid Liquid
1

Name

Molecular formula

CnH2n+2
C1H2x1+2 = CH4 C2H2x2+2 = C2H6 C3H2x3+2 = C3H8 C4H2x4+2 = C4H10 C5H2x5+2 = C5H12 C6H2x6+2 = C6H14 C7H2x7+2 = C7H16 C8H2x8+2 = C8H18 C9H2x9+2 = C9H20 C10H2x10+2 = C10H22

Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane

Consecutive members different in molar mass is 14 g mol-1 4. Structural formulae of alkanes Name Methane No. of isomers 0 Structural formulae and Name H HCH H 0 H H HCCH H H H H H HCCCH H H H H H H H HCCCCH H H H H n-butane
2

CH4

Ethane, C2H6

Propane, C3H8

Butane, C4H10

H H H H C C C H H HCH H H 2 - methyl propane Pentane, C5H12 3 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 H HCH H H C C C H H HCH H H 2,2-dimetyl propane Hexane, C6H14 5 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 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.

CH4 + 2O2 CO2 + 2H2O

CH4

O2

CO2

H2O

ii.

C2H6

+ 7/2

O2

2CO2

+ 3H2O

iii.

C4H10 + 13/2 O2 C6H14 + 19/2 O2

4CO2 6CO2

5H2O 7H2O

iv.

Answers

i. CH4 ii. C2H6

+ 2O2 + 7 O2 2

CO2

+ 2H2O 3H2O

2CO2 +

2 x C2H6 2C2H6

+ 2 x 7 O2 2 + 7 O2

2x 2CO2 + 2x 3H2O 4CO2 + 6H2O

iii.

C4H10 C6H14

+ 13/2 O2 4CO2 + 5H2O + 19/2 O2 6CO2 + 7H2O

iv. 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 CO + 2H2O 2CH4 + 3 O2 2CO + 4H2O ii. CH4 + O2 C + 2H2O

9

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; H H C H +Cl-Cl H Second stage; H H C Cl + H Third stage ; Cl H C Cl + H Fourth stage; Cl H C Cl + Cl Cl | Cl C Cl + HCl | Cl tetrachloromethane Cl | H C Cl + HCl | H dichloromethane Cl | H C Cl + HCl | Cl trichloromethane H | H C Cl + HCl | H monochloromethane

Cl2

Cl2

Cl2

10

Alkenes 1. General formulae : CnH2n [ no alkene corresponding to n = 1 as CH2 is not exist] Alkenes containing at least one carbon-carbon double bond 2. Alkenes is unsaturated hydrocarbon because the presence of the double bond. 3. Name of each members end with ene.

ethenes

No. of carbon atom 1 2 3 4

Name

Physical Molecular Molar mass / state at room formulae g mol-1 condition None C2H4 C3H6 C4H8 28 42 56 Gas Gas Gas
11

Ethene Propene Butene

5 6 7 8 9 10

Pentene

C5H10

70

Liquid Liquid Liquid Liquid Liquid 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 Ethene C2H4 Number of isomer 0 Structure formula and name H H CC H H

12

Propene C3H6

H H CCCH H H H

Butene, C4H8

3 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

13

Pentene, C5H10

5 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

14

H H H H C C C C H H HCH H H 2-methyl but -2- ene

15

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

16

H H H H C C C C C H H HCH H H H H

H H H H C C C C C H H H HCH H H H

H H H H C C C C C H H H H HCH H H

17

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 HC C C C C H H H H HCH H H

18

H H HCH H C C C C H H HCH H H H

H H HCH H H C C H C C H CH H H HH CH H H H C C C C H H H HCH H H
19

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

20

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

21

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

22

. Addition Reaction (5.2)

The carbon-carbon double bond is converted into two single bonds

23

H H H C=C H + XY

X CCY H H Alkanes (Saturated)

Alkenes (Unsaturated)

Molecule

1. 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.
24

Catalyst: platinum or nickel

Ni/Pt

C=C + H2 180oC H H Ethene Hydrogen Chemical equation:

H C C H H H Ethane

C2H4 + H2 C2H6

Example use of this process: Manufacture of margarine is through hydrogenation

25

2. Addition of halogens The process is known as halogenation

H H Br C C Br H H 1,2-dibromoethanes (saturated)

C = C + Br Br H H Ethenes Bromine (unsaturated) Chemical equation: C2H4 + Br2

C2H4Br2

Q1: Write a chemical equation reaction between but-1-ene with bromine water. Show the structural formula as well.

Q2: Halogenation process is best used to differentiate between alkanes and alkenes. Explain how it can be done?
26

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.

ii. When hydrogen chloride gas is passed through into ethenes, monochloroethanes is produced. H H H H H C C Cl H H Monochloroethanes (Saturated)

C=C + HCl H H Ethenes Hydrogen chloride (Unsaturated) Chemical equation: C2H4 + HCl

C2H5Cl

27

4. Addition of acidified potassium manganate(VII) 1. When alkenes is mixed with acidified potassium manganate(VII), its purple colour is decolourised. 2. 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
[from acidified KMnO4] [O]

+ H2O

CC OH OH alkanes-diol compound (Saturated)

Alkenes (Unsaturated)

28

Example; H H C = C + H2O + [O] H H H

H C C H OH OH Ethane-1,2-diol (Saturated)

Ethene (Unsaturated)

Q: Use propene as example.

HH H H CC C H H OH OH Propane-1,2-diol

H C C = C + H2O + [O] H H H Propene, C3H6

C3H6 + H2O + [O] C3H8O2

29

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 H H H C C H H OH Ethanol C2H5OH @ C2H6O

300 oC, 60 atm

C=C H H Ethene

+ HOH

H3PO 4

Steam H 2O
300 oC, 60 atm H3PO4

C2H4

Q: Use but-1-ene

C4H8 + H2O C4H9OH / C4H10O

30

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

31

Homologous Series

Characteristic of Homologous Series

32

33

Comparing properties of Alkanes and Alkenes

Similarities: Properties Solubility in water Solubility in organic solvent Conductivity Boiling and melting point Molecular formula Molecular mass Differences: Properties Reaction with oxygen, O2 gas Alkanes It burned with less sooty yellow flame Alkenes It burned with a more sooty yellow flame The reddishbrown colour of bromine water decolourised The purple colour of acidified potassium manganate(VII) solutions was decolourised
34

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

The reddish-brown Reaction with bromine, colour of bromine Br2 water water remains unchanged The purple colour of Reaction with acidified acidified potassium potassium manganate(VII) manganate(VII), solutions remained KMnO4 solution unchanged

ESSAY;

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

35

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 Liquid in bottle A Liquid in bottle B Observation Inference

The reddish-brown colour of bromine water Contains alkane remains unchanged The reddish-brown colour of bromine water Contains alkene decolourised

36

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.

37

6. Structural formula and molecule for few alcohol. n Name Mr Molekul Formula Structural formula H | H C OH | H

12+3+ CH3OH 1 Methanol 16+1 @ = 32 CH4O

H H 12x2 + | | Ethanol C2H5OH 5 +16 H C C OH 2 very @ +1= | | important C2H6O 46 H H H H H | | | H C C C OH C3H7OH | | | H H H C4H9OH

Propan-1ol

60

Butan-1ol Pentan-1ol Hexan-1ol

74

88

C5H11OH

102

C6H13OH
38

Q: Give names for this alcohol. OH CH3 CH2 CH CH2 CH2 CH3 Formula: C6H13OH Name : HEXAN-3-OL

39

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

40

(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

41

(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.

42

Propanol

Butanol

43

Propanol

H H H H C C C OH H H H

Molecular formula: C3H7OH Name: Propan-1-ol Molecular formula: C3H7OH Name: Propan-2-ol

H H H HCCCH H OH H

44

Butanol
H H H H H C C C C OH H H H H H H H H HCCCCH H H OH H

Molecular formula: C4H9OH Name: Butan-1-ol

Molecular formula: C4H9OH Name: Butan-2-ol

H H H H C C C OH H HCH H H

Molecular formula: C4H9OH Name: 2-methylpropan-1-ol

H OH H H C C C H H HCH H H

Molecular formula: C4H9OH Name: 2-methylpropan-2-ol

45

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, C6H12O6. 4. Zymase slowly decomposes the glucose to form ethanol and carbon dioxide. Zymase @ C2H5OH @ C2H6O 2CH3CH2OH (l) + 2CO2 (g) o 30 C

C6H12O6 (aq)

46

Delivery tube Conical flask Beaker Glucose + yeast Lime water

When the concentration of ethanol reach 15%, the yeast dies. Q: How to produce pure alcohol? A: Purified the ethanol through fractional distillation.

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.

47

 Thermometer Water out Liebig condenser Retort stand with clamp Water Product from fermentation Rounded conical Porcelain chips Bunsen burner

Fractioning collum

Water in Distillate (Ethanol)

Wire gauge

XXXXXXXXXXXXXXX

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.

48

Q: What is the function of; - thermometer - porcelain chips - Liebig condenser A: thermometer is used to ensure that temperature is always 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

49

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). H3PO4 concentrsted H2O 300 o C, 60 atm

@ C2H4 CH2 = CH2 +

C2H5OH CH3CH2OH

50

Chemical Properties 1. Combustion i. Alcohol are very flammable sustances. ii. Ethanol burns with non-smoky and blue flame and releases lot of heat. Suitable for use as fuel, described as clean fuel.

C2H5OH Ethanol

3O2 Oxygen

2CO2 + Carbon dioxide

3H2O Water

Q: Write combustion equation for hexanol C6H13OH hexanol + 9O2 Oxygen 6CO2 Carbon dioxide + 7H2O Water

2. Oxidation i. Ethanol can be oxidised into ethanoic acid by an oxidising agent. [Ethanoic acid is a family of carboxilic acids]

CH3CH2OH Etanol

+ 2[O]

CH3COOH + H2O Ethanoic acid

51

Q: Show the structural formula for the equation above. H H | | H C C OH + 2[O] | | H H H O | H C C OH + H2O | H

Q: Named 2 solutions are commonly used as oxidising agent. (i) Acidified potassium manganate(VII), KMnO4 (purple to colourless / decolourised) (ii) Acidified potassium dichromate(VI), K2Cr2O7 (orange to green) Q: Draw a labeled diagram for the process.
Ethanol + potassium dikromat(VI) + dilute sulfuric acid

Heat Distillate (ethanoic acid) Cold water

Distillate (ethanoic acid) - Colourless - Vinegar smell - Blue litmus paper turns red (acidic properties)
52

3. Dehydration

- H2O

ALCOHOL

ALKENE

1. Converted ethanol into ethene and a molecule of water. 2. The elimination of water results the formation of a carboncarbon double bond. 3. Dehydration occur when a. ethanol vapours is passed over a heated catalyst such as. i- Porous pot / porcelain chips ii- Purnice stone / aluminium oxide, Al2O3 /alumina b. Ethanol is heated under reflux at 170 oC with excess concentrated sulphuric acid.

CH3CH2OH Ethanol

CH2 = CH2 Ethene

H2O

Q : Draw the structural molecule for the process

H H | | HCCH | | H OH

H H | | H C C H + H2O
53

Q : Draw labeled diagram.

Glass wool soaked with ethanol

Porcelain chips Ethene gas Delivery tube Test tube Retort stand with clamp

Heat

Heat

Water

CARBOXILIC ACID General formula CnH2n+1COOH One hydrogen atom is replaced with functional group COOH

54

Formula: HCOOH

Formula: CH3COOH

O H C OH

H O | H C C OH | H

CARBOXYL GROUP

Why families known as carboxylic acid

55

Carboxyl group plays a vital role to gives acidic properties to carboxilic acid families. H+ + CH3COOHydrogen Ethanoate ion ion

CH3COOH Ethanoic acid

56

Molecular and Structural Formula

n Name Molecular formula C0H2(0)+1COOH = HCOOH Mr Structural formula

Methanoic acid

O 46 H C OH

C1H2(1)+1COOH 1 Ethanoic acid = CH3COOH [C2H4O2]

H O | 60 H C C OH | H

H H O | | CH COOH Propanoic 2 2(2)+1 74 H C C C OH acid = C2H5COOH | | H H Butanoic acid

57

Naming carboxilic acids

3 2 Carbon number 1

H C H Example 1: H H C H H C H H H C

H C H C

Longest continuous chains: propanoic acid

C4H8O2 / C3H7COOH

COOH
Carboxyl carbon: carbon number 1

Attached alkyl group: 2-methyl

Name: 2-methylpropanoic acid

58

Example 2:
Attached alkyl group: 2-methyl

H CH3 C

Longest continuous chains: butanoic acid

COOH
Carboxyl carbon: carbon number 1

C2H5
Name: 2-methylbutanoic acid

59

Example 3: H C2H5 C COOH

Name: 2-ethyl pentanoic acid

C3H7 Example 4: H C3H7 C COOH

Name: 2-ethyl pentanoic acid

C2H5 Ethanoic Asid Can be prepared through oxidation of an ethanol. Chemical equation:
60

CH3CH2OH + 2[O] CH3COOH + H2O Etanol ethanoic acid

K2Cr2O7 solutions + H O dilute H2SO4 H C C OH + H2O reflux H

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

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

61

Preparation of ethanoic acid through refluxing

Tissel tube Water out Label the diagram please

Liebig condenser Retort stand Water in Rounded bottom flask Absolute ethanol, C2H5OH + Acidified potassium dichromate(VI), K2Cr2O7 solution

Wire gauge

xxxxxxxxxxxxxx

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?
62

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+. CH3COO- + H+ CH3COOEthanoate Hydrogen ion ion

CH3COOH Ethanoic acid

Ethanoic acid is a weak acid. Why? - it dissociates in water partially, most of the molecules remain unchanged.
63

Reactions with metals - Dilute ethanoic acid reacts with reactive metal (Zn, Mg, Al) to produce a salt and hydrogen gas.
2CH3COOH + Mg Ethanoic acid Mg(CH3COO)2 + H2 Magnesium ethanoate

2CH3COOH + Zn Ethanoic acid

Zn(CH3COO)2 Zink ethanoate

+ H2

6CH3COOH + 2Al Ethanoic acid

2Al(CH3COO)3 + 3H2 Aluminium ethanoate

64

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

65

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

66

Reactions with alcohols [Esterification] Esterification: Carboxilic acid reacts with alcohol to produce an ester and water.
Concentrated H2SO4 Carboxilic acid + Alcohol Ester + Water

Concentrated H2SO4 : catalyst [will discuss more in next chapter]

67

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

68

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]
69

ESTER General formula CnH2n+1COOCmH2m+1

R : alkyl group in carboxilic acid R : alkyl group in alcohol

O CnH2n + 1C OH + CmH2m+1OH
(carboxilic acid) (alcohol)

O CnH2n + 1C O CmH2m+1 + H2O

(ESTER)
70

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 O CnH2n + 1 C
Derived from carboxilic acid Break up and rejoin

O
Carboxilate group, -COO-

CmH2m+1
Derived from alcohol

71

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

72

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

73

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 + H 2O | | | H H H ethyl etanoat Water

Example: iii. Methanoic acid + Ethanol ethyl methanoate + water Chemical equation:
HCOOH + CH3CH2OH HCOOCH2CH3 + H2O

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O 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 Air

Q: Draw structural molecule of i. Methyl metanoate ii. Pentyl propanoate iii. Propyl ethanoate Solutions; i. Methyl metanoate
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Methyl methanoate
From carboxilic acid Methanoic acid O H C OH From alcohol Methanol H | H C OH | H Break up and rejoin

O H | H C O C H + H2O | H methyl metanoate Air

ii. Pentyl propanoate Try now

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Prophyl ethanoate
From carboxilic acid Ethanoic acid H O | H C C OH | H From alcohol 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 Water

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Preparation of ester through reflux

Tissel tube Liebig condenser Water out Uniform heating Water bath Water in To cold the ethanol and ethanoic acid

Porcelain chip
XXXXXXXXXXXXXXX

To prevent bumping and ensure smooth boiling

Ethanol + ethanoic acid + concentrated sulphuric acid

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.

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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

- Palm oil are liquid ester. - The higher and complex ester does not produce pleasant smells
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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)

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

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Fats

: - found in animals - solid in room temperature - butter and tallow (types of fat) : - fats from plants - liquid in room temperature - palm oil, coconut oil, sunflower

Oil

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.

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O OH C R1 O OH C R2 O OH C R3

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

H H C OH H C OH H C OH H

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

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Formation of a fat molecule

H H C OH H C OH H C OH H
Break up and rejoin + Break up and rejoin

O OH C R1 O OH C R2 O OH C R3

Break up and rejoin

H O H C O C R1 O H C O C R2 O H C O C R3 H

+ 3H2O

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Importance of fats and oils - energy - nutrients - thermal insulation - protection to internal organ

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)
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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]

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Saturated Fats - Fats contain esters of glycerol and saturated fatty acids. - Example: i. Tristearin ii. Tripalmitin Tristearin
H O H C O C (CH2)16 CH3 O H C O C (CH2)16 CH3 O H C O C (CH2)16 CH3 H

( glycerol + stearic acid) (glycerol + palmitic acid)

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Tripalmitin

H O H C O C (CH2)14 CH3 O H C O C (CH2)14 CH3 O 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.

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

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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.

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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.
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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

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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 CCCC CCCC CCCC H H H H H H

Repeated unit in polymer

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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.

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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]

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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.

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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.

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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.

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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] Properties Elasticity Hardness Tensile strength Resistance to heat Vulcanised rubber More elastic Harder Stronger Unvulcanised rubber Less elastic Softer Weaker Cannot withstand temperature Easily oxidized Become soft and sticky easily

Can withstand higher temperature Resistance to Less easily oxidation oxidized Effect of organic Does not solvent become soft and sticky easily

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Q: Why?
CC CC
C S S C C S S C S C C S S C C S S C C S S C

CC

CC CC

CC

vulcanisation

CC

CC

CC

CC

Natural rubber

Vulcanised rubber

C S S C C S S C S S C C

C S S C C S S C S S C C

Rubber molecules

Cross-linkage of sulphur atoms

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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 stretched 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.

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Uses of natural rubber

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SPM Question (2006) Diagram 2 shows the stretching phases of a vulcanised rubber and an unvulcanized rubber strands.
Stretching phases Length of vulcanized Length of rubber unvulcanized rubber

Before

45 mm

45 mm

During

59 mm

60 mm

After

45 mm

50 mm

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]
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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.

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(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.
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(vii) Tabulation:
Type of rubber strip Vulcanized rubber unvulcanized rubber
Original length /mm Final Length Final length Increase in when weight is when weight is length /mm hung /mm removed /mm

45 45

59 60

14 15

45 50

Manipulated variable:

Action to be taken:

Responding variable:

Action to be taken: How the variable responds?:

Fixed variable:

Action to be taken:

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