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Is the special group of atoms available in homologous series compounds which is responsible for
the chemical properties of the compound
All compounds in homologous series have functional group except alkanes. Examples of
functional group homologous series: alcohol
Crude oil is a mixture of complex hydrocarbons with varying boiling points, depending on the
number of carbon atoms and how they are arranged.
Fractional distillation uses this property to separate the hydrocarbons in crude oil.
b. From naphtha:
Naphtha fraction is used for production of petrochemicals, such as medicines, plastics and
synthetic fibres, aside from fuels.
When naphtha is treated, not only it becomes a better fuel, it also contain more aromatic
hydrocarbons, alkene and cyclic hydrocarbons which are important for petrochemical industry.
Crude oil is mostly used as fuel, though some allocated for chemical feedstock.
Saturated vs Unsaturated
Saturated hydrocarbons
hydrocarbons which the combining capacity of the carbon atoms is as fully used as possible in
bonding with hydrogen atoms.
Unsaturated hydrocarbons
hydrocarbons which the combining capacity of the carbon atoms is not fully used, e.g. only 2 or 3
hydrogen are attached to a carbon atom.
usually indicated by double bond (=) or triple bond with another carbon atoms.
Alkanes
Characteristics
example: propane has three carbon atom, thus n=3. Then the formula of propane is C3H8
Next alkane formula differ by CH2 atoms. Eg: methane: CH4, ethane: C2H6
Structure of Alkanes
Shows how all atoms in a molecule joined together by drawing lines between atoms to represent
the bonds
Melting points and boiling points increase as the bonds become larger and heavier which
increases the forces of attraction between molecules so more energy (from heat) is needed to
separate them with the increase of strength of forces of attraction
insoluble in water but soluble in organic solvents such as tetrachloromethane as alkanes are
organic compounds
density increases down the series; all alkenes are less than 1g/cm
become more viscous going down the series as the longer molecules tangles together when it
flows
unreactive with either metals, water, acids or bases because the C C and C H covalent bonds
are harder to break
Reaction of Alkanes
Have same chemical properties they dont react with most chemicals
1) Combustion
When there is insufficient oxygen, the product is ALWAYS carbon monoxide and unburnt carbon.
Example: Butane is commonly used camping gas. State the chemical equation of combustion of butane in
air.
2 C4H10 (g) + 13 O2 (g) --> 8 CO2 (g) +10 H2O (l)
High alkanes burn less completely and gives soot (unburnt carbon) and CO
Substitution reaction the reaction in which one or more atoms replace other atoms in a
molecule
Light is needed to break covalent bond between chlorine molecule --> atoms
Alkenes
Characteristics
Structure of Alkenes
Reason: not all C atoms are bonded to the maximum number of 4 other atoms
Reactions of Alkenes
1) Combustion
Example: Ethene burns in air. Write the balanced equation for the reaction
C2H4 (g) + 3O2 (g) --> 2CO2 (g) + 2H2O (l)
Incomplete combustion forms soot and CO. Its produced more than alkane
2) Addition Reaction
a. Addition of hydrogen:
Alkenes react with hydrogen to form alkanes, called hydrogenation. Must use nickel as catalyst
and heat.
b. Addition of bromine
Phosphoric acid (H3PO4), high temperature of 300 C and 60-70 atm pressure are needed as
catalyst.
c. Addition of water
Alkene + steam is passed over phosphoric acid (H3PO4) catalyst and temperature of 300 C.
3) Polymerization
Polyunsaturated food food containing C=C bond in their molecules Eg: Vegetable oil
Hydrogen is reacted with vegetable oil with presence of nickel catalyst and heat, which adds to
C=C bond, increasing the molecular mass of the compound
With increase in mass, the compound has higher boiling point. Therefore, margarine is solid at
room temperature.
Since only some C=C bonds react with hydrogen, margarine is partially hydrogenated and each
has different hardness, depending on the number of C=C bonds.
Alkanes can be cracked into shorter chain hydrocarbons because of the higher value it has that it
can create more variety of products in petrochemical industries.
by catalytic cracking, which is, using catalyst to break alkane into simpler hydrocarbons.
The total number of carbon and hydrogen atoms from products should equal to the total number
of carbon and hydrogen atoms in cracked alkane.
E.g. Octane can be cracked into simpler hydrocarbons such as the reaction below. Suggest the
possible identity of product x.
C8H18 (l) --> C2H4 (g) + x + CH4 (g)
Number of C atoms in x = 8 2 1 = 5
Number of H atoms in x = 18 4 4 = 10
---> Product x is C5H10
Isomers
Due to different chain length, they have different physical properties (e.g. boiling point).
We therefore cant just say that C6H14 is simply hexane because there are more variations of C6H14and
each variation has its own name.
Alcohols
Characteristics
First three members of the series (so that youd have idea on the next)
Methanol, CH3OH
For alcohol, the OH is not of hydroxide ion, OH , but is covalent bond between oxygen and
hydrogen, O H
Making Ethanol
1. Fermentation of sugars with yeast
2. Reacting ethene with steam
1. Fermenting glucose
Ethene and steam are passed over phosphoric acid H3PO4 (as a catalyst) under high temperature
o
Since this is reversible reaction, both ethene and water are produced aside from ethanol.
Uses of Alcohol
As organic solvent
vehicle fuel
REACTIONS OF ALCOHOL
1) Combustion
2) Oxidation
a. Alcohol can be prepared in laboratory by warming alcohol with oxidizing agent (e.g. acidified potassium
chromate(VI)).
E.g. ethanol produces water and ethanoic acid when left in air.
C2H5OH (aq) + O2 (g) ---> 2CH3COOH (aq) + 3H2O (l)
3) Esterification
Carboxylic Acids
Characteristics
First three members of the series (so that youd have idea on the next)
Natural gas is passed over air and catalyst to form ethanoic acid and water.
2. Oxidation
Carboxylic acids react with metals to form metal ethanoate (salt) and hydrogen
E.g. Reaction between calcium and ethanoic acid forming calcium ethanoate and hydrogen
Ca (s) + 2CH3COOH (aq) ---> Ca(CH3COO)2 (aq) + H2 (g)
Carboxylic acids react with bases to form salt and water (neutralization)
E.g. Ethanoic acid reacts with sodium hydroxide to form sodium ethanoate and water.
CH3COOH (aq) + NaOH (aq) ---> CH3COONa (aq) + H2O(g)
Carboxylic acids react with carbonates and bicarbonates to form salt, carbon dioxide and
hydrogen.
E.g. Ethanoic acid reacts with sodium carbonate to form sodium ethanoate and water.
2CH3COOH (aq) + Na2CO3 (aq) ---> 2CH3COONa (aq) + CO2 (g) + H2O (g)
ESTERIFICATION
Ester is organic compound made from carboxylic acid and alcohol with the removal of one
molecule of water.
We can add sodium hydroxide and heat mixture to obtain carboxylic acid and alcohol from ester -> This is HYDROLYSIS.
Synthetic Macromolecules
ADDITION POLYMERISATION
small molecules (monomers) join together to form one molecule as the only product.
Another ethene molecules add to this unsaturated compound during polymerisation to form
bigger compound.
Repeat unit is the simplest part of the polymer which is repeated many times to form the
polymer.
We take the repeat unit to write the simplified formula of the polymer, where n is a large number.
From this repeat unit, to find the monomer formula, we add double bond between C C and
remove the bonds on each of their sides.
CONDENSATION POLYMERISATION
The joining of monomers together to form polymers along with the elimination of water molecules.
Nylon --> Dicarboxylic acid and diamine undergo condensation polymerisation to form nylon.
Terylene --> Dicarboxylic acid (acid with 2 COOH groups) and diol (alcohol with 2 OH groups)
undergo condensation polymerisation to form terylene
Terylene is used in fabrics as it is strong, resists stretching and sinking and doesnt crumple when
washed.
non-biodegradable they cannot be decomposed by bacteria --> Therefore, many plastic waste
will pollute the Earth
produce toxic gas (such as hydrogen chloride) when burnt and this contributes to acid rain.
Plastics that require CFC during production may contribute to global warming when the CFC is
allowed to escape.
Natural Macromolecules
a. Carbohydrates
Starch can also be broken down into glucose by heating with sulfuric acid. This is HYDROLYSIS.
b. PROTEINS
Only that their monomers are only amino acids joined together.
Proteins can also be broken down into amino acids by boiling protein with sulfuric acid.
c. FATS
Only that their monomers consists of glycerol and fatty acids; different from terylene.
Fats can also be broken down to sodium salts of fatty acids and glycerol by boiling it with an acid
or alkali. - This is HYDROLYSIS.
MCQ
1. Which physical property of the alkanes does not increase as relative molecular mass increase?
a. boiling point
b. flammability
c. melting point
d. viscosity
2. In the polymerization of ethene to form polyethene, there is no change in
a. boiling point
b. density
c. mass
d. molecular formula
3. Which polymer has the same type of linkage between its monomers as in a fat?
a. polyamide
b. polyester
c. protein
d. starch
4. Cholesterol is an organic molecule that occurs in the blood stream. Which type of compound is
cholesterol?
a. acid
b. alcohol
c. alkane
d. alkene
5. Which of the following can best be used to distinguish between ethane and ethene?
a. lighted splint
b. aqueous bromine
c. limewater
d. litmus solution
6. Methane is used as a fuel. What property is essential for this use?
a. it burns exothermically
b. it is a gas
c. it is odourless
d. it has a low boiling point
7. All the members of a homologous series have the same
a. empirical formula
b. general formula
c. molecular formula
d. physical properties
8. Yeast can be used to convert simple sugars to
a. ethanoic acid and oxygen
b. ethanol and carbon dioxide
c. ethanol and oxygen
d. starch and carbon dioxide
9. Which type of reaction occurs when soap is formed from fats?
a. hydrolysis
b. polymerisation
c. fermentation
d. substitution
10. Octane is an alkane present in petrol. What are the products when octane is completely
burned in air?
a. carbon dioxide and hydrogen
b. carbon dioxide and water
c. carbon monoxide and water
d. carbon monoxide, carbon dioxide, and water
11. Which compound, on combustion, never forms soot.
a. carbon monoxide
b. ethanol
c. ethene
d. methane
12. What is produced when ethanol is boiled with an excess of acidified potassium
dichromate(VI)?
a. ethane
b. ethanoic acid
c. ethene
d. ethyl ethanoate
13. Which of the following is not made from crude oil?
a. aircraft fuel
b. diesel oil
c. furniture polish
d. margarine
14. Which of the following is an ester?
a. pvc
b. soap
c. starch
d. terylene
15. Starch can be broken down into smaller molecules by heating with a dilute acid. What is this
type of reaction called?
a. cracking
b. fermentation
c. hydrolysis
d. reduction
16. A margarine is described as 'high in polyunsaturates'. What does this type of margarine
contain?
a. long chain alkane molecules
b. many alkene molecules joined by addition polymerization
c. molecules containing many C=C bonds
d. polymer molecules with -O=C-N-H- linkages
17. Vinegar is a solution of ethanoic acid made by the reaction of ethanol with air. Which gas in air
takes part in this reaction?
a. carbon dioxide
b. nitrogen
c. oxygen
d. water vapour
18. When must a substance be an alkane?
a. when it burns easily in air or in oxygen
alcohol
a. ethanoic
butanol
b. ethanoic
propanol
c. propanoic
propanol
d. propanoic
butanol
b. 1, 2, and 4
c. 2 and 4
d. 3 and 4
31. Which polymer has the empirical formula CH?
polymer formed by
a.
carbohydrate
condensation polymerization
b.
ester
addition polymerization
c.
hydrocarbon
addition polymerization
d.
polyester
condensation polymerization
39. Which of the following describes the ways in which isomers are identical and different?
identical
different
a.
chemical properties
molecular formulae
b.
molecular formulae
structures
c.
physical properties
chemical properties
d.
structure
molecular formulae
40. When an animal fat is boiled with aqueous sodium hydroxide, a soap and glycerol are formed.
This reaction is an example of
a. esterification
b. fermentation
c. hydrolysis
d. polymerization
41. In which chemical reaction does the named product formed have a lower molecular mass than
the reactant?
a. formation of an ester from ethanol
b. formation of ethanoic acid from ethanol
c. formation of ethanol from glucose
d. formation of ethanol from glucose
42. In the polymerisation of ethene to form poly(ethene), which does not change?
a. boiling point
b. density
c. empirical formula
d. molecular mass
43. Why are large alkane molecules cracked to form smaller molecules?
a. alkanes with large molecules are not useful
50.
a.
respiration
reduction
acidification
b.
respiration
oxidation
hydrogenation
c.
cracking
oxidation
neutralisation
d.
combustion
oxidation
esterification
51. Cracking is a common process in the petroleum industry. Which of the following gives the
most appropriate explanation for carrying out cracking?
a. It forms more useful fractions for commercial use.
b. There is too much of the heavier fraction of petroleum present.
c. It is easier to form useful fuel fractions through this means than through fractional distillation of
petroleum.
d. The reaction is exothermic.
MCQ Answers
1. b
2. c
3. b
4. b
5. b
6. a
7. b
8. b
9. a
10. b
11. a
12. b
13. d
14. d
15. c
16. c
17. c
18. c
19. c
20. b
21. a
22. a
23. a
24. a
25. c
26. b
27. a
28. d
29. d
30. c
31. d
32. b
33. d
34. c
35. b
36. b
37. c
38. b
40. c
41. d
42. c
43. d
44. a
45. b
46. d
47. a
48. a
49. b
50. d
51. a
substance
ethanoic acid
ethanol
ethyl ethanoate
eater
relative molecular
mass Mr
60
46
88
18
a. In an experiment, 3.0g of ethanoic acid and 4.6g of ethanol were heated together with a catalyst.
i. how many moles of ethanoic acid were used?
ii. how many moles of ethanol were used?
iii. which reactant (ethanol or ethanoic acid) was in excess?
iv. what mass of ethyl ethanoate would be made if there was 100% conversion?
v. in an experiment, only 2.20g of ethyl ethanoate were obtained. What was the percentage yield of
ethyl ethanoate?
b. Propanoic acid has the following structural formula.
Draw the structural formula of the ester formed when propanoic acid reacts with ethanol.
Solution
1ai. amount of acid used = 3.0/60 = 0.05 mole
1aii. amount of ethanol used = 4.6/46 = 0.1 mole
1aiii. ethanol
1aiv. amount of ester produced = 0.05 mole
2. Ethanol, C2H5OH is used in Brazil as a liquid fuel instead of gasoline (petrol). The ethanol is
manufactured by a fermentation process from sugar cane.
ai. describe how cane sugar can be converted into ethanol by the process of fermentation.
aii. what is the name of the gas produced during this fermentation? How would you test for this
gas?
b. When ethanol is completely burnt in air, it forms carbon dioxide and water. One mole of ethanol
will release 1370 kJ of heat energy during this reaction.
i. Construct the balanced equation for the burning of ethanol.
ii. The mass of 1 litre of ethanol is 780 g. How much heat energy will be released when 1 litre
3
b. The molecular formula of oleic acid is C17H31CO2H. How many double bonds between carbon
atoms are present in one molecule of oleic acid? Explain your answer.
Solution
4ai. reagent: sodium carbonate
observation: effervescence. Gas turns limewater milky.
4aii. An unsaturated compound is one that contains multiple bonds eg double bonds
4aiii. reagent: bromine
observation: the brown color of bromine is discharged
4b. number: 2
Explain: If oleic acid does not contain C=C double bond, its formula should be C17H35CO2H
(CnH2n+1CO2H). Since its formula has 4 hydrogen less than 33, it should therefore contain 2 double bonds.
5. The structure of fluorochloroethane is shown below
a. Suggest a name for, and sketch the structure of, the macromolecule formed when
fluorochloroethene polymerizes.
b. When 20 tonnes of fluorochloroethene polymerised, 18 tonnes of the polymer were obtained.
Calculate the percentage yield.
c. Name and give a use for a commercially available polymer containing a halogen.
Solution
5a. poly(fluorochloroethene)
5b. Theoretically, 20 tonnes of products should be obtained. Therefore % yield = 18/20 x 100% = 90%
5c. polyvinylchloride (PVC). It is used as plastics.
6. Ethyne, C2H2, burns in oxygen to give a very hot flame. The temperature is so high that the
flame can be used to cut metal.
ai. Name the two products of the complete combustion of ethyne.
aii. Describe a chemical test for one of these products
b. Calcium carbide, CaC2, is a greyish-white solid. Ethyne can be made by the reaction of calcium
carbide with water. Calcium hydroxide, Ca(OH)2 is the other product of the reaction.
i. Construct an equation, including state symbols, for the reaction between carlcium carbide and
water.
ii. The mixture obtained after this reaction was tested using Universal Indicator. What was the final
color of the Universal Indicator? Explain your answer.
Solution
6ai. carbon dioxide and water
6aii. Bubble the gas through limewater. A white precipitate would be observed
6bi. CaC2 (s) + 2H2O (l) --> Ca(OH)2 (aq) + C2H2 (g)
6bii. Blue. Ca(OH)2 is alkaline.
7a. The following terms are used in the description of organic compounds.
alcohol
amide
alkane
hydrocarbon
alkene
polymer
From this list, choose two terms which can be applied to each of the compounds below.
i. methane
ii. hexene
iii. poly(ethene)
iv. nylon
b. One of the general characteristics of homologous series is that all the members can be
represented by a general formula.
i. What is the general formula of the alkene series?
ii. Give one other general characteristics of homologous series.
Solution
7ai. alkane, hydrocarbon
7aii. alkene, hydrocarbon
7aiii. alkane, polymer
7aiv. amide, polymer
7bi. CnH2n
7bii. The members show similar chemical reactions.
8a. Heptane is an alkane with seven carbon atoms per molecule. It is a colorless liquid with a
boiling point of 100C.
i. deduce the molecular formula of heptane
ii. suggest two tests you could use to decide whether a colorless liquid was heptane or water.
Predict the results of the tests for both heptane and water.
b. Fructose is a carbohydrate. One form of fructose has the following structure.
8ai. C7H16
8aii. test 1: add anhydrous copper(II) sulphate
heptane: solid copper(II) sulphate remains white and insoluble
water: solid turns blue and then dissolves to give a blue solution
test 2: ignite with a flame
heptane: burns with a luminous flame
water: the flame dies off
8bi. C6H12O6
8bii. The molecular formula seems to suggest 6 units of carbon, and hydrogen and oxygen in the ratio 2:1
just like water C6(H20)6 ie. hydrate of carbon.
8biii. glucose
9a. Hydrogen can be manufactured by the reaction between methane and steam.
i. Name a source of the methane required for this reaction.
ii. Give the equation for this reaction between methane and steam.
iii. Calculate the maximum volume of hydrogen, measured at r.t.p. which can be obtained from 16g
of methane.
b. Margarine is manufactured using the addition reaction between hydrogen and a vegetable oil.
i. state the conditions used for this reaction
ii. what type of bond must be present in the vegetable oil for this reaction to take place?
c. The diagram represents the structure of a common plastic.
i. Name this plastic and draw the structure of the monomer from which it is made.
ii. This plastic is non-biodegradable. Explain the meaning of this term and describe the problems
which this property creates.
d. If this plastic is burned, a thick, black smoke and a very acidic gas are produced.
i. suggest the identity of the black particles in the smoke
ii. suggest the identity of the very acidic gas.
Solution
12. Ethanol, CH3CH2OH is a liquid fuel. Ethanol can be manufactured either from glucose
C6H12O6or from ethene.
a. Briefly describe the manufacture of ethanol from glucose. Include the balanced equation in your
answer.
bi. Draw the displayed formula for ethene
bii. Name the substance that reacts with ethene to make ethanol
biii. Give the conditions needed for this reaction.
Solution
12a. Yeast cells are added to a solution of glucose. The mixture is kept at 18-20C under anaerobic
conditions. Glucose will be broken down by zymase enzyme in yeast cells to form ethanol and carbon
dioxide. Ethanol is obtained by fractional distillation of the mixture.
C6H12O6 --> 2C2H5OH + CO2
12bi.
12bii. steam
12biii. 300C, 70 atmospheric pressure and phosphoric acid catalyst
13. Styrene-butadiene rubber is a synthetic rubber. It is made by polymerising a mixture of the
monomers butadiene and styrene.
a. What type of polymerization will take place when the monomers polymerise? Explain.
One possible structure for the polymer is shown below.
b. Give the full structural formula for the repeating unit in this polymer structure.
c. When the mixture of styrene and butadiene polymerises, the polymer is unlikely to contain only
this regular, repeating pattern. Explain why.
Butadiene can be made by cracking butane in a cracking tower.
di. Butane cracks to form butadiene and one other product. Write an equation to show this
reaction.
dii. Give a use of the other product of this reaction.
e. 2.90kg of butane entered the cracking tower. After the reaction, 2.16kg of butadiene had been
made. Calculate the percentage yield of butadiene.
Solution
13a. Addition polymerization. Addition polymerization is the joining together of two or more simple
molecules, called monomers, to form a long chain compound without any loss of small molecules. The
addition polymerization process can only occur when the monomer molecule is unsaturated (contain
double bonds or triple bonds)
13b.
13c. Since two different monomers are mixed together before being polymerized the chain will have the
different monomers distributed randomly along its length. Let styrene monomer be A and butadiene
monomer be B. One possible random distribution is
-A-A-B-A-B-B-A-B-A-A-B-B-B-ASometimes the same type of monomers may be polymerised to form short chains and then these chains
mixed and further addition polymerization occurs. For eg.
14ai. Heat the carboxylic acid with alcohol ethanol using a few drops of concentrated sulphuric acid as
catalyst.
14aii.
14bi. Place about 2cm of each acid in separate test tubes. Add a few drops of silver nitrate solution to
each test tube. A white precipitate will be observed in the test tube containing hydrochloric acid.
14bii. Dilute hydrochloric acid is a strong acid and ethanoic acid is a weak acid. Dilute HCl dissociates
fully in water whereas a weak acid dissociates partially in water to form hydrogen ions, H
+
Ethanoic acid dissociates partially in water to form a solution containing H ions. There are more acid
+