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Period 3 & Group 2 Selected Properties

Multiple-choice Questions
1. Which of the following statements about the Period 3 oxides (from sodium to chloride) is true? A The bonding between the molecules becomes covalent across the period. B Silicon dioxide reacts with hydrochloric acid and sodium hydroxide. C Magnesium oxide readily dissolves in water. D Sodium oxide dissolves forming a solution with the highest pH. 2. An oxide of X dissolves in water forming a solution Y which readily absorbs carbon dioxide gas. X can form Y because X A is very reactive with water. B has very negative standard reduction potential. C forms a cation with a high charge density. D has many valence electrons. 3. Which of the following about Group 2 elements is true? A Beryllium chloride is ionic. B Barium sulphate is insoluble in water. C The nitrates when heated form nitrogen dioxide gas and metal oxides. D Barium has high charge density. 4. Which of the following oxides does not dissolve in water? A SO2 C Al2O3 B SiO2 D P4O10 5. Which of the following electronic configuration of elements is most likely to react with steam than water? A 1s22s22p63s1 C 1s22s22p63s23p1 2 2 6 2 B 1s 2s 2p 3s D 1s22s22p63s23p2

Structured Question
1. (a) Strontium is below calcium in the Periodic Table. (i) Write the valence electronic configuration of strontium atom. (ii) State how strontium reacts with water and write the equation for the reaction. (iii) Write the equation for the heating of strontium nitrate. State whether strontium nitrate has a higher thermal stability compared to calcium nitrate. (b) The oxides of aluminium and sulphur have different physical and chemical properties. (i) State one difference in the physical properties of both of them. (ii) Write equations for the reactions if any, of the oxides of these elements with aqueous acid and aqueous alkali.

Essay Question
1. (a) Describe the combustion in oxygen of sodium and phosphorus, writing equations for both reactions. (b) The oxides of sodium, silicon and phosphorus differ in their reactions with water. Write equations for the reactions and explain the difference in the reactions by referring to their structure and bonding. (c) Explain how you would differentiate two separate test tubes, one containing magnesium chloride and the other, barium chloride. State the reagent, observation and write equations for both.
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ANSWER
CHAPTER 1 Period 3 & Group 2 Selected Properties
Multiple-choice Questions 1. D Sodium oxide, Na2O is basic. It dissolves readily in water forming an alkaline solution, NaOH, which has a very high pH. 2. B X is a basic oxide as it dissolves in water to form an alkaline solution which absorbs the acidic gas, carbon dioxide. X must have a very negative standard reduction potential as it is a very strong reducing agent. 3. B The sulphates of Group 2 elements are insoluble going down the group. 4. C Aluminium oxide is amphoteric. Therefore it does not dissolve in water due to its covalent nature. 5. B Group 2 element, magnesium has its oxide reacting with steam rather than water. Structured Question 1. (a) (i) 5s2 (ii) Strontium reacts vigorously with water liberating hydrogen gas. Sr + 2H2O Sr(OH)2 + H2 (iii) 2Sr(NO3)2 2SrO + 4NO2 + O2 Strontium nitrate has a higher thermal stability than calcium nitrate. (b) (i) Aluminium oxide has a high melting point but sulphur dioxide has a low melting point. (ii) Aluminium oxide is amphoteric. It reacts with both acid and alkali. Al2O3 + 6HCl 2AlCl3 + 3H2O Al2O3 + 2NaOH + 3H2O 2NaAl(OH)4 Sulphur dioxide is an acidic gas. It reacts only with alkali. SO2 + 2NaOH Na2SO3 + H2O Essay Question 1. (a) When burning sodium metal is lowered in a jar with excess oxygen, sodium glows more brightly with a yellow flame, a yellow substance, sodium peroxide, an ionic compound is formed and in limited oxygen supply, sodium oxide is formed. Both the oxides are basic. 2Na(s) + O2(g) Na2O2(s) 4Na(s) + O2(g) 2Na2O(s) Phosphorus burns readily in air to form acidic oxides. White phosphorus burst into flames in the presence of oxygen. In the presence of excess oxygen, phosphorus pentoxide, P4O10 is formed. In a limited supply of oxygen, phosphorus trioxide, P4O6 is formed. Both the oxides are acidic. P4(s) + 5O2(g) P4O10(s) P4(s) + 3O2(g) P4O6(s) (b) Sodium peroxide and sodium oxide are basic oxide. They have giant ionic lattice structures. The bonds are ionic and they are easily broken when dissolved in water. The reaction is exothermic so the heat released is enough to break the bonds. Sodium peroxide readily dissolves in water forming sodium hydroxide (an alkaline solution) and hydrogen peroxide whereas sodium oxide dissolves in water forming an alkaline solution and water. Na2O2 + 2H2O 2NaOH + H2O2 Na2O + 2H2O 2NaOH + H2O P4O10 is a simple covalent molecule with weak van der Waals forces between them. It readily dissolves in water forming an acidic solution. P4O10 + 6H2O 4H3PO4 Silicon dioxide exists as giant covalent molecules with strong Si O covalent bonds. These bonds do not break in water, hence they are insoluble in water. (c) Add dilute sulphuric acid to both the test tubes and shake them. A white precipitate will form in the test tube that contains barium chloride as barium sulphate is insoluble in water but no precipitate will form with magnesium chloride as magnesium sulphate is soluble in water. MgCl2 + H2SO4 MgSO4(aq) + 2HCl BaCl2 + H2SO4 BaSO4(s) + 2HCl

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Group 13 - Aluminium

Multiple-choice Questions
1. The element that does not belong to Group 13 of the Periodic Table is A boron C gallium B aluminium D rubidium 2. Which metal is protected by a layer of its own oxide? A Al C Au B Ag D Fe 3. Which of the following does not affect aluminium? A Oxygen C Alkali B Pure water D Acid 4. Cryolite is used in the electrolytic extraction of aluminium A to obtain pure aluminium. C to lower the melting point of bauxite. B to protect the anode. D as a reducing agent. 5. Most of the chemical properties of aluminium is due to the strong polarising power of Al3+ ion. From the following characteristics seen in aluminium compounds, which one cannot be explained by the polarising power factor? A High lattice energy of aluminium fluoride B The covalent characteristics seen in aluminium chloride bonding C The ability of the Al3+ ion to form complex compound D High hydration energy of Al3+ ion 6. In the manufacture of aluminium through the electrolysis process, the electrolyte is made up of a mixture containing cryolite, Na3AlF6, with aluminium oxide, Al2O3. One theory suggests that the reaction between the two compounds takes place as shown below. Na3AlF6 + Al2O3 3Al3+ + 3Na+ + 3O2 + 6F The above reaction equation shows that A aluminium oxide behaves as an acid. B aluminium oxide behaves as a base. C aluminium oxide and cryolite undergo redox reactions. D cryolite helps aluminium oxide to form ions. 7. Although aluminium is a very reactive metal, as shown by its standard redox potential value of 1.66 V, it is able to withstand corrosion. Which of the following statements below explains the above observation? A Al3+ ion has a high charge density. B Aluminium atoms are closely-packed. C Aluminium forms an oxide layer on its surface. D Aluminium forms an amphoteric compound.

Structured Questions
1. (a) Aluminium chloride, Al2Cl6, is produced when aluminium reacts with chlorine gas. (i) Draw the structural formula for aluminium chloride. (ii) Write a balanced equation for the above reaction. (iii) State one use of aluminium chloride. (b) If 1.0 g of aluminium is used in the reaction in (a)(ii), 2.3 g of aluminium chloride will be produced. Calculate the percentage of product formed.
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(c) Explain the following statements: (i) Aluminium chloride sublimes at 180 C. (ii) The aqueous solution of aluminium chloride shows acidic characteristics. 2. (a) Aluminium hydroxide is precipitated out when carbon dioxide gas is allowed to flow through an aluminate solution. (i) Write an equation to represent the precipitation of aluminium hydroxide. (ii) Write an equation to show the heating of aluminium hydroxide. (b) Aluminium can be obtained from aluminium oxide by electrolysis method. (i) What is the electrolyte used? (ii) What is the function of the electrolyte. (iii) What are the ions which will carry electrical charges during the electrolysis of aluminium oxide?

Essay Question
1. (a) With reference to the physical and chemical characteristics of the aluminium ion, describe the characteristics of the aluminium salt aqueous solution. (b) Explain the following using correct equations. (i) Reaction between anhydrous aluminium chloride with water. (ii) Why aluminium carbonate cannot be prepared from a solution containing Al3+ ions.

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ANSWER
CHAPTER 2 Aluminium
Multiple-choice Questions 1. D Rubidium is in Group 1. The others are in Group 13. 2. A Al is protected from corrosion by Al2O3. 3. B Aluminium does not react with pure water at room temperature. 4. C Cryolite lowers the melting point of pure bauxite from 2000 C to 900 C. 5. A High lattice energy of aluminium fluoride is due to high ionic charge and also small size of fluoride ion. 6. D 7. C Aluminium reacts with air to form a protective layer of aluminium oxide, Al2O3 on its surface. Structured Questions 1. (a) (i) Cl Al Cl Al
H2O

ions. The complex ions react with water and forms H3O+ ion. [Al(H2O)6]3+ + H2O [Al(H2O)5OH]2+ + H3O+ 2. (a) (i) 2[Al(OH)4] + CO2 2Al(OH)3 + CO32 + H2O (ii) 2Al(OH)3 Al2O3 + 3H2O (b) (i) Cryolite / Sodium hexafluoroaluminate (ii) To decrease the melting point of aluminium oxide so that electrolysis can be carried out at a lower temperature. (iii) Al3+, O2

Essay Question 1. (a) Al3+ ion is surrounded by six molecules of H2O forming [Al(H2O)6]3+ complex ion.
H2O OH2 Al OH OH2 2 OH2
3+

Cl

Cl Cl Cl (ii) 2Al + 3Cl2 Al2Cl6 (iii) As catalyst (b) From the equation 2Al + 3Cl2 Al2Cl6 2 mol Al produces 1 mol Al2Cl6 54 g Al produces 267 g Al2Cl6 1.0 1.0 g Al produces 267 54 = 4.94 g Al2Cl6 2.3 % of product = 100% = 46.6% 4.94 (c) (i) Aluminium chloride gas has strong covalent bonding within the molecule but weak van der Waals forces of attraction between molecules. (ii) The aqueous solution of aluminium chloride contains [Al(H2O)6]3+ complex

The Al3+ ion has a high charge and a small size, therefore the charge density is high. This causes Al3+ ion to have high polarising power, enabling it to pull the electrons from water molecules and weakening the O H bond in water. The H+ ion can be easily released causing the aqueous solution containing Al3+ ion to be acidic. (b) (i) Anhydrous Al2Cl6 is hydrolysed in water to form a cation [Al(H2O)6]3+ Al2Cl6 + 12H2O 2[Al(H2O)6]3+ + 6Cl (ii) CO32 is a strong base so the following reaction occurs. [Al(H2O)4(OH)2]+ + CO32 Al(H2O)3(OH)3 + HCO3

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Group 14 C, Si, Ge, Sn, Pb

Multiple-choice Questions
1. When CO2 gas is passed through limewater, a white precipitate of CaCO3 is formed. If an excess of CO2 is passed through, the white precipitate dissolves because A as more and more CO2 gas dissolves, the solution becomes increasingly acidic, hence CaCO3 changes to CaHCO3 which is soluble. B as more and more CO2 gas dissolves, the solution becomes increasingly acidic and CaCO3 will decompose. C as more and more CO2 gas dissolves, a soluble complex is formed. D the precipitate CaCO3 will react with an excess of CO2 to form CaO. 2. Muscovite, KAl2(Si3Al)O10(OH)2, is a type of mica which can be broken into thin layers. What type of force holds the thin layers together in muscovite? A Electrostatic force of attraction C Hydrogen bonds between layers B Van der Waals forces of attraction D Metallic bonds between layers 3. The advantages of ceramic over iron and steel are as follows except that A the density of ceramic is lower. B ceramic is an electrical conductor. C ceramic cannot be oxidised. D ceramic is less brittle. 4. The table below shows a few types of glass and their uses. Which of the following combination is incorrect?
Glass Use Making normal mirrors, windows, bottles and light bulbs Making decorative glass, prisms and lenses Making laboratory apparatus Making cookware

A B C D

Soda glass Lead glass Borosilicate glass Quartz glass

5. Which industrial use reflect the hardness of diamond and the softness of graphite?
Diamond Graphite Lubricant Pencil lead Electrode Moderator

A B C D

Drill head Insulator Glass cutter Abrasive

Structured Question
1. (a) Elements of Group 14 can react with chlorine to form tetrachlorides. (i) In the table below, name the process (if any) and write the equation for the reaction that has taken place
Reaction with water CCl4 SiCl4 PbCl4
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Reaction equation

(ii) Explain the differences in the reaction with water between the three tetrachlorides. (b) The composition of two types of glass X and Y is shown below.
Type of glass Glass X Glass Y Composition 14% Na2O, 12% CaO, 74% SiO2 5% Na2O, 4% CaO, 17% B2O3, 74% SiO2

(i) Glass X is called soda glass. State the name of glass Y. (ii) State two reasons for the addition of B2O3 to glass Y.

Essay Question
1. (a) What is the relative stability of the +2 oxidation state compared to the +4 oxidation state for the oxides of Group 14 elements when going down the group? (b) (i) Draw the structure of carbon dioxide and silicon dioxide. (ii) Although the bonding in carbon dioxide and silicon dioxide is covalent, carbon dioxide is a gas whereas silicon dioxide is a solid with high melting point. Explain this statement. (c) Write all the formulae for the oxides of carbon and lead and discuss the respective oxides with respect to their (i) acid-base characteristics (ii) redox characteristics Write one reaction equation for each of the above characteristics.

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ANSWER
CHAPTER 3 Group 14 C, Si, Ge, Sn, Pb
Multiple-choice Questions 1. A CO2 + Ca(OH)2 CaCO3 + H2O CaCO3 + CO2 + H2O Ca(HCO3)2 2. B Van der Waals forces exist between the layers of molecules. 3. D Ceramic is not less brittle but more brittle and breaks easily when dropped. 4. D Ouartz glass cannot withstand high temperature hence is not suitable for making cookware. 5. A Hardness of diamond enables the diamond to be used in drill heads. The ability of layers in the graphite to slide over one another gives the soft property of graphite and it is used as a lubricant. Structured Question 1. (a) (i) Reaction with water CCl4 SiCl4 PbCl4 No reaction Hydrolysis Hydrolysis Reaction equation SiCl4 + 2H2O SiO2 + 4HCl PbCl4 + 2H2O PbO2 + 4HCl (b) (i) O=C=O O Si O O Si Si Si (ii) Carbon dioxide is a simple molecule and has weak intermolecular van der Waals forces of attraction. Silicon dioxide has a giant molecular structure. (c) Oxides of carbon: CO, CO2 Oxides of lead: PbO, PbO2 (i) CO is neutral and does not dissolve in water. CO2 is a weak acid which partially dissociates in water to form carbonic acid. CO2 + H2O H2CO3 O

PbO and PbO2 are amphoteric. Both oxides can dissolve in dilute acid and dilute base. PbO + 2H+ Pb2+ + H2O PbO + 2OH + H2O Pb(OH)42 (ii) CO is a strong reducing agent. The +2 oxidation state will easily be oxidised to +4. CO + PbO Pb + CO2 CO2 can behave as an oxidising agent. CO2 + 2Mg C + 2MgO PbO is an oxidising agent. PbO + H2 Pb + H2O PbO2 is also an oxidising agent. PbO2 + C Pb + CO2

(ii) For SiCl4 and PbCl4, the central atom has empty d orbitals which can accept and share the lone pair electrons from O atoms of water molecules. For CCl4, the carbon atom does not have an empty d orbital and the C Cl covalent bond is very strong. (b) (i) Borosilicate glass (ii) To increase the softening level of glass To decrease the thermal expansion coefficient so that the glass does not break even if there is a sudden increase in temperature Essay Question 1. (a) When going down the group, the stability of the +2 oxidation state increases whereas the stability of the +4 oxidation state decreases.

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Group 15 Nitrogen and its Compounds

Multiple-choice Questions
1. Most metals burn readily in oxygen to form metal oxides. However metal nitrites are only formed when metal reacts with nitrogen at high temperature. Which of the following best explains this phenomenon? A Nitrogen atom has a stable half-filled p orbital in its electron arrangement. B Nitrogen has very high atomisation energy. C Oxygen is more electronegative than nitrogen. D Oxygen has more valence electrons than nitrogen. 2. Which of the following compounds of nitrogen has an odd electron? A NO2 C HNO3 B NH3 D N2O4 3. Which of the following shows the bonding in nitrogen dioxide? A N C N O B O N O O D O O N O O

4. Carbon and nitrogen both form dioxides. Which of the following is true of both carbon dioxide and nitrogen dioxide? A Both are linear molecules. B Both are non-polar molecules. C Both dissolve in sodium hydroxide solution. D Both central atoms achieve the octet electronic configuration. A Only 1 is correct B Only 1 and 2 are correct C Only 2 and 3 are correct D 1, 2 and 3 are correct

5. Nitrogen dioxide exists in equilibrium with its dimer, nitrogen tetroxide in the following equation: 2NO2(g) N2O4(g) The intensity of brown colour decreases when the temperature is lowered. Which of the following statements is/are true of the equilibrium? 1 The dimerisation of nitrogen dioxide is exothermic. 2 The equilibrium of the reaction shifts to the left with increased temperature. 3 The equilibrium of the reaction shifts to the right with increased pressure. 6. When excess aqueous ammonia is added to copper(II) ions solution, a dark blue solution is formed. What is the role of ammonia in this reaction? 1 As ligand 3 As a Bronsted-Lowry base 2 As a Lewis base

Structured Question
1. Nitrogen forms three common oxides: nitrogen oxide, nitrogen dioxide and dinitrogen tetroxide. (a) Name the oxides of nitrogen that have an unpaired electron at the central atom. (b) Name the oxides that have delocalisation of electrons between the N atom and the O atom.
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(c) Name the oxide that is formed in the internal combustion of automobiles. Write a balanced equation showing its formation. (d) Name the oxide that dissolves in rain water to produce acid rain. Write a balanced equation for the formation. (e) Name the oxide that is formed when ammonia reacts with oxygen in the presence of a catalyst. Write an equation for the formation.

Essay Question
1. (a) Nitrogen gas is the major component in atmospheric air. However, relatively few compounds exist as nitrides compare to oxides. Explain this phenomenon. (b) The oxides of nitrogen cause environmental pollution. (i) Identify one oxide of nitrogen that causes acid rain. (ii) Identify one oxide of nitrogen that causes photochemical smog. Explain how these oxides of nitrogen cause pollution. Illustrate your answer with balanced equations.

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ANSWER
CHAPTER 4 Group 15 Nitrogen and its Compunds
Multiple-choice Questions 1. B Nitrogen gas has triple covalent bond between two nitrogen atoms, N N. Hence it has a very high atomisation energy. 2. A Lewis structure of NO2 N O O 3. D Resonance occurs in NO2 N N N O O O O O O 4. C Structure of CO2 and NO2 are as follows: N O=C=O O O Structured Question 1. (a) (b) (c) (d) (e) NO, NO2 NO2, N2O4 NO; N2 + O2 2NO NO2; 2NO2 + H2O HNO2 + HNO3 NO; 4NH3 + 5O2 4NO + 6H2O

Essay Question 1. (a) Nitrogen gas is relatively inert compared to oxygen gas. This is because the two N atoms in nitrogen gas are held by a very strong triple bond. The N N bond has very high bond energy / very short bond length. Furthermore, the nitrogen molecule is linear and non-polar. A lot of energy is required to dissociate N2 molecule / very high atomisation energy to produce N atoms for reaction. (b) (i) NO2, nitrogen dioxide causes acid rain. NO2 dissolves in rain water to produce nitrous acid and nitric acid. 2NO2 + H2O HNO2 + HNO3 4NO2 + 2H2O + O2 4HNO3 (ii) NO2, nitrogen dioxide causes photochemical smog. Ultraviolet light causes the formation of oxygen radical from nitrogen dioxide. NO2(g) NO(g) + O(g) The oxygen radical produced then reacts with oxygen molecule to form ozone molecule. O(g) + O2(g) O3(g) The ozone combines with nitrogen dioxide and the unsaturated hydrocarbon from incomplete combustion of fuels to form smog.

CO2 can dissolve in water to form acidic solution, H2CO3. NO2 can dissolve in water to form acidic solution, HNO3. Hence both CO2 and NO2 can react with NaOH to form salts. 5. D When the temperature is lowered, NO2 which is a brown gas, dimerises to form N2O4. When N2O4 absorbs heat, it dissociates to NO2. Dimerisation of NO2 to form N2O4 loses heat (exothermic). Increased temperature shifts equilibrium to the left to absorb heat. Increased pressure shifts equilibrium to the right to decrease the pressure by decreasing the number of moles of gases. 6. B A complex ion [Cu(NH3)4]2+ is formed. Lone pair of electrons on N of NH3 is shared with Cu2+ ion, hence NH3 acts as a ligand and Lewis base.
2+

H3N Cu H3N

NH3 NH3

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Group 17: Cl, Br, I

Multiple-choice Questions
1. Astatine is the last member of Group 17 elements. Which of the following statements is true? A Astatine has the lowest melting point compared to other halogens. B Astatine is the strongest oxidising agents compared to other halogens. C Hydrogen astatide, HAt, is a colourless gas. D Silver astatide is soluble in dilute ammonia solution. 2. NaClO3 is obtained by heating NaClO. 3NaClO 2NaCl + NaClO3 What are the oxidation states of these chlorine compounds?
NaClO NaCl +1 +1 1 1 NaClO3 +5 +7 +5 +7

A B C D

1 1 +1 +1

3. Which of the following hydrides decomposes most easily when heated? A HF B H Cl C H Br D HI 4. Which of the following is not produced when potassium iodide is heated with concentrated sulphuric acid? A SO3 C I2 B NaHSO4 D HI 5. Which of the following chlorine compounds is a covalent molecule? A BaCl2 C AgCl B AlCl3 D KClO3 A Only 1 is correct B Only 1 and 2 are correct C Only 2 and 3 are correct D 1, 2 and 3 are correct

6. Which of the following property / properties decrease(s) on descending Group 17 from chlorine to iodine? 1 The boiling points of the halogens 2 The electronegativity of the halogens 3 The oxidising power of the halogens

Structured Question
1. (a) When chlorine is passed into an aqueous solution of sodium hydroxide, the smell of chlorine disappears. (i) Explain why the smell of chlorine disappears. (ii) Write an equation for the reaction. (iii) How do you classify this type of reaction?
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(b) When a red-hot platinum wire is placed inside a gas jar of hydrogen iodide, violet fumes are produced. (i) Explain the observation. (ii) Write an equation for the reaction. (iii) How do you classify this type of reaction?

Essay Question
1. Explain the following: (a) The reactivity between hydrogen and halogens decreases in the order: Cl2 > Br2 > I2 (b) When chlorine is passed into sodium iodide solution, the solution turns brown. (c) Concentrated sulphuric acid is not suitable for the preparation of hydrogen bromide from sodium bromide.

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ANSWER
CHAPTER 5 Group 17: Cl, Br, I
Multiple-choice Questions 1. C Hydrogen halides, HF, HCl, HBr and HI are all colourless gases. 2. C 3. D The longer the bond length, the weaker the bond. 4. A H2SO4 is reduced to SO2 and not SO3. 5. B Metal chlorides are usually ionic compounds. AlCl3 is covalent and exists as Al2Cl6 at room conditions. 6. C Structured Question 1. (a) (i) The chlorine gas is converted to the salts, sodium chloride and sodium chlorate(I), which are odourless. (ii) Cl2(g) + 2NaOH(aq) NaCl(aq) + NaClO(aq) + H2O(l) (iii) This is a disproportionation reaction. Chlorine is simultaneously oxidised to ClO and reduced to Cl. (b) (i) At temperatures above 200 C, H I bonds break to form hydrogen and the violet fumes of iodine. (ii) 2HI(g) H2(g) + I2(g) (iii) This is a thermal decomposition reaction. Essay Question 1. (a) Under suitable conditions, hydrogen reacts with halogens to form hydrogen halides. H2(g) + X2(g) 2HX(g) This is a redox reaction. The halogens oxidise hydrogen to hydrogen halides. The order of reactivity decreases on descending the group because the oxidising power of the halogens decreases as the sizes of the halogens increase. (b) When chlorine is passed into sodium iodide solution, the solution turns brown because chlorine oxidises iodide ions to iodine. Aqueous sodium iodide is colourless but aqueous iodine is brown. Cl2(g) + 2NaI(aq) 2NaCl(aq) + I2(aq) (c) When concentrated sulphuric acid reacts with sodium bromide, hydrogen bromide is produced. NaBr(s) + H2SO4(l) NaHSO4(s) + HBr(g) But concentrated sulphuric acid is also an oxidising agent. HBr is oxidised by concentrated sulphuric acid to form bromine. 2HBr(g) + H2SO4(l) Br2(g) + 2H2O(l) + SO2(g) So, instead of getting hydrogen bromide, a mixture of gases is produced.

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Introduction to the Chemistry of d-block Elements

Multiple-choice Questions
1. Which of the following does not indicate the properties of a transition element? A Iron reacts with dilute acid to liberate hydrogen gas. B Oxides of iron include FeO and Fe2O3. C Iron is used in the manufacture of ammonia. D A blood red colouration is formed when potassium thiocyanate is added to ferric chloride solution. 2. Which of the following statements is correct regarding transition elements? A All transition elements exhibit oxidation states of +1 to +7. B All transition elements have more than one valency. C All transition elements have completely filled 4s orbitals. D All transition elements react with dilute acid to produce hydrogen gas. 3. Which one of the following elements exhibits only one oxidation state in its compounds? A Copper B Titanium C Tin D Scandium 4. A bidentate ligand always A has bonds formed to two metal ions. B has a charge of +2 or 2. C forms complex ions with a charge of +2 or 2. D has two donor atoms. 5. Which one of the following best explains why water is a monodentate ligand? A The oxygen atom in a water molecule has only one lone pair of electrons that can be used to form a coordinate bond to a metal ion. B Each hydrogen atom in a water molecule has only one electron to form a coordinate bond to a metal ion. C The oxygen atom in a water molecule has two lone pairs of electrons but both pairs are used to form a single coordinate covalent bond to a metal atom. D The oxygen atom in a water molecule has two lone pairs of electrons but the second lone pair is not close enough to a second coordination site to form a coordinate bond. 6. What are the oxidation number and coordination number in the coordination compound, [Cu(en)(NH3)2]Cl2?
Oxidation number Coordination number 2 2 4 6

A B C D

+1 +2 +2 +2

7. When a concentrated solution of NH3 is added to a solution containing Zn(NO3)2, a colourless solution containing the complex ion Zn(NH3)42+ results. Which of the following best explains why this solution is colourless? A The 3d orbitals are full, thus cannot be split. B The 3d orbitals on the Zn atom are completely filled, thus, an electron cannot be transferred between the split 3d orbitals.
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C The Zn atom does not have any 4s electrons, thus an electron cannot be transferred between the split 4s orbitals. D The Zn atom does not have any unpaired electrons which are necessary in order to transfer an electron between the split 3d orbitals. 8. When solid CoCl2 is dissolved in water, the following equilibrium is established: Co(H2O)62+(aq) + 4Cl (aq) CoCl42(aq) + 6H2O(l)

In aqueous solution, the Co(H2O)62+ ion is pink and the CoCl42 ion is blue. Which of the following best describes what will happen when a concentrated solution of HCl is added to the CoCl2 solution without changing the volume significantly? A The colour of the CoCl2 solution will not change because the solution of HCl is colourless. B The colour of the solution will become blue. C The shape of Co(H2O)62+ is octahedral whereas the shape of CoCl42 is tetrahedral. D The number of unpaired electrons in Co(H2O)62+, but not CoCl42, will change because HCl is a strong acid. A Only 1 is correct B Only 1 and 2 are correct C Only 2 and 3 are correct D 1, 2 and 3 are correct

9. Which of the following reactions show(s) the formation of complex ion by the replacement of ligand? 1 [Pb(OH)2]2 + 2H2O2 PbO2 + 2H2O + 2OH 2 [Cu(H2O)4]2+ + 4NH3 [Cu(NH3)4]2+ + 4H2O 3 [Fe(H2O)6]3+ + SCN [Fe(SCN)(H2O)5]2+ + H2O 10. The hexaaquairon(III) ion hydrolyses as shown below. [Fe(H2O)6]3+ + H2O [Fe(H2O)5OH]2+ + H3O+

Which of the following statements about the above equilibrium is/are correct? 1 The corresponding iron(III) ion [Fe(H2O)5OH]2+ is less likely to undergo hydrolysis. 2 The iron ion undergoes a change in oxidation state. 3 The above hydrolysis is favoured under low pH conditions.

Structured Questions
1. Copper exhibits oxidation states of +1 and +2 in its compound. (a) Write the electronic configuration for Cu2+ ion and Cu+ ion. (b) Explain why hydrated copper(II) sulphate is coloured whereas copper(I) sulphate is white. (c) In aqueous solutions, Cu+ disproportionates to Cu2+ and Cu. (i) What do you understand by the term disproportionation? (ii) Write an equation to show the disproportionation of Cu+ in water. 2. (a) Complete the table.
Ion Number of electrons in the 3d subshell Number of unpaired electrons Colour of the aqueous ion Ti3+ Co2+ Cu2+

(b) The metals platinum, rhodium and palladium are transition metals that are used in catalytic converters to reduce pollution from vehicle exhausts. State and explain the role of these transition elements in this process.
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Essay Questions
1. (a) Explain what do you understand by the term stability constant? (b) When ammonia is added to a solution of nickel(II) sulphate, the solution turned from green to pale blue. Discuss the stability constant of the complex [Ni(NH3)6]2+. (c) When aqueous ammonia is gradually added to aqueous copper(II) sulphate, a blue precipitate is formed initially but dissolves in excess aqueous ammonia to give a deep blue solution. This deep blue solution lightens considerably on the addition of an aqueous solution of EDTA. Explain the observations as fully as you can. 2. (a) Two common oxidation states of chromium are +3 and +6. (i) Explain why Cr 6+(aq) ion does not exist but Cr(VI) exists as CrO42 and Cr2O72 ions. (ii) Explain with an equation, the effect of acid on the aqueous chromate(VI) ion. (b) (i) Use the standard electrode potential values from the Data Booklet to discuss the oxidation of Cr 3+ to dichromate(VI) ions by hydrogen peroxide. (ii) This oxidation of Cr 3+ by hydrogen peroxide is more satisfactorily achieved under alkaline conditions. Use your equation in (b)(i) to suggest why alkaline conditions are used.

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ANSWER
CHAPTER 6 Introduction to the Chemistry of d-block Elements
Multiple-choice Questions 1. A Other metals besides transition metals react with dilute acids to liberate hydrogen gas. 2. B Transition elements have electrons which can be removed from s orbitals and also d orbitals hence they have variable oxidation states and more than one valency. 3. D Scandium is a d-block element but it is not a transition element. It shows only one oxidation state, +3 in the Sc3+ ion. 4. D A bidentate ligand has two lone pairs of electrons on two donor atoms for sharing with central metal ion. 5. D Water molecules has two lone pairs of electrons in a tetrahedron shape orbital, hence the second lone pair of electrons is too far away (big angle) to form another coordinate bond with the central metal ion. 6. C The compound has the following structure
NH3 en C Cu NH3
2+

(c)

(i) Disproportionation is a reaction in which a substance is both oxidised and reduced simultaneously. (ii) 2Cu+ Cu + Cu2+ Co2+ 7 3 Cu2+ 9 1

2. (a) Ion Ti3+ 1 Number of electrons in the 3d subshell 1 Number of unpaired electrons Colour of the aqueous ion Violet

Pink Blue

(b) These transition metals act as heterogeneous catalysts. Dative or coordinate bonds can be formed as these metals have empty d orbitals to allow adsorption to take place. Essay Questions 1. (a) Stability constant, K, is the equilibrium constant for the formation of the complex ion from its constituent ions/atoms/molecules. The higher the K value, the more stable the complex. M(aq) + nL [MLn] K = n [M][L] MLn(aq)

2 Cl

7. B

8. B

9. C

10. A

Oxidation number of Cu = +2 Coordination number = 4 Valence electronic configuration of Zn2+ ion is 3d10. In the complex ion, the split 3d orbitals are completely filled, hence there is no transfer of electrons between the split energy levels of 3d orbitals. When HCl is added to CoCl2 solution, the Cl from HCl reacts with Co(H2O)62+(aq) to form the blue complex CoCl42. In 1, the oxidation state of Pb charges from 0 to +4, it is a redox reaction. In 2 and 3, the ligands H2O in the complexes are replaced by ligands NH3 and SCN. Hence 2 and 3 are correct. Fe2+ has a lower charge density hence less likely to undergo hydrolysis (1 is correct). Fe is still in +3 oxidation state in [Fe(H2O)6OH]2+ (2 is incorrect). If the pH is low, equilibrium is shifted to the left and hydrolysis is depressed (3 is incorrect).

at constant temperature (b) When ammonia is added to nickel(II) sulphate, equilibrium occurs. [Ni(H2O)6]2+(aq) + 6NH3(g) green [Ni(NH3)6]2+(aq) + 6H2O(l) pale blue [Ni(NH3)62+] K = [Ni(H2O)62+][NH3]6 K is the stability constant for [Ni(NH3)6]2+ complex ion. The change of colour from green to pale blue shows that the [Ni(NH3)6]2+ complex ion has a high stability constant and that the equilibrium lies to the right. NH3 is a stronger ligand than H2O. [Ni(NH3)6]2+ is more stable than [Ni(H2O)6]2+. (c) CuSO4 dissolves in water forming a blue coloured solution of [Cu(H2O)6]2+. When aqueous ammonia is added to copper(II) sulphate solution, a light blue precipitate Cu(OH)2 is formed. Cu2+(aq) + 2OH Cu(OH)2(s) The light blue precipitate Cu(OH)2 dissolves in excess ammonia to form [Cu(NH3)4]2+ complex ion which is soluble in water to give a deep blue solution.

Structured Questions 1. (a) Cu2+ : 1s22s22p63s23p63d 9 Cu+: 1s22s22p63s23p63d10 (b) The 3d orbitals of Cu+ are all fully filled. Hence no d-d transition can take place. However, the 3d orbitals of Cu2+ are not fully filled and d-d transition can occur.
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Cu(OH)2(s) + 4NH3(aq) [Cu(NH3)4]2+(aq) + 2OH(aq) When an aqueous solution of EDTA is added to the copper complex, the deep blue solution of [Cu(NH3)4]2+ turns lighter due to formation of the lighter coloured Cu(EDTA)2 complex ion. [Cu(NH3)4]2+(aq) + EDTA4(aq) [Cu(EDTA)]2(aq) + 4NH3(aq) The reaction shows the displacement of weaker NH3 ligand by the stronger EDTA4 ligand. This implies that the [Cu(NH3)4]2+ complex is less stable than the [Cu(EDTA)]2 complex. 2. (a) (i) Cr 6+ ion has very high charge density. Formation of Cr 6+ requires very high ionisation energy that results in high instability.

CrO42 and Cr2O72 have delocalised bonding, thus are more stable. (ii) 2H+ + 2CrO42 Cr2O72 + H2O In acidic condition, CrO42 converts to Cr2O72. (b) (i)
H2O2(aq) + 2H+ + 2e 2H2O(l); E red = +1.77 V 2Cr3+(aq) + 7H2O(l) Cr2O72(aq) + 14H+(aq) + 6e ; E ox = 1.33 V 2Cr3+(aq) + 3H2O2(aq) + H2O(l) Cr2O72(aq) + 8H+(aq); Ecell > 0

Cr3+ is oxidised to Cr2O72 while H2O2 is reduced to H2O. (ii) In alkaline condition, the hydrogen ion produced will be removed by the alkali. The equilibrium will shift to the right. Oxidation of Cr3+ would be easier.

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19

The Chemistry of Carbon

Multiple-choice Questions
1. One mole of a hydrocarbon produces four moles of water when burnt in excess oxygen. The formula of the hydrocarbon is A CH3CH2CH3 C CH3CH = CH2 B CH3CH2CH2CH3 D CH3C6H4CH3 2 When 60 cm3 of a hydrocarbon were burnt completely in oxygen, 240 cm3 of carbon dioxide and 0.0125 mol of water were produced. What is the molecular formula of the hydrocarbon? (The volumes of all gases were measured at room conditions. The molar volume of any gas at room conditions is 24.0 dm3) A C2H6 C C3H6 B C3H8 D C4H10 3. The compound R has the structural formula shown below.
OCH3 C=O

The functional group present in R is A carboxylic acid B aldehyde

C ester D ketone

4. What is the bond angle of the C C C bonds in CH3C CH? A 120 C 107 B 180 D 109.5 5. Which type of isomerism is shown by each of the following organic compounds?
CH3CH = CHCH3 CH3CH(NH2)COOH Geometric Geometric Optical Geometric C2H5CH = CHBr Geometric Optical Geometric Optical

A B C D

Optical Optical Geometric Geometric

A Only 1 is correct

B Only 1 and 2 are correct

C Only 2 and 3 are correct

D 1, 2 and 3 are correct

6. The reaction between hydroxide ion and the organic compound, R X can be represented by the equation R X + OH R OH + X where R is the alkyl group and X is an electronegative element. In the above reaction, the hydroxide ion acts as a 1 Bronsted-Lowry base 2 Lewis base 3 nucleophile
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7. Which of the following hydrocarbons contain(s) delocalised electrons? CH3 1

2 3

CH3 C C CH3 C(CH3)4

8. Two compounds with the molecular formula, C2H2Br2, are expected to 1 exhibit structural isomerism 2 exhibit cis-trans isomerism 3 exist in d- and l- forms

Structured Question
1. Limonene has a lemon odour and is found in oils from citrus fruits. The structural formula of limonene is shown below.
CH3

C CH3 CH2

(a) (b) (c) (d)

Write the displayed formula of the limonene molecule. Write (i) the empirical formula, (ii) the molecular formula of limonene. What type of stereoisomerism is shown by limonene? In which ways are the isomers (i) similar to each other, (ii) different from each other?

Essay Question
1. (a) The mass spectrum of a straight chain hydrocarbon shows the main peaks at m/e 56, 29, 27, 15. The percentage composition (by mass) of the hydrocarbon is as follows. C = 85.7% H = 14.3 %

Write the structural formula of a hydrocarbon that can give the results described above. Explain your answer. (b) The pKa values for three carboxylic acids are given below.
Compound Benzoic acid 4-methylbenzoic acid 4-nitrobenzoic acid pKa 4.20 4.34 3.43

Explain the relative strengths of these acids.

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ANSWER
CHAPTER 7 The Chemistry of Carbon
Multiple-choice Questions 1. A CxHy 4H2O Hence, y = 8 2. D Step 1 Calculate the number of carbon atoms per molecule of hydrocarbon 60 cm3 of CxHy produces 240 cm3 CO2. 240 That is, 1 mol of CxHy produces 60 = 4 mol of CO2. 1 molecule of CxHy contains 4 carbon atoms. Step 2 Calculate the number of hydrogen atoms per molecule of hydrocarbon 60 60 cm3 of CxHy contains 24 1000 = 0.0025 mol of CxHy. 0.0025 mol CxHy produces 0.0125 mol H2O. 1 mol of CxHy produces 5 mol of H2O. 1 molecule of CxHy contains 10 hydrogen atoms. Step 3 Formula of hydrocarbon Formula of hydrocarbon is C4H10. 3. C The structural formula can be written as C6H5COOCH3. The ester group is COO. Thus R is methyl benzoate. 4. B The carbon atom in the C C bond uses sp hybrid orbitals for bond formation. Hence, the three carbon atoms are arranged linearly. 5. C 6. C + R X + OH R OH + X OH is a nucleophile and attacks the alkyl group which has low electron density. A nucleophile is also a Lewis base. OH ion does not act as a Bronsted-Lowry base in this reaction because it does not accept a proton from RX. 7. A Only benzene ring contains delocalised electrons. 8. B H H H Br Structural isomerism C = C C = C Br Br H Br H H H Br Cis-trans isomerism C=C C=C Br Br Br H cis trans
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Structured Question 1. (a)


H H H C C C C H H H H H

C H H C H * C H H C C H H

C H

(i) C5H8 (ii) C10H16 (c) Limonene has a chiral carbon, *C. Hence it exhibits optical isomerism. (d) Limonene exists as d- and l-forms. (i) Similarity Both the d- and l-forms have the same molecular and structural formulae. They have the same physical and chemical properties. (ii) Difference The d-form rotates the plane of planepolarised light to the right. The l-form rotates the plane of planepolarised light to the left. Essay Question 1. (a) Empirical formula from composition by mass Element Number of moles C 85.7 12 = 7.14 1 H 14.3 1 = 14.3 2

(b)

Simplest ratio

Empirical formula is CH2. Molecular formula from mass spectrum: Mr as shown in the mass spectrum = 56 nCH2 = 56 14n = 56; n = 4 Molecular formula is C4H8. Fragments from mass spectrum m/e 29 : C2H5+ m/e 27 : CH = CH2+ m/e 15 : CH3+ Structural formula: CH3CH2CH = CH2. (b) The smaller the pKa value, the stronger the acid. Thus, the acid strength increases in the order: 4-methylbenzoic acid < benzoic acid < 4-nitrobenzoic acid 4-methylbenzoic acid is a weaker acid than benzoic acid because the methyl group is electron-donating (+I effect). The methyl

group destabilises the carboxylate anion by increasing the charge density of oxygen atom in the C O bond. This makes the loss of proton more difficult. Thus the acid strength decreases.

4 nitrobenzoic acid is a stronger acid than benzoic acid because the nitro group is electron-withdrawing (I effect). The nitro group stabilises the carboxylate ion and thus the acidity increases.

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23

Hydrocarbons

Multiple-choice Questions
1. A mixture containing a little ethane and a large quantity of bromine gas is exposed to ultraviolet light. Which of the following bromoalkanes is the principle product of reaction? A CH3CH2Br C BrCH2CH2Br B CH3CHBr2 D CBr3CBr3 2. The following hydrocarbons are isomers of hexane. Which of these isomers has the lowest boiling point? A (CH3)2CHCH(CH3)2 C CH3CH2CH(CH3)CH2CH3 B (CH3)2CHCH2CH2CH3 D C2H5C(CH3)3 3. 10 cm3 of methane and 10 cm3 of ethane were mixed with excess oxygen and the mixture was exploded. After cooling to room temperature, the residual gases were passed through aqueous sodium hydroxide. What was the volume of gas absorbed by aqueous sodium hydroxide? A 15 cm3 C 25 cm3 B 20 cm3 D 30 cm3 4. When X (a gas) reacts with Y, a mixture of CH2BrCH2Br and CH2BrCH2OH are produced. X and Y are probably
X Y Bromine water Sodium bromide solution Ethene Ethene

A B C D

Ethene Ethene HBr(g) Br2 vapour

5. The enthalpies of hydrogenation of cyclohexene and 1,3-cyclohexadiene are given below.


+ H2 + 2H2 cyclohexane ; H1 = 120 kJ mol1 cyclohexane ; H2 = 232 kJ mol1

The enthalpy of hydrogenation when 1 mol of benzene reacts with three moles of hydrogen is A (3 120) kJ mol1 C 208 kJ mol 3 1 B ( 232 ) kJ mol D 152 kJ mol1 2 A Only 1 is correct B Only 1 and 2 are correct C Only 2 and 3 are correct D 1, 2 and 3 are correct

6. The relative molecular mass of a hydrocarbon, P, is 54. 0.25 g of Q required 207.4 cm3 of hydrogen at s.t.p. for complete hydrogenation. The structural formula of P could be 1 CH2 = CH CH = CH2 2 CH3C C CH3 3 CH2 C = CH2 CH2
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7. Which of the following reagents react(s) with benzene by addition reaction? 1 Concentrated sulphuric acid 2 Hydrogen gas in the presence of nickel at 150 C 3 Chlorine in the presence of ultraviolet light 8. When a monosubstitued benzene, products obtained are as follows:
X E X
and

X, reacts with an electrophile, E+, the major organic

The substituent, X, may be 1 NH2 2 COCH3 3 NO2

Structured Question
1. Essential oil is a natural oil with a distinctive scent produced by certain plants. Geraniol and linalool are found in many essential oils. They are used as flavouring agents and in perfumes. The structural formulae of geraniol and linalool are shown below. (CH3)2C = CHCH2CH2C(CH3) = CHCH2OH geraniol (CH3)2C = CHCH2CH2C(CH3)(OH)CH = CH2 linalool (a) The IUPAC name for geraniol is 3,7-dimethyl-2,6-octadien-1-ol. Explain why it is named this way. (b) Based on your explanation given above, suggest the IUPAC name of linalool. (c) Give two similarities and one difference between geraniol and linalool in terms of their structures. (d) Geraniol reacts with bromine in CCl4 in the absence of sunlight to form an organic compound. What is the molecular formula of this organic compound? (e) Would you expect linalool to have any effect on plane-polarised light? Why?

Essay Question
1. (a) State three ways in which (i) cyclohexane is similar to hexane, (ii) cyclohexane is different from hexane. (b) (i) 1,1,1-trichloroethane is used in liquid paper as a solvent. Write the displayed formula of this compound. Name and write the structural formula of an isomer of 1,1,1-trichloroethane. (ii) State two ways in which the isomers are similar to each other. (c) Outline the steps for the conversion of benzene to (i) (chloromethyl)benzene, (ii) benzoic acid.

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ANSWER
CHAPTER 8 Hydrocarbons
Multiple-choice Questions 1. D With a little bromine, the main product is CH3CH2Br. With a little ethane but a large amount of bromine, CH3CH2Br produced undergoes further bromination. The main product is therefore CBr3CBr3. 2. D The greater the number of side chains, the smaller the surface area of the hydrocarbon molecule and the smaller the attractive forces between the molecules. 3. D CH4 + 2O2 CO2 + 2H2O 7 C2H6 + O2 2CO2 + 3H2O 2 Volume of CO2 = 10 + (2 10) = 30 cm3 4. A Bromine water contains Br2 and HOBr. CH2 = CH2 + Br2 CH2BrCH2Br CH2 = CH2 + HOBr CH2OHCH2Br 5. C The actual structure of benzene is considerably more stable than the Kekule structure of three carbon-carbon double bonds. Hence the enthalpy of hydrogenation of benzene is lower (less exothermic) than ( 3 120) kJ mol1. It is slightly lower than the enthalpy of hydrogenation of 1,3-cyclohexadiene but not as low as 152 kJ mol1. 207.4 6. B 207.4 cm3 of H2 = = 9.26 103 mol 22 400 0.25 Number of moles of P = = 4.6 103 54 Thus, P contains two double bonds or one triple bond. 7. C The reaction between fuming sulphuric acid and benzene is electrophilic substitution. 8. A The NH2 group is ortho- and para-directing. Structured Question CH3 CH3 1. (a) CH3 C = CHCH2CH2C = CHCH2OH
8 7 6 5 4 3 2 1

(c) Similarities Both geraniol and linalool have two carboncarbon double bonds and one OH group per molecule. Both have the same molecular formula, C10H18O. Difference They differ in the positions of double bonds and OH group, that is, they have different structural formulae. Hence, they are structural isomers. (d) Molecular formula of geraniol is C10H18O. C10H18O + 2Br2 C10H18OBr4 CH3 CH3 (e) CH3 C = CHCH2CH2C* CH = CH2 OH Linalool contains a chiral carbon atom. It is therefore optically active and will rotate the plane of polarised light. Essay Question 1. (a) (i) Cyclohexane and hexane are saturated hydrocarbons. They have similar chemical reactions. They both have six carbon atoms per molecule. (ii) Cyclohexane is a cyclic hydrocarbon but hexane is a straight chain hydrocarbon. The general formula of cyclohexane is CnH2n. The general formula of hexane is CnH2n+2. Cyclohexane and hexane have different physical properties such as boiling point and density. (b) (i) Cl H Cl C C H Cl H 1,1,1-trichloroethane Cl Cl HCCH Cl H 1,1,2-trichloroethane (ii) They have the same molecular formula, C2H3Cl3. They have similar chemical properties (c) (i) Step 1 Conversion of benzene to methylbenzene by FriedelCrafts reaction

3,7-dimethyl means two methyl groups at C3 and C7. 2,6 octadien- means an alkene with two double bonds at C2 and C6 in the longest continuous chain of eight carbon atoms. 1-ol means an alcohol (OH) group at C1. (b) CH3 CH3 CH3 C = CHCH2CH2C CH= CH2 8 7 6 5 4 3 1 2 OH 3,7-dimethyl-1,6-octadien-3-ol
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+ CH3Cl

AlCl3

CH3 + HCl

+ CH3Cl

AlCl3

CH3

+ HCl

Step 2 Chlorination of side chain


CH3 + Cl2
uv

Step 2 Oxidation of side chain to benzoic acid


CH3 + 3[O]
acidified KMnO4

CH2Cl + HCl

COOH + H2O

(ii) Step 1 Conversion of benzene to methylbenzene by FriedelCrafts reaction

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Haloalkanes

Multiple-choice Questions
1. Three haloalkane compounds are shown below. CH3 CH3CCH3 Cl III

CH3CH2CH2CH2Cl

CH3CHCH2CH3 Cl II

Which sequence shows the haloalkanes arranged in ascending order of their boiling points? A I < II < III C III < II < I B II < I < III D II < III < I 2. Chloroethane, C2H5Cl, and bromoethane, C2H5Br, are hydrolysed by aqueous potassium hydroxide to form ethanol. Which combination shows correctly the more reactive compound and the reason for the reactivity?
More reactive compound Reason Higher relative molecular mass C Br bond is weaker C Cl bond is more polar Chlorine is a stronger oxidising agent

A B C D

Bromoethane Bromoethane Chloroethane Chloroethane

3. When CH3CH(Br)CH3 reacts with cyanide ions, compound X is formed. What is the compound formed when dilute sulphuric acid is added to X? A (CH3)2CHCN C CH3CH2COOH B (CH3)2CHCOOH D CH3CH2CH2COOH 4. An aromatic compound X has the molecular formula C8H9Cl. When X is heated with acidified potassium manganate(VII) solution, compound C8H6O4 is formed. X is A C
CH2CH2Cl CH3CH2 Cl

B
CH3 CH2Cl

D Cl

CH3 CH3

5. The structure of 3-methyl-3-pentanol is shown below. OH CH3CH2 C CH3 CH2 CH3 Which of the following compounds can be used to prepare 3-methyl-3-pentanol? O A CH3MgBr and CH3CH2 C CH3
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O B CH3CH2MgBr and CH3CH2 C CH3 O C CH3CH2CH2MgBr and CH3 C CH3 O D CH3CH2MgBr and CH3CH2 C CH2CH3 6. Which of the following reagents can be used to differentiate between chloropropane and iodopropane? A Aqueous potassium hydroxide C Ethanolic silver nitrate B Ethanolic sodium hydroxide D Chlorine gas 7. (Chloromethyl)benzene reacts with aqueous potassium hydroxide according to the following equation.
CH2Cl + OH CH2OH + Cl

What reaction mechanism is involved in the reaction? A Nucleophilic substitution reaction C Electrophilic substitution reaction B Nucleophilic addition reaction D Electrophilic addition reaction 8. The rate equation for the hydrolysis of a haloalkane P is as follows. Rate = k [P] [OH] Which haloalkane could be P? A CH3CH2CH2CH2Br B CH3CHCH3 Br C CH CH CHBrCH
2 2 3

D (CH3)3CBr 9. Which haloalkane can be used as a refrigerant? A CCl4 C CH3CH2CH2Cl B CF2Cl2 D CHCl
2

Structured Question
1. (a) A compound Z has the following composition by mass. C, 29.76 %; H, 4.18 %; Br, 66.06 % (i) Determine the empirical formula of Z. (ii) Given that the relative molecular mass of Z is 242, determine the molecular formula of Z. (iii) Draw the structural formula of an alkene that can be used to prepare Z and name the alkene. (b) Chlorofluorocarbons are organic compounds that act as pollutants in the environment. (i) Name a typical chlorofluorocarbon. (ii) State one property of the chlorofluorocarbon named in (b)(i) and one use related to this property. (iii) Chlorofluorocarbons dissociate in the presence of light. Write an equation to show the photochemical dissociation of the compound in (b)(i).

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Essay Question
1. A haloalkane has the molecular formula of C4H9Br. (a) Write the structural formulae of four isomers with the molecular formula C4H9Br. (b) One of the isomers from (a) reacts with ethanolic sodium hydroxide to form three compounds with the molecular formula C4H8 according to the following equation. C4H9Br + NaOH C4H8 + NaBr + H2O (i) Identify the isomer that reacts in this reaction. (ii) Give the IUPAC name of the three compounds with the molecular formula C4H8 that can be obtained in this reaction. (c) Another isomer in (a) reacts with NaOH(aq) according to the following equation. C4H9Br + NaOH C4H9OH + NaBr (i) Explain why haloalkanes can be attacked by the OH ion. (ii) Identify the isomer that would give the highest rate of reaction when reacted with aqueous sodium hydroxide solution. Give a reason for your answer. Write the reaction mechanism for this isomer. (d) Which isomer in (a) shows optical isomerism? Identify the chiral carbon with *.

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ANSWER
CHAPTER 9 Haloalkanes
Multiple-choice Questions 1. C I is a straight chain molecule with the largest size and highest boiling point. III is a branched chain molecule with the smallest size and lowest boiling point. 2. C Cl is more electronegative than Br. Hence chloroethane is more reactive because of the C Cl bond being more polar than C Br bond. H H 3. B CH3 C CH3 + CN CH3 C CH3 + Br Br CN H H H+ CH3 C CH3 + H2O CH3 C CH3 CN COOH B 4. B
CH3 CH2Cl + [O]
X

Structured Question 1. (a) (i) C3H5Br (ii) C6H10Br2 (iii) Structural formula: Name: Cyclohexene (i) Dichlorodifluoromethane (ii) Property : Low boiling point Use : As refrigerant (iii) CCl2F2 CF2Cl + Cl

(b)

Essay Question 1. (a) Isomers of C4H9Br: CH3CH2CHCH3 Br CH3CH2CH2CH2Br

HOOC

COOH

C8H6O4

O
+

5. B CH3CH2 C+ CH3

CH3CH2MgBr

6. C

7. A

8. A

9. B

OH CH3CH2 C CH3 CH2CH3 Chloropropane reacts with ethanolic silver nitrate to produce AgCl (white precipitate). Iodopropane reacts with ethanolic silver nitrate to produce AgI (yellow precipitate). OH ion is a nucleophile. It replaces Cl in the molecule hence the reaction mechanism is nucleophilic substitution reaction. The rate equation shows the reaction is second order, depending on the concentration of P and OH ion in the slow, rate-determining step. P is a primary haloalkane, CH3CH2CH2CH2Br. CFC (chlorofluorocarbon) compound, CF2Cl2 can be used as a refrigerant.

OMgBr H2O, H+ CH3CH2 C CH3 hydrolysis CH2CH3

CH3CHCH2Br CH3 (b) (i) CH3CH2CHCH3 Br (ii) 1-butene, cis-2-butene, trans-2-butene (c) (i) The C Br is polar with the carbon atom being partially positive, thus it can be attacked by OH ion, which is a nucleophile. Br (ii) CH3CCH3 reacts with the highest rate of CH3 reaction. This is because the reaction occurs via a more stable carbonium ion. Mechanism (CH3)3CBr is a tertiary haloalkane. It reacts via nucleophilic substitution SN1 reaction. CH3 CH3 slow CH3 C Br CH3 C+ + Br CH3 CH3 tertiary carbonium ion CH3 CH3 fast CH3 C+ + OH CH3 C OH CH3 CH3 * (d) CH3CH2CHCH3 Br

Br CH3CCH3 CH3

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10

Hydroxy Compounds

Multiple-choice Questions
1. Which of the following compounds will produce an alkene in hydration? A (CH3)3COH C CH OH
2

OH

OH CH3

2. Which of the following is the major product formed when 2-butanol is refluxed with concentrated sulphuric acid at 140 C? A CH3CHCHCH3 B CH2CHCH2CH3 C CH3CH2CH2CH2 O CH2CH2CH2CH3 D CH3CH2CH(CH3) O (CH3)CHCH2CH3 3. Which of the following compound has the highest solubility in water? A CH3CH2CH2CH2OH C (CH3)3COH B CH3CH2CH(OH)CH3 D OH 4. Which sets of reagents can be used to prepare phenyl benzoate in the laboratory? A Phenol and benzoic acid B Phenol and sodium benzoate C Phenol and benzoyl chloride D Sodium phenoxide and benzoic acid 5. Which of the following compound is formed when ethanoyl chloride is reacted with
H2N CH2OH OH

A B C

H2N

CH2OCOCH3 OH

H2N

CH2OH OCOCH3

H2N

CH2OCOCH3 OCOCH3

D CH CONH 3

CH2OCOCH2 OCOCH3

A Only 1 is correct

B Only 1 and 2 are correct

C Only 2 and 3 are correct

D 1, 2 and 3 are correct

6. Which of the following compound(s) can react with ethanoic acid to produce an ester? 1 C6H5COCl 2 C6H5OH 3 C6H5CH2OH
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7. Vanillin is the active ingredient of vanilla and has the following formula:
HO CH3O CHO

Which of the following is/are true of vanillin? 1 Produce hydrogen gas with sodium metal 2 Produce an orange precipitate with 2,4-dinitrophenyl hydrazine 3 Produce a yellow precipitate with aqueous alkaline iodine

Structured Question
1. C4H10O forms two alcoholic isomers A and B as follows: A: CH3CH2CH2CH2OH and B: (CH3)3COH (a) Draw the structural formulae of two other alcoholic isomers of C4H10O besides A and B. (b) Give a chemical test that can be used to distinguish A from B. (c) Draw the structural formulae of the products formed from A and B respectively when they are reacted with concentrated sulphuric acid at 170 C. (d) Compound C is the alcoholic isomer of C4H10O that is optically active. Give a chemical test that can be used to distinguish A from C.

Essay Question
1. (a) 3-methyl-1-butanol is a primary alcohol. Name and draw the structural formulae of three primary alcohols that are isomers of 3-methyl-1-butanol. Identify the isomer that is optically active and mark the chiral centre. (b) The ester formed from the reaction of 3-methyl-1-butanol and ethanoic acid has a flavour of ripe pears. (i) Draw the structural formula of the ester formed. (ii) State the condition used in the laboratory for the preparation of this ester. (iii) Name another chemical that can replace ethanoic acid to produce the same ester. (c) Predict the reaction that will take place when 3-methyl-1-butanol is reacted with (i) sodium metal (ii) phosphorous pentachloride (iii) concentrated sulphuric acid at 170 C. (iv) acidified potassium dichromate(VI)

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ANSWER
CHAPTER 10 Hydroxy Compounds
Multiple-choice Questions 1. A Aliphatic alcohol will produce alkene during hydration. CH3 CH3 CH3 C CH3 CH3 C = CH2 + H2O OH 2. D When 2-butanol is refluxed with excess concentrated H2SO4, the major product is alkene. When excess 2-butanol is refluxed with concentrated H2SO4, the major product is ether. conc. H2SO4 2CH3CH2CH CH3 OH H H CH3CH2 C O C CH2CH3 + H2O CH3 CH3 3. A The OH group at the end of the straight chain gives the strongest hydrogen bond between the alcohol and the hydrogen in water hence the highest solubility in water. 4. C Benzoyl chloride, an acyl chloride is very reactive and reacts rapidly with phenol in NaOH solution. 5. D Ethanoyl chloride, an acyl chloride reacts with hydroxyl group, OH to form ester, R C O R. O 6. C 2 and 3 are correct because ethanoic acid reacts with OH group in alcohol and phenol to form ester. 7. B 1 is correct because the OH group reacts with Na to produce hydrogen gas. 2 is correct because the aldehyde group C H reacts with O 2,4-dinitrophenyl hydrazine to produce an orange precipitate. Structured Question 1. (a) CH3CH(OH)CH2CH3, CH2(OH)CH(CH3)2 (b) Heat with acidified potassium dichromate(VI) solution / alkaline potassium manganate(VII) solution. A will change potassium dichromate(VI) from orange to green / potassium manganate(VII) purple to colourless but B has no visible change. CH3CH2CH2CH2OH CH3CH2CH2COOH (c) A will produce CH3CH2CH = CH2. B will produce CH2 = C(CH3)2. (d) Heat with alkaline iodine solution. C will produce a yellow precipitate but A has no visible change. CH3 CH(OH) CH2CH3 CH3CH2COO + CHI3 Essay Question 1. (a) CH3CH2CH2CH2CH2OH (1-pentanol) (CH3)3C CH2OH (2,2-dimethyl-1-propanol) CH3CH2CH(CH3)CH2OH (2-methyl-1-butanol) * CH3CH2CH(CH3)CH2OH is optically active. (b) (i) CH3COOCH2CH2CH(CH3)2 (ii) Reflux with concentrated sulphuric acid (iii) Ethanoyl chloride, CH3COCl (c) (i) H2 gas is released. (CH3)2CHCH2CH2OH + Na (CH3)2CHCH2CH2ONa + H2 (ii) HCl gas is liberated. (CH3)2CHCH2CH2OH + PCl5 (CH3)2CHCH2CH2Cl + HCl + POCl3 (iii) An alkene is produced. (CH3)2CHCH2CH2OH (CH3)2CHCH = CH2 (iv) A carboxylic acid is produced. (CH3)2CHCH2CH2OH + 2[O] (CH3)2CHCH2COOH + H2O
K2Cr2O7/H+ conc. H2SO4 I2 / OH [O]

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11

Carbonyl Compounds

Multiple-choice Questions
1. Propanal, CH3CH2CHO and propanone, CH3COCH3 are isomers. Which pair of characteristics is shown by the mass spectra of the two compounds?
m/e of molecular ion m/e of molecular fragments Different Same Different Same

A B C D

Different Different Same Same

2. Which compound will give a yellow precipitate with alkaline iodine solution? O O A CH3 C OCH3 O B CH3 C OH C CH3 C NH2 O D CH3 C CH2OH

3. The structure of cyclohexanone is shown below.


O

Which statement is true about cyclohexanone? A It is an aromatic ketone. B Its molecular formula is C6H12O. C It can be oxidised to benzoic acid. D It will give a precipitate with 2,4-dinitrophenylhydrazine. 4. A compound Q has the following composition by mass. Carbon, 64.3%; hydrogen, 7.1%; oxygen, 28.6%. Q reduces Fehlings solution to copper(I) oxide. 0.1 mol Q reacts with 4480 cm3 hydrogen gas at s.t.p. with nickel as catalyst. Q is [Relative atomic mass: H, 1; C, 12; O, 16. 1 mol gas occupies 22.4 dm3 at s.t.p.] A CH2 = CHCHO C CH3CH = CHCH = CHCHO B CH CCH2OH D CH3COCH = CHCH = CHOH 5. Citral is used by honeybees as pheromone that attracts other bees. CH3 CH3C = CHCH2CH2C = CHC = O CH3 H Which reagent is decolourised by citral? A Fehlings solution B 2,4-dinitrophenylhydrazine solution C Hot, dilute acidified potassium dichromate(VI) solution D Cold, dilute acidified potassium manganate(VlI) solution
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6. The reaction between cyanide ion and phenylethanone is shown in the equation below.
CN COCH3 + CN C OH CH3

Which statement is true about the reaction? A The CN ion acts as a nucleophile where the N atom on the CN ion donates a lone pair of electrons to a carbon atom in phenylethanone. B The reaction can be carried out by using an acidic solution of sodium cyanide. C The product formed exists as geometric isomers. D The reaction is a nucleophilic substitution reaction. 7. The structure of fructose is given below. HO CH2 C CH CH CH CH2OH O OH OH OH Which statement is not true about fructose? A It has six optical isomers. B It is a reducing sugar. C It exists in equilibrium with a pentagonal ring form. D It forms an orange precipitate with 2,4-dinitrophenylhydrazine solution. A Only 1 is correct B Only 1 and 2 are correct C Only 2 and 3 are correct D 1, 2 and 3 are correct

8. An organic compound gives an orange precipitate with 2,4-dinitrophenylhydrazine but does not form a silver mirror when heated with diamminesilver(I) ions (Tollens reagent). This compound could be 1 C6H5COCH3 3 C6H5CH2CHO 2 C6H5CHO 9. Phenylethanone can be converted to 1-phenylethanol as shown below.
H C CH3 O C OH CH3

Which reagent(s) can be used to perform the above conversion? 1 Sodium in ethanol 3 Hydrogen gas and hot nickel 2 Zinc and dilute hydrochloric acid

Structured Question
1. Lactic acid is found in sour milk. It can be formed from ethanol as shown in the following reaction scheme. OH Step I Step II Step III CH3CH2OH CH3CHO Q CH3 CH C = O HCN OH
lactic acid

(a) In Step I, ethanol is converted to ethanal. (i) State the reagents used in Step I. (ii) Suggest a chemical test that can be used to differentiate between ethanol and ethanal.
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(b) In Step II, ethanal is allowed to react with HCN. (i) Draw the structure of compound Q. (ii) Write an equation for the reaction involved in Step II. (iii) Name the reaction mechanism involved in this reaction. (c) In Step III, compound Q is converted to lactic acid. (i) State the IUPAC name of lactic acid. (ii) State the reagent used in this conversion. (d) Lactic acid exhibits stereoisomerism. (i) Name the type of stereoisomerism shown by lactic acid. (ii) Draw the stereoisomers of lactic acid.

Essay Question
1. A compound P has the molecular formula C4H6O2. P reacts with hydrogen cyanide to give compound Q, C6H8O2N2. P reacts with warm acidified potassium dichromate(VI) to give an acidic compound R, C4H6O3. 2.50 g of compound R was dissolved in 250 cm3 water. 25.0 cm3 of this solution required 24.5 cm3 of 0.10 mol dm3 sodium hydroxide solution for complete neutralisation. (a) (i) Use the molecular formula of R to calculate its relative molecular mass. (ii) Determine the basicity of acid R. (b) Write two structural formulae of compound P. (c) State a chemical test that can be used to distinguish between the two isomers of P in (b). (d) Using any one isomer of P, identify compounds Q and R.

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ANSWER
CHAPTER 11 Carbonyl Compounds
Multiple-choice Objectives 1. C Propanol and propanone have the same molecular formulae, hence m/e of molecular ion will be the same. The structures of propanol and propanone are different, hence the fragments will have different m/e. 2. D Alkaline iodine will react with a ketone which has the CH3 C group. O 3. D Cyclohexanone is a ketone hence it will react with 2,4-dinitrophenylhydrazine to produce a yellow precipitate. 4. A Q reduces Fehlings solution to Cu2O hence Q is an aldehyde with the functional group, CHO. 4480 Number of moles of H2 gas = = 0.2 22 400 0.1 mol Q reacts with 0.2 mol H2 gas. Hence Q contains one double bond, C = C besides the one aldehyde group. 5. D The presence of C = C double bonds in citral causes cold, dilute acidified KMnO4 to be decolourised when the KMnO4 reacts with C = C to form diol, C C . OH OH 6. B Acidic solution of sodium cyanide forms HCN which will react with
COCH3

(i) CH3CH OH CN (ii) CH3CHO + HCN CH3CH(OH)CN (iii) Nucleophilic addition (c) (i) 2-hydroxypropanoic acid (ii) Dilute hydrochloric acid (d) (i) Optical isomerism COOH COOH (ii) (b)
C H3C OH H H C CH3 OH

Essay Question 1. (a) (i) 102 (ii) [R] = 2.50/102 1000/250 = 0.0980 mol dm3 aR + bOH H2O 0.0980 25.0 0.10 24.5 = a b a 1 = b 1 Thus, basicity of R = 1 O O

(b) CH3 C CH2 C H; O O CH3 CH2 C C H (c) Reagent: Iodine + NaOH(aq) Condition: Heat Observation: CH3COCH2CHO gives a yellow precipitate while CH3CH2COCHO does not. OH OH (d) Q: CH3 C CH2 CH; CN CN O O R: CH3 C CH2 C OH

through

nucleophilic addition mechanism. 7. A Fructose does not have six optical isomers. B, C and D are true. 8. A The compound does not react with Tollens reagent, thus it is not aldehyde (2 and 3 are incorrect). 1 is correct because ketone can react with 2,4-dinitrophenylhydrazine to produce an orange precipitate. 9. D The reaction is a reduction reaction. 1, 2 and 3 are correct since all are reducing agents. Structured Question 1. (a) (i) KMnO4/H2SO4 (ii) Ethanal gives an orange precipitate with 2,4-dinitrophenylhydrazine while ethanol does not.

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12

Carboxylic Acids

Multiple-choice Questions
1. When chlorine gas is passed into pure ethanoic acid at 100 C and in the presence of uv light, the organic compound obtained is A ClCH2COOH C CH3CH2Cl B CH3COCl D ClCH2CHO 2. The reaction scheme for the synthesis of the organic compound, Y is shown below: CH3CH2OH X Y
reflux K2Cr2O7/H+ Cl2/uv

The pH values of ethanol, X and Y increases in the order A pKa of ethanol < pKa of X < pKa of Y B pKa of ethanol < pKa of Y < pKa of X C pKa of Y < pKa of X < pKa of ethanol D pKa of X < pKa of Y < pKa of ethanol 3. Which of the following pairs of compounds cannot be used for the preparation of an ester? A Benzoic acid and phenol C Ethanoic acid and 2-propanol B Ethanoyl chloride and phenol D Benzoic acid and ethanol 4. The esterification of ethanoic acid with 2-propanol produces an ester with the formula A CH3COOCH(CH3)2 C CH3CH2COOCH(CH3)2 B CH3COOCH2CH3 D CH3CH2COOCH2CH3 5. The best method to prepare phenyl benzoate is by A refluxing benzoic acid with phenylmethanol. B refluxing benzoic acid with phenol. C mixing benzoyl chloride with phenylmethanol. D mixing benzoyl chloride with phenol dissolved in aqueous sodium hydroxide. 6. What is the molecular formula of benzenedicarboxylic acid and how many structural isomers can this molecular formula have?
Molecular formula Number of structural isomers 3 4 3 4

A B C D A

C7H6O4 C7H8O4 C8H6O4 C8H8O4

B Only 1 and 2 are correct

C Only 2 and 3 are correct


COOH OH

D 1, 2 and 3 are correct

Only 1 is correct

7. The structural formula of an organic compound is shown below.

The organic compound is expected to react with 1 bromine water 2 aqueous sodium carbonate 3 lithium tetrahydridoaluminate(III) in ether
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8. A compound with the formula CH3CH(OH)COOH will 1 act as an alcohol. 2 act as a carboxylic acid. 3 react with hot, concentrated sulphuric acid.

Structured Question
1. (a) The organic compounds, ethanol, phenol, ethanoic acid and benzoic acid, all contain the hydroxyl (OH) group. From this list of compounds, select (i) two compounds which will react with sodium hydrogen carbonate. Write equations to represent these reactions. (ii) one compound which will react with aqueous sodium hydroxide but will not react with sodium hydrogen carbonate. (iii) one compound which will react with sodium metal but will not react with sodium carbonate or sodium hydroxide. (b) Aqueous sodium benzoate can be distinguished from aqueous sodium phenoxide by using hydrochloric acid. (i) Name the organic product formed and describe what you would see in each case. (ii) Describe one chemical test which can be used to distinguish between these two organic products.

Essay Question
1. Methacrylic acid, CH2 = C(CH3)COOH, is used widely to form addition polymers. (a) (i) What is the IUPAC name of methacrylic acid? (ii) How would you prepare methacrylic acid from HOCH2CH(CH3)COOH? (b) Predict the reactions of methacrylic acid with (i) lithium tetrahydridoaluminate(III), (ii) potassium manganate(VII) solution and (iii) sodium. (c) Write the formula of the polymer formed when methacrylic acid polymerises.

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ANSWER
CHAPTER 12 Carboxylic acids
Multiple-choice Questions 1. A Chlorine attacks the alkyl group in ethanoic acid. 2. C X is CH3COOH and Y is ClCH2COOH or Cl2CHCOOH or CCl3COOH. Ethanol is the weakest acid. Hence it has the highest pKa value. Chlorinated ethanoic acid is the strongest acid. Hence, it has the lowest pKa value. 3. A Benzoic acid reacts with ethanol to form ethyl benzoate but benzoic acid does not react with phenol to form phenylbenzoate. Phenylbenzoate is prepared by Schotten-Baumann reaction. H 4. A CH3 C O H + H O C CH3 ethanoic acid CH3 2-propanol O H CH3 C O C CH3 + H2O CH3 5. D C6H5COCl + Na+ O C6H5 C6H5COOC6H5 + NaCl 6. C COOH COOH COOH
COOH COOH COOH

For sodium phenoxide Organic product: Phenol Observation: White emulsion of phenol formed. (ii) Use neutral iron(III) chloride solution. Benzoic acid: Buff-coloured precipitate formed Phenol: Purple solution formed Alternative method Use sodium carbonate solution. Benzoic acid: Effervescence and carbon dioxide gas liberated Phenol: No reaction Essay Question 1. (a) (i) 2-methylpropenoic acid (ii) By dehydration, using concentrated sulphuric acid at 180 C. H CH3 H C C COOH OH H H CH3 H C = C COOH + H2O (b) (i) Reduction to CH2 = C(CH3)CH2OH Comment Lithium aluminium hydride is the source of hydride ion (H) which acts as the nucleophile. Hence, the C = C double bond is not affected because the C = C bond is susceptible to electrophilic attack and not nucleophilic attack. (ii) KMnO4 decolourised. In cold condition, mild oxidation CH3 produces a glycol, CH2 C COOH OH OH

7. D It contains a phenol group. Hence it will react with bromine water. It contains a COOH group. Hence it liberates CO2 from Na2CO3 and is reduced to CH2OH by LiAlH4. 8. D CH(OH) is a secondary alcohol group. COOH is a carboxylic acid group. conc. H2SO4 CH3CH(OH)COOH CH2 = CHCOOH + H2O Structured Question 1. (a) (i) CH3COOH and C6H5COOH 2CH3COOH + Na2CO3 2CH3COONa + H2O + CO2

2C6H5COOH + Na2CO3 2C6H5 COONa + H2O + CO2 (ii) Phenol (C6H5OH) (iii) Ethanol (CH3CH2OH) (b) (i) For sodium benzoate Organic product: Benzoic acid Observation: White precipitate of benzoic acid formed.

On heating, cleavage of the C = C double bond occurs and a mixture of aldehydes, ketones and carboxylic acids are formed. (iii) Hydrogen gas is liberated and CH2 = C(CH3)COONa is formed. (c) H CH3 C Cn ( ) H COOH
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13

Carboxylic Derivatives

Multiple-choice Questions
1. When ethanoyl chloride is added to phenylamine, C6H5NH2, at room temperature, the organic product obtained is A C6H5NHCH3 B C6H5N(CH3)2 C CH3COC6H4NH2 D C6H5NHCOCH3 2. When acylation occurs, the hydrogen atom in the OH group of alcohol is replaced with A R C RCO2 B RCO D RCH2 3. An organic compound, W, is boiled with aqueous sodium hydroxide and the reaction mixture is allowed to cool. Upon cooling, compound X and compound Y (an alcohol) are produced. On acidification, compound X is converted to compound Z (C3H6O2). Compound Y gives a positive triiodomethane (iodoform) test. Compound W is likely to have the structural formula A CH3CH2COOCH3 B CH3COOCH3 C CH3CH2COOCH2CH3 D CH3CH(OH)CH2COCl 4. When ethyl ethanoate, CH3 CO18O C2H5, is hydrolysed with sulphuric acid, the organic product obtained is A CH3CH2COOH B CH3CO18OH C CH3CH2OH D CH3CH218OH 5. The mechanism for the reaction between ammonia and ethanoyl chloride is shown below. O O Cl HNH2 + CH3 C Cl CH3 C Cl CH3 C + Cl + H+ + H+ + H N H2 NH2 O This shows that the mechanism A involves the formation of a planar intermediate. B involves elimination reaction followed by addition reaction. C is a nucleophilic addition reaction. D is a nucleophilic substitution reaction. 6. Calculate the number of isomers (structural and stereo) for the acyl chlorides with the molecular formulae, (i) C4H7OCl, and (ii) C5H9OCl.
C4H7OCl C5H9OCl 3 5 4 5

A B C D
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2 2 3 3

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A Only 1 is correct

B Only 1 and 2 are correct

C Only 2 and 3 are correct

D 1, 2 and 3 are correct

7. Ethanoyl chloride can be used to synthesise 1 CH3COOC2H5 2 CH3COOC6H4COOH 3 C6H5NHCH3 8. When a compound is boiled with aqueous sodium hydroxide, ammonia gas is liberated. The compound(s) is/are likely to be 1 CH3CONH2 2 CH3COONH4 3 CH3CH2CH2NH2

Structured Question
1. With reference to the reaction scheme given below, answer the following questions. X (C2H4O3) 2 mol HCl
oxidation PCl5

Y (C2H2O3) 1 mol HCl


further oxidation

PCl5

Z (C2H2O4) 2 mol HCl (a) State the reagents used for the conversion of X to Y. (b) Suggest the structural formulae for X, Y and Z. (c) State the reagents and conditions required to convert Z to a neutral compound with the molecular formula, C4H6O4. (d) How and under what conditions does Z react with (i) KMnO4, (ii) concentrated H2SO4.

PCl5

Essay Question
1. An ester, X (C9H10O2), is boiled with excess aqueous sodium hydroxide. The solution is then distilled. The distillate contains a neutral organic compound, Y (C8H10O). When Y undergoes mild oxidation, compound Z (C8H8O) is obtained. Compound Z gives a positive triiodomethane test but does not give a precipitate with aqueous solution containing the complex ion, [Ag(NH3)2]+. (a) Name the class of organic compounds to which (i) Z and (ii) Y belong. (b) Hence, write the structural formula for (i) Y, (ii) Z. (c) From your answer in (b), deduce the structural formula of X. (d) How would you expect the residue from the distillation to react with (i) acidified potassium manganate(VII), (ii) concentrated sulphuric acid.

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ANSWER
CHAPTER 13 Carboxylic Derivatives
Multiple-choice Questions 1. D CH3COCl + C6H5NH2 C6H5NHCOCH3 + HCl O 2. B R OH + RCOCl R O C R + HCl 3. C O CH3CH2 C OCH2CH3 + NaOH W CH3CH2COONa + CH3CH2OH Y H+ X CH3CH2COOH Z 4. D In hydrolysis of esters, the acyl-oxygen fission occurs and the 18O isotope is present in the alcohol. O CH3 C 18OC2H5 + H2O CH3COOH + C2H518OH The intermediate is tetrahedral and not planar in shape. NH3 is a nucleophile. Structural isomers of C4H7OCl CH3CH2CH2COCl ; CH3CHCOCl CH3 Structural isomers of C5H9OCl CH3CH2CH2CH2COCl; CH3CH2*CHCOCl; CH3 [This molecule exists as optical (d and l) isomers] CH3 CH3 C COCl ; CH3CHCH2COCl CH3 CH3 CH3COCl + C2H5OH CH3COOC2H5 + HCl CH3COCl + HOC6H4COOH CH3COOC6H4COOH + HCl An amide or an ammonium salt gives ammonia gas when heated with aqueous sodium hydroxide. An amine has no reaction with aqueous sodium hydroxide. CH3CONH2 + NaOH CH3COONa + NH3 CH3COONH4 + NaOH CH3COONa + H2O + NH3 Y is COOH Z is COOH CHO COOH (c) Reagent: Methanol and a little concentrated sulphuric acid as catalyst. Condition: Heat COOH COOCH3 + 2CH3OH + 2H2O COOH COOCH3 (d) (i) When a mixture of Z (ethanedioic acid) and acidified KMnO4 is heated, decolourisation of KMnO4 occurs and ethanedioic acid is oxidised to carbon dioxide and water. 5C2O42 + 2MnO4 + 16H+ 2Mn2+ + 8H2O + 10CO2 (ii) When Z is warmed with concentrated sulphuric acid, dehydration occurs to produce carbon dioxide and carbon monoxide. COOH H2O + CO2 + CO COOH Essay Question 1. (a) (i) Z is a ketone (ii) Y is a secondary alcohol (b) (i) Y is
H CH3 C OH

5. D 6. B

(ii) Z is
O CH3 C

(c) X is
H

C O C CH3

7. B

(d)

8. B

(i) Saponification of ester X gives sodium methanoate (residue) and Y. The residue decolourises KMnO4 because methanoate is a reducing agent. Methanoate ion is oxidised to carbon dioxide and MnO4 is reduced to Mn2+ ions. 5HCOO + 2MnO4 + 11H+ 5CO2 + 8H2O + 2Mn2+ (ii) Concentrated sulphuric acid reacts with methanoate to give methanoic acid. HCOO + H+ HCOOH Carbon monoxide is liberated when methanoic acid reacts with concentrated H2SO4 which acts as a dehydrating agent. HCOOH H2O + CO

Structured Question 1. (a) Potassium manganate(VII) solution, acidified with dilute sulphuric acid. O (b) X is HO CH2 C OH
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14

Amines

Multiple-choice Questions
1. Compound P is produced when bromoethane reacts with alcoholic potassium cyanide. Which of the following is formed when P is reacted with tetrahydridoaluminate(III)? A CH3CH2CN C CH3CH2CH2OH B CH3CH2NH2 D CH3CH2CH2NH2 2. Which of the following amines is most soluble in water? A CH3CH2NH2 C (CH3)3N B (CH3)2NH D C6H5NH2 3. Which of the following pairs of chemicals will react to produce N-phenylethanamide? A NH and CH CH COCl
2 3 2

B C D

NH2 and CH3COCl CH3CH2NH2 and CH3NH2 and COCl COCl

4. Which of the following product is formed when aniline is reacted with cold nitrous acid followed by p-nitrophenol? A NO N=N-O
2

B
N=N

NO2 OH

HO N=N NO2 OH N=N NO2

5. When 1 mol of compound X is treated with nitrous acid, 1 mol of nitrogen gas is liberated. Which of the following compounds is likely to be compound X? A CH3CH2NH2 B (CH3)2NH C (CH3)3N D H2NCH2CH2NH2 A Only 1 is correct B Only 1 and 2 are correct C Only 2 and 3 are correct D 1, 2 and 3 are correct
NH2

6. Which of the following chemicals can be used to distinguish 1 2 Nitrous acid Hydrochloric acid 3 Bromine water

from CH3CONH2?

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7. Which of the following is true of aniline? 1 Soluble in hydrochloric acid 2 Soluble in sodium hydroxide solution 3 Soluble in water

Structured Question
1. Benzocaine is an active ingredient found in many sunburn ointment. It can be prepared by the following reaction scheme.
CH3
I

CH3
II

CO2H
III

CO2CH2CH3 X
IV

NO2

NO2

NH2

(a) Name the type of reaction that has occurred in step I. Hence state the reagent and the condition for step I. (b) State the reagent and the condition for step II. (c) Ethanoyl chloride is added in step III. Draw the structural formula of the intermediate compound X. Name the type of reaction that has taken place. (d) Suggest how step IV can be carried out. Name the type of reaction involved.

Essay Question
1. (a) 1-chloropropane is heated with alcoholic potassium cyanide to produce compound A. When compound A is reacted with tetrahydridoaluminate(III), compound B is formed. Compound B reacts with ethanoyl chloride to liberate white fumes and compound C is produced. Determine the structures and give the IUPAC names for compounds A, B and C. Write equations for all the reactions involved. Suggest how 1-butanamine can be prepared from compound C. Write an equation for the reaction involved. (b) State a simple test to differentiate the following pairs of substances: (i) CH3CH2NH2 and CH3NHCH3 (ii) CH CH NH and NH
3 2 2 2

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ANSWER
CHAPTER 14 Amines
Multiple-choice Questions 1. D CH3CH2Br + CN CH3CH2CN + Br P CH3CH2CN + [H] CH3CH2CH2NH2 2. A CH3CH2NH2 can form the most hydrogen bonds with water. O 3. B
NH2

(c)

CO2CH2CH3

NO2

Type of reaction: Esterification (d) React with tin / zinc with dilute hydrochloric acid Type of reaction: Reduction Essay Question

+ CH3C Cl H O N C CH3 + HCl


N-phenylethanamide

1. (a) Compound A is butanenitrile, CH3CH2CH2CN Compound B is butamine, CH3CH2CH2CH2NH2 Compound C is N-buthylethamide, CH3CH2CH2CH2NHCOCH3 CH3CH2CH2Cl CH3CH2CH2CN
alcoholic KCN

4. C

NH2 + HNO2 N2+ + NO2 OH

N2+ OH N=N NO2

5. A 1 mol of primary amine will react with HNO2 to produce 1 mol of N2 gas. CH3CH2NH2 + HNO2 CH3CH2OH + N2 + H2O 6. C
NH2

4 CH3CH2CH2CN CH3CH2CH2CH2NH2 3 CH3CH2CH2CH2NH2 CH3CH2CH2CH2NHCOCH3 + HCl

LiAlH

CH COCl

is basic and reacts with HCl to form

Reflux with aqueous sodium hydroxide solution: CH3CH2CH2CH2NHCOCH3 CH3CH2CH2CH2NH2 + CH3COONa (b) (i) React with nitrous acid and heat. CH3CH2NH2 liberates N2 gas, CH3NHCH3 has no visible change. CH3CH2NH2 CH3CH2OH + N2 (ii) Add bromine water.
NH2 produces a white precipitate,
HNO2 with NaOH(aq)

salt. CH3CONH2 is neutral and does not react with HCl (2 is correct). Bromine will react with
NH2

to form a

white precipitate while CH3CONH2 does not react with bromine (3 is correct). 7. A Aniline,
NH2

is basic since it can react

with HCl to form soluble salt (1 is correct). Structured Question 1. (a) Nitration Reagent: Concentrated nitric acid Condition: In the presence of concentrated sulphuric acid (b) Reagent: Potassium manganate(VII) Condition: Acidified and reflux / heat

CH2CH2NH2 has no visible change.


Br NH2
Br2

Br

NH2 Br

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15

Amino Acids and Proteins

Multiple-choice Questions
1. Which of the following is true about aminoethanoic acid? A It exists as a dimer in organic solvent. B It exists as a diazonium ion. C It is optically active. D It forms zwitterion. 2. The simplest amino acid, glycine, is soluble in both aqueous acid and aqueous alkali. When glycine is dissolved in aqueous sodium hydroxide solution at pH 12.5, it exists as A H3N+CH2COO C H3N+CH2COOH B H2NCH2COO D H2NCH2COOH 3. Tyrosine is a natural existing amino acid with the formula C9H11NO3. Which of the following is the most likely structure of tyrosine? A
O2N HO H2N CH2CH(OH)CH3

B C D

CH2CH(NH2)COOH CH2CH(OH)COOH OH CH2 C COOH NH2

4. 1 mol serine, HOCH2CH(NH2)COOH will A react with 2 mol of hydrochloric acid. B react with sodium metal to liberate 2 mol of gas. C react with excess nitrous acid to liberate 1 mol of gas. D react with excess Na2CO3 solution to liberate 1 mol of gas. 5. Which of the following fibers is considered a protein fiber? A Silk C Cotton B Hemp D Glycogen A Only 1 is correct B Only 1 and 2 are correct C Only 2 and 3 are correct H3C D 1, 2 and 3 are correct

6. The structural formula for threonine is

CH CH COOH HO NH2 Which of the following is/are true about threonine? 1 Threonine has amphoteric properties. 2 Threonine releases nitrogen gas when heated with nitric(V) acid 3 The repeating unit of threonine in a polypeptide chain is CH3

O O CH CH C . NH2

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7. GABA with the chemical formula H2N(CH2)3COOH is the chief inhibitory neurotransmitter in the central nervous system and also in the retina. Which of the following is/are true of GABA? 1 It exists as zwitterion. 2 It is found in protein. 3 It is optically active. 8. Which of the following statements is/are true of proteins? 1 Proteins are polyamides. 2 Globular proteins are more soluble in water than fibrous proteins. 3 When protein is denatured, the peptide sequence is destroyed.

Structured Question
1. Insulin is known to lower blood glucose level. Insulin is made up of a chain of 51 amino acids. Partial hydrolysis gives a peptide chain as shown. H O H O H H2N CH C N CH C N CH C N CH COOH CH CH3 CH2 CH3 CH2 CH3 CH2 CH CH3 COOH CH3 O

Val-Glu-Ala-Leu

(a) With further hydrolysis, this peptide chain yields four amino acids. Draw the structures of the four amino acids obtained. (b) Give the systematic names of these four amino acids (c) Classify these amino acids as either non-polar, polar, acidic or basic. Explain your answers.

Essay Question
1. Amino acids has the general formula H2NCH(R)COOH. (a) Draw the structural formulae of the first two amino acids, glycine and alanine. (b) Alanine is optically active. Explain what is meant by this term. (c) Describe what is observed and give balanced equations for the reactions of alanine with solutions of (i) sodium bicarbonate (ii) nitrous acid (d) Using alanine as an example, explain how an amino acid can act as a buffer solution. (e) (i) How many different tripeptides are possible which contain two molecules of glycine and one molecule of alanine? (ii) Draw the structures of the tripeptides formed. (iii) Discuss the reactions of the tripeptides with dilute sodium hydroxide solution under different conditions.

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ANSWER
CHAPTER 15 Amino Acids and Proteins
Multiple-choice Questions 1. D H2NCH2COOH
+

exists

as

zwitterion,

H3NCH2COO . 2. B H2NCH2COOH + OH H2NCH2COO + H2O


+

(iii) 2-aminopropanoic acid (iv) 2-amino-4-methylpentanoic acid (c) 2-aminopentanedioic acid is acidic because it has two carboxyl groups. The other 3 amino acids are non-polar and neutral with hydrophobic aliphatic R groups. Essay Question O O

or H3NCH2COO + OH H2NCH2COO + H2O 3. B General formula of naturally occurring amino acids: H2NCH(R)COOH 4. C Only 1 NH2 group to react with 1 HCl. Na reacts with the 2 OH groups to liberate 1 H2. With HNO2, 1 NH2 group liberates 1 N2. 1 COOH group reacts with Na2CO3 to form CO2. 5. A 6. A Threonine has COOH group and NH2 group (1 is correct). The NH2 group will only release N2 gas when heated with nitric(III) acid, HNO2, not with nitric(V) acid, HNO3 (2 is incorrect). The structure is not a polypeptide chain (3 is incorrect). 7. A GABA is not -amino acid, thus not found in protein. GABA does not have chiral carbon, hence not optically active. 8. B Proteins are polyamides (1 is correct). Globular proteins can form more hydrogen bonds with water hence more soluble in water than fibrous proteins (2 is correct). Denaturation causes the tertiary structure to open up and destroyed but the peptide sequence is not destroyed (3 is incorrect). Structured Question 1. (a) H2N CH COOH CH CH3 CH3 (i) H2N CH COOH CH3 H2N CH COOH CH2 CH2 COOH (ii)

1. (a) H2N CH C OH H2N CH C OH H CH3 glycine alanine (b) Alanine rotates the plane of polarised light. Alanine has a chiral or asymmetrical C* that is bonded to four different groups. (c) (i) Effervescence due to liberation of CO2 gas. H2NCH(CH3)COOH + NaHCO3 H2N CH(CH3)COO Na+ + CO2 + H2O (ii) Effervescence due to liberation of nitrogen gas. H2N CH(CH3)COOH + HNO2 HO CH(CH3)COOH + N2 + H2O (d) Alanine can react with both acid and base. H2NCH(CH3)COOH + OH H2NCH(CH3)COO + H2O H2NCH(CH3)COOH + H+ H3N+CH(CH3)COOH (e) (i) 3 (ii) GAG O H O H H2N CH2 C N CH C N CH2 COOH CH3 GGA H O H H2N CH2 C N CH2 C N CH COOH CH3 H O H H2N CH C N CH2 C N CH2 COOH CH3 (iii) With cold dilute alkali, a salt is formed. When boiled with dilute alkali, the tripeptide would be hydrolysed to amino acids. O O

H2N CH COOH CH2 CH CH3 CH3 (iii) (iv) (b) (i) 2-amino-3-methylbutanoic acid (ii) 2-aminopentanedioic acid
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AGG

16

Polymers

Multiple-choice Questions
1. The polymer containing the following repeating unit, O C C6H4 C2H4 O is a A SBR rubber C detergent B protein D polyester 2. Concentrated nitric(V) acid oxidises cyclohexanol to an organic compound which can be used to make A Terylene C polyethene B nylon-6,6 D polystyrene 3. The structure of natural rubber can be represented by the formula A CH2 CH = C CH2 n ( ) C CH2 CH = CH CH2 n ( ) CH3 B CH2 = CH CH2 CH2 n ( ) D CH2 CH = C CH2 n ( ) CH3 CH3 4. O Epoxyethane, CH2 CH2, can be polymerised under suitable conditions. The repeating unit for this polymer is O C CH2 CH2 O D CH CH OH OH 5. Which of the following statements about natural rubber is true? A Its monomer is 2-methyl-1,3-butadiene. B It is the trans-isomer of polyisoprene. C It can be synthesised by the addition polymerisation of isoprene. D It is a saturated hydrocarbon. 6. Which of the following structures represents the repeating unit of nylon-6,6? O O A C (CH2)6 C O (CH2)4 O H O H O B N (CH2)6 C N (CH2)4 C H H O O C N (CH2)4 N C (CH2)6 C H H O O D N (CH2)6 N C (CH2)4 C
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A CH CH B CH2 O CH2 O

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A Only 1 is correct

B Only 1 and 2 are correct

C Only 2 and 3 are correct

D 1, 2 and 3 are correct

7. nHO2CCH2CH2COOH + nHOCH2CH2OH COCH2CH2CO2CH2CH2O n + 2nH2O ( ) P The formation of polymer P in the above reaction can be considered as 1 esterification 2 condensation polymerisation 3 hydrolysis 8. Which of the following can be used as the initiator for anionic polymerisation? 1 BuLi+ 2 Na+NH2 3 Li+NH2

Structured Question
1. (a) Write the structure of the copolymer formed from the following reactions. (i) CH2 = CCl2 + CH2 = CHCN (ii) CH2OH + ClOC (CH2)6 COCl CH2OH (b) The partial structure of polymer X is shown below. O CH3 O CH3 || C (CH2)2 C O C (CH2)2 C O H H (i) Write the repeating unit for polymer X. (ii) Write the structural formula of the monomer for making polymer X. (c) The structural formulae of polymers Y and Z are shown below. H H C C n ( ) H CH3 Y H C (CH2)5 N n ( ) Z O

and

(i) State one use of polymers Y and Z. (ii) Draw the structures of the monomers of Y and Z and name them. (iii) Which of these two polymers is not suitable for use as a container for concentrated sodium hydroxide solution? Explain. (iv) Which polymer, Y or Z will create environmental problems? Why?

Essay Question
1. (a) Outline a reaction scheme to show how phenol can be used as starting material to make synthetic fibre. (b) Explain the mechanism of free-radical polymerisation using chloroethene as an example.

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ANSWER
CHAPTER 16 Polymers
Multiple-choice Questions O O Essay Question 1. (a) The synthetic fibre made from phenol is nylon-6,6. Step 1 Preparation of 1,6-hexanedioic acid Phenol cyclohexanol HOOC(CH2)4COOH Step 2 Preparation of 1,6-hexanediamine HOOC(CH2)4COOH ammonium 1,6-hexanedioate NC(CH2)4CN H2N(CH2)6NH2 Step 3 Reaction between HOOC(CH2)4COOH and H2N(CH2)6NH2 HOOC(CH2)4COOH + H2N(CH2)6NH2 nylon-6,6 + nH2O (b) Initiation step O O
H2 H2O NH3 H2 HNO3

1. D C C6H4 C2H4 O C C6H4 C2H4 O ester linkage 2. B Cyclohexanol is oxidised to 1,6-hexanedioic acid, one of the monomers making nylon-6,6. 3. A 4. C O 5. 6. 7. CH2 CH2 CH2 CH2 O A Natural rubber is a cis-isomer. It is a polyunsaturated hydrocarbon. D B The reaction between a carboxylic acid and an alcohol is called esterification. P is a condensation polymer. D For anionic polymerisation, the initiator is a Lewis base (nucleophile).

8.

Structured Question 1. (a) (i) H Cl H CN C C C C n ( ) H Cl H H O O

C6H5 C O O C C6H5 benzoyl peroxide 2C6H5 + 2CO2 Chain propagation step H H H H C6H5 + C = C C6H5 C C H Cl H Cl The chain propagates as successive monomers are added to the chain. H H H H C6H5 C C + C = C H Cl H Cl H H H H H C6H5 C C C C CH2 C n ( ) H Cl H Cl Cl Termination step The addition polymerisation stops when two free radicals combine. H H 2C6H5 C C H Cl H H H H C6H5 C C C C C6H5 H Cl Cl H
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(ii)

(b)

O CH2CH2 O C (CH2)6 C n ( ) O CH3 C (CH2)2 C O H (ii) O CH3 HO C (CH2)2 C O H H (c) (i) Polymer Y: For making plastic bags Polymer Z: As a synthetic fibre for making clothing (ii) H H O H C = C and HO C (CH2)5 N H monomer of Z H CH3 monomer of Y (6-aminohexanoic acid) (propene) (iii) Polymer Z because it contains the amide linkage. In the presence of concentrated NaOH, the amide linkage is broken up due to hydrolysis. (iv) Polymer Y. It is non-biodegradable and causes land pollution. (i)

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