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HWA CHONG INSTITUTION

C1 PROMOTIONAL EXAMINATION H2 CHEMISTRY 9746 PAPER 1 26 September 2008 45 min

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There are 30 questions in this paper. Answer all questions. For each question, there are four possible answers, A, B, C or D. Choose the one you consider correct and record your choice in soft pencil on the OMS. After the examination, you are required to submit only the OMS. Each correct answer will score one mark. Marks will not be deducted for wrong answers. A Data Booklet is provided. You may use a calculator. Any rough working should be done in this booklet.

This question booklet consists of 15 printed pages.

Cr2O72– + 14 H+ + 6e → 2 Cr3+ + 7 H2O What is the original oxidation state of element M? A +1 B +2 C +3 D +4 3 Which of the following ions contains the most number of unpaired electrons? A 52 3+ 24 Cr B 56 3+ 26 Fe C 59 2+ 27 Co D 63 2+ 29 Cu 4 The elements arsenic (As).0 cm3 of this solution required 21. How many molecules are present at the end of the reaction? A 3.02 mol dm–3 K2Cr2O7 to oxidize M in the compound to the +5 oxidation state. selenium (Se) and bromine (Br) have consecutive proton numbers in the Periodic Table.02 x 1023 C 9.01 x 1023 B 6.65 cm3 of 0.2 Section A 1 71 g of Cl2 reacted with 1 g of H2 to give HCl gas under standard conditions. 10.03 x 1023 D 15.013 mol of the compound was dissolved in water and the solution was made up to 100 cm3. What is the order of their first ionization energies? least endothermic A B C D As As Br Se Se Br Se As most endothermic Br Se As Br 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 .1 x 1023 2 The oxidation number of an element M in a compound was determined as follows: 0.

y and z? w A B C D 120o 120o 109. is a volatile and poisonous inorganic compound.5o 180o 180o y 120o 120o 90o 90o z 107o 109. w I O x O y H C C H P z CH3 CH3 What are the values of the bond angles w.5o 109.5o 109.5o x 104. HNCO. x.5o 104. How many σ and π bonds are present in the isocyanic acid molecule? σ A B C D 2 3 3 3 π 3 1 2 3 6 A compound has the structure shown.5o 120o 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 .3 5 Isocyanic acid.

00 g cm–3.4 7 Which of the following graphs shows the behaviour of a fixed mass of an ideal gas at two constant temperatures.72 m3 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 .72 dm3 2.72 x 10–3 dm3 2. T1 and T2 (where T2 > T1)? p T2 p T2 A T1 B T1 0 1/V 0 1/V pV pV T T2 T2 T1 C D T1 0 0 1/V V 8 The density of ice is 1. What is the volume of steam produced when 1 cm3 of ice is heated to 596 K at a pressure of 101 kPa? A B C D 272 cm3 2.

Kp. What is the value of the equilibrium constant.00 12 Compound V is converted into compound Y in three steps: 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 . which of the following gives the enthalpy change of formation of magnesium oxide? A -897 kJ mol–1 B -601 kJ mol–1 C -327 kJ mol–1 D -31 kJ mol–1 10 The enthalpy and entropy change of vaporization of ethanoic acid are +24. two-thirds of the steam remained.464 kJ mol–1 ∆Hrxn = -148 kJ mol–1 Given that the enthalpy change of formation of water is -285 kJ mol–1. according to the following equation.5 9 Consider the following reactions: Mg (s) + 2HCl (aq) → MgCl2 (aq) + H2 (g) MgO (s) + 2HCl (aq) → MgCl2 (aq) + H2O (l) ∆Hrxn = .2 kJ mol–1 and +61. C (s) + H2O (g) ⇌ CO (g) + H2 (g) At equilibrium.50 0.9 J K–1 mol–1 respectively.80 1.50 mol of carbon and 1. Which of the following gives the temperature at which ethanoic acid vaporizes? A 0.1 K C 391 K D 1498 K 11 0.00 mol of steam was placed in an empty vessel and allowed to reach equilibrium at 10 atm.25 8.39 K B 86. at the temperature of the experiment? A B C D 0.

The diagrams show the structure of two 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 .6 Step 1 Step 2 Step 3 Overall : : : : V W X V → → → → W X Y Y ∆H1 ∆H2 ∆H3 ∆Hr The energy profile diagram is as shown. Energy X W V Y Reaction pathway Which one of the following is correct? ∆H2 A B C D Endothermic Exothermic Exothermic Endothermic ∆Hr Exothermic Endothermic Endothermic Exothermic Rate Determining Step Step 3 Step 3 Step 2 Step 2 13 Many organic compounds exhibit optical isomerism.

Which compound is produced in trace amounts by a termination stage in the chain reaction? 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 .7 organic compounds. OH O HO HO O OH O OH OH estradiol citric acid What is the total number of chiral carbon centres in these two structures? A B C D 4 5 6 7 14 How many isomers (including both structural isomers and stereoisomers) are possible for a compound with molecular formula C4H9Cl? A B C D 3 4 5 6 15 Samples of the gases CH3Cl and Br2 are mixed together and irradiated with light.

Karposi’s sarcoma.8 A B C D HBr CH3CH3 CH2ClCHBr2 CHBrClCBr2Cl 16 Which substance in a vehicle exhaust results from incomplete combustion of a hydrocarbon fuel? A B C D NO N2 H2O CO 17 Alitretinoin is an antineoplastic agent used to treat lesions caused by AIDS-related disease. Its structure is shown below: 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 .

Alitretinoin may exhibit up to sixteen different stereoisomers. Alitretinoin will only undergo free radical substitution. The typical acylating agent is RCOCl. 18 Acylation of benzene undergoes the same type of reaction mechanism as for chlorination of benzene. The product of the reaction of Alitretinoin with cold dilute potassium manganate(VII) solution is optically active. Addition of hot acidic potassium manganate(VII) solution to Alitretinoin will result in the effervescence of carbon dioxide gas. O O C R + R C Cl + HCl Which of the following is the correct structure for the electrophile? A B C D RCO+ Cl+ R+ RCOCl+ 19 A synthetic route for ethanol is proposed as follows: 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 .9 HO O Which of the following statements about Alitretinoin is incorrect? A B C D In the presence of excess bromine and uv light.

the following 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 .10 ethanolic NaOH heat H C H C H H H H C H H C OH H Reagent Y Compound X ethene ethanol What could compound X and reagent Y be? Compound X H H C OH H Reagent Y A H C Br Excess concentrated H2SO4 170oC H H C H H B H C Br Concentrated H2SO4. the position of the new incoming substituent is determined by the nature of the group already present on the benzene ring. H2O 300oC. 60 atm H H C H D H C Dilute KMnO4 / aqueous NaOH Cold OH OH 20 Why does the reaction C2H5X + OH– C2H5OH + X solution when X = Cl than when X = Br? A B C D – – – take place less rapidly in aqueous The Br ion is a stronger nucleophile than the Cl ion. – – 21 During aromatic substitution. The Cl ion is more strongly hydrated in solution than the Br ion. The C–Cl bond is stronger than the C–Br bond. The C–Cl bond is more polar than the C–Br bond. followed by H2O Warm H H C Br H C H C Br Concentrated H3PO4. For example.

which synthetic sequence will produce 2-bromo-4-nitrobenzoic acid from methylbenzene? COOH CH3 Br NO2 2-bromo-4-nitrobenzoic acid A B C D nitration → bromination → oxidation bromination → oxidation → nitration nitration → oxidation → bromination oxidation → nitration → bromination 22 Which of the following correctly represents the transfer of electrons when a bromoalkane undergoes nucleophilic substitution reaction? 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 .11 reactions produce bromo compounds: CH3 CH3 Br COOH COOH Br NO2 NO2 Br Using this knowledge.

12 A H N H H C Br B C N C Br C H O C Br D O H Br C Section B 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 .

N2F4 pentane. CS2 (g) is a reducing agent in reaction III. trans-1. The response A to D should be selected on the basis of A B C D 1. 24 Which of the following pairs does the first compound have a higher boiling point than the second compound? 1 2 3 N2H4 . 2-methylbutane 1.1-dichloroethene.13 For each of the questions in this section. bromine and iodine are correct? 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 . (You may find it helpful to put a tick against the statements that you consider to be correct).2-dichloroethene 25 Which statements about the element chlorine. 2 and 3 are 1 and 2 only 2 and 3 only 1 only correct are correct are correct correct No other combination of statements is used as a correct response. one or more of the three numbered statements 1 to 3 may be correct. is 23 Below is a list of chemical reactions I to III I II III 2NaOH (aq) + 2Al (s) + 6H2O (l) Cl2 (aq) + 2OH– (aq) CS2 (g) + 3O2 (g) → → Cl – (aq) → + 2NaAl(OH)4 (aq) + 3H2 (g) ClO– (aq) + H2O (l) CO2 (g) + 2SO2 (g) Which of the following statements are true? 1 2 3 Reaction I is a redox reaction. Decide whether each of the statements is or is not correct. Reaction II is a disproportionation reaction.

26 The following mechanism was proposed for the reaction between nitric (II) oxide and hydrogen gas: 2 H2 (g) + 2NO (g) → N2 (g) + 2H2O (g) 2NO ⇌ N2 O2 N2O2 + H2 → N2O + H2O N2O + H2 → N2 + H2O fast slow fast Which of the following statements are incorrect? 1 2 3 The units of the rate constant. ∆H = +210 kJ mol–1 28 In which of the following pairs are the members geometric isomers of each other? 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 . 27 A mixture of methane and steam was allowed to reach equilibrium according to the equation below: CH4 (g) + H2O (g) ⇌ CO (g) + 3H2 (g) Which statements about this equilibrium are correct? 1 2 3 Cooling the reaction mixture will decrease the value of Kp. Increasing the pressure will decrease the yield of hydrogen. The intermediates in the reaction are N2O2 and N2O. The amount of hydrogen is three times the amount of carbon monoxide.14 1 2 3 The ionic radius of the X– ion increases from chlorine to iodine. is mol–1 dm3 s–1 . The energy released by the process X (g) + e → X– (g) increases from chlorine to iodine. k. The magnitude of the hydration energy of the X– ion decreases from chlorine to iodine. The rate constant increases with increasing pressure.

A racemic mixture is formed.15 H3C Br C C H H C Br C CH3 1 Cl Cl H3C Br C C H H3C C H3C C H 2 H3C Br H3C Br C C H H C H3C C Br 3 Cl Cl 29 Which of the following statements about the electrophilic addition of HBr to hex-3-ene are correct? 1 2 3 The intermediate contains carbon. There is only one possible intermediate that is formed. hydrogen and bromine. 30 Which of the following compounds when boiled with dilute sodium hydroxide solution followed by addition of excess nitric acid will give a white precipitate with dilute aqueous silver nitrate? 1 CH2Cl 2 Cl 3 CH3CH2I ~ End of Paper ~ 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1 .