HWA CHONG INSTITUTION

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

Do not open this booklet until you are told to do so.

READ THESE INSTRUCTIONS FIRST Complete the information on the optical mark sheet (OMS) as shown below. Write your name

Write your CT group

Write and shade your NRIC or FIN number.

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.

2 Section A 1 71 g of Cl2 reacted with 1 g of H2 to give HCl gas under standard conditions. How many molecules are present at the end of the reaction? A 3.01 x 1023 B 6.02 x 1023 C 9.03 x 1023 D 15.1 x 1023

The oxidation number of an element M in a compound was determined as follows: 0.013 mol of the compound was dissolved in water and the solution was made up to 100 cm3. 10.0 cm3 of this solution required 21.65 cm3 of 0.02 mol dm3 K2Cr2O7 to oxidize M in the compound to the +5 oxidation state. 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

Which of the following ions contains the most number of unpaired electrons?

52 3+ 24 Cr

56 3+ 26 Fe

59 2+ 27 Co

63 2+ 29 Cu

The elements arsenic (As), selenium (Se) and bromine (Br) have consecutive proton numbers in the Periodic Table. 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

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3 5 Isocyanic acid, HNCO, is a volatile and poisonous inorganic compound. How many and bonds are present in the isocyanic acid molecule?

A B C D 2 3 3 3

3 1 2 3

A compound has the structure shown.

w I O x O y H C C H P z CH3 CH3

What are the values of the bond angles w, x, y and z?

w A B C D 120o 120o 109.5o 109.5o

x 104.5o 104.5o 180o 180o

y 120o 120o 90o 90o

z 107o 109.5o 109.5o 120o

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4 7 Which of the following graphs shows the behaviour of a fixed mass of an ideal gas at two constant temperatures, T1 and T2 (where T2 > T1)?

T2

T2 A T1 B T1

0 1/V

0 1/V

pV

pV T

T2 T2 T1

D T1

0 1/V

The density of ice is 1.00 g cm3. 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 2.72 dm3 2.72 x 103 dm3 2.72 m3

2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1

5 9 Consider the following reactions: Mg (s) + 2HCl (aq) MgCl2 (aq) + H2 (g) MgO (s) + 2HCl (aq) MgCl2 (aq) + H2O (l) Hrxn = - 464 kJ mol1 Hrxn = -148 kJ mol1

Given that the enthalpy change of formation of water is -285 kJ mol1, which of the following gives the enthalpy change of formation of magnesium oxide?

-897 kJ mol1

-601 kJ mol1

-327 kJ mol1

-31 kJ mol1

10 The enthalpy and entropy change of vaporization of ethanoic acid are +24.2 kJ mol1 and +61.9 J K1 mol1 respectively. Which of the following gives the temperature at which ethanoic acid vaporizes?

0.39 K

86.1 K

391 K

1498 K

11 0.50 mol of carbon and 1.00 mol of steam was placed in an empty vessel and allowed to reach equilibrium at 10 atm, according to the following equation. C (s) + H2O (g) CO (g) + H2 (g) At equilibrium, two-thirds of the steam remained. What is the value of the equilibrium constant, Kp, at the temperature of the experiment? A B C D 0.50 0.80 1.25 8.00

12 Compound V is converted into compound Y in three steps:

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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

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. The diagrams show the structure of two

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. Which compound is produced in trace amounts by a termination stage in the chain reaction? 2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1

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, Karposis sarcoma. Its structure is shown below:

2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1

HO

Which of the following statements about Alitretinoin is incorrect? A B C D In the presence of excess bromine and uv light, Alitretinoin will only undergo free radical substitution. Alitretinoin may exhibit up to sixteen different stereoisomers. Addition of hot acidic potassium manganate(VII) solution to Alitretinoin will result in the effervescence of carbon dioxide gas. The product of the reaction of Alitretinoin with cold dilute potassium manganate(VII) solution is optically active.

18 Acylation of benzene undergoes the same type of reaction mechanism as for chlorination of benzene. The typical acylating agent is RCOCl.
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:

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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

C Br

Excess concentrated H2SO4 170oC

H C H H

C Br

Concentrated H2SO4, followed by H2O Warm

H C Br H

C Br

Concentrated H3PO4, H2O 300oC, 60 atm

H C H

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. The Cl ion is more strongly hydrated in solution than the Br ion. The CCl bond is more polar than the CBr bond. The CCl bond is stronger than the CBr bond.

21 During aromatic substitution, the position of the new incoming substituent is determined by the nature of the group already present on the benzene ring. For example, the following

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, 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

12

N H

Br

Br

Br

Br

Section B

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13 For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct. (You may find it helpful to put a tick against the statements that you consider to be correct). The response A to D should be selected on the basis of A B C D 1, 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.

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. Reaction II is a disproportionation reaction. CS2 (g) is a reducing agent in reaction III.

24 Which of the following pairs does the first compound have a higher boiling point than the second compound?

1 2 3

N2H4 , N2F4 pentane, 2-methylbutane 1,1-dichloroethene, trans-1,2-dichloroethene

25 Which statements about the element chlorine, bromine and iodine are correct?

2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1

14

1 2 3

The ionic radius of the X ion increases from chlorine to iodine. The magnitude of the hydration energy of the X ion decreases from chlorine to iodine. The energy released by the process X (g) + e X (g) increases from chlorine to iodine.

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, k, is mol1 dm3 s1 . The rate constant increases with increasing pressure. The intermediates in the reaction are N2O2 and N2O.

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 amount of hydrogen is three times the amount of carbon monoxide. H = +210 kJ mol1

28 In which of the following pairs are the members geometric isomers of each other?

2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1

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H3C

Br C C H

H C Br C

CH3

1
Cl

Cl

H3C

Br C C H

H3C C H3C C

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, hydrogen and bromine. There is only one possible intermediate that is formed. A racemic mixture is formed.

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

Cl

CH3CH2I

~ End of Paper ~

2008 HCI C1 H2 Chemistry Promotional Examination / Paper 1