FORM TP 2017171 ‘CANDIDATES ELEASENOTED PRINT jour name on the tine below and return this booklet with your answer sheet. Fala do so may resu rest cope 02212010 MAY/UNE 2017 CARIBBEAN EXAMINATIONS COUNCIL CARIBBEAN ADVANCED PROFICIENCY EXAMINATION® CHEMISTRY UNIT 2 ~ Paper 01 J hour 30 minutes 12 JUNE 2017 (p.m.) READ THE FOLLOWING INSTRUCTIONS CAREFULLY. ‘This test consists of 45 items. You will have 1 hour and 30 minutes to answer them, In addition to this test booklet, you should have an answer sheet and a data booklet. Each item in this test has four suggested answers lettered (A), (B), (C), (D). Read each item ‘you are about to answer and decide which choice is best. On your answer sheet, find the number which corresponds to your item and shade the space having the same letter as the answer you have chosen. Look at the sample item below. Sample Item Which of the following energy transitions is the HIGHEST in an organic compound? ‘Sample Answer (A) nwoos 2@0®8 oto (C) nton* ©) nom The correct answer to this item is “6 10 a*”, so (B) has been shaded. Ifyou want to change your answer, erase it completely before you fill in your new choice. When you are told to begin, turn the page and work as quickly and as carefully as you can, If you cannot answer an item, go on to the next one. You may return to that item later. You may do any rough work in this booklet Figures are not necessarily drawn to scale, ‘You may use a silent, non-programmabe calculator to answer items, DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO'SO. Copyright © 2015 Caribbean Examinations Couneil All rights reserved,The volatility of organic compounds depends on the strength of the intermolecular forces present. Which of the following ‘compounds would be the MOST volatile? (A) CH,CH,CH,OH (B) —CH.CH.CH.CH, (©) CH.CH(CH)CH, (DB) CH,CH,CH,COOH Jiems 2-3 refer to the following information about hydrocarbon Z. Hydrocarbon Z has @ relative molecular mass of 84. When 0.1 g of Z was burnt in oxygen, 0.316 g of carbon dioxide and 0.128 g of water were formed. ‘The empirical formula of Z is (A) CH ® cH, (© cH, (D) CHO ‘The molecular formula of Z is ) CH, B) CH, © CH, ©) CHO 4 6. Inthe reaction between ethene and bromine, which of the following statements about the reaction mechanism may be true? 1. A carbocation forms in the rate determining step. Il, A dative covalent bond forms between the bromide ion and ethene. IIL. Heterolytic fission of the bromine bromine bond occurs (A) Tonly (8) Land Il only (©) Mand ill only (D) 1, Mand Itt Item 5 refers to the following structural, formula of a compound. ae H-C-C CH, CHCH, a H CH, The correct IUPAC name for the compound (A) imethyl pentane ®) imethyl octane © imethyl pentane (D) 2, 4, 4trimethy! octane Which of the followng reaction mechanisms occurs between benzene and concentrated HNOJH,SO,? (A) Blectrophilic substitution (B) _ Nucleophitie substitution (©) Electrophilic addition (D) _Nucleophilic addition GO ON TO THE NEXT PAGEem 7 refers to the following incomplete equation Light + Br, ) CH= CHCH, ‘The product of the reaction above is Diazonium salts are useful in the synthesis of aromatic compounds. Which of the following compounds can be prepared from a diazonium salt? (A) COOH o (By) CH, NH, © os 7e CH, OH () Hydrogen cyanide can be added to ethanal but not to ethene because (A) ethanal is more susceptible to electrophilic attack than ethene (B) __ethanal is more susceptible to free radical attack than ethene (© ethanal is more susceptible to nucleophilic attack than ethene (D) the addition product formed with ethene would be unstable GO ON TO THE NEXT PAGE10. u ae Item 10 refers to the following table which shows the results of an investigation to analyse an organic liquid, Z. Test Observation Tnference 1. ‘Solid Na,CO, was] Rapid effervescence, gas | CO, gas liberated added to Z. evolved formed a white precipitate with Ca(OH), solution. 2. SOCI, is added to Z. | White misty fumes OH group is present The organic liquid Z is MOST likely (A) analeohol (B) a carbonate (C)__ anacyl chloride t (D) — acarboxylic acid 2-hydroxy-2-methylpropanoie acid ean be formed from propanone in two steps, X and Y, as illustrated below. on omy oH og \ 7 . ro SE > cr—cocen SPY em eee ca, il ba Yon Which of the following statements about these steps is/are true? 1. Step X involves nucleophilic addition. IL Aqueous potassium cyanide is the reagent in Step X. IIL Step Y involves hydrolysis. (A) Lonly (B) Land I only (©) Mand only (D) 1, Hand U1 GO ON TO THE NEXT PAGE,122 13, 14. 15, ‘Nylon 66 can be made by the condensation polymerization of H,N(CH,),NH, and HOOC(CH,),COOH. The repeat unit is (A) -NHJCH,). NHCO(CH,),COOH- (8B) -NH(CH,,NHCO(CH,,CO- (Q -NH\CH,),NHCO(CH,),COO- (DB) -OOC(CH,),CONH(CH,),-NH- Which of the following statements is NOT true of addition polymerization? (A) Only one type of polymer is formed, (B) The polymeris readily hydrolysed to the monomer (©) Themolecular mass of the polymer is a multiple of the monomer unit, (D) The physical and chemical properties of the polymer are different from those of the ‘monomer. When butan-I-ol is dehydrated in a suitable piece of apparatus, the product is (A) butane (B) _ butene (©) but-bene (D) — but-2-ene What would be OBSERVED when aqueous bromine is added to the following compound? ou (A) There is no visible reaction. (B) The colour of the bromine is discharged and a white precipitate is formed, (©) The colour of the bromine is discharged leaving a yellow precipitate, (D) The colour of the bromine is discharged and a colourless solution is formed. 16. tem 16 refers to the following diagram which represents a paper chromatogram of food dyes obtained using water as the solvent. A spot ofa sample was originally placed at Z. It contained the components X and Y. Solvent Front ex ey Starting Point +z Which of the following statements regarding the components of X and Y is correct? (A) Xismore strongly adsorbed by the paper than Y, and X has a larger R, value than Y. (B) __Xismore strongly adsorbed by the paper than Y, and X has a smaller R, value than Y. (©) Yismore strongly adsorbed by the paper than X, and Y has a larger R, value than X. (PD) Yismore strongly adsorbed by the paperthan X, and Y hasa smaller R, value than X. GO ON TO THE NEXT PAGE17, 18. Species which absorb light in the UV-Vis region have I. saturated bonds Il, unsaturated bonds II, non-bonded electron pairs (A) Tonly (B) Land 1 only (©) Mand only (D) i. Wand It Item 18 refers to the following information, A student used gravimetric analysis to determine the percentage by mass of calcium in chalk. The student weighed 2 g of chalk and dissolved it in HCI, then added excess ammonium oxalate to precipitate the calcium ions. The precipitate was filtered, dried and weighed. Percentage by mass was then calculated. It was found, however; that the result obtained was lower than expected. Which of the following sources of error ‘could possibly account for this difference? (A) Incomplete drying (B) Error in weighing (©) Incomplete precipitation (D) Other ions precipitating from solution 19, 20. 21 Treatment of a 10.00 g sample containing a chloride salt with excess silver nitrate solution produced 8.08 g of silver chloride. (Ag= 108, Cl=35.5) Which of the following expressions ean be used to calculate the percentage of chloride in the sample? 143.5 * 8.08 35.5 10.00 35.5 * 8.08 143.5% 10.00 a) 100 @) 100 35.5 «10.00 143.5 * 8.08, © 100 143.5 «10.00 . ABO 100 100 35.5 * 8.08 Different regions of the electromagnetic spectrum have different energies. Which of the following equations justifies the criteria for dividing the electromagnetic spectrum into regions according to wavelength? [f= frequency] (A) C#FR (8) E=ht (C) E=me® (D) hey Which of the following materials are commonly used stationary phases in chromatography? (A) Cellulose, alumina, lime (B) Silica gel, lime, alumina (©) Lime, silica gel, cellulose (D) Alumina, cellulose, silica gel GO ON TO THE NEXT PAGE22, 23. ‘The complex ion [FeSCN}* has a molar absorptivity (e) of 7.0 * 10° dm? mot" em! The concentration of its solution, which gives an absorbance of 4.2 when measured ina2cmeell, is (A) 3 10% mol dm? (B) 6 * 10% mol dm (©) 3*10*mol dm? (D) 6 * 10" mol dm? In the infrared spectrum of an organic compound, a strong band is observed at 3000 cm. The MOST likely explanation is that (A) radiation is absorbed and causes the C-H bonds to vibrate (B) protons absorb infrared radiation at this frequency (©) thecompound is being decomposed by the radiation (D) bonding electrons absorb radiation and are excited to a higher level Which of the following regions of the electromagnetic spectrum BEST matches the wavelength ranges of P, Q and R? Frequency (H2) 108 is 108 (A) Uv OR (B) IR UV tadio © IR UV x-rays (@) UV IR x-rays 25. 26. 27, 28, Which of the following processes occur in ‘# mass spectrometer before isotopes can be detected? 1. Acceleration I. Amplification IL Deffection (A) Land Il only (8) Land Il only (C) Mand 111 only () 1 Mand it In the mass spectrometer a molecular ion is formed from a compound by the (A) loss of a proton (B) gain of an electron : (C) loss ofan electron (D) fragmentation of the compound What transitions are expected from C,H.NO, in a UV-Vis spectrum? (A) naandnoo (B) no’ ando—o" andn— x" (© 9 roa anda andno" (D) xm andn—a'anda—o" ‘Compound X contains three components, P,QandR. Component Piis needed as the starting material for the synthesis of a new drug. Which of the following methods of chromatography is MOST suitable for obtaining a pure sample of Component P? (A) Column (B) Paper (©) Gaseliquid (D) Thin layer GO ON TO THE NEXT PAGE29, 30, 3. Which of the following bonds would show the STRONGEST absorption in IR spectroscopic analysis? (A) Carbon-hydrogen (B) — Sulfur-hydrogen (C) _Nitrogen-hydrogen (D) — Oxygen-hydrogen Ittakes 5 em* of 1.4 M NaOH to neutralize 150 em? of HCI with an unknown concentration. What was the original concentration of the acid? (A) 047M (8) 0.047M (©) 0.014M (D) 0.0014M A sample of crude oil contains mainly C,H... In which crude oil fraction would ‘you expect to find this sample? (A) Bitumen only (B) Kerosene and bitumen (C) __Naptha and gasoline (D) Refinery gas 32. 33. Which of the following factors is LEAST important in locating a company where iton is extracted from its ore? (A) Cheap energy resources (B) _ Closeness to the market (C) Availability of transport (D) Proximity to the raw materials From the reaction given below, @ high pressure would give the best yield, but in industry, a moderate pressure is used. N,@) + 3H,(@) F* 2NH,e) Why isa moderate pressure used in industry rather than high pressure? (A) [tis too expensive to produce high pressure, (B) The reaction would be uncontrollably fast. (©) The reaction would be too slow to generate adequate NH, (D) _Itiseasierto remove the NH, from the reaction container. Item 34 refers to the following test for pollutants on a sample of water. TEST ‘OBSERVATION INFERENCE, HCI(ag) was added to the water sample drop by drop. ‘A white ppt. formed 34. What is the MOST appropriate inference based on the above observation? (A) Pb* ions present (B) PO, ions present (©) NO, ions present (D) — CN*ions present GO ON TO THE NEXT PAGE35, 36. 37. 38. What is the product of the following (unbalanced) equation? A1,0,H,0 (5) + H,0 (1) + OH (aq) > (A) Al,H,0C) (B) A1(OH),G) (C) Al, (OH),s) (D) AI@H)-(aq) Item 36 refers to the manufacture of chlorine by the electrolysis of brine using the diaphragm cell. The anode is made up of (A) steel (B) graphite (©) __ platinum with a coating of asbestos () titanium with an inert coating of ruthenium(1V) oxide Chlorine is MOST widely used for the manfacture of (A) solvents and sodium chi (B) solvents and polyvinylchloride (©) sodium chloride and poly- inylchloride (D) sodium chloride and chloro- fluorocarbons Which of the following methods are used in water purification? L_ Distillation I. Filtration UL. UV radiation (A) Land 11 only (B) Land Ut only (©) Mand 11 only (D) 1, Mand ul A991 MAA BE 9007 39. 40. 4. In which layer of the atmosphere is ozone detrimental to human health and vegetation? (A) Mesosphere (B) _Thermosphere (©) Troposphere (D) Stratosphere In one of the steps involved in the ‘manufacture of sulfuric acid, sulfur dioxide and oxygen are mixed to form sulfur trioxide according tothe following equation 280,(g) + 0,(@)_ 2S0,¢g) Which of the following options describes the effect of adding the catalyst VO, to the mixture? Equilibrium | Reaction Yield Rate (A)_ [Increases Increases, (B)_[ No change Tnereases (©) [No change No change (D) [increases ‘No change Chlorine can be produced by the diaphragm. method and mercury cell electrolysis. Which of the following statements is/are true regarding the diaphragm cell method? 1 less energy efficient, Il. Itis more energy efficient IIL, Ttislessharmful tothe environment, (A) Lonly (B)— Tonly (©) Tand Ill only (D) Mand Itt only GO ON TO THE NEXT PAGE42. 43. 44, IF YOU FINISH BEFORE -10- Chlorofluorocarbons (CFCs) with relatively high proportions of chlorine are potentially more damaging to the ozone layer. Which of the following reactions gives evidence of this? (RCL represents a CFC.) (A) _ Initiation step — RCL (g) > R(@) + Cl@) (B) Propagation — 0,(g) + Cl(g) > ClO“) + 0,(g) + COG) + Of) > Cl) + O,(8) (C) Termination — Cr(g) + CH,(g) + HCI (g) +CH, (D) Termination — ClO" + NO, > ClONO, Which of the following is NOT manufactured using ammonia? (A) ethanol (B) explosives (©) fertilizers (D) livestock feed Which of the following processes is NOT involved in the manufacture of ethanol? ‘i (A) Fermentation (B) Aerobie oxidation of sugar (C)__ Catalytic hydration of ethene (D) Addition of biological catalysts (enzymes) ‘Thermal pollution results in (A) increased fish population (B) _ nochange in dissolved oxygen (C)__ less dissolved oxygen in water (D) more dissolved oxygen in water END OF TEST rIME IS CALLED, CHECK YOUR WORK ON THIS TEST.