UNIVERSITI MALAYA PEPERIKSAAN SEMESTER PERTAMA. PROGRAM ASASI SAINS PUSAT ASASI SAINS TAHUN AKADEMIK 2008/2009 FIKAX0112 : KIMIA ASAS 2 OKTOBER 2008 MASA : 2% JAM ARAHAN : Kertas ini terbahagi kepada DUA BAHAGIAN. Jawab SEMUA\ soalan dalam BAHAGIAN A dan mana-mana EMPAT (4) soalan dari BAHAGIAN B. Soalan boletr dijawab dalam Bahasa Malaysia atau Bahasa Inggeris. ‘Semua jawapan hendaklah ditulis dalam kertas jawapan yang dibekalkan. (Kertas peperiksaan ini mengandungi 10 soalan di dalam 21 halaman bercetak).FKAX0112/02 SECTION A (@) Consider the structure of aldosterone given below: CH,OH ¢=0 nt Ho. HC o Aldosterone () Give the molecular formula of aldosterone. (ii) Name the types of functional groups present in the molecule. (4 marks) (>) (i)_Rewite the structure of prostaglandin using skeletal formula. HO. SCH. Gig GHCH2CH=CHCH,CHCH)CH,COH A CHCH=CHCHCH,CH,CH:CH:CH, HOW bu Prostaglandin Using condensed formula, write the structure of an isomer of CyHis which has five primary carbons, one secondary carbon, one tertiary carbon and one quartenary carbon atom. Gi) (3 marks)© @ ) FKAX0112/04 Name the type of each reaction given below: * Om Oo Gi) crycscH ONNE, CHsc=ccH; + NH) + NaBr CBr Nicomplex (ii) 3HC=CH > (3 marks) Consider the following reaction scheme of an alkene. CO ecincr, CH f HCl GHCH-CH, ———* B+ € (oaion oro (major) ee pe GCH,CHs + Or piiion tu, (major) (Give the IUPAC name for the alkene. (ii) Write the structural formulas for A — E ii) State the reagents and conditions for J and I (8 marks) Arrange the following compounds in the order of increasing boiling point: (i) Hexane, heptane, 2-methylpentane (ii) 2-Methylpropene, cis-2-butene, trans-2-butene iy (2 marks)@ ) FKAX0112/06 Give the IUPAC name of each compound below: (® __sec-butylisopropylacetylene (i) CH=CH; ii) CH;Br ° NO2 (3 marks) Complete the following reaction equations: HSO4 (i) CHs;C=CH + HO ———> > HgSO, ‘NaNH> CH3CH,Br (i) CHyC=CH ———> ae ii) CHs Ch — uv I Ch/FeCls (iv) NE #20 + 3B ——> (7 marks)@ (b) © FKAX0112/08 A sample of chlorine gas is analysed in a mass spectrometer. The sample composed of two isotopes with the mass of the isotope *°Cl is 34.96 amu and mass of isotope "Cl is 36.97 amu. The isotopic abundances of °C] and >7C1 isotopes are 75% and 25%, respectively. (Calculate the atomic mass of chlorine. (ii) Sketch the niass spectrum of the sample of Cls* ions. (4:marks) A gaseous compound containing carbon and hydrogen has a molecular mass of 26 amu. Combustion of 25.3 g of this compound yields 85.6 g CO2 and 17.5 g 120. (i) Whatis the molecular formula of the compound? (ii) Write the balanced equation for its combustion. Relative atomic mass : C = 12.00, H = 1.00, O = 16.00 (4 marks) When dinitrogen pentoxide, N20s, a white solid is heated, it decomposes to nitrogen dioxide and oxygen. 2N,0s(s) > 4NO2g) + Ong) If a sample of N2Os produces 1.618 g of oxygen, how many grams of NO> are formed? Relative atomic mass: N = 14.00, O = 16.00 (2 marks)@ ) FKAX0112/10 SECTION For the reaction given below: u I @ Gi) @ @ aD Gi) (CHj)N + HBr ——> CHCH,Cl + AICh ——> Describe the reaction by drawing curved arrow(s) to show the movement of electrons. Write the possible products of each reaction. (6 marks) State the type of compound and draw the functional group isomer of the following compounds ° HOCCHCH Hs [>—ock.cts ‘Arrange the following carbanions in order of increasing stability and briefly give the reason. CH;CH,CHCH,NO) CHCHCCHs ONCHCHCHs CH;CHCH,CH ii) CHy CH @ i) (iii) (iv) Write the structures of four geometrical isomers of molecular formula CsHio. (9 marks)@ (b) © FKAXO112/12 What is the IUPAC name for the following compounds? @ — CICH,CH()CH:Br Gi) ne{ Yoo CH,CHy (iii) “or CH Zt H® ~~ CH,CH(CH;), dy) CH, i? e HCH, (vy) BrCHCH=CHCHCH, (S marks) Three hydrocarbons X, ¥, Z have molecular formula CsHi2. Hydrocarbon X does not decolourise dilute solution of potassium manganate(VII) at room temperature. Hydrocarbon Y decolourises dilute solution of potassium manganate(VII) and shows geometrical isomerism. Hydrocarbon Z decolourises dilute solution of potassium manganate(VIl) but does not show geometrical isomerism. (Suggest the identity of X, Y and Z. (i) Write equation for the reaction of Z with dilute potassium ‘manganate(VI). (4 marks) Write an equation to show how each of the following alcohols may be obtained as the only hydration product of a suitable alkene: (i) (CH3CH(OH)CH2CH3 (ii) | CHyCHyCH(OH)CH,CH2CH3 (3 marks)@ @) (b) FKAXO0112/14 Starting with a suitable alkene, write an equation to show how each of the following compounds may be synthesized: @ pr Cro OH ii) Cl i) C} ae Mixtures of alkenes may be produced by dehydration of alcohols. @ Gi) Gi) @ wo ii) ww) Show how the dehydration of alcohol P forms alkene @ using a 1,2- hydride shift. IH ot USO, CY + 0 Q ‘What other alkene is also formed along with @ in problem (i)? ‘What alkenes would be formed from P if no carbocation rearrangement occurred? (6 marks) State the Markovnikov’s rule Use the Markovnikov’s rule to predict the products when 1- methylcyclohexene reacts with the following reagents. 1 Aqueous bromine Tl Steam in phosphoric acid as catalyst Write equations for the reactions of hydrogen bromide with I cyclohexene I I-methyleyclohexene. Which of these two reactions is faster? Explain your answer. Draw the structure of product formed when 1-methylcyclohexene is I treated with dilute potassium permanganate at room temperature. Tl boiled with concentrated potassium permanganate followed by acidification. (9 marks)@ () © @ (>) FKAX0112/16 Write the equations for the following electrophilic substitution reactions of benzene: t (Methylation Gi) —_‘Nitration (ii) Bromination : (4% marks) Choose ONE of the reactions in (a) and answer the followings: (i) Write equation for formation of the electrophile. Gi) Show with curved arrow the electrophilic attack on benzene (arene). (ii) Write the contributing resonance structures of the arenium ion. iv) Show with curved arrows formation of product and restoration of benzene ring. (6 marks) With reaction equations and description of observation, give a simple test to distinguish the following pairs of compounds: () | CHyC=CCH; and CHyCHC=CH “@~0 Write the equations of reactions involved in the synthesis of propyne from 2-propanol (CHsCH(OH)CHs). (4 marks) (4 4 marks) Starting with benzene, two separate syntheses are carried out according to reaction sequences A and B. Reaction sequence A: (1) Alkylation @) Oxidation @) —_ Bromination© ) FKAXO112/18 Reaction sequence B: ()_—_Bromination Q) Alkylation 3) Oxidation () Write the structures and name the final products/product of reactions sequence A and B. (i) Write the reaction equations for ei sequence A or sequence B. (6 marks) Dichloromethane, CHCl, is a component of many paint-stripping solvents. It is, made industrially by the free radical chlorination of methane. (Describe the reaction mechanism of its formation, appropriately labeling each step in the mechanism. (ii) Draw the structures of two possible organic side products in the reaction. (S marks) Carbon disulfide, CS;, bums in oxygen. Complete combustion gives the reaction CSx(g) + 30g) > COx(g) + 280,(e) In an experiment, 15.0 g of carbon disulfide is reacted with 35.0 g of oxygen. (What is the theoretical yield (in grams) of SO2 that can be obtained from this reaction. (ii) ‘The actual yield of sulfur dioxide is 25.0 g. What is the percentage yield of the reaction? Relative atomic mass: C = 12.00, $= 32.00, O= 16.00 (5 marks) The density of 8.5% by mass of ammonium chloride, NHiCl, solution is 1.024 g/mL. What are the molarity and molality of NH,CI solution? Relative molecular mass: NH4Cl= 53.45, H0 = 18.00 (5 marks)© FKAX0112/20 In an experiment on volumetric analysis to find the percentage of iron in a sample of iron wire, the following result was obtained: 1.450 g of the wire was dissolved in excess of dilute sulphuric acid and the solution made up to 250 mL. 25 mL of this solution required 24.50 mL of 0.0196M of KMnO, for oxidation. Calculate the percentage of iron in the sample. Relative atomic mass: Fe = 55.85 (5 marks) seeneeeeeeeeees