a UNISA FINAL % CHE1502 (474468) OCTOBER/ NOVEMBER 2017 GENERAL CHEMISTRY IB ‘STUDENT NUMBER IDENTITY NUMBER. Marks: ‘Question No Examiners FOR USE BY EXAMINATION INVIGILATOR Subject Number of paper Date of examination Total WARNING 1A candidate who vsthout authonsaton takes ino the examination venue any book, dccumont oF object which coukd assist nn the exaimnaton, and dows not nar over such material to the inglator before ie oltre commencement a! the examination wail Be gly of intinging the Urvversy 5 exarnmaten reyulatons and wi Oe uable to purshment as delernad by Gouncl 2 Rough work may be done ony onthe exaranation question paper and must be labeled a& such 3 Nonotes may be made on ary part of tye body such asthe nands or on any garment 4 This pagefpaper is the propenty of the Unverey and under no exeumetancas may the candidate ream to take «out ofthe examination NB PLEASE COMPLETE THE ATTENDANCE REGISTER ON THE BACK PAGE, TEAR OFF AND HAND TO THE INVIGILATORUNIVERSITEITSEKSAMENS ~— UNISA \fen UNIVERSITY EXAMINATIONS CHE1502 (474468) October/November 2017 GENERAL CHEMISTRY IB Duration 2 Hours 100 Marks. EXAMINERS FIRST PROF CA SUMMERS SECOND PROF GJ SUMMERS Use of a non-programmable pocket calculator is permissible Closed book examination ‘This examination question paper remains the property of the University of South Africa and may not be removed from the examination venue EXAMINATION PAPER UNIQUE NUMBER 474468 The examination paper consists of 25 pages plus 5 pages for rough work (pp 26-30) plus instructions for completion of the mark reading sheet The examination paper consisis of two parts SECTION A 30 multiple choice questions answer on a marking reading sheet Each question 1s allocated TWO marks SECTION B Whitten questions answer in spaces provided on the examination paper 40 marks The multiple choice questions have four possible answers In each case, provide only ONE answer to each question HH The use of molecular models is permissible ANSWER ALL QUESTIONS IN SECTION A AND SECTION B2 CHE1502 OCT / NOV 2017 SECTION A This section consists of 30 MULTIPLE CHOICE QUESTIONS ‘Answer ALL the questions in this section on the MARK READING SHEET Unique Number 474468 1 Identify the CORRECT statement below a) (2) (3) (4) ‘There are 3 distinct s orbitals exist in the second electron shell, where n = 3 The electron configuration of carbon is 1s%2s?2p? A carbon-hydrogen bond (C-H) is polar A carbon-bromine bond (C-Br) is non-polar 2 Which of the following DOES NOT represent the appropnate hybridization state of the carbon atoms in the structures shown below? (1) 2) 3) a) H cing + s8thybribzed wow sp? hybridzed ® hybridized Gy * SP? yb H + sphybrdeed {TURN OVER]3 In the structure below, the formal charges are (1) #1onBanddono (2) -1onBand0onO (3) -1onBand +1 onO (4) +1 onBand-1 onO CHE 1502 OCT/ NOV 2017 Which of the following pairs of compounds are constitutional isomers? (1) and @ oe ge GA oH C—H a CHycH, CH @ and (4) and —CHy [TURN OVER}- 4 CHE 1502 OCT /NOV 2017 For questions 5 and 6, consider the following reaction: + Hc 5 The structure of the Lewis base (nucleophile) in the reaction is a) CHy (2) @ (4) 6 The structure of the conjugate base in the reaction 1s a) 2 CHy: (TURN OVER]5 CHE1502 OCT /NOV 2017 Which of the following processes is the correct representation of heterolysis / heterolytic bond breaking? (1) oH (2) e + od (3) i 4 Lee, Br er! H—C—Br ! I (4) 4 ore if iw 4 What is the IUPAC name of the molecule shown below? (1) 4-ethyl-4-methyihexane (2) 4ethyl-3-methylheptane (3) 3-methyl-4-ethytheptane (4) 2,3-diethylpentane [TURN OVER}6 CHE1502 OCT / NOV 2017 Which of the following structures is NOT a conformation of the compound, CH,CH,CH,CH,? (1) @) (3) (4) H. CH CH 4 [TURN OVER}10 " 7 CHE 1502 OCT /NOV 2017 Which of the following conformations of 2-10do-propane, CH;CH,CH,|, the represents the ANTI- conformation? (1) 2 3) (4) Hy, 4 Drew 1 1 H. cl 4 H 4 CHa en, ir Hi Consider the compounds, (CH,),NH and CH,CH,CH, Which statement is CORRECT? a) @) @ O) CH,CH,CH, can form hydrogen bonds with water (CH,),NH is not capable of undergoing hydrogen bonding with water (CH,),NH is insoluble in water (CH,).NH ts more soluble in water than CH,CH,CH, [TURN OVER}12 13 8 Identity the MOST STABLE carbon radical (1) 2) 3) 4) oo What is the major organic product formed in the following reaction? ight (Cllg),CH CH CH + Bry a) (CHs)p CH CH,CH,Br (2) Br—CHy CH-CH.CHy CHa (3) {CHsl CHCH-CHy Br 4) Br (CHs-C~CH.CHs CH CHE1502 OCT /NOV 2017 {TURN OVER]9 CHE1502 OCT / NOV 2017 14 Which of the following reactions 1s an example of an elimination reaction? a) CHSCHaFHCHs + NaOCHy -CHAOH Br OCHs (2) Hy cH GHyCH_OH Ae CHy—G—Br + NaOH = of i CHy CHCl, @) CHBr LCHECN Kon @0e a, + KBr Ho (4) cl “Nf —_—2_ yw a [TURN OVER]15 16 10 CHE1502 OCT / NOV 2017 Alkyl halides may undergo nucleophilic substitution reaction according to the following reaction R—x + HO — R—OH + OK Which compound 1s the LEAST REACTIVE under these conditions? 0) Br SA 2) Br Ph—C—CHs H (3) ie Coe # (4) Hy Ph—C—cr CH Consider the following reaction Ona et eoutiitte ratte What is the major product formed in the reaction? [TURN OVER}7 W CHE1502 OCT / NOV 2017 a) : (2) . (3) (4) Which of the following reactions DOES NOT proceed via an Sx2 reaction mechanism? a) CH,CHeBr + NaSH + OHCHSH + NaBr @) 1 pM Rear ates Eee @) (CHy),CHBr + NaCN = = (CH).CHEN. + NaBir (4) Ce Oe tr (TURN OVER]12 CHE1502 OCT / NOV 2017 18 What is the major product formed in the following reaction? ee. Na _OCHCHs Br ay (3) (4) ae 19 Which of the following alcohols 1s produced by the acid catalyzed hydration of the following compound? poe ay 2) [TURN OVER)20 13 CHE 1502 OCT / NOV 2017 3) CHjCHy ou enero What is the major product formed in the following reaction? (4) Ha, CH 4 Her oo — 4 ‘CHy a) 2) (3) SENHA he (4) [TURN OVER}21 14 CHE1502 OCT / NOV 2017 Alkenes undergo addition reactions in the presence of bromine What is the MAJOR, product formed in the following reaction? Br — (1) Cit (2) Br 2 ; (3) Bray Br (4) Bray (TURN OVER]23 15 CHE1502 OCT /NOV 2017 ‘The absolute configuration of a chiral carbon 1s defined as R- or S- according to the Cahn-Ingold-Prelog rules What is the IUPAC name for the following compound? CH,CH:CHy oH c, 2 Ho Nou, ciicscH, (1) (8) octan-5-o1 (2) (A) octan-4-01 (3) (R)octan-5-o1 (4) (S)octan-4-o1 What is the major organic product formed in the following reaction? H,S0, io a) (2) (4) KREK 2, [TURN OVER)24 25 16 CHE 1502 OCT / NOV 2017 ‘What are the major products formed in the following reaction? ON or cher, eal (1) OH (Cr + cHucnoH (2) 1 fe + cmcnon (3) on ce + exyen (4) 1 ie + CH,CHI What reagents can be used for the following conversion? q crete —c: Seereealltl ae tial (1) 1 Hy, Ni, # Na,Cr,0,, HSOs (2) Ho", H,SO,, HO (3) 1 CH,MgBr, 1 CO, (4) 1 Oy, # (CH,),S [TURN OVER}26 27 17 CHE1502 OCT / NOV 2017 What is the MAJOR product in the following reaction? CHyCH,c==ccH, ‘ea Bre (1) } (2) Br a, (3) Br, H ee (4) 7 Which of the following compounds is the WEAKEST acid? (1) 2 , g £ cr 2) ° Aw @) ° LWA, (4) ° : 2 (TURN OVER}28 29 18 CHE1502 OCT / NOV 2017 What is the correct structure of (Z)-3,4-dimethylhept-3-enoic acid? () ‘COOH 2 aw (3) COOH cHscH~ SS (4) SS coon Which species is formed in the following process? a) (TURN OVER}19 CHE1502 OCT /NOV 2017 (2) () 4) In the reaction of an amide with a strong acid, protonation takes place at the oxygen instead of the nitrogen atom because (1) Oxygen is less electronegative than nitrogen (2) H* only becomes attached to an O and never to a N atom (3) The non-bonding electrons on nitrogen 1s more available (4) The following occurs [60] [TURN OVER]20 CHE1502 OCT /NOV 2017 SECTION B Answer ALL the questions in the SPACE PROVIDED AFTER EACH QUESTION Question 1 [20] (a) Draw the Lewis structure of the following compound 5 a (3) {b) The compound shown in (a) above can undergo resonance delocalization Show the resonance delocalization with all the possible resonance forms of the compound Show the movement of electrons with curved arrows (6) {TURN OVER]at CHE 1502 OCT / NOV 2017 {c) Formulate a detailed mechanism of the following nucleophilic substitution reaction 6) (@) Draw the structure of butan-2-ol and indicate whether or not the molecule has a chiral (asymmetric) carbon atom Explain your answer (4) (TURN OVER}22 CHE1502 OCT / NOV 2017 (e) Draw the enol form of the following compound a o (2) Question 2 [20] (a) Draw the structure of a diene with a trans double bond and a cis double bond (b) Consider the compound with the proposed name 1,1-dimethyl-2-chlorohex-3-ene () Draw the structure of the compound that 1s consistent with the proposed name given above 2) [TURN OVER]23 CHE 1502 OCT / NOV 2017 () Explain what 1s wrong with the name provided (state each violation of the IUPAC nomenclature rules) and give the correct IUPAG name for the compound @ [TURN OVER}(a) 24 CHE1502 OCT / NOV 2017 Use curved arrows to show how bond(s) break and/or form in the process shown below (2) CHy, H CH H Sieg ‘\e_! eal teen c—c—H CHCHY CH Ga | CH; Draw the structure of the MAJOR product formed in the following reaction CHy, H HBr —_> peroxides cH "CH2CHs (2) (TURN OVER]25 CHE 1502 OCT /NOV 2017 () Draw the complete mechanism for the following reaction sequence by showing the conversion of the starting alkyne to the formation of the final product cmcscn NN: CHyBr i () Name the following compound according to the IUPAC nomenclature rules 9 i J 4 CHy—CH—cH Dpatea ge CHyCH, @ [40] TOTAL MARKS [100] © NSA 2017 [TURN OVER}26 CHE1502 OCT / NOV 2017 ROUGH WORK [TURN OVER]27 CHE 1502 OCT / NOV 2017 ROUGH WORK [TURN OVER}28 CHE 1502 OCT /NOv 2017 ROUGH WORK [TURN OVER]29 CHE1502 OCT / NOV 2017 ROUGH WORK [TURN OVER}30 CHE1502 OCT / NOV 2017university oF souta arrica U NISA. EXAMINATION MARK READING SHEET PART 1 (GENERAL/ALGEMEEN) DEEL 1 med ‘azo UNIVERSITEIT VAN SUID-AFRIKA EKSAMEN-MERKLEESBLAD tana (Q] semanas GQ 0 «co» cas er tos fas eta ets fas etueta acta fb ex: ean eds cas ers ezn cas] fase cdo asso Keds cs games casas] [ac omy Sh fee bee aay [asa Gea sess 1 NOAM cs coco] [on Ss MOAR sc ls os ees eco ls ers eos eer lb eas sae sch [oy areas lcs ces asec lps eps en eps ef tee ob ad rch 181s 9] For use by examination invigilator Vir gebruik deur eksamenopsiener 4 impoRTANT 1 USEOmLY AN HB PeMeN To COMPLET Ta SHEET 6 HEC raat THe uweue meargR HAs BEN rlLeD mv conncerir 4 sonorous PART 2 (ANSWERS/ANTWOORDE) DEEL 2 2 Meneasvoe om ' kowtmoteen OAT vo ROWEKiE SWOSNTTNOMMER ERSTE HEE 6 Kontmo.eer bat ot ueexe NoumIER REG GELS ee TEEreS yt eae Tao fa or eae 1 EEO 2 oes ‘eemed lg aneat tanaed |2 ganas i iiaed |2 gaeas PEE) |p Gees iEha | Ee oar [eee rguaaa [seems igugaa |i gases Py |? ees PEEL [2 EES eee ieee raugeaa |# eyes igaged |: ayia eee | PE ew eee. sae tc ie QO mrss LOOT ss hanes enay ieee] sie eo esl then aieh a iienen en a Si ediageck Heb eb ean areal Shere ete si cien ace than are Ai dds ew ee ised ooo Hit Gs eo Hath > en Range a heb ah te equim cae thane se] eee ebb fh ere eb ce} Shen a geek? eueee wee sees aeane see % a Sea] R fer siscaiag ca ea n Me dieneaen a 4 We qvaraien ai 5 MO dich asen Bets erreas canes ep er easea es D saan ae feb Grete] R tare ia Hanae By taesen area 136 eb es ® dara soe Gre Bares sane cp ane es B haga ca egrear ea ca 5 ese eb st a mana = chee e tm ararearease 12 tana eaes IB ttecp seca sty Ht aie as co a B mevan ar Us chen aca a gras aan te trees 2 Danas eo | = th toararre o iB mae * im faery tea % tm sear ep care BD naae IR trees cna & manana IB Magen B Siaun aes Wage r aia aia sl we 98 cise ety cas iw @ magma 6 & manana ct B wena cy ie tharcaaMARK READING SHEET INSTRUCTIONS Your mark reading sheet is marked by computer and should therefore be flled in thoroughly and correctly USE ONLY AN HB PENCIL TO COMPLETE YOUR MARK READING SHEET PLEASE DO NOT FOLD OR DAMAGE YOUR MARK READING SHEET ‘Consult the lustration of a mark reading sheet on the reverse ofthis page and follow the instructions step by step when working on your sheet Instruction numbers @ to @ refer to spaces on your mark reading sheet which you should film as fallows © Wate your paper code n these eight squares, for mstance © the paper member pertains only to first-level courses consisting of two papers write [OTT] forthe rst paper and [0] 2 | forthe second AF only one paper, then leave blank © Filln your imtiats and sumame © Fittanthe date of the exammnation © Fitinthe name ofthe examination centre © WRITE the digits of your student number HORIZONTALLY (from leftto nghi) Begin by Gilling ithe firs digit of your student namber i the ist square on te lef then fil the other dis, each one n 2 separate square @ in cack vertical column mark the digit that corresponds tothe digt m your student number as follows 4 © WRITE your unique paper number HORIZONTALLY NB. 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