a UNISA CHE1502 OCTOBER / NOVEMBER 2018 GENERAL CHEMISTRY 1B ‘STUDENT NUMBER FTI ets ELLA a ae I Question No Examiners: FOR USE BY EXAMINATION INVIGILATOR Subject + + ‘Number of paper Date of examination Examination centre + WARNING + A-candidote whe without authonsaton Iskes iio the examination venue any Rack, document or object which could assist him 1 the xsmnation, and does no hand aver such ratenal 1 Die nwa store the offical commericertent of the examination wil be gully Of ininngng tee Unveretys examneton regulations and wl be lable to punshment as determined by Counc 2 Rough work may be done only on the extmansten question paper and must ne abliad as such 3 Nonotes may be made on any ar ofthe body, such asthe hands or on any garment 4 This pagelpaper isthe property ofthe Universi and under no crcunstances may the candidate ream itor take tout of the examination NB PLEASE COMPLETE THE ATTENDANCE REGISTER ON THE BACK PAGE, TEAR OFF AND HAND TO THE INVIGILATOR,UNIVERSITY EXAMINATIONS, UNIVERSITEITSEKSAMENS. UNISA lex CHE1502 (490797) OctobertNovember 2018 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 The examination paper consists of 27 pages plus 5 pages for rough work (pp 23-27) plus instructions for completion of the mark-reading sheet The examination paper consists of two parts: SECTION A: 50 marks: 25 multiple-choice questions The multiple-choice questions have four possible answers. Provide only ONE answer to each question Answer multiple-choice questions on the mark-reading sheet ‘SECTION B: 50 marks: Written questions Answers to the questions must be provided in the designated spaces on the examination Paper The use of molecular models is permissible ANSWER ALL QUESTIONS2 CHE1502 OCTOBER/NOVEMBER 2018 SECTION A What type of bonding 1s exhibited by CHsONa? (1) polar covalent bond (2) hydrogen bond (3) amuxture of covalent and sonic bonds (4) tonic bond Which of the following reactions 1s an example of heterolytic bond breaking? —> a (2) Chee + 80H =) CHsOH (3) one ——- CH 7 c® (4) Br + CHs —_—- Br—CHy‘The carbocation is an example of (ay 2) 8) (4) an Arrhenius base an electron-pair acceptor a nucleophile a Bronsted-Lowry base (CHE1502 OCTOBER/NOVEMBER 2018 The CORRECT STRUCTURE of the compound 1,3-cyclohexadiene is? (1) (2) @) (4) oo (TURN OVER]4 CHE1502 OCTOBER/NOVEMBER 2018, Which of the following structures is an example of a conjugated system? () 6 2) Oo (3) ® SS A (4) ZZ ‘Which of the following structures contain TWO sp? and ONE sp? hybridized carbon atoms? (1) H cry ct», 2) CHy;—c=c—H @) 9 I CHy—C—cH, (TURN OVER](4) 2 nf So CHE1502 OCTOBER/NOVEMBER 2018 Which of the following pairs of structures represent eclipsed conformations? a) (2 @ (4) # H and " H a H ci Gey fC and or H oe and H HY 4 and CH 4, cl a H CHy CHy Br H ot H, CHy 4 H [TURN OVER]6 CHE1502 OCTOBER/NOVEMBER 2018 Alkyl halides may undergo nucleophilic substitution reactions according to the following pathway: 70% eee eee re erige R—OH + HK 30% CHjOH Which alkyl halide is the LEAST REACTIVE when reacted with an aqueous alcohol solution via the Sy1 mechanism? a) (2) ° CHsCH,—I 4) Hg, te f CHy ‘Which one of the following reactions DOES NOT occur readily via the Sx2 mechanism? (1) ° Cheb — HoH + er (2) hy, HyC er e HO, ‘of ‘OH ra ° = + er 0 [TURN OVER]7 CHE1502 OCTOBER/NOVEMBER 2018 @ 7 Ho, gH ‘OH g iiiittel H0 () > 0 10 Whatis the IUPAC name of the following molecule? a. (1) 2-bromo-7-chloro-6-hydroxy-4.5,7-trimethyinonane (2) 8-bromo-3-chioro-3,5,6-trimethyl-6-propyinonan-4-ol (3) 6-bromopropyl-3-chloro-3,5,6-tnmethylnonan-4-ol (4) 4-bromopropyl-7-chloro-4,5,7-tnmethyinonan-6-ol 11 Which of the following alcohols 1s resistant to oxidation by chromic acid? a) joo ©-onon @) [TURN OVER]8 CHE1502 OCTOBER/NOVEMBER 2018. @) CHZOH Q @ 1H ¢ 12. What is the major product formed in the following reaction? {(CHs)yCOK te | a) 2) @ 4) OL OL 13 Which of the following molecules has a chiral (asymmetnc) carbon atom? a) 4 {TURN OVER](2) Na NHCH,CHs @) 4) CHa __-cOoH a (CHE1502 OCTOBER/NOVEMBER 2018 14 The absolute configuration of a chiral carbon is defined as R- or S- according to the Cahn- Ingold-Prelog rules. What is the name for the following compound? (1) (R)3-bromo-4-propytheptane 2) (RY+bromo-5-ethyloctane (3) (S)-4-bromo-5-ethyloctane (4) (S)-3-bromo-4-propylheptane 15 Which of the following amines 1s the LEAST soluble in water? (1) (CHsCH2CH)aN (2) (CoH)2NH (3) CHoNHe [TURN OVER]47. 10 CHE1502 OCTOBER/NOVEMBER 2018 (4) (CeHs)2NH . Which of the following compounds 1s classified as a primary amine (1) CHaNHe (2) (CHsCH2):NCHs (3) CoHsNHCHs (4) CHsCH2CH2CN Which of the following reaction steps is the first step in the mechanism of the reaction of ‘CHsCHCHsCH=CHe with Hs0°? (qt) H @ CHy—cH—c —— cH cH CHC, (2 9 HO LS a @ CHy—CHy—cH=£cH, + —— = cy 0H, CH CH, 3) HO Cy —c—cH=cH, 5% = cc cH SH, H [TURN OVER]18. "1 ‘CHE1502 OCTOBER/NOVEMBER 2018 @ 4 | 4 aN, e | cH —cH—cH=LoH, HHH, — SHH, ‘The mechanism for the E2 reaction of 1-chloropropane with hydroxide anion in the presence of heat is a) @ 3) (4) (TURN OVER]19 20 12 CHE1502 OCTOBER/NOVEMBER 2018 What 1s the major organic product formed in the following reaction? “re HgSo, NaBHy H,0 / THE (1) “tT ‘OH (2) AX (3) Aw (4) OH ‘Which of the following reactions will NOT produce the final product as shown? ay 1) NaNH, NH (TURN OVER}13 CHE1502 OCTOBER/NOVEMBER 2018 1) NaNH pies HaCH- 2) PhCH2Br NaOCH,CH crc — 1) NaNH, 2) (CHs)Br sch — 21 What is the MAJOR product formed in the following reaction? CH ye—C—on 1) NaOH Hy 2) CH3CH)CH)Br qa) ° @) [TURN OVER]23 (3) (4) 14 CHE1502 OCTOBER/NOVEMBER 2018 ian -——OCH,CH,CHs CH Ch, HsC——C——OCH(CHs)2 CH What is the IUPAC name for the following compound? a @ @) @) OH 9 4-ethyl-5-hydroxy-4-oxooct-3-ene S-ethyl-4-hydroxyoct-4-en-3-one 4-hydroxy-5-ethyloct-4-en-6-one S-hydroxy-4-ethyloct-4-en-3-one What is the structure of the major organic product formed in the following reaction? (1) 1) NaNHy 2) CHL {TURN OVER]15 CHE1502 OCTOBER/NOVEMBER 2018 @) 24 Which of the following compounds 1s the weakest acid? (1) (2) 3) ‘OH [TURN OVER]16 CHE1502 “ OCTOBER/NOVEMBER 2018 ‘OH 25. Which reaction intermediate is formed in the following reaction? ¢ j am mR on a) (2) 3) 4) —09 ‘CHsCH,—C—cl [60] [TURN OVER]17 CHE1502 OCTOBER/NOVEMBER 2018 SECTION B QUESTION 4 (25) (a) _ Draw the Newman projections of the most stable and least stable conformations of butane about the C2-C3 bond @) {b) Draw all the resonance structures to show electron delocalization in the following molecule Show the movement of the electrons using curved arrows for each individual step Oo \ 6) (TURN OVER]18 CHE1502 OCTOBER/NOVEMBER 2018 (c) Draw any three constitutional isomers for a compound with the molecular formula of CsH1« Give the IUPAC name for each compound ©) (d) Draw the geometric isomers of the following compound CHsCH2CH=CCHCI and name each isomer according to the IUPAC nomenclature @19 CHE1502 OCTOBER/NOVEMBER 2018 (e) Consider the following reaction. Br, Seeeeteeeeeeeee oe light ‘Show the structure of the MAJOR product formed in the reaction 2) () Draw the structure of any ether Give the IUPAC name of the compound | @) QUESTION 2 [25] (a) Outline a detailed mechanism for the following reaction’ NRF IEEE eeeeer eat eeeeeeedta PEL | | [TURN OVER](b) 20 CHE 1502 OCTOBER/NOVEMBER 2018 Draw the structures of the following compounds. () 5-bromo-2,4-dimethyipentanal (i) methyl ethanoate (4)24 CHE 1502 OCTOBER/NOVEMBER 2018 (€) Propose a detailed mechanism for the following reaction Name the major product according to the !UPAC rules and outline the stereochemistry at each chiral centre in the major product. . Bra — @)2 CHE1502 OCTOBER/NOVEMBER 2018 (@)__Iltustrate keto-enol tautomerism with appropnate structures (2) (2) Outline a detailed mechanism for the following reaction and name the major product according to the IUPAC rules OH HS, (conc) @) TOTAL MARKS [100] TURN OVER]23 CHE1502 OCTOBER/NOVEMBER 2018 ROUGH WORK24 CHE1502 OCTOBER/NOVEMBER 2018 ROUGH WORK25 CHE 1502 OCTOBER/NOVEMBER 2018 ROUGH WORKROUGH WORK 26 OCTOBER/NOVEMBER 2018 [TURN OVER]27 ‘CHE1502 OCTOBER/NOVEMBER 2018 ROUGH WORKUNIVERSITY OF SOUTH AFRICA UNI SA fo EXAMINATION MARK READING SHEET ‘Zizatlane UNIVERSITEIT VAN SUID-AFRIKA EKSAMEN-MERKLEESBLAD Pema ca ol foie nent avases aah, Hen oe eb eas > gummy as topos ae bets “bea ‘oa ees isso se gn cha) co es cep 8s See ch epee sete ot eh fps ets [es as ebs es case edo sap fogs fests ess ncn es ots ta] fests Pre i Manna Qa oS: 3 fora ip cf eben aris af MORTAR For use by examination invigilator Vir gebruik deur eksamenopsiener 4 Sarma 2 mares : 2 hanes = thao = S marae sy o © cer eas ew cy 4 Ghani t Rana Bo dha gien cy ® dares Bar asaresy a Sage 4 Bo dress cess Mo epg ets ay ahaa Sy wares dren gen sh Ho diane si Bodine Rodina Sy ena2 epsse aeese ma ais! naan thar hana neenes Sea Sena teens eouse ueeD: zeess arose geen an a] Hien ss ee Hie ig aes, Hise eo ey Gian aca Hoagie ane Hig anes cha ara enemas] Shan ace ee eed aida an esrerracs sper ea es Hidven cai Heeb a cais tsetse |” SUG aa aim ey mene aie Sharan ase cheba aeby Diag] poe Wasa ace Moa baal Maran] Most beens chaneresenfs =! | ne ci gvcceear ee Maal oe sR ag Baste caesy ty as Becseaca B idigrace Wee eg Bo vcbanig a be Mog 2 DS asgp Baty whan cpa oe! fom ay pareares cena: Cf i mia area manna a ahaa Q. 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