a UNISA |= CHE1502 (474458) MAY / JUNE 2019 GENERAL CHEMISTRY IB eee eee FOR USE BY EXAMINATION INVIGILATOR Subject Number of paper Date of examination Examination centre WARNING 1A candidate who without authonsation takes mnt the examination venue any Book, document or object which could assist hm mn the ‘amination, and doesnot hand aver such malena tote ngstorbelore the offal commencement sf the tarrseasor wk este ‘Wfnngng te Univers examanaton reguiabons and wil be liable punish es determined Sy ices 2 Rough work may be done only on the exammnaton queston paper and must be labeled as such 3 Nonotes may be mede on any part ofthe body, such asthe hands, arom any garmont 4 This papefnaper i the propeny of he Unveraty and under no ercumstances may the candat retain & of tke @ ot ofthe examination ‘MB PLEASE CONPLETE THE ATTENDANCE REGISTER ON THE BACK PAGE, TEAR OFF AND HAND TO THE INVIGILATOR.UNIVERSITY EXAMINATIONS UNIVERSITEITSEKSAMENS. ~— a UNISA lSnn CHE1502 (474458) May/June 2019 General Chemistry IB nee al au nee vee coe PREM 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 28-32) plus instructions for completion of the mark-reading sheet ‘The examination paper consists of two parts: SECTIONA: 60 marks 30 multiple-choice questions Each multiple-choice question has four possible answors. Provide only ONE answer to each question Answer multiple-choice questions on the mark-reading sheet SECTIONB: 40 marks 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CHE1502 MAY/JUNE 2019 SECTION A Consider the structure of CHsCl Which statement is correct? (1) Swx valence electrons of the carbon atom are involved in the hybridization process (2) The hybndization state of the carbon atom 1s sp? (3) Apprbond is formed by the overlap of a 2p atomic orbital of the carbon atom with the s- atomic orbital of the chlorine atom (4) The carbon-chionne bond 1s a polar bond Which of the following reactions is an example of heterolytic bond breaking? (0) Che + 9SH + CHaSH @ e ° CHy—cl ——» CH + Cl @ Hy Hy Hy Cty ——$> ech; + ooo CHs CH3 4) ° e er + CH er-—cH, [TURN OVER]CHE1502 MAY/JUNE 2019 Which of the following structures is NOT an example of a conjugated system? a) Ay i) ams ol ‘Which of the following structural formulas 1s the CORRECT structure? (2) @) (4) a [TURN OVER]‘CHE1502 MAY/JUNE 2019 @) @) ° “0: I oH WON \ @ e_. CH3——N==0 Which of the following s NOT an example of the concept of resonance? a) @) 3) ITURN OVER]CHE1502 MAY/JUNE 2019 @) cHy—C—oH <> cHy—C=8H Predict the hybridization state, geometry and bond angles for the central atoms in 2-butene (1) The carbon atoms are sp? hybndized, with tngonal planar geometry and a bond angle of 109° (2) Carbon 2 is sp? hybridized with a bond angle of 120° and linear geometry (3) Carbon 3 is sp* hybndized with a bond angle of 120° and a tetrahedral geometry (4) Carbon 2 and 3 are sp? hybndized, with trigonal planar geometry and a bond angle of 120° ‘Which structure is an INCORRECT representation of the following compound? (CHah(CHEHCH:CHy CH a) CHs H. CHs cHy H CH(CH)2 (2) 4 cH, Hy CHCHs cus H (TURN OVER]CHE1502 MAY/JUNE 2019 @) CHa H. CHy cHy H CH{CHs @ AN ‘What is the IUPAC name of the following compound? CHs i CHy HyC" H a (1) 3-chloro-2-ethyl4,5-dimethylhexane 2) 4-chioro-S-ethyi-2,3-dimethylhexane @) — 4-chloro-3,5,6-timethylheptane (4) 3-chloro-2,3,5-tnmethyiheptane (TURN OVER]10. " ‘CHE1502 MAY/JUNE 2019 Which of the following sets of reagents and reaction conditions will complete the following reaction? a) @) 8) (4) Lay —- [~T* Ch, Nior Pt catalyst CHSC, light ‘Aqueous HCI, heat Ch, light ‘Which of the following substrates will react the FASTEST via the Sv1 mechanism? a) (2) (3) (4) (CeHs)sCCH20H (CsHs)eCHCH2Cl (Cets)sCSH (CeHs)aCCl ‘Which one of the following reactions occurs predominantly via the Sx2 mechanism? (ty cher — cH,OH + Br [TURN OVER]12 CHE1502 MAYIJUNE 2019 (2) Cth, Br a M, ne ‘tg OH Yn, Ho C Ho, 2. np OH “4, ° a er 4.0 ro 4) aa “2 OO +20 ‘Which of the following products is NOT formed in the followang reaction? CHs unncrchy + + CHO" _CHsOH ra (a) CCH ok, [TURN OVER]13 4 CHE1502 MAYHJUNE 2019 2 ma Yomel WO Nor hee cH 4 i, 2 Noo woos (4) cts chy ——enors 4 Which of the following compounds has the highest boiling point? (1) (CHs)pCHCH2CHs (2) (CHs)2CHCH20H (3) CHs-COOH (4) (CHs)sCC! ‘Which of the following compounds 1s the MAJOR product formed in the following reaction? Naget ‘Br [TURN OVER]CHE1502 MAY/JUNE 2019 (ty + (2) x Et 3) a 15 The mechanism for the E2 reaction of 1-bromopropane with the methoxide anion in the presence of heat is a) 2) {TURN OVER]16 W CHE1502 MAY/JUNE 2019 @) 4) Alkenes react with hydrogen halides to give alkyl halides as products What is the MAJOR ‘organic product formed in the following reaction? TC ae Br (a) (2) [TURN OVER]7 18 12 CHE1502 MAY/JUNE 2019 @) Te @) Consider the following catalytic hydrogenation reaction. CH3 ‘cH ‘Which of the following statements ts CORRECT? (1) The reaction proceeds via a catalyzed isomenzation process (2) The syn addttion of hydrogen gives the cis isomer as the major product (3) The catalyst speeds up the reaction by stabilizing the major product of the reaction (4) The trans isomer is formed as the minor product in a racemic mixture ‘What is the mayor organic product formed in the following reaction? ee H9SO. NoBH, 20 |THE [TURN OVER](a) (2) @) (4) ‘CHE1502 MAY/JUNE 2019 Which of the following reactions does NOT occur? a (2) @) @) ee ee CH3C: Na + CH;CO;H ——= CH,C==CH + CHsCO)Na Co ee CHsC==C Na + CH;OH ———» CH,C==CH + CHjO Na ee concen + NeW, = ———> cHC=EC Na+ NH eo cHc==cH + MOH = ——m cHc=EC he + HO [TURN OVER}20 2 4 CHE 1502 MAYAJUNE 2019 Which of the following reagents are used to convert 2-butyne to trans-2-butene? (1) He, NE (2) He, Lindlar’s catalyst (3) Ns (liquid) (4) Ly, NH (liquid) Alcohols undergo dehydration reactions in the presence of acid and the reaction proceeds via the most stable carbocation intermediate, Which of the following alcohols undergoes ‘carbocation rearrangement reactions during acid catalyzed dehydration reactions? 0} HoH cH; —o— a 4d (2) 8 ctor ba 8) 4 crete ten, bi “4 [TURN OVER)15 ‘CHE1502 MAY/JUNE 2019 22 Which of the following molecules is achiral? a) se @) 3) 4) pn Xe 23. Which of the following structures show the (S) configuration at the chiral center? an er Ho, e L ay (2) [TURN OVER}16 CHE1502 MAY/JUNE 2019 @) : oe : ae @) HO. oo CIH,C 24 Which of the following alcohols ts NOT oxidized by pyridinium chlorochromate (PCC)? oo a @) o~ @) Ae @ AK [TURN OVER}7 ‘CHE1502 MAY/JUNE 2019 25 Ethers undergo cleavage reactions in the presence of acids What are the MAJOR products formed in the following reaction? (box + Ht oe oN + CHyCHOH SAL B+ ction bw 26. Whats the IUPAC name for the following compound? (1) (2) @) 4) (1) S-vinyl-2-hexyn-5-al (2) 4-propynylpent-2-enal (TURN OVER]18 CHE1502 MAY/JUNE 2019 (8) 4-methyihex-5-yn-2-enal (4) 4-methylhept-2-en-5-ynal 27 Which of the following reactions yields PhCOOCHs as the major product? a OH + HCOOH ———> (2) OOH + cHOH (3) o (4) + Ker | [TURN OVERI28 29 19 CHE1502 MAY/JUNE 2019 ‘Which reaction intermediate 1s formed in the following reaction? eryc—C—oCHs NaH ® cHycHy—g—OcH, @ fi ® ° Le cise — Fac OH « ° ct —E— 00H OH Which of the following compounds 1s classified as a secondary amine a) NH A ITURN OVER]CHE1502 MAY/JUNE 2019 (2) “—~™NHe @) CHa, ,CHy Do (a) CH, 30 Which of the following amines 1s most soluble in water? (1) CaHsNHCHs (2) (CaHs)sN (3) CHsNH» (4) (CH3CH,CH,),NH [60] [TURN OVER]a CHE1502 MAY/JUNE 2019 SECTIONB QUESTION 4: (2) Use Newman projection formulas and draw the most stable and least stable conformations, about the C2 - C3 bond, of 3-methylpentane @) (b) Draw the three dimensional structure of (S)-2-bromobutane according to the Cahn-Ingold- Prelog convention (2) [TURN OVER}22 CHE1502 MAY/JUNE 2019 (©) Draw the geometric isomers of the following compound: CHsBrC=C(CH2CHs)CHBrCHs and name each isomer using the cis-trans or E-Z nomenclature @) (@) Draw the Lewis structure and all the resonance structures of each of the following molecules Show the electron delocalization and movement of the electrons using curved arrows for each individual step i ) NHy-—C==CH, () CHy—NO, @ (w) CHy—o—C—cH, H [TURN OVER]23 CHE1502 MAY/JUNE 2019 (6) () Consider the following reaction: Br, i Draw the structure of the MAJOR product formed in the reaction 2) [TURN OVER]24 ‘CHE1502 MAY/JUNE 2019 (9 Define the concept of the inductive effect 2-Chloroacetic acid is more acidic than acetic acid Why? 2) [20] [TURN OVER]25 CHE1502 MAY/JUNE 2019 QUESTION 2: {a) Name the following compound according to the IUPAC rules @ (b) Outline a detailed mechanism for the acid catalyzed hydration of 2-methyl-2-butene and name the mayor product according to the IUPAC rules 6) [TURN OVER]26 CHE1502 MAY/JUNE 2019 (©) Draw the structure of propyl 2-chloro-4-methyipentanoate @) (d) Propose a detailed mechanism for the reaction of 2-bromo-3-methylbutane with ethanol in the presence of heat Name the major product according to the IUPAC rules 6) ITURN OVER]a7 CHE1502 MAYI/JUNE 2019 (€) Outline a detailed mechanism for the following reaction Cy (1) NaNH (@) CHCH,CH,COH ° @)Hs0 @ (f) Illustrate the concept of keto-enol tautomerism with appropnate structures (2) [20] TOTAL MARKS = [100] e UNIsA 2019 [TURN OVER]28 CHE1502 MAY/JUNE 2019 ROUGH WORK [TURN OVER],29 ‘CHE1502 MAY/JUNE 2019 ROUGH WORK ROUGH WORK [TURN OVER]CHE1502 MAY/JUNE 2019 [TURN OVER],34 ‘CHE1502 MAY/JUNE 2019 ROUGH WORK ROUGH WORK [TURN OVER]32 CHE1502 MAY/JUNE 2019