2011-AL 2B Please stick the barcode label here. CHEM PAPER 2B HONG KONG EXAMINATIONS AND ASSESSMENT AUTHORITY | | HONG KONG ADVANCED LEVEL EXAMINATION 2011 Cardeaonomeer | | 1 CHEMISTRY A-LEVEL PAPER 2 le — Question-Answer Book 2B Markers Examiner's Use Only Use Only 1.30 pm — 4.30 pm (3 hours) | ir This paper must be answered in English re Cot? 1. There are TWO sections in this paper, Section A and Section B. | BO 2. Section A carries 60 marks, and Section B carries 40 marks. T B10 3. Questions for Section A and Section B are printed in Question-Answer Books 2A and 2B respectively. B11 ‘Answer ALL questions in both sections. aon 4 Some constants, characteristic infra-red absorption I wavenumber ranges, standard reduction potentials B13. and a Periodic Table can be found on pages 18, 19 and 20 of Question-Answer Book 2A. B14 5. Question-Answer Books 2A and 2B will be collected B15 ‘separately at the end of the examination. Instructions for Section B : B Total 6 After the announcement of the start of the examination, you should first write your Candidate Number in the space provided on page 1 of this Question-Answer Book, and stick barcode labels in the spaces indicated on pages 1, 3, 5 and 7 7. Write your answers in the spaces provided in this Question-Answer Book. Do not write in the margins. ‘Answers written in the margins will not be marked. 8. Supplementary answer sheets will be supplied on request. Write your Candidate Number, mark the question number box and stick a barcode label on each sheet, and fasten them with string INSIDE this book. 8. No extra time will be given to candidates for sticking Checker’s Use Only the barcode labels or filing in the question number 7 boxes after the ‘Time is up’ announcement. Checker No. | | B Total! OFBSRRMKM PRANK Hong Kong Examinations and Assessment Authority All Rights Reserved 2011 2011-AL-CHEM 2B-1 1Answers writen in the margins will not be marked. SECTION B Answer ALL questions. Write your answers in the spaces provided 9. Ethylbenzene can be converted to phenylethene, which is also known as styrene, via the following synthetic route: CH;CHy CHBrCHs Hh Sip oO Sup? ; (®)— Forstep 1, (suggest reagent(s) and reaction conditions required, and (ii) outline @ mechanism of the reaction, and suggest why (I-bromo)ethylbenzene, not @-bromo)ethylbenzene, is the major product. (S marks) (6) Suggest reagents) and reaction conditions required for Step 2 (1 mark) (© Styrene undergoes polymerisation to give polystyrene. Suggest reagent(s) and reaction conditions required. (1 mark) ‘Answers written in the margins will not be marked. 2011-AL-CHEM 28-2 2 Page Total ‘Answers written in the margins will not be marked.Answers written in the margins will Please stick the barcode label here. ‘Answers written in the margins “Answers writen in the margins will not be marked. 2011-AL-CHEM 2B-3 Goontothenen page >| Page TotalAnswers written in the margins will not be marked. 10. Compound A contains carbon, hydrogen and oxygen only. It reacts with 2,4-dinitrophenylhydrazine to give a yellow precipitate, but shows negative results when treated with acidified KzCr,Or(ag). The ‘mass spectrum of A is shown below. relative intensity (26) 100 80 29 60 40 20: 10 2030 Deduce ONE possible structure of A. 37 86 CE a a ee) mlz 90 (S marks) ‘Answers written in the margins will not be marked. 2011-AL-CHEM 28-4 Page Total ‘Answers writien in the marginsPlease stick the barcode label here. “Answers writen in the margins Answers written in the margins ‘Answers written in the margins will not be marked. 2011-AL-CHEM 28-5 5 Goontothenedpage > | Page TotalAnswers written in the margins will not be marked, lly active alcohol B reacts with ethanoyl chloride to give optically active ester D. ° q prs ee eee : 5 (a) Draw the three-dimensional structure of B. (1 mark) () The following three mechanisms, (1), (2) and (3), have been proposed for the alkaline hydrolysis of D: ° 2 7 os a caulS2euccHxcs) cHC-6® + (HeCHyCH OF » | (CoH,(CH,)CHOH ° i as @ cHC-OLcHCH CH) —— CHEB + CoHigCHCHOH ASH 2 o I CHECHEN Cas) —P CHC LO—CHICH CHD ‘OH. OH ° ° Wo. i 7 CHjC—6® + (CjH5(CH;)CHOH = CH,C—OH + (CH (CH:)CO® i H (@ For each of the proposed mechanisms (1), (2) and (3), discuss the stereochemistry of the (CoHs)(CHs)CHOH formed, Gi)__A sample of (C:H.)(CH,)CHOH is obtained from the hydrolysis of D with NaQH(aq). ‘What information about the mechanism of the hydrolysis can be inferred from a comparison of the optical activity ofthe sample with that of B? (8 marks) ‘Answers written in the margins will not be marked. 2011-AL-CHEM 28-6 6 Page Total ‘Answers written in the margins will not be marked.Answers writen in the margins will not be marked. Please stick the barcode label here. ‘Answers written in the margins will not be marked. ‘Answers written in the margins will not be marked. 2011-AL-CHEM 2B-7‘parLeU 2q 10U jm SUIRIEW 247 UF UOWLIM SIOMSUY Poyeu 99 jou IM SUSIE Ty WT UST SRST ‘Answers written in the margins will not be marked. Page Total 2011-AL-CHEM 28-8not be marked. Answers written in the margins wi 12, Suggest a synthetic route with no more than five steps to accomplish the following conversion: Br oH I I CHSCH,CHCH, —> CHCHLCCO CH (4 marks) not be marked, ‘Answers written in the margins wi “Answers written in the margins will not be marked. 2011-AL-CHEM 23-9 L) Goontotenedpage Page TotalAnswers written in the margins will not be marked. 13. Compound E undergoes electrophilic aromatic substitution to give compound F as the major product. Co + 3 E F (a) Propose a mechanism for this substitution. (3 marks) (b) Suggest why this substitution takes place intramolecularly instead of intermolecularly, (1 mark) ‘Answers written in the margins will not be marked. 2011-AL-CHEM 28-10 10 Page Total ITnot be marked ‘Answers written in the marginsAnswers written in the margins will not be marked. “Answers written in the margins 2011-AL-CHEM 2B-11 ill not be marked. i Page Total not be marked. ‘Answers written in the margins wi Goontothenetpage >|Answers written in the margins will not be marked. ) Consider the compound shown below: Arrange hydroxyl groups, a B and y, in order of increasing acidity. Explain your arrangement marks) Phenolphthalein is an acid-base indicator. It exists predominately as species G in aqueous solutions of pH 6 to 8 Ce Ox, wd G ° In aqueous solutions of pH 10 to 12, phenolphthalein exists mainly as the conjugated base of G, and appears pink. It is known that phenolphthalein exists mainly as species J instead of species K in alkaline solutions. Explain why this is the case. (2 marks) ‘Answers written in the margins will not be marked, “Answers written in the margins will not be marked. 2011-AL-CHEM 2B-12 12 pepe)Answers written in the margins will not be marked. “Answers writien in the margins will nat be marked ‘Answers writen in the margins will not be marked. ‘Goontotenedpage >| Page Total 13 2011-AL-CHEM 28-13,Answers written in the margins will not be marked. 15. Polyacrylamide, polyacrylonitrile and polypropene are three polymeric materials used as textile fabries. sfonerg= fone fener CONH, cH, polyacrylamide polyacrylonitrle polypropene (@) Arrange these polymers in order of increasing tensile strength. Explain your arrangement. (4 marks) (b) One of these polymers displays the IR spectrum shown below. Deduce which polymer this is. 100 = transmittance (9%) 20 4000 3000 2000 1000 wavenumber / em"! (@ marks) ‘Answers written in the margins will not be marked. 2011-AL-CHEM 2B-14 14 ‘Answers writen in the margins will not be marked, Page Totalthe margins will not be marked. ‘Answers written in the margins wi END OF PAPER ‘Answers written in the margins will not be marked. 2011-AL-CHEM 2B-15 15 Page Total