UNIVERSITI TUNKU ABDUL RAHMAN ACADEMIC YEAR 2021/2022 MAY 2021 TRIMESTER FINAL ASSESSMENT FHSC1124 ORGANIC CHEMISTRY TUESDAY, 21 SEPTEMBER 2021 TIME: 9.00 AM ~ 12.00 PM (3 HOURS) FOUNDATION IN SCIENCE ‘andidates: REMINDER: You are reminded to read and adhere to the Final Assessment Instructions to. Candidates that has been made available through the UTAR Portal before the commencement of Final Assessment (FA). The detailed instructions for this FA are as follows: General 1. This Final Assessment (FA) is an Individual, time restricted assessment which consists of SIX (6) questions. Each question carries 25 marks. 2. You are required to answer the questions as follows: Question 1 and Question 2: Answer ALL questions. Question 3 and Question 4: Answer ONE (1) question only. Question 5 and Question 6: Answer ONE (1) question only. In cases where a choice of questions is provided, only answers to the initially chosen question will be marked. Any addition questions will not be considered. Only ONE (1) online submission is allowed. Submit the ANSWER SCRIPT by 12.00 pm, 21 SEPTEMBER 2021. 3. During the period of this FA, if you require any clarification from your lecturer(s), the contact details can be obtained from the FA guide/FA guidelines available on WBLE. 4, You may refer to any books, lecture notes, published materials, online resources etc. when answering the questions. Candidates are reminded that Copy-and-Paste, Consultation, Discussion and Sharing of Answers with others are STRICTLY PROHIBITED in this FA. This final assessment paper consists of 6 questions on 10 printed pages.FHSC1124 ORGANIC CHEMISTRY. Answer Script File 5. Please refer to the FA guide/FA guidelines for the submission format of the answer script file. Note: Please keep the file size NOT exceeding 30MB per file. 6. Please check your Index Number generated by the Division of Examinations, Awards, and Scholarships (DEAS). You MUST name your answer script file using the following file name for submission: Index Number_FHSC1124_ORGANIC_CHEMISTRY Answer Script File Submission 7. Your answer script file has to be submitted following the platform(s) as stated in the FA guide/FA guidelines before the due time/date. 8. Please make sure you submit the correct, complete and final version of your answer script to the platform(s) as stated in the FA guide/FA guidelines. Contents of Answer Script 9. The first page of your submission is the Final Assessment Cover Page. You MUST use the template given and fill in the following information: Your Programme (Foundation in Science) Your Index Number © Your Name © Your Student ID 10. The second page of your submission is the Final Assessment Declaration Statement. You MUST use the template given, and digitally sign on the form to indicate the authenticity of your submitted work is without plagiarism. 11, Each question should be answered starting on a new page. 12, For answer scripts that require/contain drawings, equations and calculations with short text descriptions, you can hand-write your answers and then use the scanner apps in your smartphone to take a scanned copy, or you can type if necessary and include the scanned copy taken in the Word document, as part of your submitted answers. 13. Please include a page number on each and every page of your answer script. Ensure that each page of answer scripts is in sequence prior to online submission. This final assessment paper consists of 6 questions on 10 printed pagesFHSC1124 ORGANIC CHEMISTRY WARNING OF PLAGIARISM 14, Answer scripts shall be uploaded to Tumitin to check for the originality of submitted answers. In the case of suspected plagiarism, the evidence will be submitted to the Examination Disciplinary Committee of the University. Disciplinary action shall be taken against any candidate who is found to have plagiarized in the answer submitted. Hence, candidates are reminded to abide by all University Rules and Regulations and any instructions/guidelines relating to examinations/assessments, This final assessment paper consists of 6 questions on 10 printed pages.FHSC1124 ORGANIC CHEMISTRY Question 1 and Question 2: Answer ALL questions. Ql. (@) Give the IUPAC name for the following compounds. @ sat wo Gi) Any (b) Draw the structure for the following compounds. @ —3-Bromo-S-methylbenzonitrile (ii) Cis-cyclopent-4. ene-1,3-dicarbonyl dibromide (ii) N-Cyclohexyl-N,3-diiodobutanamide (2 marks) (2 marks) (2 marks) (2 marks) (2 marks) (2marks) This final assessment paper consists of 6 questions on 10 printed pages.FHSC1124 ORGANIC CHEMISTRY QL. (Continued) (©) Draw all the possible stereoisomers for the compound A below. Label the chiral centre with an asterisk (*) if any. CH,CH=CHC(OH),CH=C(CHs)2 N ‘CH,COCH, ‘Compound (9 marks) (@ Draw TWO (2) possible structural isomers that contain a four-carbon ring with the molecular formula of CsHsN. (4 marks) [Total : 25 marks] This final assessment paper consists of 6 questions on 10 printed pages.FHSC1124 ORGANIC CHEMISTRY 2. (@ Given below are three organic compounds with the same number of carbon ) © @ atoms. 4-methylpentanol, 3-methylpentanal and hex-3-ene ‘Arrange the above compounds in the ascending order of boiling points and explain your answer. (6 marks) Compare the acidity of the following compounds and explain your answer. ° HO. 0 ‘OH we o i oO Compound J Compound IT (9 marks) Vanillin is commonly used in food industries to get the flavour of vanilla. When vanillin is treated with LiAIHs, a primary alcohol B is produced. Suggest a suitable chemical test to differentiate vanillin and alcohol B. State the reagent(s), condition(s) and expected observation(s) for each compound. HO, HO, . - ~ocH, . - “ocH Vanillin Alcohol B (4marks) Suggest a chemical test to differentiate the following pairs of compounds by stating the reagent(s) and expected observation(s).. (®_ Phenylamine and 1-phenylethanamine (3 marks) (ii) 3-Hydroxycyclohexanone and 4-hydroxyhexan-2-one (3 marks) [Total : 25 marks] This final assessment paper consists of 6 questions on 10 printed pages.FHSC1124 ORGANIC CHEMISTRY Question 3 and Question 4: Answer ONE (1) question only. @. @ ©) Compound € with the molecular formula of CsH120 is an acyclic carbonyl compound. It consists of four primary carbon atoms and gives positive iodoform test. (@ Show a three-step reaction scheme on how compound C can be synthesised using 2-chloro-2-methylpropane. State clearly the reagent(s) and condition(s) involved in each step. (7 marks) (ii) Outline the complete mechanism for the NaOH-catalysed condensation reaction of compound C. (8 marks) Depending on the reagent(s) and condition(s) provided, cyclobut-2-enone is able to undergo addition reaction in two different ways, either via the electrophilic mechanism or the nucleophilic mechanism. @ Explain why cyclobut-2-enone can undergo both electrophilic addition and nucleophilic addition. ( marks) (ii) Outline the mechanism for the chlorination of eyclobut-2-enone, (S marks) (Total : 25 marks} This final assessment paper consists of 6 questions on 10 printed pages.FHSC1124 ORGANIC CHEMISTRY 4 @ © @ Gi) Upon reflux with NaOH, an optically active compound D with molecular formula of CsHoBr produces a eyclic primary alcohol E. Outline the mechanism to depict the production of alcohol E from compound D. (6 marks) Show a synthesis pathway for the conversion of alcohol E into (1,2-dimethyleyclopropyl)methanamine. State clearly the reagent(s) and condition(s) involved in each step. CHyNHp (1,2-dimethyleyelopropy!)methanamine (7 marks) Sulphonation of benzene produces benzenesulphonic acid. @ @ Gi) Outline the mechanism for the nitration of benzenesulphonic acid. (6 marks) Name the product formed in Q4. (b) (i). (2 marks) Explain why the nitration of phenol occurs at a much higher rate compared to the nitration of benzenesulphonie acid. (4 marks) [Total : 25 marks} This final assessment paper consists of 6 questions on 10 printed pages.FHSC1124 ORGANIC CHEMISTRY Question 5 and Question 6: Answer ONE (1) question only. QS. (a) __ The structure of compound Fis shown below. 4 OH noth |, kc —G-—C—C—CH | | ca ou Compound F Draw the product(s) for the reaction of compound F with: (potassium hydroxide, KOH in ethanol. (5 marks) (i) hydrogen cyanide, HCN. (2 marks) (&) Based on the reaction scheme below: NaH G H,0 Hy —KilnO./H y+ 0 (Tertiary Refiux Reflux cs halide) = Hol Reagent I Ch UV light OH OH 0 ee Y + mo ° @ Draw the structure of G, H, Land J. (8 marks) (ii) Suggest the Reagent I used in the above reaction. (2 marks) (© Compound X is an unsaturated hydrocarbon with the molecular formula of CrHiy that reacts with hot acidified potassium manganate(VII) to form compound L, C4HsO and M, CsHsO2. Compound L gives positive results with Brady’s reagent and iodoform test while compound M turns blue litmus paper to red. Compound M undergoes reduction to form compound N. Deduce the structure of compounds K, L, M and N. (8 marks) [Total : 25 marks] This final assessment paper consists of 6 questions on 10 printed pages.10 FHSC1124 ORGANIC CHEMISTRY Q6. (a) The structure of compound 0 is shown below. OH OH H Oo on | Hyxec—C—¢—C-—C —0—CH,CH Loh Compound O () Draw the product(s) for the reaction of compound O with: (A) _ Dimethylamine, (CH3):NH. (4 marks) (B) Acidified KMn0,. (2 marks) (ii) Name the type of reaction in Q6. (a) (i) (B). (1 mark) (b) Based on the reaction scheme below: ‘SO3H Q , Hae J ether R Reagent IT 450 KCN, ethanol HeCH2G, Reni Bre Fry NAOH, ethanol SOsH ——*—m (Primary NaCHcthanol » ¢ UVlight halide) (@ Draw the structure for P,Q, Rand S. (8 marks) (ii) Suggest the Reagent I used in the reaction, (2 marks) (© A straight-chain ketone T with molecular formula of CsHiyO undergoes reduction with sodium borohydride, NaBHs to form compound U. Compound U reacts with phosphorus tribromide, PBr; to form compound V and phosphorous acid. Compound V is further treated with ethanolic sodium hydroxide solution to give the major product W. Deduce the structure of compounds 7, U, Vand W. (8 marks) [Total : 25 marks} This final assessment paper consists of 6 questions on 10 printed pages.