CONFIDENTIAL, UNIVERSITI KUALA LUMPUR MALAYSIAN INSTITUTE OF CHEMICAL AND BIOENGINEERING TECHNOLOGY FINAL EXAMINATION JANUARY 2019 SEMESTER COURSE CODE : CLB 10803 COURSE NAME : ANALYTICAL & ORGANIC CHEMISTRY PROGRAMME LEVEL : BACHELOR DATE : 26 JUNE 2019 TIME : 09.00 AM - 12.00 PM DURATION : 3 HOURS INSTRUCTIONS TO CANDIDATES 1, Please read CAREFULLY the instructions given in the question paper. 2. This question paper has information printed on both sides of the paper .. This question paper consists of TWO (2) sections; Section A and Section B. 4, Answer ALL questions in Section A in the answer booklet provided. . Answer THREE (3) questions in Section B in the answer booklet provided. 6. Answer all questions in English language ONLY. 7. Periodic table and IR frequencies table have been appended for your reference. THERE ARE 9 PAGES OF QUESTIONS, EXCLUDING THIS PAGE.JANUARY 2019 CONFIDENTIAL, SECTION A (Total: 40 marks) INSTRUCTION: Answer ALL questions. Please use the answer booklet provided. Question 1 (a) (b) (c) (a) Determine the structural formula of the following compounds; i _2hydroxycyclopentanone (2 marks) 4,2,2-trifluoropentane (2 marks) ji, 1-ethoxy-1-methoxycyclohexane (2 marks) iv. 2-methyloct-5-ene-3-yne (2 marks) Differentiate between cis and trans isomers and E and Z isomers for alkenes using suitable diagram(s) and example(s). (8 marks) The characteristics of an alcohol may change according to the number of carbon atoms or the number of hydroxy groups present in the molecule. With the increasing number of hydroxy groups in an alcohol, explain; i. the trend of the boiling point of the alcohol (1 mark) ii, the trend of the solubility of the alcohol (1 mark) Explain briefly the difference(s) between Friedel-Crafts alkylation and Friedel-Crafts acylation. (2 marks) CLB10803 ANALYTICAL & ORGANIC CHEMISTRY Page 1 of 9JANUARY 2019 CONFIDENTIAL Question 2 (a) (b) (°) (d) (e) Describe enol. (2 marks) Discuss hydrolysis and saponification reactions including the general equations for both reactions. (4 marks) Ester can be produced by the acid-catalysed condensation reaction involving carboxylic acids and alcohols. Predict the structures of esters that formed from the reactions below and state the names. i. CHsCOOH and CHsCH.OH (2 marks) ii, CgHsCOOH and CHsCH.CH;OH (2 marks) Discuss the main products for the following elimination reactions by providing any relevant diagram(s) or example(s) to support the answer. i. Dehydration of 1-methyleyclohexanol (3 marks) ji. Dehydrohalogenation of vicinal dibromide (3 marks) A solution with a concentration of 2.33 x 10 mol/dm® have an absorbance of 0.698 at 575 nm. Given the path length is 2.5 cm. Calculate; i. the %T of the solution. (2 marks) ii the molar absorptivity of the solution. (2 marks) CLB10803 ANALYTICAL & ORGANIC CHEMISTRY Page 2 of 9JANUARY 2019 CONFIDENTIAL SECTION B (Total: 60 marks) INSTRUCTION: Answer ONLY THREE (3) questions. Please use the answer booklet provided. Question 3 (a) Name the compounds below following the IUPAC nomenclature. Oo Br Oo iii, OH f At HO- CHCH,CCH, cH; CH " | Br 0 — CH,CH, ik ck el wv. cH a cf WN CH,CH,~ C—CH al OH (8 marks) (b) Provide a balance chemical equation for the reactions below. i. Reduction of methyl benzoate (2 marks) ii. Williamson synthesis of sodium ethoxide (2 marks) iii, Oxidation of ethyl benzene (2 marks) iv. Hydrolysis of ethanamide under basic condition (2 marks) (©) There are six ether isomers with the molecular formula of CsH120. Draw only four of these six isomeric ethers (4 marks) CLB10803 ANALYTICAL & ORGANIC CHEMISTRY Page 3 of 8JANUARY 2019 CONFIDENTIAL Question 4 (2) Gas Chromatography (GC) is an example of instruments that use chromatography techniques in separating components of a mixture. i Explain Gas Solid Chromatography (GSC) and Gas Liquid Chromatography (GLo), (4 marks) ii, ‘Analyse two methods that can be implemented to obtain GC optimisation. (2 marks) il. Give two differences of selective detector and non-selective detector. (2 marks) iv. Figure 1 shows a portion of a chromatogram obtained from a temperature- programmed analysis of wide range of n-hydrocarbons. Injection splitless was used on a medium polar column. Discuss the possible reason(s) for the strange baseline observed in the second part of the chromatogram. Cw Cm Cu Cx | Cu | Cos Lovebe Ww) Figure 1 (4 marks) (b) Nuclear Magnetic Resonance (NMR) is the most powerful technique used to obtain structural information and can be used in understanding the structure of a component. i. Differentiate the principles between ‘H and "C NMR. (6 marks) il. State two applications of NMR in the medical diagnostic industries. (2 marks) CLB10803 ANALYTICAL & ORGANIC CHEMISTRY Page 4 of 9JANUARY 2019 CONFIDENTIAL Question 5 (2) High-performance Liquid Chromatography (HPLC) is an instrument in analytical chemistry that separate, identify, and quantify different components of a mixture. i Distinguish between partition chromatography and adsorption chromatography with the aid of necessary diagram(s). (4 marks) ii Differentiate the type of samples that can be analysed by HPLC and GC. (4 marks) il, Provide one method of ionization used in mass spectroscopy detector. (1 mark) (b) Fourier Transform Infrared Spectroscopy (FTIR) is @ powerful instrument regularly used in identifying organic compounds. i In FTIR analyses, liquid and gas samples are prepared in a different way prior analysis. Explain briefly the sample preparation methods for liquid and gas samples, (4marks) ji. Differentiate between stretching and bending vibrations mode. (4 marks) ii, Identify three major principle peaks from Figure 2 below. Absorbance aa we Aenuabere (Ue) i + Figure 2 (3 marks) CLB10803 ANALYTICAL & ORGANIC CHEMISTRY Page 5 of 9JANUARY 2019 CONFIDENTIAL Question 6 (2) Ultraviolet Visible spectroscopy (UV-VIS) is an instrument used in analytical chemistry for the quantitative determination of analytes, i. Differentiate between double beam and single beam UV-VIS with the aid of relevant diagrams). (4 marks) ii. Define ‘negative absorbance’ for a sample analysed using UV-VIS. (2 marks) iii, State one method that can be implemented to overcome the ‘negative absorbance’, (2 marks) iv. State the function of monochromator in UV-VIS. (2 marks) (b) Figure 3 shows the standard calibration curve of zinc obtained using Atomic Absorption Spectroscopy (AAS). 09 08 07 06 05 Absorbance 04 03 02 5 10 15 20 25 30 35 40 45 50 55 Concentration / ppm Figure 3 CLB10803 ANALYTICAL & ORGANIC CHEMISTRY Page 6 of 9JANUARY 2019 CONFIDENTIAL i. Explain the need(s) to construct a standard calibration curve before analysing any samples using the AAS. (2 marks) il Analyse the accuracy of the standard curve with the aid of a brief explanation in the answer. (4 marks) iif, Determine the concentration of zinc in the sample if the absorbance of the ‘sample obtained was 0.33. (2 marks) iv. Provide two applications of AAS in the food industries. (2 marks) END OF EXAMINATION PAPER CLB10803 ANALYTICAL & ORGANIC CHEMISTRY Page 7 of 9CONFIDENTIAL JANUARY 2019 APPENDIX! ‘Sayles apIUOV. 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Page 8 of 8 CLB10803 ANALYTICAL & ORGANIC CHEMISTRYJANUARY 2019 CONFIDENTIAL APPENDIX II Characteristics Infrared Absorption Frequencies Bond Compoundtype Frequency range (cm) C-H ‘Alkanes 2960 - 2850 (s) stretch 1470 - 1350 (v) scissoring and bending CH3 Umbrella Deformation 7380 (m-w) - Doublet -isopropyl, *- Butyl C-H Alkenes 3080 - 3020 (i) streich 1000 - 675 (s) bend |C-H ‘Aromatic ring 3100 - 3000 (m) stretch Phenyl Ring Substitution | 870 - 675 (s) bend Bands Phenyl Ring Substitution | 2000 - 1600 (w) - fingerprint region Overtones C-H Alkynes 3333 - 3267 (s) stretch 700 - 610 (b) bend ‘Alkenes 1680 - 1640 (m,w) stretch Alkynes 2260-2100 (w sh) stretch ‘Aromatic rings 1600, 1500 (w) stretch Alcohols, Ethers, Carboxylic acids, Esters 7260-1000 (8) stretch C=0 Aldehyde, Ketone, Carboxylic | 1760 - 1670 (s) stretch Acid, Ester O-H Monomeric - Alcohols, | 3640 - 3160 (s,br) stretch Phenols 3600 - 3200 (b) stretch Hydrogen bonded - Alcohols, Phenols 3000 - 2500 (b) stretch Carboxylic acids N-H ‘Amines 3500 - 3300 (m) stretch 1650 - 1580 (m) bend o-N ‘Amines 1340-1020 (m) stretch C-N Nitriles 2260 - 2220 (v) stretch NOz Nitro compounds 7660 - 1500 (s) asymmetrical stretch 1390 - 1260 (s) symmetrical strech CLB10803 ANALYTICAL & ORGANIC CHEMISTRY Page 9 of 9