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1 UNIVERSITI MALAYA UNIVERSITY OF MALAYA PEPERIKSAAN IJAZAH SARJANA MUDA SAINS EXAMINATION FOR THE DEGREE OF BACHELOR OF SCIENCE SESI AKADEMIK 2010/2011 : SEMESTER 1 ACADEMIC SESSION 2010/2011 : SEMESTER 1 SCES2339 : KIMIA ORGANIK INDUSTRI I INDUSTRIAL ORGANIC CHEMISTRY I November/ Disember 2010 November/ December 2010 MASA : 2 jam TIME : 2 hours ARAHAN KEPADA CALON : INSTRUCTIONS TO CANDIDATES : Kertas soalan ini mengandungi dua bahagian, Bahagian A dan Bahagian B. This paper contains two sections, Section A and Section B. Jawab kedua-dua bahagian mengikut arahan yang diberi di bawah setiap bahagian. Answer both sections according to the instructions given in each sections. (Kertas soalan ini mengandungi 6 soalan dalam 7 halaman yang dicetak) (This question paper consists of 6 questions on 7 printed pages)

2 SCES2339/02 BAHAGIAN A (50 MARKAH) SECTION A (50 MARKS) Jawab SEMUA soalan. Answer ALL questions. 1. (a) Fenol boleh dihasilkan melalui Proses Dow dengan menggunakan toluena sebagai bahan pemula. Proses keseluruhan adalah seperti ditunjukkan di bawah: Phenol can be manufactured through the Dow Process by using toluene as the starting material. The overall process is as depicted below. H 2 O, air, Y Bincangkan dengan justifikasi samada fenol merupakan bahan kimia pukal, halus atau khas. Is phenol a bulk, fine or specialty chemical? Provide a justification for your answer. (3 markah/ marks) Kenalpastikan Y dan gambarkan peranannya dengan menggunakan persamaan kimia. Namakan jenis tindak balas yang terlibat. Identify Y and illustrate its function using suitable chemical equations. Name the reactions involved. (4 markah/ marks)

3 SCES2339/03 (b) Gambarajah yang berikut menunjukkan Proses Wacker Chemie Satu-Peringkat yang dilaksanakan oleh Loji Kimia AA. The following figure shows the one-stage Wacker Chemie Process conducted by AA Chemical Plant. Kenalpastikan bahan pemula, reagen menghad, pemangkin dan hasil untuk proses tersebut. Identify the raw materials, limiting reagent, catalyst and product of the process. (3 markah/ marks) Hitungkan darjah penukaran, hasil dan pilihan berdasarkan data yang diberi. Calculate the degree of conversion, yield and selectivity percentages based on the data given. (5 markah/ marks) (iii) Hasil proses Wacker Chemie yang dijangka adalah lebih kurang 95%. Komen peratusan hasil yang diperolehi di. Jelaskan sebab keputusan sedemikian. The expected yield of a Wacker Chemie process is about 95%. Comment on the yield obtained in. Explain the cause of such result. (5 markah/ marks)

4 SCES2339/04 (iv) Bincangkan ciri-ciri utama bagi pemangkin yang digunakan dan penjanaan semula dengan menggunakan persamaan-persamaan kimia yang sesuai. Discuss the major characteristics of the catalyst used and its regeneration by using suitable chemical equations. (5 markah/ marks) 2. (a) Industri kimia menggunakan pelbagai proses pengoksidaan untuk menghasilkan bahan perantaraan dan bahan kimia yang berguna. Benzena, naftalena dan o-xilena merupakan contoh-contoh bahan suap bagi prosesproses pengoksidaan. The chemical industry makes use of various oxidation processes to yield useful intermediates and chemicals. Benzene, naphthalene and o-xylene are examples of feedstock subjected to oxidation processes. Bandingkan proses pengoksidaan bagi benzena, naftalena dan o-xilena. Berikan persamaan kimia, keperluan bahan pemula, pemangkin dan hasil pengoksidaan (termasuk hasil sampingan). Compare the oxidation process of benzene, naphthalene and o-xylene. Provide the respective chemical equation, requirement of raw materials, catalyst and oxidative products (including side products). (6 markah/marks) Bincangkan kebaikan / keburukan penghasilan ftalik anhidrida dari pengoksidaan o-xilena fasa gas. Discuss the advantages or disadvantages of the production of phthalic anhydride from gas phase o-xylene oxidation. (4 markah/marks) (b) Persamaan kimia yang berikut menunjukkan penghasilan akrilonitril, suatu bahan perantaraan yang penting bagi pembuatan homo dan ko-polimer seperti fiber akrilik, getah nitril, plastic-plastik ABS dan SAN. The following chemical equation shows the production of acrylonitrile, an important intermediate for the manufacture of homo and copolymer such as acrylic fibres, nitrile rubber, ABS and SAN plastics.

5 SCES2339/05 Kenalpasti dan takrifkan jenis tindak balas yang dialami oleh propena dalam pengeluaran akrilonitril. Tuliskan mekanisme kimia yang terlibat. Identify and define the type of reaction that propene undergoes in the production of acrylonitrile. Provide a reaction mechanism. (5 markah/marks) Bincangkan akibat buruk sekiranya ammonia yang tidak bertindak balas tidak dikeluarkan dari aliran hasilan. Cadangkan suatu cara pengeluaran dan pengasingannya. Discuss the adverse effect produced if unconverted ammonia is not removed from the product stream. Suggest a method for its removal and isolation. (5 markah/marks) 3. Proses pembuatan yang melibatkan tindak balas berbalik senantiasa merupakan cabaran teknikal dalam industri kimia organik. Dengan menggunakan satu proses yang tertentu, jelaskan mana-mana dua masalah yang dijangka dan seterusnya bincangkan cara penyelesaian. The manufacturing process involving a reversible reaction is always a technical challenge in the organic chemical industry. By using a specific process, explain any two expected problems and discuss ways to overcome them. (5 markah/marks)

6 SCES2339/06 BAHAGIAN B (50 MARKAH) SECTION B (50 MARKS) Jawab SEMUA soalan. Answer ALL questions. 4. Tulis nota pendek mengenai pengeluaran bahan asas daripada: Write short notes on the production of raw materials from: pengkarbonan arang batu carbonation of coal Penyulingan minyak mentah distillation of crude oil (15 markah/ marks) 5. Sebatian yang mempunyai nombor oktana rendah boleh ditukarkan kepada sebatian bernombor oktana tinggi melalui proses pengalkilan bermangkin. Low octane number compounds can be converted into high octane number compounds through catalytic alkylation process. (iii) (iv) Nyatakan keadaan tindak balas yang diperlukan bagi proses ini. Indicate the process condition needed for this process. Lukis struktur hasil yang terbentuk apabila isobutana dan propena diguna sebagai bahan suapan. Draw the structures of the products formed when isobutane and propene are used as feedstocks. Beri mekanisme bagi menjelaskan pembentukan hasil di. Explain the formation of the products in part mechanistically. Nyatakan satu hasil sampingan dan jelaskan bagaimana pengeluarannya dapat dikurangkan. Give one side product and explain how the production of the side product can be minimized. (20 markah/ marks)

7 SCES2339/07 6. Salah satu kaedah pengeluaran asid asetik adalah melalui kaedah pengoksidaan fasa-cecair dengan menggunakan butana sebagai bahan suapan. One of the methods used to produce acetic acid is through liquid-phase oxidation by using butane as the feedstock. Tulis persamaan tindak balas bagi proses di atas. Nyatakan keadaan tindak balas yang digunakan bagi proses ini. Write the reaction equation for the above process. Indicate the process condition used in this process. Beri mekanisme bagi menjelaskan pembentukan asid asetik. Give a mechanism for the formation of acetic acid. (15 markah/ marks) TAMAT END

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