(Kertas soalan ini mengandungi 7 soalan dalam 8 halaman yang bercetak) (This question paper consists of 7 questions on 8 printed pages)

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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 2016/2017 ACADEMIC SESSION 2016/2017 : SEMESTER I : SEMESTER I SCES3355 : KIMIA ORGANOLOGAM GUNAAN APPLIED ORGANOMETALLIC CHEMISTRY Dis 2016/Jan 2017 Dec 2016/Jan 2017 Masa: 2 jam Time: 2 hours ARAHAN KEPADA CALON: INSTRUCTIONS TO CANDIDATES: Kertas soalan ini mengandungi Bahagian A dan B. This paper consists of Section A and B. Jawab soalan mengikut arahan yang diberikan dalam setiap bahagian. Questions should be answered according to the instructions given in each section. (Kertas soalan ini mengandungi 7 soalan dalam 8 halaman yang bercetak) (This question paper consists of 7 questions on 8 printed pages)

2 BAHAGIAN A (50 MARKAH) SECTION A (50 MARKS) Jawab SEMUA soalan dalam bahagian ini. Answer ALL questions in this section. 1. (a) Huraikan 4 fungsi kompleks logam dalam proses biologi. Describe 4 roles of metal complexes in biological processes. (4 markah/marks) Bincangkan faktor-faktor yang menyumbang kepada toksikologi logam dalam sistem biologi. Discuss the factors that contribute to metal toxicology in the biological system. 2. Jadual di bawah menunjukkan kepekatan perencatan minimum (IC 50 ) bagi siri triorganofosfanaaurum(i) dengan natrium ditiokarbamat dan ubat kawalan (cisplatin) terhadap sel kanser payudara, MCF-7R. Kaji data yang diberikan dengan cara mengambil kira elemen-elemen penting yang menyebabkan sebatian-sebatian tersebut menunjukkan aktiviti anti-proliferatif. (*Rujuk struktur molekul sebatian di bawah). The minimum inhibitory concentration (IC 50 ) of triorganophosphanegold(i) series of sodium dithiocarbamate and control drug (cisplatin) against breast cancer cells, MCF-7R is displayed in the following table. Interpret the data given by incorporating all the important elements or criteria that are crucial for the test compounds to exhibit anti-proliferative activity. (*Refer to the molecular structures of the tested compounds below). 2/8

3 (a) (c) Compound IC 50 (µm) Compound (a) 4.4 ± 0.4 Compound 13.6 ± 0.2 Compound (c) 9.3 ± 0.3 Ligand (sodium dithiocarbamate) >80 Cisplatin 19.6 ± 0.4 (10 markah/marks) 3/8

4 3. Merujuk pada struktur auranofin di bawah: With reference to the structure of auranofin below: (a) Tunjukkan bagaimana auranofin disintesis dengan menggunakan reagen kalium tetrakloroaurat (KAuCl 4 ) sebagai bahan pemula. Show the synthetic scheme of auranofin by using potassium tetrachloroaurate (KAuCl 4 ) as the starting material. (2 markah/marks) Bincangkan farmakodinamik auranofin sebagai agen rheumatoid arthritis. Discuss the pharmacodynamics of auranofin as a rheumatoid arthritis agent. (10 markah/marks) (c) Terangkan perbezaan antara pengaruh trans dan kesan trans. Explain the differences between trans influence and trans effect. (4 markah/marks) 4. Merujuk pada struktur molekul cisplatin di bawah, By referring to the following molecular structure of cisplatin, 4/8

5 (a) Tunjukkan bagaimana cisplatin disintesis dan mengapa isomer-cis lebih digemari berbanding isomer-trans. Outline the synthetic procedure of cisplatin and mention why cis-isomer is preferred over trans-isomer. (2 markah/marks) Transplatin tidak mempunyai aktiviti anti-kanser. Cadangkan bagaimana transplatin boleh dijadikan sebagai sebatian yang sitotoksik terhadap sel kanser. Transplatin is lacking of biological activity as an anticancer agent. Suggest how transplatin could be improved to possess cytotoxicity towards cancer cells. (2 markah/marks) (c) Huraikan mekanisma tindak balas cisplatin sebagai agen anti-kanser. Explain the mechanistic pathway of how cisplatin acts as an anticancer agent. (10 markah/marks) 5/8

6 Jawab SEMUA soalan dalam bahagian ini. Answer ALL questions in this section. BAHAGIAN B (50 MARKAH) SECTION B (50 MARKS) 5. (a) Terangkan secara ringkas mengapa ligan CO juga dipanggil ligan asid-. Explain briefly why a CO ligand is sometimes called -acid ligand. (3 markah/marks) Gariskan kompleks yang mempunyai ikatan M-CO yang paling lemah. Terangkan jawapan anda. Underline the complex that have the weakest M-CO bonding. Explain your answer. (i) Re(CH 3 )(CO) 5 or Mn(F)(CO) 5 (ii) WCl 3 (CO) 3 or Mo(CMe) 2 (CO) 4 (iii) Na[Co(CO) 4 ] - or Mn(CO) 4 (PMe 3 ) 2 (c) Namakan jenis ligan karbonil ini dan terangkan secara ringkas mengapa ia tak bersimetri? Name this type of carbonyl ligand and explain briefly why it is unsymmetrical? ~150 o C O M M (3 markah/marks) 6/8

7 6. (a) Alkil fosfina, R 3 P, adalah ligan yang sangat serba boleh. Dengan mengubah ketiga-tiga kumpulan-r nya, terangkan bagaimana ini boleh menjejaskan keupayaan penderma- dan kebolehterimaan- fosfina itu. Alkyl phosphine, R 3 P, are very versatile ligands. By varying the three R-groups, explain how this can affect the -donor ability and -acceptability of the phosphine. Beberapa purata biasa jarak ikatan M-PR 3 untuk baris pertama ditunjukkandi bawah. Terangkan secara ringkas perubahan tentang jarak ikatan M-P mereka. Some typical first row M-PR 3 average bond distances are shown below. Explain briefly about the variation in their M-P bond lengths. Ti-P 2.6 Å Cr-P 2.4 Å V-P 2.5 Å Ni-P 2.1 Å (c) Lengkapkan langkah-langkah untuk a dan b: Complete the steps for a and b: (d) Untuk menyediakan kompleks alkil logam yang stabil, kita perlu mengelakkan alkil dengan hidrogen-. Cadangkan TIGA jenis ligan yang kerap digunakan untuk mencegah penghapusan hidrida-. ln order to prepare stable metal alkyl complexes, we need to avoid alkyls with - hydrogens. Suggest THREE common types of ligands used to prevent -hydride elimination. 7/8

8 7. (a) Lengkapkan skema untuk penkarbonilan Monsanto untuk metanol yang dimangkinkan oleh pemangkin rodium. Rujukkan dan berikan penjelasan ringkas untuk apa yang berlaku pada setiap kitaran. Outline a scheme for the Monsanto carbonylation of methanol which is catalysed by a rhodium catalyst. Indicate and give a brief account of what happens at each step during the cycle. (10 markah/marks) Dalam proses Cativa yang lebih elok, pemangkin iridium digunakan. Apakah kelebihan menggunakan iridium berbanding rhodium? In the improved Cativa process, iridium catalyst is employed. What are the advantages of using iridium instead of rhodium? (4 markah/marks) TAMAT END 8/8

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