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1 UNIVERSITI MALAYA UNIVERSITY OF MALAYA PEPERIKSAAN IJAZAH SARJANA MUDA SAINS EXAMINATION FOR THE DEGREE OF BACHELOR OF SCIENCE PEPERIKSAAN IJAZAH SARJANA MUDA SAINS DENGAN PENDIDIKAN EXAMINATION FOR THE DEGREE OF BACHELOR OF SCIENCE WITH EDUCATION SESI AKADEMIK 2016/2017 : SEMESTER 1 ACADEMIC SESSION 2016/2017 : SEMESTER 1 SCES3324 : KIMIA SEBATIAN SEMULAJADI NATURAL PRODUCT CHEMISTRY Dis 2016/Jan 2017 Masa: 2 jam Dec 2016/Jan 2017 Time: 2 hours ARAHAN KEPADA CALON: INSTRUCTIONS TO CANDIDATES: Jawab SEMUA soalan Answer ALL question Untuk Soalan 1, sila jawab di kertas jawapan dan Lampiran I - VI. For Question 1, please answer in the answer script and Attachments I - VI. Sila kepilkan Lampiran I VI bersama-sama dengan skrip jawapan anda. Please attach Attachments I VI together with your answer script. (Kertas soalan ini mengandungi 5 soalan dalam 6 halaman yang dicetak) (This question paper consists of 5 questions on 6 printed pages)

2 1. (a) (b) Kamu dibekalkan dengan satu set data NMR ( 1 H, 13 C, COSY, HSQC, and HMBC) yang sepadan dengan salah satu sebatian di atas (Lampiran I VI). Berdasarkan spektrum yang dibekalkan (Lampiran I VI), tentukan sebatian (A atau B) yang sepadan dengan data spektrum yang disediakan. Jelaskan jawapan anda. Sebagai sebahagian daripada jawapan anda, anda dikehendaki menandakan setiap puncak dalam spektrum NMR 1 H dan 13 C (Lampiran I dan II). Sila kepilkan semua spektrum-spektrum ini (Lampiran I VI) bersamasama dengan kertas jawapan anda. You are provided with a set of NMR data ( 1 H, 13 C, COSY, HSQC, and HMBC), which corresponds to one of the above compounds (Attachments I VI). Based on the spectra provided in Attachments I VI, determine which of the two compounds (A or B) corresponds to the spectral data provided. Explain your answer. As part of your answer, you are required to assign each peak in the 1 H and 13 C NMR spectra (Attachments I and II). Please attach all spectra (Attachments I VI), together with your answer script. Spektrum 1 H-NMR di Lampiran I mengandungi satu puncak lebar sekitar ~ 3.80 ppm. Mengapakah puncak yang berkenaan kelihatan lebar dan bagaimanakah anda membuktikan bahawa puncak lebar tersebut adalah kepunyaan kumpulan OH? The 1 H-NMR spectrum in Attachment I contains a broad peak around 3.80 ppm. Why does this peak appear broad and how do you prove that this broad peak belongs to the OH group? (28 markah/marks) 2. (a) Sejarah penemuan sebatian semula jadi adalah penuh dengan ceritacerita 2/6

3 yang luar biasa di mana penemuan sebatian semula jadi memberikan impak kemajuan yang mendalam dalam bidang biologi dan terapi. Terangkan secara ringkas (dengan contoh) peranan sebatian semula jadi sebagai sumber ubat-ubatan atau ubat-ubatan petunjuk. The history of natural product discovery is full of remarkable stories of how the discovery of a natural product profoundly impacted advances in biology and therapy. Briefly describe (with an example) the role of natural products as the source of drugs or drugs leads. (6 markah/marks) (b) (i) Apakah komponen utama dalam minyak pati? Berikan satu kaedah pengekstrakan minyak pati daripada sample tumbuh-tumbuhan. (c) What are the main components in essential oils? Provide a methodology to extract essential oils from a plant sample. (ii) Terangkan secara ringkas, kelebihan dan kelemahan Pengekstrakan Bendalir Adigenting (CO 2 ). Briefly describe the advantages and disadvantages of Supercritical Fluid Extraction (CO 2 ). (10 markah/marks) Kelaskan setiap sebatian-sebatian yang berikut (C G) mengikut kelas sebatian semulajadi (cth., terpena, alkaloida, dsb.). Classify the following compounds (C G) according to the class of natural product to which they belong (e.g., terpenes, alkaloids, etc.). 3/6

4 (6 markah/marks) 3. Berikan mekanisme terperinci bagi biosintesis asid lemak berikut dan kenalpasti kesemua enzim utama yang terlibat. Cadangkan reagen bahan kimia yang setara dengan blok binaan biologi dan ko-faktor bagi mekanisme yang terlibat. Provide a detailed mechanism for the biosynthesis of the fatty acid shown below, identifying all key enzymes. Suggest chemical reagents equivalent to the biological building blocks and co-factors you have used in your reaction mechanism. (10 markah/marks) 4. Lukiskan mekanisme untuk oksidatif fenolik berganding untuk transformasi dari (1) kepada (2), dan (3) kepada (4). Kenalpasti ko-faktor dan/atau enzim tertinggal yang terlibat dalam penukaran dari (4) kepada (5), dan (5) kepada (6). Draw out oxidative phenolic coupling mechanisms for the transformation of (1) to (2), and (3) to (4). Identify the missing co-factors and/or enzymes involved in the conversion (4) to (5), and (5) to (6). 4/6

5 (10 markah/marks) 5. (a) Lukiskan mekanisme tindak balas bagi transformasi dari (7) kepada (8), dan (8) kepada (9), langkah penting dalam sintesis kolesterol R. B. Woodward. Bagaimanakah anda menukar (9) kepada (10)? Draw out reaction mechanisms for the transformation of (7) to (8), and (8) to (9), key steps in R. B. Woodward s cholesterol synthesis. How would you convert (9) to (10)? (15 markah/marks) (b) Langkah terakhir dalam sintesis biomimetic progesteron W. S. Johnson ditunjukkan di muka surat yang berikut. Berikan semua reagen yang tertinggal (H M) dan mekanisme bagi transformasi dari (13) kepada (14). Apakah fungsi plumbum tetraasetat bagi penukaran dari (14) kepada (15)? The final steps in W. S. Johnson s biomimetic progesterone synthesis are shown in the following page. Provide all missing reagents (H M) and the mechanism for the transformation of (13) to (14). What is the function of lead tetraacetate in the conversion of (14) to (15)? 5/6

6 (15 markah/marks) TAMAT END 6/6

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