EXAMINATION FOR THE DEGREE OF BACHELOR OF SCIENCE WITH EDUCATION PEPERIKSAAN IJAZAH SARJANA MUDA SAINS DENGAN PENDIDIKAN

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1 UNIVERSITY OF MALAYA UNIVERSITI MALAYA EXAMINATION FOR THE DEGREE OF BACHELOR OF SCIENCE WITH EDUCATION PEPERIKSAAN IJAZAH SARJANA MUDA SAINS DENGAN PENDIDIKAN SESI AKADEMIK 2011/2012 : SEMESTER 2 ACADEMIC SESSION 2011/2012 : SEMESTER 2 SCES2246 : FUNCTIONAL GROUP CHEMISTRY KIMIA KUMPULAN BERFUNGSI June 2012 Jun 2012 TIME : 2 hours MASA : 2 jam INSTRUCTIONS TO CANDIDATES: ARAHAN KEPADA CALON : This question paper consists of Section A and Section B. Kertas soalan ini mengandungi Bahagian A and Bahagian B. Answer the questions according to the instructions given in each section. Jawab soalan mengikut arahan yang diberikan dalam setiap bahagian. (This question paper consists of 10 questions on 9 printed pages) (Kertas soalan ini mengandungi 10 soalan dan 9 halaman yang dicetak)

2 SCES2246/02 SECTION A (50 MARKS) BAHAGIAN A (50 MARKAH) Answer ALL questions from this Section. Jawab SEMUA soalan daripada bahagian ini. 1. Consider the following structural formulas. Pertimbangkan formula struktur berikut. Which of these compounds cannot be oxidized easily? Explain. Manakah diantara sebatian di atas tidak boleh teroksida dengan mudah? Jelaskan. Provide the structures for the common oxidation products of the compounds above. Tuliskan struktur untuk hasil pengoksidaan yang biasa dari sebatian di atas. (6 marks/markah) 2. Consider the following chemical reactions. Pertimbangkan tindak balas berikut..

3 SCES2246/03 Which of these reactions will favour elimination and which will prefer a nucleophilic substitution? Antara tindak balas di atas, yang manakah akan mengikuti tindak balas penyingkiran dan yang manakah akan mengikuti tindak balas penukargantian nukleofilik. Are the reactions A and B following a first or a second order reaction? Explain. Adakah tindak balas A dan B mengikuti tindak balas tertib pertama atau kedua? Jelaskan. Provide the structure(s) of all main reaction products and indicate the stereochemistry clearly where appropriate. Tuliskan struktur untuk semua hasil utama dan tunjukkan stereokimia di mana sesuai (14 marks/markah) 3. Gulose is a aldohexose with a stereochemical configuration of (AABA). Gulosa adalah suatu aldoheksosa dengan konfigurasi stereokimia (AABA). Draw the Fischer projection of L-gulose. Lukis unjuran Fischer bagi L-gulosa. Construct the Haworth projection of -L-gulopyranose. Bina unjuran Haworth bagi -L-gulopyranosa. Assign the absolute configuration for C-4 in L-gulose. Tandakan konfigurasi mutlak bagi C-4 dalam L-gulosa. (10 marks/markah) 4. Examine the following amino acids. Pertimbangkan struktur asid amino berikut.

4 SCES2246/04 Which of the compounds above are not common natural amino acids? Sebatian manakah di atas merupakan asid amino semula jadi yang tidak biasa? Classify all common amino acids above into categories? Kelaskan semua asid amino semula jadi di atas kepada kategori. (8 marks/markah) 5. How are amino acids connected in a protein? Draw the structure of a dipeptide. Bagaimana asid amino yang berkaitan dengan protein? Tuliskan struktur kimia untuk satu dipeptida. (d) What is the primary structure of a protein? Apa adalah struktur primeri untuk protein? Name two different secondary protein structures and indicate the difference between them. Namakan dua struktur sekunder untuk protein dan tunjukkan perbezaan di antara mereka. Name all major interaction types responsible for the 3-dimensional structure of proteins. Namakan semua jenis interaksi utama yang bertanggungjawab bagi struktur protein 3-dimensi. (12 marks/markah)

5 SCES2246/05 BAHAGIAN B (50 MARKAH) SECTION B (50 MARKS) Answer question 6 (compulsory) and any two other questions. Jawab soalan 6 (wajib) dan mana-mana dua lagi soalan. 6. Provide missing reagents and products for the reactions below. Identify all functional groups in (g) and (h). Draw out a reaction mechanism for reaction (g). Cadangkan reagen dan hasil bagi tindak balas berikut. Tentukan semua kumpulan berfungsi dalam tindak balas (g) and (h). Lukis mekanisme untuk tindak balas (g). (18 marks/markah)

6 SCES2246/06 7. Explain the following observations. Terangkan pemerhatian yang berikut. (ll) is a weaker acid than (l). (ll) ialah asid yang lebih lemah dari (I). (lll) is a stronger acid than (l). (III) ialah asid yang lebih kuat dari (I). (lv) is a weaker acid than (V). (IV) ialah asid yang lebih lemah dari (V). (d) (VI) is a stronger acid than (II). (VI) ialah asid yang lebih kuat dari (II). (e) (VII) is a weaker acid than (VIII). (VII) ialah asid yang lebih lemah dari (VIII). (16 marks/markah)

7 8. Identify all functional groups in compounds (i) to (vii). Kenalpasti setiap kumpulan berfungsi dalam sebatian (i) to (vii). SCES2246/07 Provide a mechanism for the transformation of (ii) to Ibruprofen. Berikan mekanisme bagi transformasi (ii) kepada ibruprofen. Provide a mechanism for the transformation of (v) to (vii) and identify the missing reagent A. Berikan mekanisme bagi transformasi (v) kepada (vii) dan apakah reagen A. (16 marks/markah)

8 SCES2246/08 9. Provide reaction mechanisms for the transformation of (ii) to (iii) and (ii) to (B). Berikan mekanisme tindak balas bagi transformasi (ii) kepada (iii) dan (ii) kepada (B). Identify the missing reagent A and product B. Suggest a synthetic route from (ii) to (iv). (More than one step may be necessary). Kenalpasti reagen A dan hasil B. Cadangkan kaedah sintesis dari (ii) kepada (iv). (Lebih dari satu langkah mungkin perlu). (16 marks/markah)

9 SCES2246/ Describe methods (reagents) for the transformations shown below. Draw out mechanisms for reactions (d) and (e). Berikan reagen untuk transformasi dibawah. Lukis mekanisme tindak balas bagi (d) dan (e). (16 marks/markah) END TAMAT

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