(Kertas soalan ini mengandungi 4 soalan dalam 9 halaman yang dicetak) (This question paper consists of 4 questions on 9 printed pages)

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1 UNIVERSITI MALAYA UNIVERSITY F MALAYA PEPERIKSAAN IJAZAH SARJANA MUDA SAINS EXAMINATIN FR THE DEGREE F BACHELR F SCIENCE PEPERIKSAAN IJAZAH SARJANA MUDA SAINS DENGAN PENDIDIKAN EXAMINATIN FR THE DEGREE F BACHELR F SCIENCE WITH EDUCATIN SESI AKADEMIK 2013/2014 : SEMESTER 2 ACADEMIC SESSIN 2013/2014 : SEMESTER 2 SCES2220 : KIMIA RGANIK II RGANIC CHEMISTRY II Jun 2014 June 2014 MASA : 2 jam TIME : 2 hours ARAHAN KEPADA CALN : INSTRUCTINS T CANDIDATES : Jawab SEMUA soalan. Answer ALL questions. (Kertas soalan ini mengandungi 4 soalan dalam 9 halaman yang dicetak) (This question paper consists of 4 questions on 9 printed pages)

2 1. (a) Lukiskan hasil organik (A H) yang terbentuk dari tindak balas berikut. Draw the organic products (A H) formed in each reaction. (8 markah/marks) (b) Berikan reagen-reagen (a h) dalam tindak balas di bawah: Give the reagents (a- h) in the reaction below: Br (b) (a) H (c) Ts (d) (e) NBS Br (f) H H (g) (h) H H + enantiomer (9 markah/marks) 2/9

3 (c) Tindak balas berikut tidak memberikan hasil utama seperti yang ditunjukkan. Jelaskan kenapa begitu, dan lukiskan struktur hasil utama yang sepatutnya terbentuk. The following reactions do not afford the major product that is given. Explain why this is so, and draw the structure of the major product actually formed. CH 3 Br t-bu CH 3 C(CH 3 ) 3 Br CH 3 CH 3 H I (8 markah/marks) 2. (a) Lukiskan mekanisme lengkap bagi setiap tindak balas berikut. Draw a detailed mechanism for each of the following reaction. CH 3 H CH 3 CH 2 + H CH 3 CH 2 H H CH 2 CH 3 (10 markah/marks) (b) Jelaskan sintesis bagi salah satu dari sebatian berikut daripada benzene. Describe the synthesis of one of the following compound from benzene. (5 markah/marks) 3/9

4 (c) Apakah hasil-hasil (I L) bagi sintesis di bawah? What is the product (I L) of the following synthesis? HN 3, H 2 S 4 2 I J K L Fe 3 Pd/C H 2 2 Fe 3 H N (5 markah/marks) (d) Lukiskan hasil bagi setiap tindak balas penurunan pengaminaan berikut. Draw the product of each of the following reductive amination reaction. (5 markah/marks) 4/9

5 3. (a) Berikan hasil dan reagen yang tertinggal bagi mana-mana enam (6) dari tindak balas di bawah. Provide missing products and reagents for any six (6) of the reaction sequences below. (12 markah/marks) 5/9

6 (b) Cadangkan kaedah (atau berikan reagen) bagi sintesis mana-mana empat (4) hasil dari tindak balas di bawah. Lebih dari satu langkah mungkin diperlukan. Suggest methods (or provide reagents) for the synthesis for any four (4) products from the reaction sequences below. More than one step may be necessary. (12 markah/marks) 6/9

7 4. (a) Kaedah sintesis bagi bridged heterocycle (VIII) di berikan di bawah. A synthesis of the bridged heterocycle (VIII) is provided below. SCES2220 (i) Berikan mekanisme samada bagi langkah (I) kepada (II) ATAU langkah (II) kepada (III). Provide a mechanism for either step (I) to (II) R step (II) to (III). (2 markah/marks) (ii) Berikan mekanisme samada bagi langkah (III) kepada (IV) ATAU (VI) kepada (VII) Provide a mechanism for either step (III) to(iv) R (VI) to (VII). (4 markah/marks) 7/9

8 (iii) Berikan reagen-reagen (A) dan (B) Provide the missing reagents (A) and (B). (2 markah/marks) (iv) Berikan mekanisme bagi penukaran (VII) kepada (VIII) Provide a mechanism for the transformation of (VII) to (VIII). (4 markah/marks) (b) (i) Sintesis laktam ditunjukkan di bawah. A lactam synthesis is shown below. Percubaan menukarkan (i) kepada (ii) di atas, menggunakan LiAIH 4, tidak menghasilkan (ii) tetapi menghasilkan sebatian lain The attempted conversion of (i) to (ii) above, by means of LiAlH 4, did not produce (ii) but led to a different product! Berikan struktur bagi hasil ini. Kenalpasti reagen yang tertinggal, A dan B, lain yang diperlukan untuk menjayakan penukaran (i) kepada (ii). Lukiskan mekanisme bagi pembentukan (iii) dari (ii). Provide a structure for this product. Identify the missing reagents, A and B, required for a successful transformation of (i) to (ii). Draw out a mechanism for the formation of (iii) from (ii). (6 markah/marks) 8/9

9 (ii) Persamaan kimia dibawah menunjukkan Robinson Annulation. The chemistry below illustrates the Robinson Annulation. Berikan mekanisme bagi semua langkah tindak balas di atas. Provide reaction mechanisms for all the reaction sequences above. (8 markah/marks) TAMAT END 9/9

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