(Kertas soalan ini mengandungi 6 soalan dalam 8 halaman yang dicetak) (This question paper consists of 6 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 PEPERIKSAAN IJAZAH SARJANA MUDA SAINS DENGAN PENDIDIKAN EXAMINATION FOR THE DEGREE OF BACHELOR OF SCIENCE WITH EDUCATION SESI AKADEMIK 2015/2016 : SEMESTER 2 ACADEMIC SESSION 2015/2016 : SEMESTER 2 SCES2220 : KIMIA ORGANIK II ORGANIC CHEMISTRY II Jun 2016 June 2016 Masa : 2 jam Time : 2 hours ARAHAN KEPADA CALON : INSTRUCTIONS TO CANDIDATES : Jawab SEMUA soalan. Answer ALL questions. (Kertas soalan ini mengandungi 6 soalan dalam 8 halaman yang dicetak) (This question paper consists of 6 questions on 8 printed pages)

2 1. Sebatian A menjalan tindakbalas S N 2 atau E2 bergantung kepada reajen. Compound A undergoes S N 2 or E2 reaction depending on the reagents. SCES2220 (a) Lukis struktur B, C, D dan E Draw the structure of B, C, D and E. (b) Tetapkan stereokimia A, B dan C, dan konfigurasi D dan E. Assign the stereochemistry of A, B and C, and the configuration of D and E. (c) Lukis mekanisme untuk tindakbalas E2 dan S N 2 di bawah. Draw the mechanism of the following E2 and S N 2 reactions. D CH 3 O - Na + Br CH 3 OH B E A C E2 reaction S N 2 reaction (20 markah/marks) 2. 1-Metilsikloheksena menjalani tindakbalas hidroborasi/oksidasi dan oksimerkurasi/penurunan untuk menghasilkan C dan D. Sebatian A dan B merupakan sebatian perantaraan dalam penghasilan sebatian C dan D. 1-Methylcyclohexene undergoes hydroboration/oxidation and oxymercuration/reduction reactions to give compounds C and D, respectively. Compounds A and B are the intermediates for the formation of compounds C and D. (a) (b) Lukis struktur A-D Draw structures A-D. Tentukan stereosenter dalam sebatian C dan D, dan tetapkan stereokimia untuk steresentre yang ditentukan. Identify the stereocentre in compounds C and D, and assign the stereochemistry of these stereocentres. 2/8

3 (c) Jelaskan perbezaan dalam strategi sintesis tindakbalas hidroborasi/oksidasi dan oksimerkurasi/penurunan dibawah untuk penghasilan sebatian C dan D. Highlight the differences in the synthetic strategy of the hydroboration/oxidation and oxymercuration/reduction reactions adopted below for the formation of compounds C and D. BH 3 THF A H 2 O 2 -OH C CH 3 1-methylcyclohexene Hg(OAc) 2 H 2 O B NaBH 4 D (20 markah/marks) 3. n-butanol boleh ditukar kepada n-propilamina melalui tindakbalas penyusunan semula Hofmann atau Curtius. Lukis skema tindakbalas untuk kedua-dua penukaran. n-butanol can be transformed to n-propylamine via Hofmann or Curtius rearrangements. Draw both transformation reaction schemes. CH 3 CH 2 CH 2 CH 2 OH CH 3 CH 2 CH 2 NH 2 n-butanol n-propylamine (10 markah/marks) 3/8

4 4. Bagi struktur produk atau reagen untuk mana-mana 4 urutan tindak balas di bawah. Provide missing products and reagents for any 4 of the reaction sequences below. (a) (b) (c) (d) (e) 4/8

5 (f) (g) (12 markah/marks) 5. Cadangkan kaedah (atau bagi reagen) untuk sintesis bagi mana-mana 4 produk dari urutan tindak balas di bawah. Mungkin lebih daripada satu langkah adalah diperlukan. Suggest methods (or provide reagents) for the synthesis for any 4 products from the reaction sequences below. More than one step may be necessary. (a) (b) (c) 5/8

6 (d) (e) (f) (g) (12 markah/marks) 6/8

7 6. Sintesis ketone trisiklik melalui derivatif anthracyclinone ditunjukkan di bawah A synthesis of a tricyclic ketone en route to an anthracyclinone derivative is shown below. (i) Bagi mekanisme untuk langkah-langkah (I) hingga (II) dan langkah (II) hingga (III). Provide a mechanism for steps (I) to (II) and step (II) to (III). (7 markah/marks) 7/8

8 (ii) Cadangkan satu reagen atau urutan tindak balas yang berbeza bagi penukaran (iv) hingga (vii). Suggest a different set of reagents or a different sequence of reactions for the conversion of (iv) to (vii). (9 markah/marks) (iii) Bagi mekanisme untuk transformasi (viii) hingga (ix) dan (x). Provide a mechanism for the transformation of (viii) to (ix) and (x). (10 markah/marks) TAMAT END 8/8

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