Jawab soalan 1 dan mana-mana 3 (tiga) daripada soalan-soalan berikut Answer question 1 and any 3 (three) of the following questions

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1 UNIVERSITI MALAYA UNIVERSITY OF MALAYA PEPERIKSAAN IJAZA SARJANA MUDA SAINS EXAMINATION FOR TE DEGREE OF BACELOR OF SCIENCE PEPERIKSAAN IJAZA SARJANA MUDA SAINS DENGAN PENDIDIKAN EXAMINATION FOR TE DEGREE OF BACELOR OF SCIENCE WIT EDUCATION SESI AKADEMIK 2015/2016 : SEMESTER I ACADEMIC SESSION 2015/2016 : SEMESTER I SIC1003 : KIMIA ORGANIK I ORGANIC CEMISTRY I Dis 2015/Jan 2016 Dec 2015/Jan 2016 Masa: 2 jam Time: 2 hours ARAAN KEPADA CALON: INSTRUCTION TO CANDIDATES: Jawab soalan 1 dan mana-mana 3 (tiga) daripada soalan-soalan berikut Answer question 1 and any 3 (three) of the following questions (Kertas soalan ini mengandungi 5 soalan dalam 8 halaman yang dicetak) (This question paper consists of 5 questions on 8 printed pages)

2 1. (a) Lukiskan struktur bagi sebatian A hingga O di bawah dengan stereokimia yang betul di mana yang mungkin: Draw the structure of compounds A to O below with the correct stereochemistry wherever possible: (i) (C) (B), ROOR i. g(oac) 2, O ii. NaB 4 (A) 2 i. B 3, TF ii. 2 O 2, O - (D) O CCl 3, KO 2, Pd / C (E) (F) (6 markah/marks) (ii) (2 markah/marks) (iii) (3 markah/marks) 2/8

3 (iv) (L) + (M) major minor C 2 C 2 Cl AlCl 3 O C 2 C AlCl 3 Cl (N) Zn(g) Cl, (O) (b) Tunjukkan curved arrows yang terlibat dalam tindak balas berikut: Show the curved arrows involved in the following reactions: (6 markah/marks) Tentukan samaada sebatian berikut berkonfigurasi R atau S pada pusat kiral mereka Assign R or S configuration to the chiral center in each of the following molecules: O i. ii. iii. COO 3 C COO N 2 CN 3/8

4 2. (a) Lukiskan struktur bagi sebatian-sebatian berikut: Draw the structures of the following compounds: (i) (ii) (iii) (iv) 4-ethyl-2,2-dimethylhexane 4-isopropyl-3-methylheptane 2-Ethyl-7-iodobicyclo[2.2.1]heptanes 1,3,9-trimethylbicyclo[4.4.0]decane (b) Berikan hasil atau hasil-hasil penghalogenan mono bagi setiap tindak balas berikut, abaikan stereoisomer. Give the monohalogenated product(s) of each of the following reactions, ignoring the stereoisomers. + NBS? peroxide + 2 h C? + NBS peroxide? + NBS? peroxide + Cl 2 h? C + Cl 2 h? (6 markah/marks) Lukiskan struktur bagi semua hasil yang mungkin terbentuk dari pengklorinan mono alkana-alkana berikut. Draw the structure of all possible products that can be obtained from monochlorination of the following alkanes. i) ii) 3 C C C 2 C iii) 3 C C C 2 C iv) (6 markah/marks) 4/8

5 (d) Alkuna hujung bertindak balas dengan air bromin bagi menghasilkan keto bromo seperti yang ditunjukkan di bawah. Cadangkan mekanisme bagi tindak balas tersebut. Terminal alkynes react with 2 and water to yield bromo ketones as shown below. Propose a mechanism for the reaction. C C 2, 2 O O C 2 3. (a) Selaras dengan peraturan Cahn-Ingold-Prelog, tentukan keutamaan pada setiap kumpulan penukarganti berikut: In accordance with the Cahn-Ingold-Prelogs rules, assign priorities to the following sets of substituents: (i), -, -C 2, -C 2 C 2 O (ii) COO, -CO 2, -C 2 O, -O (iii) CN, -C 2 N 2, -C 2 N, -N 2 (iv), -C 2, -Cl, -C 2 Cl (b) Alanina, sejenis asid amino dalam protin, adalah kiral. Lukiskan keduadua enantiomer bagi alanine mengunakan ketetapan standart garisan tebal, biasa dan putus-putus, dan juga dalam bentuk formula unjuran Fisher. Alanine, an amino acid found in proteins, is chiral. Draw the two enantiomers of alanine using the standard convention of solid, wedge and dashed lines, and also in the form of Fisher projection formula. 2 N O C C O 5/8

6 Anda diberikan satu campuran rasemat bagi 2-butanol dan asid (2R,3R)- (+)-tartarik. Cadangkan satu kaedah untuk memisahkan enantiomer R & S bagi 2-butanol menggunakan teknik resolusi. You are given a racemic mixture of 2-butanol and (2R,3R)-(+)-tartaric acid. Propose a method to separate the R & S enantiomers of 2-butanol using the resolution technique. O COO O COO (2R,3R)-(+)-tartaric acid (10 markah/marks) (d) Penambahan kepada 3-bromosikloheksena menghasilkan hanya trans-1,2-dibromosikloheksana. Cadangkan mekanisme tindak balas tersebut dan jelaskan kenapa tidak ada regioisomer lain yang terbentuk. Addition of to 3-bromocyclohexene yields only trans-1,2- dibromocyclohexane. Propose a mechanism for the reaction, and explain why none of the other regioisomers are produced. (7 markah/marks) 4. (a) Cadangkan struktur bagi alkena yang memberikan hasil yang ditunjukkan. Terdapat lebih dari satu jawapan dalam kes-kes tertentu. Suggest structures for alkenes that give the following reaction products. There may be more than one answer for some cases. 6/8

7 (b) Penambahan kepada 1-fenilpropena menghasilkan hanya (1-bromopropil)benzene. Cadangkan mekanisme bagi tindak balas ini, dan jelaskan kenapa regioisomer lain tidak terbentuk. Addition of to 1-phenylpropene yields only (1-bromopropyl)benzene. Propose a mechanism for the reaction, and explain why none of the other regioisomer is produced. Kenalpasti reagen-reagen yang dinomborkan i-v dalam skema berikut: Identify the reagents represented by the numbers i-v in the following scheme: O (i) (ii) (iii) (iv) (v) (10 markah/marks) (d) Daya penarik sek bagi lalat rumah biasa adalah sejenis hidrokarbon dengan formula C Apabila ditindak balaskan dengan larutan akuas berasid KMnO4, dua hasil diperolehi, (C 2 ) 12 COO dan (C 2 ) 7 COO. Cadangkan struktur bagi penarik sek tersebut. The sex attractant of the common housefly is a hydrocarbon with the formula C On treatment with aqueous acidic KMnO 4, two products are obtained, (C 2 ) 12 COO and (C 2 ) 7 COO. Propose a structure of the sex attractant. 5. (a) Antara sepsis berikut, yang manakah aromatic? Jelaskan jawapan anda. Among the following species, which one is aromatic? Explain your answer. N i) ii) iii) iv) v) 7/8

8 (b) Berdasarkan kepada tindak balas di bawah, jelaskan mengapa penukarganti CF 3 adalah pengarah meta manakala penukarganti OMe adalah pengarah orto/para. Tunjukkan kesemua struktur resonans yang mungkin dalam penjelasan anda. Based on the reactions below, explain why the CF 3 substituent is a meta director while the O substituent is an ortho/para director. Show all the possible resonance structures in your explanation. CF 3 CF 3 NO 3 / 2 SO 4 NO 2 O O O NO 3 / 2 SO 4 NO 2 + NO 2 (8 markah/marks) Jelaskan pemerhatian berikut. Explain the following observations. + C 2 C 2 Cl AlCl 3 / O C C 2 C 2 + major minor (7 markah/marks) (d) Tunjukkan bagaimana sebatian aromatik berikut boleh disediakan (sebagai hasil utama), menggunakan benzene sebagai bahan pemula. Show how the following aromatic compound can be prepared (as major product), using benzene as the starting material. C 2 C 2 TAMAT END 8/8

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