(Kertas ini mengandungi 7 soalan dalam 10 halaman yang dicetak) (This question paper consists of 7 questions on 10 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 SCES1220 : KIMIA ORGANIK I ORGANIC CHEMISTRY I Jun 2016 June 2016 Masa : 2 jam Time : 2 hours ARAHAN KEPADA CALON : INSTRUCTIONS TO CANDIDATES : Jawab SEMUA soalan. Answer ALL the questions. (Kertas ini mengandungi 7 soalan dalam 10 halaman yang dicetak) (This question paper consists of 7 questions on 10 printed pages)

2 1. (a) Sebatian A Compound A Bulatkan sekurang-kurangnya 5 kumpulan berfungsi dan namakan setiap satu kumpulan berfungsi tersebut. Tandakan kesemua pusat kiral dengan * dan tentukan konfigurasi R,S bagi setiap pusat kiral. Circle at least 5 functional groups and name each of them. Mark all chiral centers with * and assign R,S configurations to each chiral center. (14 markah/marks) 2. (a) Pilih struktur yang sepadan dengan spektrum inframerah yang ditunjukkan. Terangkan jawapan anda. Choose the structure that best fits the infrared spectrum shown. Explain your answer. (i) A B C D 2/10

3 Spektrum inframerah 1 Infrared Spectrum 1 (ii) A B C D 3/10

4 Spektrum inframerah 2 Infrared Spectrum 2 (6 markah/marks) 3. (a) Senaraikan diena yang berikut mengikut turutan penurunan kereaktifannya di dalam tindak balas Diels-Alder. Terangkan jawapan anda. List the following dienes in order of decreasing reactivity in a Diels-Alder reaction. Explain your answer. (6 markah/marks) (b) Lukis struktur aduk yang terhasil di antara diena yang paling reaktif (dari a) dan dienofil yang berikut. Draw the structure of the adduct formed between the most reactive diene (from a) and the following dienophile. (4 markah/marks) 4/10

5 4. Tulis formula struktur untuk 2 konformasi bagi trans-1-tert-butil-3- metilsikloheksana. Yang mana satu konformasi yang lebih stabil? Terangkan jawapan anda. 5. Write structural formulas for the two chair conformations of trans-1-tert-butyl-3- methylcyclohexane. Which one of the conformations would be more stable? Explain your answer. (4 markah/marks) Sebatian B Compound B Ramalkan hasil-hasil yang terbentuk dari tindak balas sebatian B dengan reagen-reagen yang berikut. Predict the product/s formed when compound B is reacted with the following reagents. (i) (ii) (4 markah/marks) (iii) (4 markah/marks) (2 markah/marks) 5/10

6 (iv) (4 markah/marks) (v) (2 markah/marks) 6. (a) Terangkan perbezaan di antara tindakbalas pengionan dan asid-bes. Bincangkan mekanisma tindakbalas bagi tindakbalas yang berikut dengan menggunakan anak panah bengkok. Explain the difference between ionization and acid-base reaction. Discuss the reaction mechanism of the following reaction by using curly arrows. (b) Apakah penghibridan bagi setiap satu atom karbon samada bagi (i) atau (ii) yang berikut? What is the hybridization of each carbon atom in the following either (i) or (ii) compound? (i) (ii) 6/10

7 (c) Terangkan mana-mana tiga yang berikut: Explain any three of the following: (i) ph dan pk a ph and pk a (ii) (iii) (iv) Nukleofil Nucleophile Konjugasi bes Conjugated base keasidan bagi sesuatu asid Acidity of an acid (d) Terangkan salah satu yang berikut: Explain any one of the following: (i) pk a bagi HI < pk a bagi HF pk a of HI < pk a of HF (ii) pk a bagi HF < pk a bagi CH 4 pk a of HF < pk a of CH 4 (e) Tuliskan struktur Kekule bagi setiap satu sebatian yang berikut: Write the Kekule s structure for each of the following compounds: (i) CH 3 CHO (ii) CH 3 OCH 3 (iii) (CH 3 ) 3 COH (iv) CH 3 CH(OH) CH 2 CN (v) CH 3 COOCH 3 (25 markah/marks) 7. (a) Susunkan sebatian yang berikut, dengan memberi penjelasan, mengikut aturan penurunan reaktiviti bagi penggantian nukleofilik: Arrange the following compounds, with explanation, in order of decreasing reactivity toward electrophilic substitution: Benzana, Metoksibenzana dan Bromobenzana Benzene, Methoxybenzene, and Bromobenzene 7/10

8 (b) Terangkan sumbangan struktur resonan, hibrid resonan dan tenaga resonan. Lukiskan sumbangan struktur resonan bagi mana-mana dua sebatian yang berikut. Bincangkan kestabilan relatif untuk sumbangan struktur resonan bagi setiap satu sebatian tersebut. Explain contributing resonance structures, resonance hybrid and resonance energy. Draw the contributing resonance structures for any two of the following compounds. Discuss the relative stability of the contributing resonance structures for each of these compounds. (i) RCO 2 - (ii) RCONH 2 (iii) C 6 H 5 NH 2 (c) Bincangkan mekanisma tindak balas bagi tindak balas berikut dan terangkan mengapa o- dan p-bromonitrobenzana tidak terbentuk dalam tindak balas ini. Discuss the reaction mechanism for the following reaction and explain why o- and p-bromonitrobenzene could not form in the reaction. (25 markah/marks) 8/10

9 Apendiks 1 Appendix 1 9/10

10 TAMAT END 10/10

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