(Kertas soalan ini mengandungi 6 soalan dalam 9 halaman yang dicetak) (This question paper consists of 6 questions on 9 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 2016/2017 : SEMESTER I ACADEMIC SESSION 2016/2017 : SEMESTER I SIC1003 : KIMIA ORGANIK I ORGANIC CHEMISTRY I Dis 2016/Jan 2017 Dec 2016/Jan 2017 Masa: 3 jam Time: 3 hours ARAHAN KEPADA CALON: INSTRUCTION TO CANDIDATES: Jawab SEMUA soalan. Answer ALL the questions. (Kertas soalan ini mengandungi 6 soalan dalam 9 halaman yang dicetak) (This question paper consists of 6 questions on 9 printed pages)

2 1. Molekul A Molecule A (a) Berapakah pusat kiral bagi Molekul A di atas? Tandakan *. How many chirality centers does the above Molecule A have? Mark them with *. (5 markah/marks) Bulatkan kumpulan-kumpulan berfungsi pada molekul tersebut dan namakan. Circle the functional groups in the molecule and name them. (5 markah/marks) 2. (a) Apakah itu nombor oktana? What is octane number? (1 markah/marks) Jangkakan mana satu sebatian di bawah ada ahli oktana yang lebih tinggi. Terangkan jawapan anda. Predict which of the below compounds will have a higher octane member. Explain your answer. 2/9

3 Sebatian B Compound B Sebatian C Compound C Sebatian D Compound D (c) Berikan jangkaan hasil tindak balas daripada tindak balas di antara sebatian D dengan bahan tindak balas yang berikut: Predict the probable products from the reactions of compound D with the following reagents. (i) (3 markah/marks) 3/9

4 (iii) (4 markah/marks) (iv) (v) (3 markah/marks) (d) Tindak balas di antara sebatian E dengan HCl akan menghasilkan sebatian F dan G dan bukan hanya sebatian F sahaja. Terangkan pemerhatian tersebut. Compound E, upon reaction with HCl, gave two products; compounds F and G instead of only compound F. Explain this observation. (3 markah/marks) 4/9

5 3. (a) Tentukan konfigurasi R, S bagi setiap pusat kiral pada molekul berikut. Yang mana satu pasangan merupakan enantiomer, diastereomer dan sebatian meso? Assign R, S configurations to each chirality center in the following molecules. Which pairs are enantiomers,diastereomers and meso compounds? (i) (iii) (iv) (12 markah/marks) Lukiskan struktur konformasi yang paling stabil bagi trans-1-tert-butil-4- klorosikloheksana. Terangkan jawapan anda. Draw the most stable conformation of trans-1-tert-butyl-4-chlorocyclohexane. Explain your answer. (4 markah/marks) (c) Berikan jangkaan hasil daripada tindak balas Diels Alder berikut. Predict the product of the following Diels Alder reaction. (4 markah/marks) 5/9

6 4. Rujuk kepada tindak balas balas di bawah dan jawab soalan berikut. Refer to the reactions below and answer the following questions. (i) Berikan reagen untuk a, b dan c. Give the reagents for a, b and c. Lukis struktur untuk H, I, J, K dan L, atau tulis tidak ada tindak balas Draw the structures for H, I, J, K and L, or write no reaction (iii) Berikan nama IUPAC untuk L. Give IUPAC name for L. (iv) Cadangkan mekanisma bagi pembentukan H. Suggest the mechanism for the formation of H. (20 markah/marks) 6/9

7 5. (a) Lukiskan struktur resonans bagi yang berikut. Draw the resonance structure for the following. (i) (iii) (6 markah/marks) Apakah struktur resonan yang paling stabil bagi setiap satu pasangan? What is the most stable resonance structure in each pair? (i) 7/9

8 (c) Label setiap reaktan dalam tindak balas kimia di bawah sebagai nukleofil atau elektofil. Label each reactant in the chemical reaction below as either nucleophile or electrophile. 6. (a) Sebatian-sebatian dibawah adalah asid karboksilik; susunkan mereka mengikut turutan keasidan. The following compounds are carboxylic acids; arrange them in order of increasing acidity. Explain. (3 markah/marks) Mana satu molekul dibawah adalah aromatik, antiaromatik, atau tidak aromatik. Terangkan jawapan anda. Which of the following molecules are aromatic, antiaromatic or nonaromatic. Explain your reasoning. (4 markah/marks) 8/9

9 (c) Bagi setiap sebatian, nyatakan jenis hibridisasi untuk atom utama, domain elektronik dan geometri molekul. For each compound, state the hybridization of the central atom, the electronic domain geometry, and the molecular geometry. (i) HCHO ClF 3 (6 markah/mark) (d) Mana satu molekul dibawah mempunyai ikatan kovalen berkutub, ikatan kovalen tidak berkutub atau ikatan ionik? Which of the following molecules possess polar covalent bond, nonpolar covalent bond or ionic bond? (i) ICl LiF (iii) CH 3 OH (iv) C 2 H 6 (v) CCl 4 (vi) H 2 (6 markah/marks) TAMAT END 9/9

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