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 1 ACADEMIC SESSION 2016/2017 : SEMESTER 1 SCES1220 : KIMIA ORGANIK I ORGANIC CHEMISTRY I Dis 2016/Jan 2017 Dec 2016/Jan 2017 MASA : 2 jam TIME : 2 hours ARAHAN KEPADA CALON : INSTRUCTIONS TO CANDIDATES : Jawab SEMUA soalan. Answer ALL the questions. (Kertas ini mengandungi 6 soalan dalam 9 halaman yang dicetak) (This question paper consists of 6 questions on 9 printed pages)
1. Molekul A Molecule A (a) Berapakah pusat kiral bagi Molekul A di atas? Tandakan *. Berapakah stereoisomer yang mungkin terdapat pada Molekul A tersebut? How many stereogenic centers does the above Molecule A have? Mark them with *. How many stereoisomers of the Molecule A are possible? (8 markah/marks) (b) Bulatkan kumpulan-kumpulan berfungsi pada molekul tersebut dan namakan. Circle the functional groups in the molecule and name them. (6 markah/marks) (c) Jangkakan penyerapan IR dalam cm -1 bagi mana-mana 2 kumpulan berfungsi. Predict the IR absorption in cm -1 of any 2 of the functional groups. (d) Apakah itu nombor oktana? What is octane number? (1 markah/marks) (e) 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
Sebatian B Compound B Sebatian C Compound C (3 markah/marks) 2. (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 stereogenic center in the following molecules. Which pairs are enantiomers,diastereomers and meso compounds? (ii) (iii) (iv) (12 markah/marks) (b) 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. (8 markah/marks) 3/9
3. Sebatian D Compound D (a) 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: (ii) (iii) 4/9
(iv) (v) 4. Rujuk kepada tindak balas balas di bawah dan jawab soalan berikut. Refer to the reactions below and answer the following questions. Berikan reagen untuk a. Give the reagent for a. (ii) Lukis struktur untuk E, F, G, H, I, J and K. Draw the structures for E, F, G, H, I, J and K. 5/9
(iii) Berikan nama IUPAC untuk J. Give IUPAC name for J. (iv) Cadangkan mekanisma bagi pembentukan F. Suggest the mechanism for the formation of F. (20 markah/marks) 5. (a) Lukiskan struktur resonans bagi yang berikut. Draw the resonance structure for the following. (ii) (iii) (6 markah/marks) (b) Apakah struktur resonan yang paling stabil bagi setiap satu pasangan? What is the most stable resonance structure in each pair? 6/9
(ii) (4 markah/marks) 6. (a) 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? KF (ii) CHCl 3 (iii) C 2 H 5 OH (iv) C 4 H 10 (v) H 2 (10 markah/marks) (b) 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. BH 3 (ii) CCl 4 (6 markah/marks) (c) 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) 7/9
Apendiks 1 Appendix 1 8/9
TAMAT END 9/9