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1 UNIVERSITI MALAYA UNIVERSITY OF MALAYA PEPERIKSAAN IJAZAH SARJANA MUDA SAINS EXAMINATION FOR THE DEGREE OF BACHELOR OF SCIENCES SESI AKADEMIK 2016/2017 ACADEMIC SESSION 2016/2017 : SEMESTER I : SEMESTER I SCES3329 : KIMIA ORGANIK FIZIK PHYSICAL ORGANIC CHEMISTRY 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 Questions (Kertas ini mengandungi 4 soalan dalam 5 halaman yang dicetak) (This question paper consists of 4 questions and 5 printed pages)

2 1 (a) Jawab SAMA ADA (i) ATAU Answer EITHER (i) OR (i) Bincangkan mekanisme tetrahedral untuk hidrolisis beralkali bagi metilbenzoat. Bincangkan penggunaan teknik pelabelan isotop untuk menyokong mekanisme tetrahedral. Discuss the tetrahedral mechanism for the alkaline hydrolysis of methylbenzoate. Describe the use of isotopic labeling technique to support the tetrahedral mechanism. ATAU/OR Berikan penerangan mekanistik bagi nilai pemalar tindakbalas Hammett ( X ) yang diperolehi bagi tindakbalas berikut: Give the mechanistic explanation of Hammett reaction constant ( X ) values obtained for the following reactions: Y X p-no o-no Terangkan tindakbalas penyingkiran syn dan anti. Bincangkan mekanisme untuk tindakbalas berikut: Explain syn and anti elimination reaction. Discuss the mechanism for the following reaction: (12 markah/marks) 2/5

3 2. (a) Untuk tindakbalas yang berikut: For the following reaction: hukum kadar empirikal empirical rate law adalah the empirical rate law is [NH 2 OH] k obs = (1) 1 + [NH 2 OH] di-mana k obs ialah pseudo-first-order rate constant, dan adalah pemalar empirikal. Cadangkan satu mekanisme yang sesuai yang boleh membawa kepada persamaan kinetik yang setara dengan persamaan (1) where k obs is pseudo-first-order rate constant, and are empirical constants. Propose a possible reaction mechanism that could lead to a kinetic equation similar to equation (1). (12 markah/marks) Takrifkan kesan isotop kinetik primari. Berikan penjelasan mekanisme bagi tindakbalas berikut jika nilai k H /k D = 1.0. Define primary kinetic isotope effect. Give the mechanistic explanation of the value of k H /k D = 1.0 for the following reactions: C 6 H 6 + NO 2 + k H C 6 H 5 NO 2 + H + C 6 D 6 + NO 2 + k D C 6 D 5 NO 2 + D + 3/5

4 3. (a) Sebatian A, B dan C dilarutkan dalam keadaan berasid pada ph 5. Compounds A, B and C were dissolved in acidic condition at ph 5. (i) Jangkakan hasil daripada A, B dan C. Predict all products from A, B and C. (3 markah/marks) Kirakan pemalar kadar bagi hidrolisis sebatian B pada kepekatan berkesan tindakbalas 1.6 x 10 8 M dan t 1/2 ialah 30 minute manakala t 1/2 bagi A adalah 300 tahun. Calculate the rate constant for compound B with effective molarity of the reaction at 1.6 x 10 8 M and t 1/2 is 30 minutes while t 1/2 for A is 300 years. (9 markah/marks) (iii) Hidrolisis sebatian B 1200 kali lebih pantas daripada C. Kirakan pemalar kadar bagi hidrolisis C. Jelaskan jawapan anda. Hydrolysis of compound B is 1200 time faster than C. Calculate rate constant of hydrolysis of C. Justify your answer. the (4 markah/marks) (iv) Nyatakan jenis pemangkinan yang berlaku terhadap B dan C. State the type of the catalysis that happens to B and C. (1 markah/marks) Kehadiran Zn 2+ boleh memangkin penghidratan piridina-2-aldehid. The presence of Zn 2+ may catalyze the hydration of pyridine-2-aldehyde. (i) Berikan hasil akhir tindakbalas ini. Suggest the final product from the reaction. (2 markah/marks) 4/5

5 Jelaskan semua faktor berserta mekanisme tindakbalas jika berkaitan yang menjadi asas kepada pemangkinan ini. Describe all the factors and show the reaction mechanism when necessary for the basis of the catalysis. (11 markah/marks) 4. (a) Jelaskan metanolisis sebatian D dalam kehadiran satu enzim tiruan E. Explain the methanolysis of compound D in the presence of an artificial enzyme, E. (10 markah/marks) Terangkan bagaimana struktur misel boleh memangkin suatu tindak balas dan berikan kesemua anggapan yang diperlukan dalam suatu pemangkinan misel. Describe how micellar structure can catalyze a reaction and give all the required assumptions in a micellar catalysis. (10 markah/marks) TAMAT END 5/5

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