(Kertas soalan ini mengandungi 3 soalan dalam 11 halaman yang bercetak) (This question paper consists of 3 questions on 11 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 ACADEMIC SESSION 2015/2016 : SEMESTER II : SEMESTER II SCES3120 : KIMIA ORGANIK III ORGANIC CHEMISTRY III Jun 2016 June 2016 Masa: 2 jam Time: 2 hours ARAHAN KEPADA CALON: INSTRUCTIONS TO CANDIDATES: Jawab semua soalan. Answer all question. (Kertas soalan ini mengandungi 3 soalan dalam 11 halaman yang bercetak) (This question paper consists of 3 questions on 11 printed pages)

2 1. (a) Isikan tempat kosong (A F) bagi setiap sebatian atau reagen yang tertinggal dalam sintesis berikut. Fill in the blanks (A F) for each compound or reagent that is missing in the following synthesis. (9 markah/marks) (b) Percubaan pengasilan pada karbon α suatu aldehid selalu gagal. Apakah hasil sebenar dalam percubaan pengasilan yang ditunjukkan di bawah dan bagaimana anda boleh dengan jayanya memperolehi sebatian yang dikehendaki? Attempted acylation at alpha-carbon of aldehyde often fail. What would be the actual product of the attempted acylation shown below and how would you successfully make the target molecule? (5 marks) (5 markah/marks) (c) Berikan hasil utama bagi lima (5) dari tindak balas berikut: Give the major product for five (5) of the following reactions. 2/11

3 (iii) (iv) (v) (vi) (vii) (5 markah/marks) 3/11

4 (d) Bagaimana dapat anda sintesis sebatian N daripada p- methoxybenzaldehyde? Tunjukkan analisa retrosynthesis dan juga semua reagen dan keadaan tindak balas. How would you synthesize N from p-methoxybenzaldehyde? Show the retrosynthetic analysis as well as all appropriate reagents and reaction conditions. (6 markah/marks) (e) Bagaimanakah dapat anda sintesis sebatian O daripada fenolik keton. How would you synthesize O from the phenolic ketone P? (5 markah/marks) 2. (a) Yang mana asetat A atau B akan menghasilkan (S)-sianohidrin C apabila mengalami hydrolisis berenzim. Which of the acetates A or B will yield an (S)-cyanohydrin C on enzymatic hydrolysis. (3 markah/marks) 4/11

5 (b) Beri reagen atau hasil yang sesuai bagi mana-mana 5 reagen atau hasil (D J) dalam tindak balas di bawah Give suitable reagents or products for any 5 reagents or products (D J) in the reactions below. (iii) (iv) (10 markah/marks) (c) Beri mana-mana 6 hasil (K-S) dalam turutan tindak balas di bawah. Provide any 6 of the missing products (K S) in the reaction sequences below. 5/11

6 (iii) 6/11

7 (iv) (12 markah/marks) (d) Beri penjelasan bagi tindak balas di bawah dengan merujuk kepada mekanisme yang terlibat. Provide explanations for the reactions below by reference to the reaction mechanisms involved. (10 markah/marks) 7/11

8 3. (a) Jelaskan mana-mana 2 dari yang berikut: Explain any 2 of the following: (iii) (iv) Mekanisme tindak balas Reaction mechanism Teori keadaan peralihan Transition-state theory Prinsip mikroskopik berbalik The principle of microscopic reversibility Tindakbalas elektrosiklik Electrocyclic reaction (4 markah/marks) (b) Tindakbalas di bawah adalah dijangkakan berlaku seperti mekanisme yang ditunjukkan. The reaction below is believed to occur by the mechanism shown. Dalam menentukan langkah penentuan kadar, kadar tindak balas telah ditentukan bagi satu siri substrat dengan X- penukarganti yang berbeza. Plot Hammet seperti di bawah telah diperolehi. In order to determine the rate determining step, the rate of reaction was measured for a series of substrates with different X- substituents. The Hammett plot shown below was obtained. 8/11

9 Plot Hammett yang diperolehi adalah tak-linear dan cekung ke bawah. Bagi penukarganti dengan nilai σ < +0.5, nilai ρ telah diperolehi. Bagi penukarganti dengan nilai σ > +0.5, nilai ρ telah diperolehi. Komen mengenai sifat plot Hammet ini yang berkaitan dengan mekanisme tindak balas. The Hammett plot obtained for this reaction is a nonlinear plot of the concave downwards type. For substituents with σ values < +0.5, a ρ value of was obtained. For substituents with σ values > +0.5, the ρ value was found to be Comment on the nature of the Hammett plot in relation to the reaction mechanism. (10 markah/marks) (c) Jawab SAMA ADA atau. Sila jawab soalan (iii). Answer EITHER or. Please answer question (iii) Gambarkan ayat di bawah dengan menggunakan rajah tenaga: Illustrate the following statement with an energy diagram: Kesan isotop kinetik berpunca dari tenaga titik sifar yang berbeza bagi ikatan C-H dan C-D. Kinetic isotope effects originate in different zero point energies for C-H and C-D bonds. (4 markah/marks) Mekanisme bagi penitratan elektrofilik adalah ditunjukkan di bawah. Kesan isotop kinetik telah dijalankan bagi membandingkan kadar tindak balas antara C 6 H 6 dan C 6 D 6. Apakah jenis KIE yang dijangkakan (jenis KIE dan anggaran magnitud) jika langkah 9/11

10 pertama adalah pengehad kadar? Bagaimana pula jika langkah kedua adalah pengehadan kadar? The mechanism for electrophilic nitration is shown below. A kinetic isotope effect (KIE) study was carried out by comparing the rate of the reaction with C 6 H 6 and C 6 D 6. What type of KIE would you expect (KIE type and approximate magnitude) if the first step is rate limiting? What if the second step is rate limiting? (4 markah/marks) (iii) Dua tindak balas sebatian diazo dengan asid karboksilik ini menghasilkan gas nitrogen dan ester. Dalam kedua-dua kes, kadar tindak balas adalah bersandar kepada kepekatan sebatian diazo dan asid karboksilik. Gunakan maklumat bagi setiap tindak balas untuk mencadangkan mekanisme dan bincangkan tentang perbezaan antara keduanya. The following two reactions of diazo compounds with carboxylic acids give gaseous nitrogen and esters as products. In both cases the rate of reaction is dependent on the concentration of both diazo compound and carboxylic acid (Rate = k[diazo compound][rco 2 H]). Use the data for each reaction to suggest mechanisms and comment on the difference between them. ρ = 1.6 (10 markah/marks) 10/11

11 (d) Jawab SAMA ADA atau Answer EITHER or Lukis rajah tenaga bebas-koordinat tindak balas bagi kedua-dua tindak balas di bawah menggunakan maklumat yang diberi. Anggap bahawa tindak balas keseluruhan adalah eksergonik. Draw a free energy-reaction coordinate diagram for both of the reactions below using the information provided. Assume that the overall reaction in each case is exergonic. Sebatian A bertindak balas membentuk campuran B dan C. Pada 80 o C, B adalah hasil utama. Pada 0 o C, C adalah hasil utama. Compound A reacts to form a mixture of B and C. At 80 o C, B is formed as the major product. At 0 o C, C is the major product. A dan B adalah dalam keseimbangan dengan C. Pemalar keseimbangan (K 1 ) adalah C bertindak balas dengan pada langkah penentuan kadar bagi menghasilkan E. E dan F adalah dalam keseimbangan dengan pemalar keseimbangan (K 2 ) sebanyak 10,000. A and B are in equilibrium with C. The equilibrium constant (K 1 ) is C reacts with D in the rate determining step to give E. E and F are in equilibrium with an equilibrium constant (K 2 ) of 10,000. (7 markah/marks) Bincangkan mekanisme S N 1 dan terbitkan hukum kadar bagi tindak balas berikut: Discuss the S N 1 mechanism and derive the rate law for the following reaction. (7 markah/marks) TAMAT END 11/11

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