SCES2260 : KAEDAH SPEKTROSKOPI DALAM KIMIA ORGANIK SPECTROSCOPIC METHODS IN ORGANIC CHEMISTRY
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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 2012/2013 : SEMESTER 2 ACADEMIC SESSION 2012/2013 : SEMESTER 2 SCES2260 : KAEDAH SPEKTROSKOPI DALAM KIMIA ORGANIK SPECTROSCOPIC METHODS IN ORGANIC CHEMISTRY Jun 2013 June 2013 MASA : 2 jam TIME : 2 hours ARAHAN KEPADA CALON : INSTRUCTIONS TO CANDIDATES : Jawab SEMUA soalan. Answer ALL questions. (Kertas soalan ini mengandungi 7 soalan dalam 9 halaman yang dicetak) (This question paper consists of 7 questions on 9 printed pages)
2 1. Spektrum UV-Vis berikut menunjukkan dua peringkat dari pewarna hijau malachite. Formula struktur peringkat kedua ditunjukkan dalam skim tindak balas beribut. The following UV-Vis spectra represent two different stages of malachite green, a common dye. The structural formulas of both stages are shown in the reaction scheme below. (10 markah/marks) (a) Tentukan spektrum UV-Vis I dan II untuk formula struktur A dan B. Assign the UV-Vis spectra I and II to the structural formulas A and B. Berikan penjelasan berdasarkan struktur molekul bagi perbezaan pada spektrum UV-Vis bago A dan B. Gunakan skema MO untuk ilustrasi. Give an explanation based on molecular structure for the differences in the UV-Vis spectra for A and B. Use MO schemes for illustration. I II 2/9
3 2. (a) Berikan formula struktur bagi hasil C dan D. Provide structural formulas for both products C and D. Terangkan serapan ciri dalam spektrum IR untuk sebatian A hingga D menunjukkan getaran kumpulan berfungsi. Explain characteristic absorptions in the IR spectra of compounds A to D by indicating the functional group vibration they are related to. 3. Berikan penjelasan mekanistik bagi ion serpihan berikut. Give a mechanistic explanation for the following fragment ions. (a) O O m/z = 86 m/z = 58 O m/z = 100 (1) m/z = 43 (2) m/z = 58 (3) m/z = 85 3/9
4 4. Diberikan di bawah adalah IR, MS dan 1 H-NMR spektrum bagi sesuatu sebatian yang tidak diketahui. Given below are the IR, MS and 1 H-NMR spectra for an unknown compound. (a) Berikan nama dan formula struktur bagi sebatian. Provide the name and the structural formula for the compound. Jelaskan spektrum IR, MS dan NMR berdasarkan formula ini. Explain the IR, MS and NMR spectra based on this formula. 4/9
5 5. Struktur A Stucture A (a) Ramalkan anjakan kimia bagi H a, H b, H c, H d, H e, H f, H g dan H h. Predict the chemical shifts of H a, H b, H c, H d, H e, H f, H g and H h. (c) Gambarkan corak pengkupelan semua proton dan terangkan jawapan anda. Describe the coupling patterns of all the protons and explain your answer. Di antara H d, H e dan H f yang manakah adalah paling terperisai dan ternyahperisai. Terangkan jawapan anda. Between H d, H e and H f which one will be the most shielded and which will be the most deshielded. Explain your answer. (23 markah/marks) 6. Struktur B Stucture B 5/9
6 Rajah 1 Figure 1 Tentukan puncak spektrum karbon dalam rajah 1. Terangkan jawapan anda. Assign the carbon peaks of the spectrum shown in Figure 1. Explain your answer. (7 markah/marks) 7. Sebatian ini mempunyai formula molekul C 9 H 11 NO 2. Diberikan spectrum IR, 1 H NMR dan data spectral 13 C. Dalam spectrum 1 H, puncak d ialah dublet, e ialah triplet, f ialah singlet dan g ialah dublet. Dengan maklumat yang diberikan tentukan struktur molekul ini. Tentukan semua puncak proton dan carbon dan ramalkan pemalar pengkupelan bagi setiap puncak di kawasan aromatik. This compound has the molecular formula C 9 H 11 NO 2. Included are the infrared spectrum, 1 H NMR and 13 C spectral data. In the 1 H spectrum, peak d is a doublet, e is a triplet, f is a singlet and g is a doublet. Using this information, elucidate the structure, Assign all the proton and carbon peaks and predict the coupling constants of peaks in the aromatic region. 6/9
7 CH 3 /CH (positive) CH 2 (negative) C q (no peak) CH (positive) 7/9
8 Lampiran A Appendix A 8/9
9 Lampiran B Appendix B TAMAT END 9/9
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