(Kertas soalan ini mengandungi 6 soalan dalam 11 halaman yang dicetak) (This question paper consists of 6 questions on 11 printed pages)
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1 UNIVERSITI MALAYA UNIVERSITY F MALAYA PEPERIKSAAN IJAZAH SARJANA MUDA SAINS EXAMINATIN FR THE DEGREE F BACHELR F SCIENCE SESI AKADEMIK 2013/2014 : SEMESTER 2 ACADEMIC SESSIN 2013/2014 : SEMESTER 2 SCES2260 : KAEDAH SPEKTRSKPI DALAM KIMIA RGANIK SPECTRSCPIC METHDS IN RGANIC CHEMISTRY Jun 2014 June 2014 MASA : 2 jam TIME : 2 hours ARAHAN KEPADA CALN : INSTRUCTINS T CANDIDATES : Jawab SEMUA soalan. Answer ALL questions. (Kertas soalan ini mengandungi 6 soalan dalam 11 halaman yang dicetak) (This question paper consists of 6 questions on 11 printed pages)
2 1. Pertimbangan spektrum UV dan formular struktur berikut. Examine the following UV spectra and structural formulas. A B H 3 C CH N 3 Na 3 S N N CH 3 N CH 3 H 3 C CH N N 3 + CH 3 Cl CH 3 I II (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. (b) (c) Ramalkan warna sebatian A dan B berdasarkan UV-Vis spektra I dan II. Jelaskan ramalkan anda. Predict the colours of compounds A and B based on the UV-Vis spectra I and II. Explain your prediction. Jelaskan perbezaan dalam spektrum UV-Vis untuk A dan B dari formula struktur. Gunakan skim M untuk ilustrasi. Give a molecular structure-based explanation for the differences in the UV-Vis spectra for A and B. Use M schemes for illustration. (15 markah/marks) 2/11
3 2. Tindak balas berikut disediakan dua produk, D dan E. Spektrum IR untuk dua produk tersebut dan sebatian permula C disediakan di bawah. The following chemical reaction provided two products, D and E. The IR spectra of both products and the starting material C are provided below. CN C = H 2 D + E [H + ], C D E (a) Berikan formula struktur bagi hasil tindak balas D dan E. Provide structural formulas for both reaction products D and E. (b) Terangkan serapan ciri dalam spektrum IR untuk sebatian C hingga E menunjukkan getaran kumpulan berfungsi. Explain characteristic absorptions in the IR spectra of compounds C to E by indicating the functional group vibration they are related to. F = G = (c) Jelaskan perbezaan untuk getaran karbonil daripada benzaldehid, F (1703 cm -1 ), dan karbaldehid sikloheksana, G (1727 cm -1 ). Explain the difference for the carbonyl vibrations of benzaldehyde, F (1703 cm -1 ), and cyclohexane carbaldehyde, G (1727 cm -1 ). (20 markah/marks) 3/11
4 3. (a) Spektrum NMR III dan IV mencerminkan stereoisomer metil 2-butenoate, H dan K, yang struktur diberikan di bawah. Tentukan spektra bagi sebatian berikut dan jelaskan. The NMR spectra III and IV reflect the stereoisomers of methyl 2- butenoate, H and K. Assign the spectra to the compounds and explain your assignment. H = K = H 3 C CH 3 H 3 C CH 3 4/11
5 Pertimbangkan formula struktur dan spektrum NMR berkaitan berikut. Consider the following structure formula and related NMR spectra. L = CH 3 CH 3 (b) (c) Tentukan semua puncak dalam spektrum NMR V dan VI berdasarkan struktur L. Assign all peaks in the NMR spectra V and VI based on structure L. Ramalkan kepelbagaian untuk semua atom hidrogen alkil dalam struktur L dan tunjukkan keamatan puncak relatif yang sepadan untuk semua isyarat dengan maksimum 5 puncak. Predict the multiplicity for all alkyl hydrogen atoms in structure L and indicate the corresponding relative peak intensities for all signals with maximum 5 peaks. (25 markah/marks) 5/11
6 4. Diberikan di bawah adalah H-NMR, IR dan MS spektrum bagi sesuatu sebatian tidak diketahui. Given below are the H-NMR, IR and MS spectra for an unknown compound. (a) (b) Berikan nama dan formula struktur bagi sebatian tersebut. Provide the name and the structural formula for the compound. Jelaskan spektra IR, NMR dan MS berdasarkan formula yang diberikan dalam a. Explain the IR, NMR and MS spectra based on the formula given in a. (15 markah/marks) 6/11
7 5. Diberikan di bawah adalah spektra IR dan NMR bagi sebatian tidak diketahui dengan jisim molekul 139. Given below are the IR and NMR spectra of an unknown compound with a molecular mass of 139. (a) (b) Cadangkan struktur bagi sebatian tidak diketahui. Propose a structure for the unknown compound. Jelaskan spektra (IR, NMR dan MS) berdasarkan struktur yang dicadangkan. Explain the spectra (IR, NMR and MS) on basis of your structure proposal. (15 markah/marks) 7/11
8 6. Berikan penjelasan mekanistik bagi ion serpihan berikut. Give a mechanistic explanation for the following fragment ions. m/z = 130 m/z = 74 m/z = 110 m/z = 154 (10 markah/marks) 8/11
9 INFRARED SPECTRSCPY ABSRPTIN TABLE 9/11
10 NUCLEAR MAGNETIC RESNANCE SPECTRSCPY ABSRPTIN TABLES 10/11
11 TAMAT END 11/11
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