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 2014/2015 : SEMESTER 2 ACADEMIC SESSION 2014/2015 : SEMESTER 2 SCES2260 : KAEDAH SPEKTROSKOPI DALAM KIMIA ORGANIK SPECTROSCOPIC METHODS IN ORGANIC CHEMISTRY Jun 2015 June 2015 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 11 halaman yang dicetak) (This question paper consists of 7 questions on 11 printed pages)

2 1. Tindak balas berikut memberikan dua hasil, C dan D. Spektrum IR untuk produk kedua-dua hasil, sebatian bermula A dan sebatian perantara B diberikan di bawah. The following chemical reaction sequence provided two products, C and D. The IR spectra of both products, starting material A and intermediate B are provided below. (a) (b) (c) Mengenal pasti ciri-ciri getaran bagi sebatian A hingga D dan menetapkan kumpulan berfungsi yang berkaitan. Identify characteristic vibrations for compounds A to D and assign the related functional groups. Terangkan peralihan untuk ciri-ciri anjakan yang ditunjukkan dalam sebatian A dan B. Menggunakan formula struktur. Explain the shift for the indicated major absorption in compounds A and B. Use structural formulas. Berikan formula struktur bagi hasil tindak balas C dan D.Jelaskan jawapan anda. Provide structural formulas for reaction products C and D. Explain your answers. HO O ONa O HCl SOCl 2 HO OH C + D A B (15 markah/marks) 2/11

3 2. Spektrum UV-Vis berikut menunjukkan dua peringkat dari suatu pewarna. Skim tindak balas yang berkaitan ditunjukkan di bawah. The following UV-Vis spectra represent two different stages of a dye. The related reaction scheme is shown below. (a) (b) (c) Jelaskan perbezaan dalam spektrum UV-Vis untuk E dan H dari formula struktur. Gunakan skim MO untuk ilustrasi. Give a molecular structure based explanation for the differences in the UV-Vis spectra for E and H. Use MO schemes for illustration. Ramalkan warna pewarna H. Jelaskan berdasarkan spektrum UV-Vis. Predict the colour of dye H. Explain based on the UV-Vis spectrum. Lakarkan spektrum sebatian pemula G dan ramalkan warnanya. Jelaskan ramalan anda. Sketch the spectrum of precursor G and predict its colour. Explain your prediction. OMe OMe HNO 2 H 3 C OH NH 2 NO 2 N + N NO 2 NC O N CH 3 E F G MeO NO 2 HO N N CH 3 N O H H 3 C CN (10 markah/marks) 3/11

4 3. Diberikan di bawah adalah 1 H-NMR, IR dan MS spektrum bagi sesuatu sebatian unknown. Given below are the 1 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 spektrum IR, NMR dan MS (EI) berdasarkan formula yang diberikan dalam a. Explain the IR, NMR and MS (EI) spectra based on the formula given in a. (15 markah/marks) 4/11

5 4. Berikan penjelasan mekanistik bagi dua ion serpihan berikut. Give a mechanistic explanation for two of the following fragment ions. m/z = 132 O.+ m/z = 228 m/z = 256 m/z = 185 (10 markah/marks) 5. (a) (b) (c) Ramalkan nombor isyarat dan multiplisiti dalam spektrum 1 H NMR bagi sebatian (I J) di atas. Predict the number of signals and their coupling patterns in the 1 H NMR spectra of the compounds (I J) above. Ramalkan bilangan isyarat dalam spektrum 13 C NMR bagi sebatian (I J) di atas. Predict the number of signals in the 13 C NMR spectra of the compounds (I J) above. Anggarkan pemalar kupelan (dalam Hertz) tiga-ikatan ( 3 J) bagi sebatian (I J) above. Estimate the three-bond ( 3 J) coupling constant (in Hertz) of the compounds (I J) above. (19 markah/marks) 5/11

6 6. (a) Kenalpastikan spektrum 1 H NMR (i iii) di bawah bagi sebatian K, L, dan M, masing-masing. Jelaskan jawapan anda. Identify which of the 1 H NMR spectrum below (i iii) belong to compounds K, L, and M, respectively. Explain your answer. Spectrum/Spektrum i 1H 1H 1H Spectrum/Spektrum ii 1H Spectrum/Spektrum iii 1H (6 markah/marks) 6/11

7 7. Sebatian N dan P adalah isomer dengan formula molekul C 5 H 9 N. Spektrum IR, 1 H, dan 13 C NMR sebatian ini adalah seperti ditunjukkan di bawah. Compounds N and P are isomers with the molecular formula C 5 H 9 N. The IR, 1 H, and 13 C NMR spectra of these compounds are shown below. (a) (b) Berdasarkan maklumat yang diberikan, tentukan struktur sebatian N dan P. Based on the information provided, determine the structures of compounds N and P. Tentukan semua isyarat dalam spektrum 1 H dan 13 C NMR sebatian N dan P. Assign all peaks in 1 H and 13 C NMR spectra of compounds N and P. 7/11

8 Spektrum IR sebatian N IR spectrum of compound N Spektrum 1 H NMR sebatian N 1 H NMR spectrum of compound N Spektra 13 C NMR dan DEPT-135 sebatian N 13 C NMR and DEPT-135 spectra of compound N 2C 8/11

9 Spektrum IR sebatian P IR spectrum of compound P Spektrum 1 H NMR sebatian P 1 H NMR spectrum of compound P Spektra 13 C NMR dan DEPT-135 sebatian P 13 C NMR and DEPT-135 spectra of compound P (25 markah/marks) 9/11

10 Appendik/ Appendix: 10/11

11 TAMAT END 11/11

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