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1 UNIVERSITI MALAYA UNIVERSITY OF MALAYA PEPERIKSAAN IJAZAH SARJANA MUDA SAINS EXAMINATION FOR THE DEGREE OF BACHELOR OF SCIENCE SESI AKADEMIK 2011/2012 : SEMESTER 1 ACADEMIC SESSION 2011/2012 : SEMESTER 1 SCES2260 : KAEDAH SPEKTROSKOPI DALAM KIMIA ORGANIK SPECTROSCOPIC METHODS IN ORGANIC CHEMISTRY Januari 2011 January 2011 MASA : 2 jam TIME : 2 hours ARAHAN KEPADA CALON : INSTRUCTIONS TO CANDIDATES : Jawab SEMUA soalan. Answer ALL questions. (Kertas soalan ini mengandungi 5 soalan dalam 9 halaman yang dicetak) (This question paper consists of 5 questions on 9 printed pages)
2 SCES2260/02 1. (a) Proton yang manakah dalam sebatian di bawah akan kelihatan sebagai i) septet; ii) heptet pada spectrum 1 H NMR. Lukiskan spectrum 1 H NMR bagi sebatian tersebut. Which proton(s) of the compound below would appear as i) septet; ii) heptet in the 1 H NMR spectrum. Draw the 1 H NMR spectrum of this compound. (b) Semua sebatian organik di bawah adalah isomer struktur yang mempunyai formula molekul C 7 H 12 O 2. All the organic molecules below are structural isomers with the molecular formula C 7 H 12 O 2. A B C D
3 SCES2260/03 i. Sebatian yang manakah akan menunjukkan hanya dua puncak singlet pada spectrum 1 H NMR? Which compound would show only two singlets peak in their 1 H NMR spectrum? ii. iii. Berapakah puncak yang anda jangkakan akan kelihatan pada spectrum 1 H NMR dan 13 C NMR bagi sebatian A dan B? How many signals would you expect to find in the 1 H NMR and 13 C NMR spectrum of A and B? Lukiskan spectrum 1 H NMR bagi sebatian C dan tunjukkan bentuk pengkupelam bagi setiap puncak. Draw the 1 H NMR spectrum of compound C and show the splitting pattern for each peak. 2. (a) Spektrum 1 H NMR di bawah adalah bagi sebatian asid 2-kloropropanoik dan asid 3-kloropropanoik. Tentukan spektrum manakah untuk asid 2-kloropropanoik dan yang mana untuk asid 3-kloropropanoik. The 1 H NMR spectrum shown below is of 2-chloropropanoic acid and 3-chloropropanoic acid. Indicate which spectrum belong to 2-chloropropanoic acid and which belong to 3-chloropropanoic acid. Explain you answer.
4 SCES2260/04 (b) Spektrum proton NMR bagi isopropil butanoat ditunjukkan di bawah. Tentukan proton a e kepada puncak yang bersesuaian. Proton NMR spectrum of isopropyl butanoate is shown below. Assign proton a e to their corresponding peaks. (5 markah/marks)
5 SCES2260/05 (c) Spektra 1 H NMR dan IR bagi suatu sebatian dengan formula molekul C 9 H 10 O ditunjukkan di bawah. Dari formula molekul ditentukan bahawa sebatian mempunyai darjah ketaktepuan 5. Cadangkan struktur bagi sebatian ini. Proton NMR and IR spectra of a compound with the molecular formula C 9 H 10 O are shown below. From the molecular formula the compound has five degree of unsaturation. Propose the structure of this compound.
6 SCES2260/06 3. Apabila dilarutkan dalam CDCl 3, sebatian K yang berformula molekul C 4 H 8 O 2 memberikan spectrum yang mengandungi puncak dublet pada 1.35, singlet pada 2.15, singlet lebar pada 3.75, dan kuartet pada Bila dilarutkan dalam D 2 O, spectrum 1 H NMR yang sama diperolehi kecuali puncak pada 3.75 telah hilang. Spektrum IR sebatian tersebut menunjukkan keserapan kuat pada 1720 cm-1. When dissolved in CDCl 3, a compound (K) with molecular formula C 4 H 8 O 2 gives a 1 H NMR spectrum that consists of a doublet at 1.35, a singlet at 2.15, a broad singlet at 3.75 (1H), and a quartet at 4.25 (1H). When dissolved in D 2 O, the compound gives a similar 1 H NMR spectrum, with the exception that the signal at 3.75 has dissappeared. The IR spectrum of the compound shows a strong peak near 1720 cm -1. (a) Cadangkan struktur bagi sebatian K. Propose a structure for compound K. (b) Jelaskan kenapa puncak NMR pada 3.75 hilang apabila D 2 O digunakan sebagai pelarut. Explain why the NMR signal at 3.75 disappears when D 2 O is used as the solvent. 4. (a) Spektra jisim, IR dan 1 H NMR di bawah adalah untuk sebatian yang sama. Tentukan struktur sebatian tersebut. The mass, infrared, and proton NMR spectra below were all generated by the same compound. Determine the identity of that compound.
7 SCES2260/07 (b) Tentukan struktur bagi sebatian yang mempunyai spectra IR, dan 1 H NMR ditunjukkan di bawah yang berformula molekul C 11 H 14 O 2. Determine the structure of the compound which generates the IR and proton NMR spectra shown in the figure and has the molecular formula given (C 11 H 14 O 2 ). IR Spectrum
8 SCES2260/08 1 H NMR Spectrum 5. (a) Spektrum jisim sebatian B menunjukkan puncak M + pada m/z 88, satu puncak pada m/z 73 dan base peak pada m/z 59. Spektra IR bagi sebatian B mempunyai keserapan yang lebar pada cm -1. Spektra 1 H NMR bagi B menunjukkan puncak seperti berikut: triplet pada 0.9, suatu singlet pada 1.1 dan kuartet pada 1.6. Nisbah keluasan puncak-puncak tersebut adalah 3:7:2 masing-masing. Cadangkan struktur sebatian B. The mass spectrum of compound B shows an M + peak at m/z 88, a peak at m/z 73 and the base peak at m/z 59. The IR spectrum of B shows a broad peak between 3200 and 3559 cm -1. The 1 H NMR spectrum of B shows the following peak: a triplet at 0.9, a singlet at 1.1, and quartet at 1.6. The area ratio of these peaks is 3:7:2, respectively. Propose a structure for B.
9 SCES2260/09 (b) Spektrum IR hasil X tidak mempunyai keserapan pada cm -1 tetapi menunjukkan keserapan pada 1370 dan 1380 cm -1, yang merupakan ciri bagi kumpulan gem-dimetil. Spektra jisim X mengandungi puncak : Suatu kluster pada m/z 270, 272 dan 274 dengan keamatan relatif puncak kira-kira 1:2:1. Kluster lain pada m/z 191 dan 193 dengan keamatan puncak yang hampir sama. The IR spectrum of product X has no absorption at cm -1 but does absorb at about 1370 and 1380 cm -1, which is characteristic of gemdimethyl groups. The mass spectrum of X contains these peaks: A cluster at m/z 270, 272 and 274 with relative peak intensities of about 1 : 2 : 1. Another cluster at m/z 191 and 193 with about equal peak intensities. OH OH 60% HBr X Spektra NMR menunjukkan: The NMR spectra show: i. Pada spektra 1 H, suatu puncak singlet pada 1.70 dan 1.80, dengan keamatan relatif 3:1. In the 1 H spectrum, singlets at 1.70 and 1.80, with relative areas of 3 : 1. ii. Spektra 13 C mempunyai puncak pada 32 (CH 3 ), 40 (CH 2 ), dan 54 (C kuarterner) The 13 C spectrum has peaks at 32 (CH 3 ), 40 (CH 2 ), and 54 (quaternary C). Apakah struktur X? Cadangkan mekanisme bagaimana ia terbentuk. What is the structure of X? Suggest a mechanism for its formation. (15 markah/marks) TAMAT END
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UNIVERSITI MALAYA UNIVERSITY OF MALAYA PEPERIKSAAN IJAZAH SARJANA MUDA SAINS EXAMINATION FOR THE DEGREE OF BACHELOR OF SCIENCE SESI AKADEMIK 2009/2010 : SEMESTER 1 ACADEMIC SESSION 2009/2010 : SEMESTER
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