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 SCES1220 : KIMIA ORGANIK I ORGANIC CHEMISTRY I Jun 2015 June 2015 MASA : 2 jam TIME : 2 hours ARAHAN KEPADA CALON : INSTRUCTIONS TO CANDIDATES : Jawab SEMUA soalan. Answer ALL the questions. (Kertas ini mengandungi 4 soalan dalam 8 halaman yang dicetak) (This question paper consists of 4 questions on 8 printed pages)
1. (a) Lukiskan molekul-molekul yang berikut: Draw the following molecules: (ii) (iii) (iv) (v) (vi) 4-bromo-3,3-dietil-6,6-dimetil-5-propilnonana 4-bromo-3,3-diethyl-6,6-dimethyl-5-propylnonane 1-bromo-7-iodospiro[4.5]decana 1-bromo-7-iodospiro[4.5]decane 6-floro-5-metil-3-heptuna 6-fluoro-5-methyl-3-heptyne (Z)-1-bromo-2-kloro-3,3-dimetil-1-pentena (Z)-1-bromo-2-chloro-3,3-dimethyl-1-pentene (1E,3Z)-1-iodo-2,5-dimetil-1,3-hexadiena (1E,3Z)-1-iodo-2,5-dimethyl-1,3-hexadiene (5R)-5-bromo-1-hexuna (5R)-5-bromo-1-hexyne (8 markah/marks) (b) Dengan menggunakan formula unjuran Newman, lukis semua konformasi terpirau apabila sebatian di atas diputarkan (pada ikatan yang ditunjukkan di atas) serta nyatakan konformasi terpirau yang paling stabil. By using the Newman projection, draw all the staggered conformations when the compound above is rotated about the bond shown above, and indicate the most stable staggered conformation. (4 markah/marks) 2/8
(c) Jelaskan pemerhatian yang berikut. Explain the following observations. (4 markah/marks) 2. (a) Lukiskan struktur-struktur resonan dan resonan hybrid yang munasabah untuk molekul-molekul di bawah: Draw all possible resonance structures and resonance hybrid for the following molecules: (9 markah/marks) (b) Jawab soalan di bawah berdasarkan molekul yang berikut (anda dikehendaki melakar semula molekul tersebut di skrip jawapan). Answer the questions below based on the following molecule (you are required to re-draw the molecule in the answer script). 3/8
Bulat dan namakan kumpulan berfungsi yang ada pada molekul di atas. Circle and name the functional groups present in the molecule above. (ii) Kenalpasti kesemua pusat stereogenik (tandakannya dengan *), dan berikan konfigurasi (R atau S) bagi SEMUA pusat stereogenik untuk molekul berkenaan. Identify all the stereogenic centers (mark it with an *), and assign the configuration (R or S) for ALL the stereogenic centers in the molecule. (10 markah/marks) (c) Yang manakah istilah-istilah berikut dapat menggambarkan pasangan sebatian yang ditunjukkan di bawah: enantiomer, diastereomer, isomer berjuzuk, atau sebatian yang sama. Which of the following terms best describes the pair of compounds shown below: enantiomers, diastereomers, constitutional isomers, or the same compound? (5 markah/marks) 4/8
(d) Berikan reagen atau produk (A G) untuk transformasi berikut: Give reagents or products (A G) for the following transformations: (8 markah/marks) 3. (a) Cadangkan sebatian H dan I. Lukiskan mekanisme tindak balas daripada H ke sikloheksena. Suggest compounds H and I. Draw reaction mechanisms from H to cyclohexene. (4 markah/marks) (b) Tentukan elektrofil, nukleofil serta hasil jangkaan daripada tindak balas di bawah. Identify electrophile, nucleophile, and expected products for the following reactions. (ii) (6 markah/marks) 5/8
(c) Lukiskan mekanisme tindak balas di bawah. Draw the mechanism for the following reactions. (ii) (20 markah/marks) 4. (a) Bincangkan proses penyingkiran tindak balas berikut. Discuss the elimination process for the following reaction. (10 markah/marks) (b) Kategorikan sebatian di bawah kepada terkonjugasi, terasing atau terkumpul. Categorize the compounds below into conjugated, isolated, or cumulated. (3 markah/marks) 6/8
(c) Lengkapkan persamaan tindak balas di bawah. Complete the reaction equations below. (ii) (iii) (iv) (v) (vi) (vii) (7 markah/marks) 7/8
(d) Tentukan salah satu sebatian berikut yang merujuk kepada spektrum ini. Indicate which of following compounds is responsible for the spectrum shown below. 2950 cm -1 1705 cm -1 1193 cm -1 TAMAT END (2 markah/marks) 8/8