‘KIM3200A ‘SULIT UMT UNIVERSITI MALAYSIA TERENGGANU PEPERIKSAAN AKHIR FINAL EXAMINATION SEMESTER I SESI 2017/2018 (SARJANA MUDA) ‘SEMESTER I 2017/2018 SESSION (BACHELOR) NAMA KURSUS KIMIA ORGANIK ASAS. COURSE BASIC ORGANIC CHEMISTRY KOD KURSUS : KIM3200A COURSE CODE TARIKH : 17 JANUARI 2018 (RABU) DATE 17” JANUARY 2018 (WEDNESDAY) TEMPAT : DEWAN SULTAN MIZAN VENUE MASA : 3.00- 5.00 PETANG (2 JAM) 3.00-5.00 PM (2 HOURS) NO. MATRIK MATRIC NO. NAMA PROGRAM PROGRAMME NO. MEJA SEAT NO. ARAHAN KEPADA CALON INSTRUCTIONS TO CANDIDATES i, Sila jawab semua soalan, Answer all questions. ii, Semua jawapan hendaklah ditulis dalam buku soalan. All answers must be written in the question booklet. JANGAN BUKA BUKU SOALAN INI SEHINGGA DIBERITAHU DO NOT OPEN THE QUESTION PAPER UNTIL INSTRUCTED KERTAS SOALAN INI MENGANDUNGI 11 MUKASURAT BERCETAK THIS QUESTION PAPER CONSISTS OF 11 PRINTED PAGES“KIM3200A QUESTION 1 [25 MARKS] a) Drawa structural formula for each of the following compounds. (Lukiskan formula struktur untuk setiap sebatian yang berikut.) | 1-cyclopropyl-3-methylcyclobutane | 2,6-dimethyl-3-heptyne | trans-2-pentene 3-methyl-3-hexene pare-bromo-tert-butylbenzene cis-2-methyl-3-hexene ‘SULIT (14 marks) aan*KIM3200A ‘SULIT b) Give an TUPAC name for the following compounds and determine their configurations (R/S) if possible. [Berikan nama IUPAC bagi sebatian-sebatian berikut dan tentukan konfigurasinya (RI 5) jika ada.] | | \ | OA | | | TUPAC name: | TUPAC name: | ° | | | | | j it, Viv. | | Br. JCH2CH2CH3 | cl | Th | | ‘CHa k | \ | TUPAC name: | | | | TUPAC name: | | | L _ —4 _ — CH3CHp- | ‘CH2CH2CH3, | | | | | \ TUPAC name: (11 marks) Slt*KIM3200A SULIT QUESTION 2 [25 MARKS] a) Taxol, an isolated compound from the bark of the Pacific Yew tree, is an anticancer drug used in the treatment of ovarian cancer. Identify and name circled functional groups 1-6 in the following structure. (Taxol, satu sebatian yang berasal dari kulit pohon Pacific Yew, adalah ubat anti kanser yang digunakan dalam rawatan kanser ovari. Kenal pasti dan namakan kumpulan berfungsi yang telah dibulatkan 1-6 dalam struktur berikut.) (6 marks) b) Study the molecule below. Answer all the following questions. (Kaji molekul di bawah.Jawab semua soalan berikut.) CH3CN i. Draw a Lewis structure for this molecule. (Lukiskan struktur Lewis bagi molekut inl.) (3 marks) ii. Predict the hybridization state of each carbon. (Ramalkan penghibridan bagi setiap atom Karbon.) (2 marks) ail+ KIM3200A, SULIT lil, Predict the geometry for each carbon atoms in the molecule. (Ramaikan geometri bagi setiap atom Karbon di dalam molekul tersebut.) (2 marks) ©) Study the molecule and compare the Hs and Hy protons below. (Kaji molekul dan bandingkan protor-proton Ha dan Hy i bawah.) 9 Hy Ha 0 i. Draw the TWO (2) possible conjugate bases for this molecule. [Lukiskan DUA (2) bes konjugat yang berkemugkinan bagi molekut ini.} | ~~ Conjugate base 1 | Conjugate base 2 (4 marks) ji, Which proton is more acidic? Explain by comparing the stability of the conjugate base. (Proton yang manakah lebih berasid? Jelaskan dengan membandingkan kestabilan bes konjugat.) (2 marks) slaKIM3200A SULIT d) Draw all possible resonance structures for each of the following molecules. (Lukiskan struktur-struktur resonan yang mungkin untuk setiap molekul berikut,) s i CHe ii. A447 (6 marks) QUESTION 3 (25 MARKS) a) Study the structure of 2,3-dimethylbutane below and answer all questions. [Kaji struktur bagi 2,3-dimetilbutana di bavah dan Jawab semua soalan.] 2,3-dimethylbutane Draw a Newman projection from €2-€3 point of view and state whether it is in staggered or eclipse conformation, (Lakarkan unjuran Nevaman dari pandangan C2-C3 dan nyatakan samada ianya konformasi terpirau atau gerhana.) (2 marks) 6fil“KIM3200A SULIT il, Draw other THREE (3) Newman projections by free rotation (60°) of sigma bond at C2-C3. [Lakarkan TIGA (3) unjuran Newman yang lain dengan putaran bebas ikatan sigma (60) pada C2-C3.] (6 marks) ii, Identify which 2,3-dimethylbutane conformations suit with the energy level a, b, cand d in the following energy diagram. (Tentukan konformasi 2,3-dimetilbutana yang manakah bersesuaian dengan aras tenaga a, b, ¢ dan d di dala diagram tenaga berikut., ) (4 marks) Energy Potential 180 120 60 0 60 120 180 pihedral angle (%) TAL‘KIM3200A ‘SULIT b) Answer the following questions by referring to the structure of molecule A. (Qawab semua soalan yang berikut berpandukan kepada struktur molekul A.) CHs Cis Molecule & Draw chair conformations for TWO(2) cis-isomer and ONE(1) transisomer. (Lakarkan konformasi kerus! bagi DUA(2) cis-isomer dan SATU(L) trans- isomer.) (6 marks) ii. Identify and label which are the most stable, moderately stable and less stable conformer. (Kenalpasti dan labelkan konformasi yang mana paling stabil, sederhana dan kurang stabil.) (3 marks) ©) Answer the following questions by referring to the structure of motecule B. (Jawab semua soalan yang berikut berpandukan kepada struktur molekul B.) Hci Hs Molecule 8 g/t‘KIM3200A ‘SULIT i. Draw the least stable chair conformation for Molecule B. (Lakarkan konformasi kerusi yang ‘paling tidak stabil bagi Molekul B. ) (2 marks) ji. State the factors that contributed to the unstable chair conformation. (Nyatakan faktor-faktor yang menyumbang kepada konformasi kerusi yang tidak stabil.) (2 marks) QUESTION 4 [25 MARKS] a) Provide the structures of the intermediate 1, intermediate 2, major and minor products for the following synthetic scheme. (Berikan struktur bagi perantaraan 1, perantaraan 2, hasil minor dan hasit major ‘bagi skim sintetik yang beriku). OMe ti - Intermediate 1 intermediate 2 | Be Bre v rainor produc aor product (8 marks) oft*KIM3200A ‘SULIT b) Predict the product(s) of the following reactions. (Ramatkan hasil bagi tindakbalas-tindakbalas yang berikut.) lar cata ; O-wet) Hz, Lindlar catalyst NHg Liquid H2SO,, H20, HeSO4 és CHoBr (10 marks) 10/1* KIM3200A SULIT ©) Provide the suitable reagents for the following synthetic scheme (Berikan reagen-reagen yang sesuai bagi skema sintesis berikut). , Ld} 6k (6 marks) d) Name the following reaction (Namakan tindakbalas berikut) ae _— Lewis acid Reaction name: (1 mark) -Kertas soalan tamat- ail