UNIVERSITI MALAYSIA TERENGGANU PEPERIKSAAN AKHIR FINAL EXAMINATION SEMESTER I SESI 2016/2017 (SARJANA MUDA) SEMESTER I 2016/2017 SESSION (DEGREE PROGRAMME) - IIMA ORGANI ASAS ~ BASIC ORGANIC CHEMISTRY KIM3200A 08 JANUARI 2017 (AHAD) 08 JANUARY 2017 (SUNDAY) DEWAN SULTAN MIZAN 3,00 — 5.00 PETANG (2 JAM) 3.00 - 5.00 PM (2 HOURS) ARAHAN KEPADA CALON DATES i, Sila jawab semua soalan Answer ail ii, Semua jawapan hendeklah ditulis dalam buku jawapan yang disediakan All answers must be viritten in answer booklet provided JANGAN BUKA BUKU SOALAN INI SEHINGGA DIBERITAHU DO NOT OPEN THE QUESTION PAPER UNTIL INSTRUCTED KERTAS SOALAN INI MENGANDUNGI 13 MUKASURAT BERCETAK THIS QUESTION PAPER CONSISTS OF 13 PRINTED PAGESSULIT KIM3200A CONFIDENTIAL QUESTION 1. (25 MARKS) a) Study the molecule below. Answer all the following questions. (Kaji molekut di bawah, Jawab semua soatan berikut.) Net AA, i. Draw TWO (2) possible conjugate base. (Lukis DUA (2) bes konjugat yang berkemungkinan.) (4 marks) ii, Compare both protons Ha and Hy that are shown in the following compound. Identify the most acidic proton. Explain your answer. (Bandingkan proton H, dan Hy yang ditunjukkan di dalam molekul tersebut. Tentukan proton yang lebih berasid. Jelaskan jawapan anda.) (3 marks) 2143KIM3200A8 SULIT CONFIDENTIAL b) Consider the following reaction below. Draw FIVE (5) resonance structures for the conjugate base of cyclopentadienyl anion. (Pertimbangkan tindak balas di bawah. Lukiskan LIMA (5) struktur resonan untuk ‘bes konjugat bagi siklopentadient anion.) (10 marks) 4 ~ OHO ©) Consider the following molecules. (Pertimbangkan moleku-molekul berikut.) (CHsCH2.0-CH.CHs Oa t t A B |. Predict the hybridization type of A and B atoms. (Ramatkan penghibridan bagi A dan B). (2 marks) 3113KIM3200A ‘SULIT CONFIDENTIAL ii, Predict the molecular geometry of each molecule above. (Ramatkan geometri moleku! bag! setiap motekul di ates.) (2 marks) lil. Identify which compound exhibit molecular dipole moment. Indicate the direction of all dipole moments and draw the net dipole moment for its molecule. (Tentukan motekul manakah yang mempunyal momen dwikutub. Tunjukkan Semua arah momen dwikutub dan lukis net momen dwikutub bagi molekul tersebut.) Q (4 marks) an3KIM3200A SULIT CONFIDENTIAL QUESTION 2 (25 MARKS) a) Study the given chemical structure and answer all questions. (Kaji stuktur Kimia yang diberikan dan jawab semua soalan.) i. Draw FOUR (4) possible Newman projection for conformations by looking down the C2-C3 bond. (Lakarken EMPAT (4) kemungkinan unjuran Newman bag! konformast- konformasi melalul pandangan ikatan C2-C3). (8 marks) 5/13KIM3200A SULIT CONFIDENTIAL ii, Identify the conformation that suit with the labeled energy level (A, By © and D) In the following energy diagram. (Tentukan konformasi yang sesuai dengan aras tenaga yang dilabelkan (A, 'B, C dan D) di dalam diagram tenage berikut,) (4 Marks) Energy Potential v 180 120 60 0 60 120 180 pyihedyal angle X° b) Study the following compound and answer all questions, (Kaji sebatian berikut dan jawab semua soatar.) 1,3-dichtorocyclohexane i. Draw THREE(3) possible chair conformations for the given compound, (Lakarkan TIGA(3) konformas! kerusi yang mungkin bagi sebatian tersebut.) (6 Marks) 6113KIM3200A SULIT ©) CONFIDENTIAL Based on question 2b(i), identify the most stable, moderate and least stable chair conformations, Label each chair conformation. (Berdasarkan soalan 2b(i), tentukan konformasi yang mana paling stably ‘sederhana dan kurang stabil. Labelkan setiap Konformas! kerusi tersebut.) (3 Marks) Explain the factor that contribute to the mest stable chair conformation. (Terangkan faktor yang menyumbang kepada konformas! kerusi yang paling stabi) (2 Marks) Draw a Newman Projection of the most stable molecule of ci-1,4-di mathyleyelohexane through Ci-C2 and C5-C4. (lakarkan unjuran Newman yang paling stabil bagi cis-1,4-dlmeti ssikloheksania melalui C1-C2 dan C5-C4.) (2 Marks) 7443KIM3200A ‘SULIT CONFIDENTIAL QUESTION 3 [25 MARKS] a) Draw a correct structure for each of the following compounds. (Lukiskan straktur yang betul untuk setiap sebatian yang berikut) i -phenyihexane | | | | | | (8 marks) 8/13KIM3200A ‘SULIT b) Give an IUPAC name for the following compounds. (Berikan nama IUPAC bagi sebatian-sebatian berikut.) ” ~ ] AT | Cee | . | CHyCHy | | ‘CH,CH»CHs | TUPAC name: | TUPAC name: | | | [ee (14 marks) ‘ ©) Assign E or Z configuration for the following molecules. (Tentukan konfigurasi € atats Z untuk molekukmolekui aj bawah.) = ~— (2 marks) 9013KIM3200A Draw a correct Fischer Projection for the following molecules. i | (9-2-butanol | SULIT CONFIDENTIAL (Lukiskan Unjuran Fischer yang betul bagi molekul-motekul yang berikut) (4 marks) 10/13KIM3200A SULIT CONFIDENTIAL QUESTION 4 [25 MARKS] a. Provide all structures for the following synthetic scheme. (Berikan semua struktur untuk skema sintetik berikut. OL a |_——-——» Intermediate | Intermediate 2 ae er? minor product major product (8 marks) 1/13KIM3200A SULIT CONFIDENTIAL b. Predict the product of the reactions given below. (Ramalkan produk tindak balas yang diberikan di bawah.) Ho, Lindlar catalyst i H3CC=CCH; § ————_——-~ _ Li, NHg Liguid ii, H,CC=CCHs | Mee H,804, Hz0, HeSO4 HsCCSCH _— fo NaNH, a HgCC2CH OO CH3Br (10 marks) 12/13KIM3200A SULIT CONFIDENTIAL c. Provide the reagents for the following synthetic scheme, (Berikan reagen untuk skema sintetik berikug). (6 marks) : (9S oS : NOz cf er d. Provide the name for the following reaction (Bertkan nama bagi tindak bates berikuly A Lewis acid ao (4 mark) ~ Kertas Soalan Tamat~ End of Question Paper 13/13