SCES1220 : KIMIA ORGANIK I ORGANIC CHEMISTRY I

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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 2013/2014 : SEMESTER 1 ACADEMIC SESSION 2013/2014 : SEMESTER 1 SCES1220 : KIMIA ORGANIK I ORGANIC CHEMISTRY I Disember 2013/Januari 2014 December 2013/January 2014 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 7 halaman yang dicetak) (This question paper consists of 4 questions on 7 printed pages)

2 1.(a) Struktur sebatian A adalah seperti di bawah. The structure of compound A is shown below. Berikan nama IUPAC untuk sebatian A. Give the IUPAC name for compound A. Nyatakan kesemua keadaan hibrid setiap atom dalam sebatian tersebut. State all the hybridization state for each atom in the compound. (7 markah/marks) Senaraikan sebatian-sebatian berikut mengikut takat didih relatif dalam urutan menurun. List the following compounds in descending order of their relative boiling point. (3 markah/marks) (c) Lukiskan kesemua resonan penyumbang untuk ion B. Draw resonance contributors for the ion B. (5 markah/marks) 2/7

3 2.(a) Lukiskan kesemua konformer terpirau dan gerhana hasil putaran sebatian pentana pada ikatan C-2 - C-3. Plotkan rajah tenaga keupayaan untuk putaran tersebut melalui pusingan 360, bermula dari konformasi paling kurang stabil. Draw all the staggered and eclipsed conformers that result from rotation about the C-2 - C-3 bond of pentane. Plot a potential-energy diagram for rotation of the C-2 - C-3 bond of pentane through 360, starting with the least stable conformer. (10 markah/marks) Lukiskan dua konformasi kerusi trans-1,4-dimetilsikloheksana. Nyatakan yang mana lebih stabil. Jelaskan. Draw the two chair conformations of trans-1,4-dimethylcyclohexane. State the most stable conformation. Give the reason. (5 markah/marks) (c) Berikan nama bersistematik untuk setiap sebatian di bawah. Give the systematic name for each of the following compounds. (3 markah/marks) (d) Lukiskan struktur molekul untuk setiap yang berikut. Draw molecular structures for each of the following. (S)-2-bromo-1-pentena (S)-2-bromo-1-pentene (2R,3R)-2,3-dikloropentana (2R,3R)-2,3-dichloropentane dua isomer akiral 3,4,5-trimetilheptana two achiral isomers of 3,4,5-trimethylheptane (4 markah/marks) 3/7

4 (e) Dua stereoisomer terhasil daripada tindakbalas HBr dan (S)-2-bromo-1-pentena. Satu daripada stereoisomer adalah aktif optik dan yang satu lagi tidak. Lukiskan struktur, nyatakan konfigurasi dan jelaskan perbezaan dalam sifat optik berkenaan. Two stereoisomers are obtained from the reaction of HBr and (S)-2-bromo-1- pentene. One of the stereoisomers is optically active and the other is not. Draw the structures, indicate their configuration and explain the difference in their optical properties. (8 markah/marks) 3.(a) Lukiskan struktur untuk setiap sebatian di bawah. Draw the structures of the following compounds. (iv) (E)-1,2-dibromo-3-isopropil-2-hexena (E)-1,2-dibromo-3-isopropyl-2-hexene (2Z,4E)-1-kloro-2,4-heptadiena (2Z,4E)-1-chloro-2,4-heptadiene 5,6-dimetil-2-heptuna 5,6-dimethyl-2-heptyne 6-kloro-2-metil-3-heptuna 6-chloro-2-methyl-3-heptyne (4 markah/marks) Nyatakan bahan pemula, reagen dan hasil dalam persamaan-persamaan di bawah. Indicate the starting materials, reagents and products in the equations below: 4/7

5 (iv) (v) (vi) (c) Tindakbalas hidrasi sebatian I bermangkin asid menghasilkan dua isomer alkohol seperti di bawah. Acid-catalyzed hydration reaction of alkene I produces two isomeric alcohols as shown below. Takat suhu didih Boiling point, o C Takat suhu lebur Melting point, o C Pemula Pre-cursor Hasil utama Major product Hasil sampingan Minor product Cadangkan pemangkin J yang digunakan. Suggest the catalyst J used in the reaction. Terangkan mengapa takat suhu didih dan lebur sebatian I lebih rendah daripada hasilnya. Lukiskan diagram untuk menerangkan situasi ini. Explain why the boiling and melting points of I are lower than the products. Draw a diagram to explain this situation. Tuliskan mekanisme tindakbalas untuk menunjukkan K sebagai produk utama. Write a mechanism to show why K is the major product. (14 markah/marks) 5/7

6 (d) Sebatian L hingga Q adalah diena yang boleh dibahagikan kepada kategori: terkonjugasi, terasing dan terkumpul. Bahagikan sebatian-sebatian di bawah mengikut kategori tersebut. Compounds L to Q are dienes that can be divided into three categories: conjugated, isolated and cumulated dienes. Assign the category of the compounds below according to the classes mentioned above. 4.(a) Tentukan elektrofil, nukleofil dan hasil jangkaan daripada persamaan-persamaan di bawah. Identify the electrophile, the nucleophile and the expected products of the following equations. Berikan sebatian pemula dan hasil-hasil daripada persamaan-persamaan di bawah. Give the starting material and products in the equations below. (3 markah/marks) 6/7

7 (c) Ion merkuri memangkin tindakbalas di bawah. Cadangkan mekanisme tindakbalas tersebut. Mercuric ion catalyses the reaction below. Suggest the mechanism of the reaction. (10 markah/marks) (d) Tentukan sama ada struktur-struktur di bawah adalah aromatik atau antiaromatik. Jelaskan. Indicate the following whether they are aromatic or antiaromatic. Explain. (iv) TAMAT END 7/7

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