CONFIDENTIAL, SS] ASIDEC 2018/CHM301 UNIVERSITI TEKNOLOGI! MARA FINAL EXAMINATION COURSE ORGANIC CHEMISTRY II COURSE CODE ‘CHM301 EXAMINATION DECEMBER 2018 TIME : 2HOURS INSTRUCTIONS TO CANDIDATES 1 This question paper consists of two (2) parts: PART A (8 Questions) PART B (2 Questions) 2 ‘Answer ALL questions in the Answer Booklet. Start each answer on a new page. 3 Do not bring any material into the examination room unless permission is given by the invigilator. 4 Please check to make sure that this examination pack consists of j) the Question Paper ii) an Answer Booklet — provided by the Faculty 5. ‘Answer ALL questions in English. DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO This examination paper consists of 6 printed pages (© Hak Cipta Universit Teknologi MARA CONFIDENTIAL,CONFIDENTIAL 2 ASIDEC 2018/CHM301 PART A QUESTION 1 a) State the general structure and the functional group for carboxylic acid, (2 marks) b) State the common name for butanoic acid and ethanoic acid. (2 marks) ) List one of the uses of carboxylic acids. (1 mark) QUESTION 2 a) List four (4) common classes of compound that are classified as carboxylic acid derivatives. (4 marks) b) Draw the general structure for one of the compounds listed above. (1 mark) QUESTION 3 a) Suggest the structural formula for cis-1,4-cyclohexanediol and 3-phenyl-2-butanol. (3 marks) b) Classify m-methylphenol and 2-methyl-2-propanol as primary (1°), secondary (2°) or tertiary (3°) alcohol. (2 marks) QUESTION 4 a) Show the balanced chemical equation for the reaction between benzoyl chloride and cyclohexanol (3 marks) ») S-cyclopropyl propanoyl chloride can be prepared from the reaction between carboxylic acid and thionyl chloride. Sketch a suitable carboxylic acid that can be used for the reaction. (2 marks) © Hak Cipta Universiti Teknologi MARA CONFIDENTIAL,CONFIDENTIAL, 3 ASIDEC 2018/CHM301 QUESTION 5 Identify the starting materials, reagents or products to complete the following reactions. a) oO Body + H,0 = ———» Compound c b) yO Reagent ——» 4 Ne ° ° ° ° A cmonmae + hoy —= CS” d) °. . NO + 2 ger — #80", Compound + ©=SOH Oo ether e) oO de cr + CompoundG —___, oO (5 marks) QUESTION 6 a) Base hydrolysis of amide will release a pungent and choking odor gas as its side product. Suggest a balanced chemical reaction for base hydrolysis reaction of butanamide. (3 marks) b) Identify reagent needed to convert an amide into a nitrile compound, (2 marks) (© Hak Cipta Universit Teknologi MARA CONFIDENTIAL,CONFIDENTIAL 4 ASIDEC 2018/CHM301 QUESTION 7 a) Sketch all the steps required for the following synthesis. om — ors Compound H (3 marks) b) Write the IUPAC name for compound H in (a). (2 marks) QUESTION 8 Consider the reaction scheme below. Ds corer Lone OH HS, Reaction K| heat 4 Compound J a) Determine the structural formula for compound L and J. (3 marks) ) Illustrate the product formed in reaction K if H2SOs is changed to phosphorus tribromide, PBra in the presence of pyridine. (2 marks) (© Hak Cipta Universiti Teknologi MARA CONFIDENTIAL,CONFIDENTIAL, 5 ASIDEC 2018/CHM301 PARTB QUESTION 1 Consider the following compounds. Hs NHe ch.cHy 2 Compound X Compound Y Compound Z a) Determine the IUPAC name for compound Z. (2 marks) b) Produce a chemical test to distinguish between compound Y and Z by providing the name, reagents and expected observation. (3 marks) c) Compound X can be prepared from an amide by Hofmann degradation reaction. Predict the chemical equation for the reaction. (2 marks) d) Construct the products formed when compound Y reacts with isopropyl ethanoate. (3 marks) (© Hak Cipta Universiti Teknologi MARA CONFIDENTIALCONFIDENTIAL, 6 ASIDEC 2018/CHM301 QUESTION 2 Compound P is a ketone with the molecular formula of CoHsCOCHs. It can be synthesized from the reaction of acid chloride Q with compound R. In a separate reaction, compound P 's reduced to compound S by using Reagent T. Compound P also undergoes condensation with hydrazine to produce compound U. a) Write the IUPAC name for compound P. (2 marks) ») Illustrate the structural formula for compound Q, R, $ and U. (4 marks) ©) Identify the reagent T. (2 marks) 4) Determine the observation if compound P reacts with Tollen's reagent. (2 marks) END OF QUESTION PAPER (© Hak Cipta Universiti Teknologi MARA CONFIDENTIAL,