CONFIDENTIAL, ASIJUN 2015/CHM412 UNIVERSITI TEKNOLOGI MARA FINAL EXAMINATION COURSE : ORGANIC CHEMISTRY FOR TECHNOLOGY COURSE CODE : CHM412 EXAMINATION JUNE 2015 TIME : 2HOURS INSTRUCTIONS TO CANDIDATES 1 This question paper consists of eight (8) 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 i) 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 5 printed pages {© Hak Cipta Universiti Teknologi MARA CONFIDENTIALCONFIDENTIAL 2 QUESTION 1 Give the IUPAC names for the following compounds: cue b) CHs OCH; NO, crn HO’ qd) ° NH, i e) ? QUESTION 2 Draw the structures for the following compounds: a) 5-isopropyl-2-methylcyclohexanol b) Trans-3-heptene ©) 2-propylpentanenitrile d) N-ethyl-N-methylcyclopentylamine e) 2-methylpropanoylehloride (© Hak Cipta Universiti Teknologi MARA ASIJUN 2015/CHM412 (10 marks) (10 marks) CONFIDENTIALCONFIDENTIAL, 3 ASIJUN 2015/CHM412 QUESTION 3 The following questions are based on Structure A below. B 14 oO HAC, ©, you a See Oy SD > ° oo ‘Structure A a) List four functional groups in Structure A. (4 marks) b) Give the hybridizations and bond angles for carbons labeled as A, B, C and D. (4 marks) ©) State if the nitrogen atom in Structure A is an electrophile or nucleophile. Explain your answer. (2 marks) QUESTION 4 a) Explain the following observations: i) 2-hydroxypropanoic acid is a stronger acid than propanoic acid. ii) State if 2,2,4-trimethylpentane has a higher or lower boiling point than that of octane. Explain your answer. (6 marks) b) i) Write the geometrical isomers for the compound with molecular formula CzH.Ch. ii) Draw two isomers with molecular formula C;H,O, to illustrate functional group isomerism. iii) Consider compounds CHsCH(OH)COOH and CH;CH,COOH. Draw the 3-D structure of the chiral compound and mark the chiral center with an asterisk. (6 marks) (© Hak Cipta Universiti Teknologi MARA CONFIDENTIAL