IJC H2 Chem 2012 Prelim P3 QP

INNOVA JUNIOR COLLEGE JC 2 PRELIMINARY EXAMINATION 2 in preparation for General Certificate of Education Advanced Level Higher 2 CANDIDATE NAME CLASS IN DEX NUMBER CHEMISTRY 9647/03 Paper 3 Free Response 14 September 2012 2 hours Candidates answer on separate paper. Additional Materials: Writing Papers Data booklet Cover Page READ THESE INSTRUCTIONS FIRST Write your name and class on all the work you hand in. Write in dark blue or black pen on both sides of the paper. You may use a soft pencil for any diagrams, graphs or rough working. Do not use staples, paper clips, highlighters, glue or correction fluid. Answer 4 out of 5 questions. Begin each answer on a fresh sheet of paper. You are advised to show all working in calculations. You are reminded of the need for good English and clear presentation in your answers. You are reminded of the need for good handwriting. Your final answers should be in 3 significant figures. At the end of the examination, fasten all your work securely together. The number of marks is given in the brackets [ ] at the end of each question or part question. This document consists of 13 printed pages and 1 blank page. Innova Junior College [Turn over

2 PRELIM 2 © INNOVA 9647/03/2012 [Turn over Answer 4 out of 5 questions. 1 (a) N,N-dimethyltryptamine is a psychoactive drug whose primary action is to alter cognition and perception. Depending on the dose and method of administration, its subjective effects can range from short-lived milder psychedelic states to powerful immersive experiences. (i) Suggest a reason why N,N-dimethyltryptamine is soluble in acidic solutions. (ii) Would you expect N,N-dimethyltryptamine to have a high or low melting point? Explain your answer in terms of structure and bonding. [4] (b) para-Methoxyamphetamine first came into circulation in the early 1970s and went by the street names of "Chicken Powder" and "Chicken Yellow" and was found to be the cause of a number of drug overdose deaths in the United States and Canada at that time. It can be synthesised by the following route. (i) Suggest reagents and conditions for steps II and III. (ii) What type of reaction is step II? (iii) Suggest why compound J is converted into K before step II is carried out. (iv) What type of stereoisomerism does para-methoxyamphetamine exhibits? Draw the structures of the stereoisomers of para-methoxyamphetamine. [6]

3 PRELIM 2 © INNOVA 9647/03/2012 [Turn over (c) Propene is an important starting product in the petrochemical industry and is often used as the raw material for a wide variety of products. (i) Name and describe the mechanism of the reaction between propene and hydrogen bromide.