2022 JPJC JC2 H2 Chem P3 Question Paper

© Jurong Pioneer Junior College [Turn Over NAME CLASS 21S JURONG PIONEER JUNIOR COLLEGE JC2 PRELIMINARY EXAMINATION 2022 CHEMISTRY 9729/03 Higher 2 Paper 3 Free Response Questions 19 September 2022 2 hours Candidates answer on the Question Paper. Additional Materials: Data Booklet 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 HB pencil for any diagrams or graphs. Do not use staples, paper clips, glue or correction fluid. Answer all questions in the spaces provided on the Question Paper. If additional space is required, you should use the pages at end of this booklet. The question number must be clearly shown. Section A Answer all questions. Section B Answer one question. A Data Booklet is provided. The use of an approved scientific calculator is expected, where appropriate. At the end of the examination, fasten all your work securely together. The number of marks is given in brackets [ ] at the end of each question or part question. For Examiner’s Use 1 21 2 20 3 19 4 or 5 20 Penalty (delete accordingly) Lack 3sf in final answer –1 / NA Missing/wrong units in final ans –1 / NA Bond linkages –1 / NA Total 80 This document consists of 29 printed pages.

2 © Jurong Pioneer Junior College 9729/03/J2 PRELIMINARY EXAM/2022 Section A Answer all the questions in this section. 1 (a) Bromoethane reacts with “acetylide” anion, CH 3C≡C:− to form new carbon−carbon bonds. This reaction takes place in two steps. In step 1, an acid-base reaction occurs. CH 3C≡C:− is formed from the reaction of propyne and a strong base, sodium amide, NaNH2. step 1: CH3C≡CH + :NH2− → CH3C≡C:− + NH3 In step 2, the intermediate anion reacts with bromoethane to form the product. step 2: CH3CH2Br + CH3C≡C:− → CH3CH2C≡CCH3 + Br− For Examiner’s Use Name and suggest the mechanism for step 2. Show relevant dipoles, using curly arrows to indicate the movement of electron pairs. [3] ...................................................................................................................................... …………………………………………………………………………………………………. …………………………………………………………………………………………………. …………………………………………………………………………………………………. …………………………………………………………………………………………………. …………………………………………………………………………………………………. ………………………………………………………………………………………………… …………………………………………………………………………………………………. …………………………………………………………………………………………………. …………………………………………………………………………………………………. (b) 4-bromopentanol can be used to synthesise Compound C as shown in Fig. 1.1. Br OH O O A B C step 1 step 2 step 3 4-bromopentanol Fig. 1.1 Suggest the structures for compounds A, B, and reagents and conditions for steps 1, 2 and 3 in this route. [4]