Test 3 233 2023

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School

University of British Columbia *

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233

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Chemistry

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Oct 30, 2023

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pdf

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8

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1 THE UNIVERSITY OF BRITISH COLUMBIA Department of Chemistry June 9, 2023 CHEM 233 Test 3 Time Limit: 40 minutes Exam Instructions 1. Check that this examination paper consists of 8 total pages, printed on both sides. 7. You may keep your exam booklet. 2. Answer all questions on the Answer Sheet that accompanies this examination booklet. 8. DO NOT fold the Answer Sheet. 3. The last page of this examination booklet is a periodic table . You may detach this page. 9. Please write clearly on the Answer Sheet so that Gradescope can read your answers. 4. Calculators are not allowed. 5. Molecular model kits are permitted. These kits may also contain pre-built structures. 6. No electronic communication devices are permitted on the desk area when writing. Cell phones must be set to silent and out of reach for the entire writing of the exam. ANY ANSWERS WRITTEN IN THIS EXAMINATION BOOKLET WILL NOT BE GRADED, FOR ANY REASON Rules Governing Formal Examinations 1. Each examination candidate must be prepared to produce, upon the request of the invigilator or examiner, his/her/their UBCcard for identification. ii. Purposely exposing written papers to the view of other examination candidates or imaging devices; 2. Examination candidates are not permitted to ask questions to the examiners or invigilators, except in cases of supposed errors or ambiguities in examination questions, illegible or missing material, or the like. iii. Purposely viewing the examination papers of other candidates; 3. No examination candidate will be permitted to enter the examination room after the expiration of one-half hour from the scheduled starting time, or leave during the first half hour of the examination iv. Using or having visible at the place of writing any books, papers or other memory aid devices other than those authorised by the examiner(s), and; 4. Examination candidates must conduct themselves honestly and in accordance with established rules for a given examination, which will be articulated by the examiner or invigilator prior to the examination commencing. Should dishonest behaviour be observed by the examiner(s) or invigilator(s), pleas of accident or forgetfulness shall not be received. v. Using or operating electronic devices including but not limited to telephones, calculators, computers, or similar devices other than those authorized by the examiner(s) – (electronic devices other than those authorized by the examiner(s) must be completely powered down if present at the place of writing). 5. Examination candidates suspected of any of the following, or any similar practices, may be immediately dismissed from the examination by the examiner/invigilator, and may be subject to disciplinary action: 6. Examination candidates must not destroy or damage any examination material, must hand in all examinations papers, and must not take any examination material from the examination room without permission of the examiner or invigilator. i. Speaking or communicating with other examination candidates, unless otherwise authorized; 7. Examination candidates must follow any additional examination rules or direction communicated by the examiner(s) or invigilator(s).
2 Section A: Multiple choice . Circle your answers where appropriate. In some cases, more than one letter could be entered as an answer to a multiple choice question. Do not guess: credit for incorrect answers will be removed from credit for correct answers. Questions are not equally weighted in marks; it is not 1 mark per answer . Q1-5 [30 marks] 1 . For the reaction below: A . There will be one product only. B . There will be a mixture of stereoisomers. C . The reaction will proceed via syn addition. D . The product will be an alkane. E . The product will be an oxidation product. 2 . For the reaction below: A . There will be one product only. B . There will be a mixture of stereoisomers. C . The reaction will proceed via syn addition. D . The product will be an alkane. E . The product will be an oxidation product. 3 . For the reaction below: A . There will be one product only. B . There will be a mixture of stereoisomers. C . The product will be an alcohol. D . The product will be reduction product. E . The product will be an oxidation product. Et H 3 C H 2 Lindlar’s Catalyst Et H 3 C Na, NH 3 O NaBH 4 EtOH
3 4 . For the reaction below: A . There will be one product only. B . There will be a mixture of stereoisomers. C . The product will be an aldehyde. D . The product will be a carboxylic acid. E . The product will be an oxidation product. 5 . For the reaction below: A . There will be one product only. B . There will be a mixture of stereoisomers. C . The product will be an aldehyde. D . The product will be a carboxylic acid. E . The product will be an oxidation product. Questions 6 to 11 (18 marks): A biosynthetic pathway to generate menthol is outlined below. Classify each step in this path as: ( A ) oxidation, ( B ) reduction or ( C ) not a redox reaction. OH PCC CH 2 Cl 2 OH Jones Oxidation CH 3 CH 3 CH 2 CH 3 CH 3 CH 2 OH CH 3 CH 3 CH 2 O CH 3 CH 3 CH 2 O CH 3 CH 3 CH 3 O CH 3 CH 3 CH 3 O CH 3 CH 3 CH 3 OH [ 6 ] [ 7 ] [ 8 ] [ 9 ] [ 10 ] [ 11 ]
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