TERM TEST II (March 13th 2020)

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University of Toronto, Scarborough *

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Chemistry

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Jan 9, 2024

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1 Term Test cover sheet for Instructor’s Name Date of Final Examination Start Time of Examination Location of Examination Number of pages of Examination Aids Permitted The University of Toronto’s Code of Behaviour on Academic Matters applies to all University of Toronto Scarborough students. The Code prohibits all forms of academic dishonesty including, but not limited to, cheating, plagiarism, and the use of unauthorized aids. Students violating the Code may be subject to penalties up to and including suspension or expulsion from the University. CHMB41H3 Dr. Nirusha Thavarajah Friday March 13 th , 2020 7:00 pm IC130 11 Unboxed molecular models
2 NAME________________________ STUDENT NUMBER____________________ Tut Grp________ ORGANIC CHEMISTRY I CHMB41H3 TERM TEST II March 13 th 2020 TIME ALLOWED: 120 MINUTES NO CALCULATORS ALLOWED NO PAGERS OR MOBILE PHONES ALLOWED Instructions: Make sure you have your name, tutorial section number & student number on the scantron sheets, answer sheets and on the question booklet. For PART I (22 Marks): 11 MCQ. Transfer your answer sheet on to the scantron provided. For PART II (48 Marks): 5 Short Answer Questions. Write your answers for all the questions on the answer sheet provided. You may detach the answer sheet. Question sheets will not be graded. You may write in pencil or ink (blue or black only. Do Not use red). If you write in pencil remarking claims will not be acceptable. You may use unboxed molecular models. A periodic table is provided on page 8. At the end of the test, place the Scantron, & the Answer sheet inside the test booklet and HAND IN EVERYTHING.
3 Part I Multiple Choice (22 Marks, 2 Mark Each): Your multiple-choice answers MUST be transferred to the scantron sheet during the time allotted for the test. ONLY THE ANSWERS ON THE SCANTRON AND ANSWER SHEET WILL BE SCORED. 1. How many chirality centres does penicillin have? a) 1 b) 2 c) 3 d) 4 e) 5 2. Which one of the following pairs of compounds are enantiomers?
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4 3. Which one of the following pairs of compounds are diastereomers? 4. Determine which one of the following compounds is chiral.
5 5. Assign E or Z configurations for the labeled doble bonds A & B on retinoic acid. a) A has Z configuration & B has E configuration b) A has E configuration and B has Z configuration c) A and B both have E configurations d) A sand B both have Z configurations 6. Which of the following mechanisms does not have an error?
6 7. Which of the following is an insignificant resonance contributor for the structure of aniline shown below? 8. Predict the most likely site of protonation (addition of H+) in the following compound. a) A b) B c) C d) D e) E
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7 9. Compare the pair of equilibria provided below and determine if there would be a difference in their dynamic equilibrium constant. Select one of the statements that best describes the given reactions. a) Reaction 1 has a greater dynamic equilibrium constant than reaction 2 b) Reaction 2 has a greater dynamic equilibrium constant than reaction 1 c) Both have the same magnitude for their equilibrium constants d) It is impossible predict the favoured direction of the dynamic equilibrium for reactions 1 & 2, based on the information provided. 10. Compare the pair of equilibria provided below and determine if there would be a difference in their dynamic equilibrium constant. Select one of the statements that best describes the given reactions. a) Reaction 1 has a greater dynamic equilibrium constant than reaction 2 b) Reaction 2 has a greater dynamic equilibrium constant than reaction 1 c) Both have the same magnitude for their equilibrium constants d) It is impossible predict the favoured direction of the dynamic equilibrium for reactions 1 & 2, based on the information provided.
8 11. Which one of the following reactions given below, best represents the reaction between an acid and the most suitable basic site on the antidepressant citalopram? PART II SHORT ANSWER (48 MARKS): PLACE YOUR ANSWERS ON THE ANSWER SHEET PROVIDED. ONLY THE ANSWERS ON THE ANSWER SHEET WILL BE SCORED. 1. (6 Marks) Convert the following structure to a Fischer projection.
9 2. (6 Marks) Draw the structure of (2R, 4S)-2-chloro-4,5-dimethylhexan-2-ol 3. (4 Marks each) For each of the following reactions, add mechanistic arrows to show the flow of electrons. Where appropriate, include lone pairs, as well as any formal charges missing from the reactants or products. a) b) c) 4. (6 Marks each set) Rank the following molecules in terms of increasing acidity (1=least, 2= intermediate, & 3= most). Place the rank numbers on the space provided on the answer sheet. 5. (6 Marks for each set) Rank the following molecules in terms of increasing basicity (1=least, 2= intermediate, & 3= most). Place the rank numbers on the space provided on the answer sheet.
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10
11 CHMB41H3 TERM TEST II ANSWER SHEET MARCH 13 th 2020 NAME_____________________________ STUDENT NUMBER_________________________ Tut Grp_______ MCQ 1 2 3 4 5 TOTAL /22 /6 /6 /12 /12 /12 /70 PART II: SHORT ANSWER QUESTIONS. WRITE YOUR ANSWERS IN THE SPACE PROVIDED. 1. (6 Marks) 2. (6 Marks) 3a) (4 Marks) 3b) (4Marks) 3c) (4 Marks) 4a) (6 Marks) _______ _______ ______ 4b) (6 Marks) _____ ______ _____ 5a) (6 Marks) ______ _______ ______ 5b) (6 Marks) ______ _______ ______