2023 F - CH202-4-6 - Final Worksheet Ch7-10 - Org

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University of Michigan *

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Jan 9, 2024

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Fall 2023 CH202/4/6 Organic Chemistry I Final Exam Preparation Worksheet 2 of 2 This document includes questions from Chapters 1-6. This worksheet does NOT mean to provide a complete review of the final exam. Studying only this worksheet is NOT a sufficient preparation for the final exam. This worksheet will not be covered by the review tutorials. Midterm 1 review tutorial and Midterm 2 review tutorial have covered questions from Chapter 1-6. If you are uncertain about any questions in this document, you are welcome to visit me during my office hours. There are some questions that you have encountered before this point. When answering these questions, ensure that you train yourself not to recall the answer, and ensure that you force yourself to analyze the questions and follow the logic stepwise to arrive at the final answer. 1. Which choice shows the transition state for the given S N 2 reaction? A. B. C. D. 2. Which of the solves is more appropriate for the following S N 2 reaction? A. B. C. D. Acetone, (CH 3 ) 2 CO, because it is a polar aprotic solvent. Acetone, (CH 3 ) 2 CO, because it is a polar aprotic solvent. Acetic acid, CH 3 COOH, because it is a polar aprotic solvent. Acetic acid, CH 3 COOH, because it is a polar aprotic solvent. Page 1 of 14
3. What is the mechanism for the elimination reaction shown? A. B. C. D. Page 2 of 14
4. Which reagents are appropriate to carry out the conversion shown? A. NaCl in water B. NaCl in ether C. HCl in water D. TsCl/pyridine followed by NaCl 5. Provide suitable reagents for the following transformation. A. Step 1: B. Step 1: HBr, HBr, ROOR, Step 2: Step 2: NaOMe NaOMe C. Step 1: HBr, Step 2: t -BuOK D. Step 1: HBr, ROOR, Step 2: t -BuOK 6. Which alkyl halide would proceed with the faster rate of S N 1 reaction? I II A. I is faster because it has less steric hindrance. B. II is faster because it has less steric hindrance. C. I is faster because it involves a more stable carbocation. D. II is faster because it involves a more stable carbocation. Page 3 of 14
7. Predict the major product for each of the following reactions. reaction major product a) b) c) d) 8. Provide suitable reagent(s) to perform each of the following transformations. reaction Reagent(s) a) Page 4 of 14
9. For the following mechanism, identify the sequence of arrow-pushing patterns: A. Proton transfer B. Rearrangement C. Nucleophilic attack D. Loss of leaving group 10. Draw the curved arrow on the incomplete mechanism below to complete the mechanism. Page 5 of 14
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