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Exam2reviewoutline - INSTRUCTOR: Daniel H. Ess Start...

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Unformatted text preview: INSTRUCTOR: Daniel H. Ess Start Date: October 27 at 3:00 pm. End Date: October 29 at 1:59 pm. Late End Date: October 30 until the testing center closes. Remember you can only do this once per semester. Exam Instructions: At the top of this page write your first and last name along with your 4 ­digit code that you made up. Write this 4 ­digit code on every subsequent page. You may use models. You may not use a calculator. If any answers are written on the back of a page you must indicate it on the front of the page. Otherwise, the answer will not be graded. Do not attach additional papers to the test. Make your answers clear, concise, and complete. You will be graded not only on your answers, but also on the means by which you communicate them. This typically means you must draw a structure or diagram to go along with short explanations. Remember a complete answer also involves drawing resonance structures and mechanisms (including use of arrows) if necessary, even if not explicitly asked for. Part of your grade requires you to recognize when these explanations are pertinent. Also remember that the exam is comprehensive and some explanations require principles you also learned from block 1. If multiple products are possible from a reaction make sure to label major and minor or make the decision that only one product is reasonable. Exam 2 Stats: 10 Questions. Multi parts. Naming question Predict the products, reactants/reagents (chapters 7, 8, and 9) Chapter 6 questions = 2 Chapter 7 questions = 1 Chapter 8 questions = 3 Chapter 9 questions = 1 Minimum principles. Chapter 6/7 1. Curved arrow mechanisms. 2. HOMO ­LUMO interactions. 3. SN2 mechanism, transition state, potential energy surface profiles, rate equations, and what controls rate. 4. Activation energy, activation enthalpy, and activation free energy compared with reaction energy, enthalpy and free energy. Remember simple equations. 5. Kinetics versus thermodynamics. 6. Rate ­determining steps. 7. Identity and properties of leaving groups. 8. C ­X bonds. 9. Identity and properties of nucleophiles. 10. Comparison of rates for combination of nucleophiles and electrophiles. 11. SN2 versus SN1 reactions, transition states, mechanism and stereochemistry. 12. Solvolysis reactions. 13. Rates of SN1 reactions. 14. Hammond postulate. 15. Hyperconjugation. Chapter 8 1. SN1/E1: reactions, transition states, mechanism and stereochemistry. 2. Alkene stability, E/Z 3. SN2/E2: reactions, transition states, mechanism and stereochemistry. 4. Bases DBN and DBU 5. Antiperiplanar and beta hydrogen elimination. 6. SN2/ SN1/E2/ E1. Determine mechanism and product. Chapter 9 1. Naming alcohols, ethers, and epoxides. 2. Ether synthesis and mechanism. 3. Epoxide synthesis and mechanism. 4. ROH dehydration reactions 5. Acid Catalysis 6. Carbocation 1,2 ­alkyl/hydride shifts 7. Dehydration by POCl3 8. ROH conversion to alkyl halides by HX and SOCl2 9. Multistep synthesis using ROH starting material 10. TsCl reagent 11. Ethers in strong acid 12. Epoxide reactions: basic versus acidic conditions. ...
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