organic midterm 2 practice

organic midterm 2 practice - Chemistry 2201 MWF 940-1030...

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Unformatted text preview: Chemistry 2201. MWF 940-1030. Practice Midterm 11. Chapters 1-8. 1. Which mechanism does this reaction undergo? 13F Nal —_—_-. DMSO at SNZ mechanism b. E1 mechanism 0. E2 mechanism d. SNI mechanism a. a polar protic solvent b. a polar aprotic solvent ct Both of the above d. No solvent is necessary 3. What type of reacti0n is shown below? Br CH3 _ tert'BuOH + 0 CH3 ————.. CH3 a, a substitution reaction b. an addition reaction c. an elimination reaction d a halogenation reaction OH 4. What reagents would you use to perform the following transformation? HCECH __.. i 1. CH3CH2Cl 2. Hz, Lindlar Catalyst 1. NaNHZ, NH3 2. CH3CH2C1 3. Li, NH3 1. NaNHz, NH3 2. CH3CH2Br 3. Li, NH3 1. H2,Pd/C 2. NaNHz, NH3 3. CH3CH2Br P‘PP‘P 5. Which are the best reagents for this reaction? H— —\—\—\ _CH \O . HzO, H2804 a b. 1. Hg(OAc) 2,H20 2. NaBH4, H0- c. 1.BH3,THF 2.H202,HO- d. None of the ab0ve 6. Which of the following is unreactive as a dienophile in a Diels-Alder reaction? _ o O o : HZCZCHZ x0 U \ B C D O A 7. Which product in the following reaction is the thermodynamic product? :\:+HCI___..CI\—\\¥+ hi A 8. Given the pKa values of the following process, the equilibrium of this reaction lies: H20 NH'2 ——> H0" NH3 pKa=15.7 pKa=38 3.. Towards the left b. Towards the right (3. This reaction does not proceed dt Somewhere in the middle 9. What is the chiral assignment of the indicated carbon on the following molecule? HO Ego a. R configuration b. It is not a chiral center c. S configuration d. (-) Levorotatory 10. How does a meso compound rotate light? a. Depends on the configurations on the asymmetric centers b. Always dextrorotatory c. It does not rotate light d. In all directions at the same time 11. What would be the products of the reactions below? Include any stereochemistry. If there is no reaction, write NR. H2504, H20 H2, Lindlar Catalyst «— \\ —_—» H9504 /HaCH2| V HBr 12. Predict the major product of the following reaction and provide a suitable curly arrow mechanism for your answer. @+é—~ 13. In one sentence, describe why this reaction does not take place as written. 1. 3H3, THF —'*‘——> 2. r1202, HO‘ 14. Which of these alkyl halides are most reactive towards the SNZ mechanism? Explain your reasoning. Br Br 15. Using any reagents you so desire, propose a synthesis route for the following process. Indicate the product you form with each step of your synthesis. HCECH —> H 16. Propose a product for the following reaction. Provide a suitable curly arrow mechanism for your answer. H20, H2504 17. Provide the correct reagents/structures for the following processes. 1. NaNHZ, NH3 KMnO4, H3O+ HCECH —- ha 2. 0131 — 1' H20, H2504 E1 ? j ———n- 1|:J 2 ...
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This note was uploaded on 02/19/2009 for the course CHEMISTRY 2201 taught by Professor Wilson during the Fall '08 term at Temple.

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