Chem_261_2003_practice_exam_III

Chem_261_2003_practice_exam_III - Chemistry 61 Section 1...

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Chemistry 61, Section 1 Name(print) Exam 3 I. Show the PREDOMINANT products for the following reactions using line-angle drawings only. Show stereochemistry if it’s relevant. Put NO REACTION if appropriate. (3 pts ea; 45 total) CH O 1 . 1 . CH 3 CH 2 MgCl, ether 2 . H + , H 2 O O CH 2 CH 3 xs HI 2 . Note: Give TWO predominant products 3 . H 3 C OH H 2 SO 4 heat 4 . O CH 3 HBr 5 . H H H H CH 3 CH 3 H Br H H H H NaOCH 3 heat 6 . Cl R S NaCN 7 . NBS, heat CCl 4 NOTE: Use flat product drawing; don't draw chair.
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8. 9. OH + HBr 10. Cl Cl + Na 2 S heat 11. 12. 13. 14. 15. OH SOCl 2 , pyridine H 2 SO 4 HgSO 4 MgBr + CH 3 OH OH OH HIO 4 Na/NH 3(l) OH
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II. Multiple Choice Questions: Put the one LETTER answer on the answer sheet for each problem below. (3 pts ea; 30 total) 1. Which of the alkyl chlorides listed below undergoes dehydrohalogenation (elimination) in the presence of strong base to give 2-pentene as the ONLY alkene product? C. 3-chloropentane. E. 1-chloro-3-methylbutane.
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