Organic 2b - 1 City College of New York Fall 2009 CHEM...

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General, Organic, & Biological Chemistry
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Chapter 15 / Exercise 4
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City College of New York Fall 2009 CHEM 26300: Organic Chemistry II Dr. Sean Boson Ch. 14: Ethers and Epoxides Ch. 15: Conjugated Systems Ch. 16: Aromatic Compounds Ch. 17. Reactions of Aromatic Compounds 100 Points 10-06-09 Part A: Multiple choice questions. All questions are of equal value. A product is always referred to as the major product for any reaction. Select the best answer and circle it. (33 x 3 = 99 points) 1. What is the correct IUPAC name for the following compound? o 3,4 S A) 3-methyl-3,4-epoxypentan-l-ol B) 5-hydroxy-3-methyl-2,3-epoxypentane C) 1-(2-hydroxyethyl)-l,2-dimethyloxirane { 1
2. What is the product inthe reaction below?
3. Determine the product in the reaction below. c.
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General, Organic, & Biological Chemistry
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Chapter 15 / Exercise 4
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4. Determine the products in the reaction below. CH;aOCHzCHs + HI 5. What compound is formed when 2,2-dimethyloxirane is treated with ethanol containing a trace of HCI? 1+ @2-ethox Y -2-methyl-l- propanol B) l-ethoxy-2-methyl-2-propanol '+ /0, /CI+. ut- tH10h.ot\ 2
6. When pent-l-ene is treated with mercury(lI} acetate in methanol and the resulting product is reacted with NaBH4, what is the primary organic compound which results? I
7. What is the complete systematic IUPAC name for the following compound? C- A) 4-( l-methylethoxY)-4-iso propyl-4-methyl pent-2 -ene B) 4-isopropyl-2,4-dimethylhept-S-en-3-ol C) isopropyl-(4-isopropyl-4-methylbut-2-enyl) ether E) 4-isopropyl-4-methylbut-2-en-isopropyl ether f"XIf 5 - 4-
-\- -t 8. Which of the following carbocations is most stable? D.
9. Which of the following is the most reactive dienophile in the Diels-Alder reaction? o-0H c.
10. How would you favor the formation of the of the following reaction?

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