Chem 332 Exam I 2 WITH ANSWERS

Chem 332 Exam I 2 WITH ANSWERS - Chem 332 Exam I 2/19/2008...

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Chem 332 Exam I 2/19/2008 NAME:_______________________________________ FIRST 2 LETTERS OF LAST NAME PART I reactions and nomenclature 1. Draw the following compounds given the specific or generic name. (16) parabenzoquinone diazonium salt O O CH 3 N N HSO 4 FOR EXAMPLE SALTS MUST HAVE A CATION AND AN ANION enol methyl phenyl ether EITHER OF THE BELOW IS A PERFECTLY GOOD ENOL OH OH O CH 3 phenyl = C 6 H 5 For the following give the missing component. If there is more than one significant product write both. (55) 2. N N HSO 4 Br CuBr 1 OF 8
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3. NO 2 F NaOCH 3 NO 2 O CH 3 4. Br CH 3 O Na + CH 3 O 5. CH 3 N NaOCH 3 N HSO 4 CH 3 O CH 3 6. CH 3 N CuCl N HSO 4 CH 3 Cl 7. N N HSO 4 KI Br + Br I 2 OF 8
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8. F F F F F F 1mole 1mole NaOCH 3 CH 3 OH, 65° C F F OCH 3 F F F Only one OCH 3 available per hexafluorobenzene so only 1 substitution is made 9. H 3 C Br excess KNH 2 NH 3 , cold temp H 3 C NH 2 H 3 C NH 2 and 10. O heat O 11. enolization HO 12. N N Cl HBF 4 Br heat F Br PART II reaction mechanisms 13. Illustrate the flow of the electrons in the Claisen rearrangement starting with the normal allyl-aryl ether as seen in the problem in Part I.(8) O 3 OF 8
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14. In question 9 above you should have had 2 isomeric answers. These products form from an intermediate compound. A. Show how this intermediate compound is formed under the given reaction conditions. B. What is the name given to this type of compound? C. Show mechanistically how the 2 isomeric products are formed from the intermediate compound (16) A. Show formation of intermediate compound CH 3 Br H NH 2 CH 3 B. Name Benzyne C. show how the isomeric products are formed from the intermediate CH 3 NH 2 amide acts like nucleophile and attacks either position. ammonia, NH
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This note was uploaded on 05/07/2008 for the course CHEM 332 taught by Professor Kisslings during the Spring '08 term at Binghamton University.

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Chem 332 Exam I 2 WITH ANSWERS - Chem 332 Exam I 2/19/2008...

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