test 302-3s08-solutions

test 302-3s08-solutions - Name: _ Chemistry 302 - Solutions...

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Name: _______________________ Chemistry 302 - Solutions Test 3 – March 18, 2008 (85 pts.) 1. Name the following. (4 pts. each) (a) (b) OH HO N OH O 2 N 3-benzyl-5-(2-hydroxyethyl)-1-naphthol 2-(1-hydroxy-2-propenyl)-4-nitropyridine 2. Starting with benzene and using anything else you need, synthesize Tylenol (acetaminophen) in good yields. (12 pts.) HO N H O HO N H O Br 2 FeBr 3 Br NH 2 - NH 3 NH 2 Cl O Br 2 FeBr 3 KMnO 4 NH 2 Br 2 FeBr 3 NO 2 Br Br Zn(Hg) HCl NH 2 HO HO - heat NO 2 HO
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3. (a) A student is attempting to make A from benzene and 2-methyl-2-pentene using an anhydrous acid as the catalyst. The student keeps getting B as the only product. Use mechanisms to show why. (6 pts.) A B H + Markovnikov Addition -H + B (b) Show how the student could synthesize A in good yields. You may use anything you need. (8 pts.) O FeBr 3 Br 2 Br 1) Mg/Et 2 O 2) OH OH 1) H 2 SO 4 / 2) H 2 /Pt 4. (a) Label each species below as aromatic, antiaromatic or nonaromatic. Give a valid reason for each label. (15 pts.) O E D C B A N O N H 2
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A is aromatic. There are 6 electrons in a conjugated, cyclic 6-atom system. There are no
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This note was uploaded on 04/10/2008 for the course CHEM 302B taught by Professor Wilde during the Spring '08 term at Carroll MT.

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test 302-3s08-solutions - Name: _ Chemistry 302 - Solutions...

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