sol_08 - CHEM 5.12 PROBLEM SET #8 Due in Friday April 25th...

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Unformatted text preview: CHEM 5.12 PROBLEM SET #8 Due in Friday April 25th at 4 pm 1. (4pcinte) For the following cyclic compounds: a) Designate whether each is aromatic or not aromatic b) Draw structures cf the molecule (as illustrated in the hex) labeling the hybridization state at each atom in the ring, the unhybridized p orbitals and any non- bonding electrons. ‘ GATlC fl 2. (6 points)Design synthesis of the compounds shown on the left. You may use the compounds shown in the square brackets and any other stan ard reagents :09, t» UVS V Hint; think back to how you can introduce a halide into an alkane..... 3. (3 points) When compound I is treated as shown below, a mixture of isomeric products of identical molecular formula are obtained. EXPLAIN My fikcub 1. Na+OMe“/MeOH I}??? —-—-———-——«——--)> 2. neutralize to pH 7 okkfeé {‘2 @g 3:00:33. a“? {3 amwné mmg o 4. (3 points) For the following reactionshow the stepwise mechanism leading to the I 15'ng formation of the product indicated. B r2/FeBr3 5. (4 points) Below are listed five different phenols and the pKa of the phenolic —OH proton. Explain why the pKa values are so different using resonance and inductive effect arguments (AND DRAWING STRUCTURES T0 iLLUSTRATE THESE) as necessary. pKa 10 Hint - write out the full structure of Bficwmcee ,J-a eke $W WA““%“‘£ ‘1 the ~N02 fin éuefiaw eggs; in, Fijaflgl m gawk fitiéic, e.— eemmtéiex emegame 3% cemxu ‘7 O :3 ‘3 la {is W@§5M,,5W M, M M“ M, ““““““ M fin Ckkomsdmfikuw" «- Cg. M11“); sVeQXV§e mate. a}? elf? ‘59E‘3xgbvn 3 WW» Mififbfi. WC 9 “awvwmmwmmm‘.._ . “WWWMW fig Moflmc e: ‘eu‘ir me» she; 1.93m “ 13?; Extra problems from the book: 10.10, 10.13, 10.38, 10.42, 10.44, 16.5, 16.7, 16.5, 16.34, 16.36. we??? . Mc3\€ $42412) \ CL. A“ N63,?» ( E‘AX/ W W MO““‘*"“M fimeefisma “31% wmfif Nut, an g‘fi‘f’kb‘ “N02. ...
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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sol_08 - CHEM 5.12 PROBLEM SET #8 Due in Friday April 25th...

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