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CH 310N POW-10_key - CH 310N — POW 10 Williams Fall 2010...

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Unformatted text preview: CH 310N — POW 10 Williams Fall 2010 Due: 8 AM, Tues 11.09.10 Name (print): Signature: Do Homework In Pen Please write the first three letters of your last name in the boxes CH 310N — POW 10 ms Fall 20 0 ' Due: 8 AM, Tues 11.09.10 Mum, LUM: ngk W 071: ohvedwv; 1. Propose a synthesis of 4-bro o-1—nitro-2-viny benzene rom benzene. (3 p 5% ’ N01,, 01/} [QL \‘ZV ~—~ max/M- gv/CW ':::t7 Q MT 923352 @Ktfi‘fl is ’Pav k 0x I K 9““? ram, wean ow fifiamfi aux/JAR} \ ,— . W mm ‘3 (i: 0&3 £15; VDV . are} N) W. Awe H; mm C(Lm WWW/LR. NDL 97v Nb), CH 310N — POW 10 Williams Fall 2010 Due: 8 AM, Tues 11.09.10 2. Mechanism. Use the arrow pushing formalism to indicate electron flow in the EAS reaction shown below. Include resonance structures for intermediates where necessary, and don’t forget all lone pairs and charges! (4 pts) —-—h> H2304 OZN . ® /:/‘©\.l 60' 501 H 0"“ l (4% I ll ' .. \O" a Hb/Jéa‘ue N® C I: 0 ll C D" \l ”H . 1'0. —9 (3.) ® ,9 7 1““ «9&3: of me ‘A H w {EL \4 “380% r .2 40%!- H \ u‘ ‘ l 10“ / 6.69 a}: CH 310N - POW 10 Williams Fall 2010 Due: 8 AM, Tues 11.09.10 3. Electron donating groups are highly activating and direct substitution at the ortho and para positions. Show why aniline favors para (ortho is also favored, but you do not need to account for this here since the same effects are present in the para substitution) over meta attack in electrophiiic aromatic substitution. Use the sulfonation reaction below to demonstrate the reason for the observed "direction" of substitution. (Hint: resonance structures of the key intermediate is the key here!)(3pts) NH2 NH; NH2 $03, st04 a —>. soan SO3H . mum - W ‘t Nth, Observed Not Observed mul "- gl‘fl’l'i, ENHL . ctr—D i Q?) l CD l H {)7} Seatl 503“ m. .. Nilq, man ”We W ‘3 H €31 H if e 7’” 35% Sow ...
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