Week 7 Worksheet Answers - Organic Chemistry II Week 7...

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Unformatted text preview: Organic Chemistry II Week 7 worksheet Not for credit Draw an example of the key electrophile for‘each of the following types of electrophilic aromatic substitutions: Bromination Nitration ' .(Friedel—Crafts alkylation Friedel~crafts acylation ~~ .. A t: -- 9 I? 6% e 9 ~55 9 A / («3 anti) Shawls Car—boatith an a am, {all m Draw the mechanism of the Friedel—Crafts acylation of-the the reaction shown below. Show the formation of the acylium ion, followed by electrophilic aromatic substitution. _ ' 0 AlCl3 + ————~——->- 0| Aniline and nitrobenzene both contain a nitrogen substituted benzene ring; however, bromination of each of these compounds resuits in dramatically different products. Use resonance structures of the cation intermediate of each to justify why aniline brominates at the orth'olpara positions and nitrobenzene brominates in the meta position. 0 See (Prion-Jud Given that bromination of aniline results in 2-bromoaniiine and 4—bromoaniline, how could you prepare 3-bromoaniline? NH2 N02 N02 Bra FGBra Br ___._... NHg Bfg , ' - A ‘ . FeBr3 . - Br 9C2 HNo3 H2804 M‘H cud/Led 10t2 CF3 AICI3 Cl Bra Fe B r3 '—NH Cl HNQ3 H2804 Place the following reagents in the correct order to best prepare the following compound in the reaction shown: CIQIFeCIa, HN03/H2804, CH3C(O)CI, Ni/Hz, Cl 0: —>. w Wan—>- -———|- @NH HN03/H2304, HNOg/H2804, NaOCH3/CH30H, Bra/3363!}, \ O GK 0 O I H (a )0] flfil “C1 ——> CPA: —c( CE CI] \l/ 0 O O x. H 9‘ / / / + O—Afivc! A103 C; HafiD/ . 9’” C“ H Cochon \ a <\—> gig «4—47 L’r l Q—s :17 CAWMW ® H i Egg; w BC H Br Br * B( H 4‘ 7142, ® Can be M‘IJ‘TOJL m 03 [main bromivxocf‘t‘o n (sec/avg. (rm addt-I‘lofi (3% jflagfivesj H. 69 502 W1 \‘ K3“ W, H é“> \5 <9 *’ (—5 H “ V“ 3" 3‘” Ev [JQ‘MLVL Mar—H; Sakai-(H'Ld'eck) Can? c1157.; 6?— OO “Janie. W43 Garbons buJL is never Jc/bcdz'fied girl—O M M’+”"OS&V}_ I geu con—(20$ (wepam 3"bmmoam'h‘rm; b3 fmdme. “3&“oaammon d)? M *bv0M0n1%b£n%QAa ‘. “Hz 1 N01- “OL ” \Q; Pisa) 1:.) Br Hf E’ BF lg HMQ3 (Hz :4 /d - \W “*5 ~—~ l W fin N02 9002 (VI/:11"? l HL/ ' dff‘eG Mj / C! o .5 l 17; i\ C! L‘ W 2. LA. I YMH‘ \ O _ jr kfiéfd—‘l/a 31" E” Hlu03 0"" WM. “0 Mo EV 2‘ “w 2 ~_/ “(30H— ._ Waa/Copl/H‘fiz QVOMQJLLC Wat M€1.5Cnluiznflxf flow/4K Ont? Jpssféle 605W Magma“ Mr%dfw}qg /l/.;fro grow arré P FES€m+ ...
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Week 7 Worksheet Answers - Organic Chemistry II Week 7...

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