shaiaiii - 1. (10 pts) Label the following compounds as...

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Unformatted text preview: 1. (10 pts) Label the following compounds as having aromatic, antiaromatic, or simple olefinic (double 1 (7" each bonding) character. 2. (15 pts) Consider the following pairs of reactions. Write down the products and circle the reaction that is faster in each pair. If you think that no reaction will occur, write & and provide a couple of words to explain. ' .__.> / heat in EtOH EtSNa + BrCHZCH3 EtONa + BrCHZCH3 +t Q” “rad- ProM «QM 246k +\ cor Con/14 Caster Rx" +}(L £0, 00th{’ *NR W'Mwmfii— HS 3 3. (20 pts) Provide a detailed mechanism for the following transformation. H H 0 Br 4. (40 pts) Provide the products for the following reactions. Show all ma'or roducts and stereoisomers. ' “ALSO on)! 706mm!- /" CH U 3 / wot—7 :F leq; V. ———-> ., Heat a WQOMQ, (.lS/1QAMS : @ ’I/CHS ® ° wanna Mfing/Mmom E3) (ml/o, FULL CD _____> .1an : E2 Pm, h" {LELA'noM OH om3 + (CH3)3COK ® ® , EanWIoME’D—G .0” v SEW WQ 3 \/ m/ 3 mm Mags 1;? H20 workup "gamma MW/ GD “No2. O EtMgBr + "um / C7 +Oifo_‘* \ a 180M305 @ Missme :1 5 MiSS'IMQ’, MAJOR/led: : no MAW Problem‘j continued. + Hg(OAc)2 +EtOH ——> 2. NaBH4 3. H20 workup 5. (15 pts) Diethyl-ether forms peroxides slowly in the presence oxygen. Give a mechanism and explain using a molecular orbital interaction diagram why the organic radical reactive intermediate in this process is more stable than typical isolated carbon centered radicals. HO\ O 7 (7+5 l . i i]; gj { ‘f x? ,‘x I flashy firm 3 ’ Extra Credit. (10 pts) A graduate student was attempting to polymerize a solution of ethylene-oxide with catalytic anhydrous acid. However he ran the reaction too dilute and found that his reaction gave molecule A rather than polymer. Using the spectroscopic data given identify molecule A and provide a detailed mechanistic explanation for its formation. 1H NMR 3.92 ppm (s), 13c NMR 67.15 ppm 10C)” ' fl Molecul‘l/ 16W” I“ 100 ’0 m T M+= 88 RelatNe Intensity mo MI“.’ 50—4 I 2553 27 1955 as 1299 54 : 2§|A 41 [733 7D 1254 17 2389 45 1453 so 1124 4 2955 23 1446 as 11184 49 / 2751 31 1374 Bl mag 94 27 36 56 135: 75 605 33 / 6 2505 34 1323 8‘ 877 S 0—?— y y ‘ —-. r—.— I—. . v , woo 3000 eoon ,____,_ . 1 L 5 W 1000 EEO hflVENunI ER! -|| C) E \t «4 ; % jig—’7 0/- l s ...
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shaiaiii - 1. (10 pts) Label the following compounds as...

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