Sp_09prog-1_answers

Sp_09prog-1_answers - 322b Practice First Progress Test...

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Unformatted text preview: 322b Practice First Progress Test, Spring 2009 La) Arrange In order or decreasmg stability (take account of resonance structures!) (a) (CH3)2C=CH—CI-12o (b) (CH3)2C=CHCH'CH3 (C) H2C= CHCHZ' (d) 'CH=CHC(CH3)3 (e) (H3030 (f) 'CH= CH2 5 > a\> a») 8 > a’) / b) (a) (b) (C) ”behemoth * (CH3) 30+ 5>a> e$> a>dl>aa + OH CH2=C+H CHa_ CH=CH—CH2 d (e) (f) () 2. Arrange in order of decreasing basicity: NaOH, CH3Li, C1',NH2K, CH3COONa, CHSCH=CH_Li, CHsc‘iCL' , (a) (b) (C) (d) (e) (g) ebew 07W“ 3. Indicate the hybridization symbol of the starred atoms .3 “In :9?" 35% £79 * w H C :5 o ' * a if [(0 m 3 =0: 22¢ :7 * * H H30 ; 5f\CH3 a. 2 * «5 3.5. [D 4 erte electronic structures 0 (include formal charges) " ‘ ,1}? g 5:" 1345‘) 2:513; 63) £1250: N/fio Nole-‘S! H80; ? Ngz' C)” CN W .3? Mi m» ,5, Y)“ ... f4 @ ‘ m” NH TV a “I” {F H N O H 3 N03 6‘ Write the resonance structures of «5573’ I r 9 g-‘f’ : t 3 a ”:3 . f .' +~$ T K” H N02 I ""6“ M} N EM} 1"” ff”! “F“? O + 3* MO 0 U Q ‘ 7.Write the structures of the predominant product including stereochemistry where appropriate. If no reaction occurs indicate “no rxn” £2 73; 433W a. CH30H=CHCH=CH2 + HBr ———-——> three products 8% b. CC|4 PX + W + Br2 Ne: Vi» C©+ --—-v—-> 2products O '5'“ Q Ea light or + 3’2 ‘——""‘—" all possible products and indicate the predominant one ROOR .52: \ d ’ + u,” g r . if»: e. Wartil" ' M f 2/: Q Q? Q: +3'2 —-————> <“—:></ gt 1%” ‘ . fl/z (one equnv) CCI4 three products 4.. o L Q: + 0:1, ____> No Br» 0 fa»; 8a Synthesize from hydrocarbons of 3 carbons or less as the only carbon source and any other needed reagent. /\><0H /’\---£> N85 Wig/’34»? ”“7"" f/VH‘QKZ: Roe/E" 51;, 0 H29 xu?(:%)z 648 i W i Q03 i 214“ W F ' “my“ #250 9/ H 8b- SVNtheSize / starting with Q as the only carbon source and any other needed reagent. M ”w gag O Kgfiéfc‘ - ’ \ 26-57 W wk: V} Waxy 03% w“ + Q“ we“ W“ ‘ ‘ ” FCC 9.1ndicate which of the following is (A) aromatic (B) anti—aromatic (C) non—aromatic Ommmoo ”(e 0") UV) 8%? 10. Write the mechanism of? ...
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