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sample_1 - 322b Practice First Progress Test Spring 200 '...

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Unformatted text preview: 322b Practice First Progress Test Spring 200 ' l.a) Arrange in order of decreasing stability (Take account of resonance structures!) (a) (CH3)2C=CH—CH2' (b) (CH3)2C=CHCH'CH3 (c) H2C= CHCHZ' (d) 'CH=CHC(CH3)3 (e) (H3C)3C. .CH': CH2 Answer: (b) > (a) > (c) > (e) > (d) > (f) b) (a) (b) (C) + + CH20H=CH2 (d) (e) (f) + + + H CH2=CH CH2=CH'CH3 Answer: (b) > (c) > (a) >(d) > (f) > (e) 2. Arrange in order of decreasing basicity: NaOH, CH3Li, C1“, NHZK, CH3COONa, CH3CH=CHLi (a) (b) (C) (d) (e) (0 Answer: b> a? K> a> e> c 4F> d. 3. Indicate the hybridization symbol of the starred atoms 3 2 Sp * * Sp 2 H 2 /0 H30 3" *)=o * sp 3 * / \ — .— sp C\ C—-C——-C 552 H H C/ * \CH 2* 3 Sp 3 Sp * spa 4. Write electronic structures of (include formal charges): C02 HNO3 NO" H804“ N02" CN" / \ — O =C =0 - "" + / \ ,0 | " .— \ / /\ + OI INEOI —— —- ’N’ |C=N' @\N¢ ug—s—gH KIj — I g -' 5. Circle and name the functional groups. Also indicate the oxidation number at the starred atoms. H ester (EH3 aldehyde )3: * Ocha * N anhydride 0 alkene l ether 0 * ketone 0 o Ox. No: +1 -1,+3 0, +2 +3 6. Write the resonance structures of 7.Write the structures of the predominant product. If no reaction occurs indicate “no rxn” a. b ' KMhO4 12-904 —-—-—> NO RXN cold CH3 °' PCC d. H30+ | CHZOH —-> fiz-CHs +CHaMgBr —> ——> $-CH3 O OH CH0 3 f. 1)NaBH4 ——-—> HCri coons 2) H30 e~ LiA|H4 H30” o (>st —> -—-> CHZOH excess HOCH 00on3 54321 2 2 r 3 g. CHSCH=CHCH=CH2 + HBr > 5M1 + 5W + 5 \ 4 2 1 Br 0,1”, 7- 3 4 I h Iightor +Br2 —-—> i. CCI4 p . O ROOR Q 0 “3'2 M Rx” Br I Br BI’ hv (Em—>5) “Q woo CCI4 fléy Endo-isomer 8. Synthesize from alcohols of 4 carbons or less as the only carbon source and any other needed reagent. a. (CH3)3C-—CH20H(C H3)2 :> (t-BU)2CuLi + BrCH20H(CH3)2 til 3 t-BuOH + PBr3 <21 t-BuBr + Li metal <23 ZABuLi + Cul HOCHgCH(CH3)2 + PBr3 2. I b. Synthesize /\>< starting with alcohols of 3 carbons or less as the only carbon / OH source and any other needed reagents /’\/OH<::=I¢%“\/Br ¢= /\/MgBr+ f => \O: “‘“20'04 + Mg/Etzo __> i391» 9.1ndicate which of the following is (A) aromatic (B) anti-aromatic (C) non—aromatic + QQQQQQ (A) (B) (A) 10. Write the mechanism of : b m:- +Br2 J3» :j + Q+BF ROOR / Br J (9.9 / NBS-> Br' H “331; ...
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sample_1 - 322b Practice First Progress Test Spring 200 '...

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