322B_Sp_09_1ST_PRACT

322B_Sp_09_1ST_PRACT - a CH 3 CH=CHCH=CH 2 HBr three...

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1 322b Practice First Progress Test, Spring 2009 1.a) Arrange in order of decreasing stability (Take account of resonance structures!) (a) (CH 3 ) 2 C=CH-CH 2 (b) (CH 3 ) 2 C=CHCH CH 3 (c) H 2 C= CHCH 2 (d) CH=CHC(CH 3 ) 3 (e) (H 3 C) 3 C (f) CH= CH 2 b) H CH 2 CH=CH 2 CH 2 =CH (CH 3 ) 3 C + CH 3- CH=CH-CH 2 + (a) (b) (c) (d) (e) (f) 2. Arrange in order of decreasing basicity: NaOH, CH 3 Li, Cl - , NH 2 K, CH 3 COONa, CH 3 CH=CHLi, CH 3 C CLi , (a) (b) (c) (d) (e) (f) (g) 3. Indicate the hybridization symbol of the starred atoms * * * C * O * H C C * C * H 3 C H 3 C * CH 3 H O * 4. Write electronic structures of (include formal charges): CO 2 HNO 3 NO + HSO 4 - NO 2 - CN - 5. Circle and name the functional groups. O CO 2 CH 3 C H O N O CH 3 O * * * * * NH
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2 6. Write the resonance structures of O N O H H NO 2 7.Write the structures of the predominant product including stereochemistry where appropriate. If no reaction occurs indicate “no rxn”
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Unformatted text preview: a. CH 3 CH=CHCH=CH 2 + HBr three products d. + Br 2 light or b. + Br 2 + HCl e. c. NBr O O hv 2 products ROOR CCl 4 CCl 4 all possible products and indicate the predominant one f. O O O 3 g. + O O h. + t-BuLi C 2 H 5 Br NH i. t-BuOK j. CH 3 C CH + k. + Br 2 CCl 4 (one equiv) three products l. O O O + 4 OH 8a Synthesize from hydrocarbons of 3 carbons or less as the only carbon source and any other needed rea.gent. 8b. Synthesize O H H as the only carbon source and any other needed reagent. starting with 9.Indicate which of the following is (A) aromatic (B) anti-aromatic (C) non-aromatic N O O . 10. Write the mechanism of: Br Br Br + HBr a. + Br 2 b. + Br NBS ROOR...
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322B_Sp_09_1ST_PRACT - a CH 3 CH=CHCH=CH 2 HBr three...

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