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322B_spring 09_2ND_PRACTICE

322B_spring 09_2ND_PRACTICE - CH=O 3 f CH 2 Br O O CN...

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1 322b Practice Second Progress Test Spring 2009, Chapters 15-17 1. Rank in order of decreasing stability : CH 3 CCH 3 CCH=CH 2 CH 2 + + CH 3 + CH 2 + CH 3 CH + a b c d e 2. Circle and name the functional groups. , , , CH=P(Ph) 3 , , , CH 3 CHO OH OCH 3 O O NOH CHCN NCH 3 O OH OH OH 3. Write acceptable structures of: a) 2-methyl-3-pentanone b) 3-butenal c) 3-methyl-2,4-pentane dione d) acetone e) 4-penten-2-one 4. Write the resonance structures of H Br OH CH 2 [CH 3 CO] + a. c. d. . b. 5. (10) Give the structure of the dominant tautomer in each case: OH O OH O O O
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2 6. Write the mechanisms including all intermediates, formal charges, curved arrows: CCH 3 O CH=O + Ph 3 P=C CH 3 CH 3 CH=C CH 3 CH 3 a. b. c. d. O + O _ + (Ph) 3 PO CHO H + CH=O OH CHCN CH 3 OH H + OCH 3 HCN OH CH=CH CO + H2O 7. Write the structures of the predominant product. b. CHO a. c. d. O + H 2 NNHCONH 2 e. Ph 3 P + CH 3 CHBrCH 3 CH O + 2CH 3 OH OH - RLi H 3 O + H + H + O O aqueous / heat
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Unformatted text preview: CH=O 3 f. CH 2 Br O O CN 1.DIBAL-H 2. H 2 O g. 1) NaOH 2) H 3 O + h. CH 3 COCl + AlCl 3 i. O CH O H 3 O + H 2 NOH j. (CH 3 ) 2 CHCN k. l. CH 3 C CNa + CH 3 COCH 3 H 2 O H 3 O + Zn/Hg HCl MgBr + H 3 O + Br OH _ heat m. CH=PPh 3 CH 3 C CH 3 O heat n. CH=CH 2 o. CH(CH 3 ) 2 + Cl 2 hv p. CCH 3 CH 2 O O 2 N q. + CH 3 COCl heat + Conc. HBr + HBr ROOR AlCl 3 OH-4 a. Synthesize CH 3 CH 2 CH = CCH 2 OH starting with alcohols of 3 carbons or less as the only carbon source and any other needed reagent. Synthesize using any acyclic starting product and any other needed reagent. c. Synthesize from any suitable reagents using the Wittig reaction. b. 8 CH 3 CH 3 C O CH 3 CH 3...
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322B_spring 09_2ND_PRACTICE - CH=O 3 f CH 2 Br O O CN...

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