Example Final 1 (1) - CHEM 223 ‘08 FINAL p 1 sec(27 1...

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Unformatted text preview: CHEM 223 ‘08 FINAL p. 1 sec (27) 1. Provide unambiguous names for the structures shown below. Use stereodesignators as needed. 0 ..H <1 caz H a ' >\ )V CHO N01 0 QCOZH /u\./C“Zu‘ C1. (27) 2. Fill in missing reagents and/or products in the following synthetic transformations; 0 / Ho CHLCLL2L O z, H3o+ CHEM 223 FINAL p. 2 sec (12) 3. What kind of reaction is the one below? Suggest a mechanism. Me M‘ M H2504 ——_——————’ 0" Me. (09) 4. Diazomethane, CH2N2, has both hydrogens attached to the carbon and a linear C-N-N skeleton. Draw its Lewis structure (with resonance structure(s), if required). (12) 5. Design a synthesis — you may need to use a ‘protecting group’ strategy. “WWCOZEt é Wall" 0 0H (11) 6. Rank in order of increasing basicity (1 for the strongest base, 4 for the weakest base) t-Buo‘ CF3CH20‘ C6H50H t—BuOH _——__.—- —_-—___ _...——.._ _..~-—.. CHEM 223 FINAL p. 3 see (24) 7. Designing syntheses. You have the following organic starting materials available. . 6 HO CH3C0a" © 2 vac 2 CH3CH2qH 1 </ 2 Haj You also have NaCN, tBuOK/tBuOH, and any non—carbon compounds and reagents you need. Now design syntheses of two (2) of the following structures 0H CH / HOCHZCHZOCHZCHZOH and or *fi’ and/or \ l C” H 35 N02 (16) 8. Indicate whether the pairs of structures shown below are conformers (C), enantiomers (E), identical (I) or diastereomeric (D). It is possible that more than one designation may apply. on ‘1" a (.14on c CH2"H a) 4.): / CH0 CHEM 223 FINAL p. 4 sec (08) 9. Here’s a reaction that you haven’t seen before. The aromatic bromide is dissolved in ether and the rest of the steps are done sequentially withmit isolating the intermediate products. C02 is carbon dioxide, a gas, which is bubbled into thereaction mixture once the magnesium metal has dissolved. Show how the (—C02H)-group becomes attached to the benzene ring. c4430 2. add 601 ‘ cuao 4. 3, H3O (13) 10. Rationalize the large difi‘erences in acidity that are seen in the pKa’s of the ammonium ions shown here. 6—) @ NHMQ 63 (Name ” \ 7" cu CH NHMe. ‘7sz -31) ' 50 10.0 (06) 11. Underline the alkyl bromide (below) which reacts faster with. NaN 3 ? (04) 12. Show what an allylic cation is — use a specific example. (09) 13. Rationalize the following experimental observation. Br Br (fie LB“ own if CHEM 223 FINAL p. 5 sec (10) 14. What (if anything) is wrong with the synthetics plans shown immediately below. <2" / la a“ Bra, - I. M5 - \ —————~ C 0H H20 3? z. H3CI-IO o (H COG. / ‘ HOB)01 3 \ “250% Ala3 NaZ N02, (08) 15. The structures of benzoic acid and perbenzoic acid are shown below. Based on these structures, do you expect perbenzoic acid to be more or less acidic than benzoic acid? Answer (say ‘more’ or ‘less’) —-> .' O“ "O'. .‘ 0.. 06%? ‘H x \ -. ' \ \ .. .- perbenzoic acid benzoic acid . . , 55ml, cuacuo " ca, (10) 16. Provrde amechamsm for g T? X 4- H20 (06) 17. What does the reagent “hydrogen gas with a platinum metal catalyst” do? CHEM 223 FINAL p. 6 sec (08) 18. Bromine in a mixture of diethyl ether and ethanol reacts rapidly with one of the unsaturated hydrocarbons show below, but not at all with the other. Which and Why? ©© (09) 19. The reaction shown below represents an “unusual” result for treating a ketone with LiAlH4inTHF. o LLlAll-lq/Et-LO o ———-——-——> @M‘2 2. H30* ah Me. Me What product would you have predicted? Try to explain the formation of the product shown. (06) 20. Illustrate, with a specific example, an SNl reaction. ...
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Example Final 1 (1) - CHEM 223 ‘08 FINAL p 1 sec(27 1...

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