sample2 - 322D Practice Second Progress Test Spring [email protected]

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Unformatted text preview: 322D Practice Second Progress Test Spring 2005 /@7 1. Rank in order of decreasing stability : + + CH3§+CH3 C! H2+ CH3§CH=CH2 EH2 CHsfH e a b c d JuA‘f ruo’ maél j/w/Z"C> ¢> €> maMcz r‘i‘MCS 2. Circle and name the functional groups. 4 e nctt 0m . O=o , CHacHO , O<82H3 , O<gj flee, 7/95 (/9448) K3 £07“ Wk / 7914426647422 O=NOH , QcHCN , Q—CH=0, O—CH=P Ph)3 owe gaudy/m Marya yaw 3. Write acceptable structures of: a) 2-methyl-3-pentanone A A N H 0 b) 3—butenal / 0 f1) 0 c) 3-methyl-2,4-pentane dione /l CH3, COCH 3 d) acetone Y \. / o ' lJ 4. Write the resonance structures of 4; J— Iv +- Br H H’ “1' «J CH2 C —" CH2 Cf]; C :C; W © / + $ Z "" $ 3/ a. [[7 +0” '53. C>'CH2 .__- C. G d. [CH300]+ — 4. 3:, L1 OH 8/» ©=c4lz @ CH; :0, E <3: Caz @Qb H —- CH2 4. pl 5. (10) Give the structure of the tautomers in each case: '2. 6. Write the mechanisms including all intermediates, formal charges, curved arrows: L“ <3er ”—04 / OH H3 \CH —» 0mg: mm 3 r\ / 3 H3 15' Cal PP)»; + HECHZCHZOH 3» w + H20 C/\ O OH M a :2 Awe H+ O + H20 > / OCH3 [’o/H 25¢ [37 as 2H3 *‘9 <_ ’3 HO " OF" “* » CHZOH + _. N Alf/COL) Hz C O=O+H2NNHCONH2 » C/CHJ d_ Ph3P+CH3CHBrCH3—> ii» 77/73 F " \Cf/3 + é J e- O + H» QM 0“ J f. [:>O’CHZBr 1) NaOH 0 5 flfOHé” (9 #0101) 2) H30+ 1.D| - / \ z 9- Q—m—m—r <3 0 2. H20 '— ' —> —-————-—-> __ u. CHSCOCI + HCI IO H30+ H2NOH / \ CH: N014 —_CH\O H 0+ : 3 (a Q—MQBI'O +(CH3)2(:HCN—> 5 .— H 0 CE C-— (C43) |. CHaccha +CH3000H3—>-————2——> 5’2’5 EH 2— m. ‘ CH — —CH __ CH=PPh3 + 3 fi 3 A > /__\ CH -CéQfigjz O n. QCH=CH2+ConQ HBr O. hv OH' / __,.C :2 C 00%:ng + 02 ——> . _} #2 A ._ CH3 p' ... c c ' C>*CfCH3 + Conc. HBr ROOR > © H H2 9” | CH2 AICI wOoQ + m——» [email protected]—@fi% 3 0 8. Indicate order of decreasing Bransted acidity: CH3000H3 (CHSCO)3CH H3C —fi—CHZCH =CH2 a b- O c CHscOCHchCHS H3C-fi]: ‘CHchZ—fi "CH3 d 0 e 9. gym/WM 15>J> C) q)?— Synthesize from benzene and any other reagent: (54‘ bay/Ha: 2? ol/\ QC]? 4, CH3CflZCOCe “14533. F4863 _:;> {3 cyzlfl+ CM" ...
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