118CMT2_Ch22_&_23

118CMT2_Ch22_&_23 - ta Give an acceptable IUPAC or...

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Unformatted text preview: ta. Give an acceptable IUPAC or COMMON name for each of the following compounds. No panial credit. E!) 0 ll <9 Q—CH26H2MCH3CH92 CH3C£|2HCOCsz cugmzah-N-N CHch, (b) In the boxes to the right of each of the following parts. write the number of the compound which corresponds to the correct answer. (l )The intermediate which is a whene. Note that formal charges mshown. i”: g“) CHaCHz"C‘ CH3 4;: CHJ‘O-‘f? : 1 CH3 CH, CH, 1 2 3 ‘ t H—C .-_=.c‘. (2) The W acid. 00 00 00 OO ' u n It a II I I ll CHgocCHchCHg CHJCCHchCH3 cupcuzccu; CH3er CHzCH, 1 2 3 ‘ (3) file Wcarbanion \ 0 O O O O 0 Chemistry 118C Workshop Second Problem Set Chapters 21, 22, and 23 Jim Hollister Skills Center u: :I [CHJCH2CCHCH3 Na' [CHJCCHCOCsz Mao [eugocHocm Na' [mm] Na’ CI . 3 ‘ 1 2 (4) The compound derived from a mixed Claisen condesation reacfion? l? ‘2 ‘3 9 ‘3 CoHs-CHZC'CHCOCH, O'Hs-CfHCOCHJ t:me E] 0.14, CH: ma, 1 2 3 (5) The compound derived from a Malonic Ester synthesis ‘3 3 ° 1 2 ° 3 ° 4 0 2. Show the steps and reagents used to synthesize the product on the left from compound on the right. OH b) -—________——_—:*> m CH3 ' t c) CH3CCHCH2CH2 HCH3 "—“_____—___>—_* acetoacetic acid H2CH3 "\th you need. Mr. Terwmlger. is a human culnz: u gentle. reassuring [0| warm smile that shows concern — all of I'm alum. were not put of my medical training." Wk rhifl 3. Show the product formed and a detailed mechanism. grg a) <3 %£“%~\L“s a“ 5mg,“ + \\ \\ Wfl \S/ b) Give a detailed mechanism for the reaction shown below. Use only the reagents given. 0 O C"'3 H3 Na+ COZCH3 COZCH3 NaOCH3,heat CH3OH I. (30 pts). Draw the structure of the expected organic product(s) formed in the followmg reactions. Unless mentioned otherwise, you can-assume that all reagents are present in excess. If no reaction occurs, write "No Reaction". 1. NaCN : 1)- C6H5-CHzBr l 2. LiAlH4 3. Ple l 2) LN N3 I %’ LA.me “A .QWL'L I l , 2‘ \CHQ CCNHL \M 3 2..\¥,¥\2.\) ' cm, 4) anou mama: § '2.) V’cflAL Y : N02 i / \)\ 2 E \k (M a MC / u- 3 Br; light (A . . 1. NaOH 2. CH2=CHCH2C1_ 7\ ‘ H heat %\ Product'ofrcaaion ${.abovc CH: 1. mos.stO4 2. excess Br2.FeBr3 9) 3. H2. PI 1. NaNOz.HCl ,b°e lfihfit l6} P‘rodnctofreacfioaflmbovc ) W12, mkME REKBQOTS \Z cmé‘x‘nws \Q “weesscur \ l 9 7 l. (9 poimsfiCompletc the IUPAC or Common namehgiven fog caeh Of-Lhc following compounds. UL ll CH3 . | '- CHsNCH2CH2CH3 - Dimethyl - 1 - ll - a + - I 11. CH3N(CH3)3C1 [rimemyl_____.____chloride l J" “ iii + “ ' CH3 = N = N methane 5 . (10 pts) Number the molecules in each group shown below as requested. a) Number in order of acid strength. [ 1 = strongest acid 5 = weakest acid ] 02H H n H, ' 02 N02 3 b) (Zl points) (a) Write a clear mechanism for the reaction_of gara-chloro-nitrobenzene with warm aqueous sodium hydroxide to give para-nitrophenol.‘ (b) Explain, using resonance structures, why it is that meta-chl‘or’o-nitrobenzene does not undergo the same reaction with hydroxide. ' (C) In the boxes beneath the foll0wing compounds, assign an order of reaCtivity With aqueous sodium hydroxide. Write "l" for the compound you think would react fastest, "2", "3", and then "4" for the slowest. L_ Ct at Cz 'u’e‘ Cf. ’ly Ct N02 - H . _N02 N02 CH3 F‘\\\ W 35301 \“h‘vJ/vaH VQ @flkwfi; -\' CE /\\. 'l—fié \ \/ ‘Q/ “SA 5 «X \,1)‘sg,%\>,\&,g , 9,33% :2, WAR) \-——> \ “th: \ch AYES N02, {x’oumaw NEED To Know. HAL-Tb SP6? 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[10° 1900 I06 00 40° TELL$ \r'ou THERE ORE (K 0Nsz er mm? mm; or: CRRG Eases) 0“) 66.5w E LO Es.) RE 9mm) WT Tb\£ E .I' 000 wumgevz TBA—S \(ov TREK: \S N0 000 Nmuv. s m“ 15 Inle@.21 0F N\WOG- . m/e@.25 122m/e@.18 12! mlc@.l7 105 a.er 1.0 CHE Mug; \ODRKSADP WE (,T'\C.E $RDELEM SSE MM \—\ 0L.\_.\ sTE—R IR. FNEAT . 1o,_'._..._ -W _,_,._ .. . .._l_.n..._m- ._ .4-.._.‘--._..-.. . - _‘ « - _.-V_l , ,..V ._ _ _-____J.V.______ ___.....'__.._‘.‘ woo woo uoo 1200 won 300 no WAVENUMBERS rinl . . ‘ . . . . I .1... . , .9 ;‘ 3 . ..;V,.\V §.. . .‘ 04.1.--.“ -...V-,1..‘-..__-, _,L...‘-.A..._ .4“...,4._‘.,.__I .; .._A_ . ....1..,J L.......J_.L.,ll__l.__...;‘___ 11., 2000 160 140 120 100 80 60 40 20 0 QGNNR“ @ 1 = i l i v , m-MT. \H8 ‘1. \huRETHAN one LBREEET ANSWER ...
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This note was uploaded on 01/31/2011 for the course CHE 118c taught by Professor Nasiri during the Spring '08 term at UC Davis.

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118CMT2_Ch22_&amp;_23 - ta Give an acceptable IUPAC or...

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