Solutions_Manual_for_Organic_Chemistry_6th_Ed 423

Solutions_Manual_for_Organic_Chemistry_6th_Ed 423 - 18-43...

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Unformatted text preview: 18-43 C6HJ002 indicates two elements of unsaturation. Theo elRements ofiounatsat1708ioem·1The s asiketgloene,inorthpossibiolyoftw2o: ketinodicatsienacehitghhly symmetrioxygensecule. are tThe siI nglet at 2n.15 ius rat n. ysuggest nextn to tcarbonylratand the si3nglenesat 2.67 iereegratitnwgotoctwmol and w absorpt probabl methyl s e , t nt o likely to be CH2 on the other side of the carbonyl. H3C -C -CH2 -CH2 -C -CH3 Since the molecular formula is double this fragment, the molecule must be twice the fragment. Two questofions Whythe e n 4 6? iengrat on provi not absol te numbers,chemiarialse.shifWhydoisnotdon'isplnttietthgrattwioootmet:er;hylhaeendnesnotshow:s forspletIinthtaneg?oriAdjacent,des aappearhydrogens,eutswith hydrogens.ts, identical c each h t signal cyclohexane as singl . 18- 4dehyde or a a o JO 2Oa ndic el ns unsatu A b an al ehyde; suggest The aneal4unknownformulketbeCne,HIbutone.inegatatievse 5Tolelementtesstofprecludesrattihoen.possisoliliidty2,of4-DNPdderivativtheerefore, s th must a ket The NMR ishowsbenzenecatal et7h.yl3 pattemulattip8le1.t)0. The tsirinpgleet)t and 3.7.5i s a CHq2uartetquiandfar downfield, monosubsty deshideltdhedtyby two groups. Assemble the pieces:l at tute e pi 5H, rn , but ), te a apparentl 0- CH2 C (5 NMR > o II (5 o II is 23 ratio, identical 8 ( (3H, 18-45 0 )H" CH,CH3 . ( (a) H /C ,�CH2 C H2 rn/z 86 )H>-. �CH3 . (b) � CH CH3/C,�,CH2 CH C rn/z 114H3 + + + II o (5 (5 2 (2H, [ II I .. II o + I .. I 418 H CHCH3 H J:CH2 CH2 rn/z44 mass 42 0....... H . CH/CH3 CH/ C'CH 3, CH2 CH3 mass 42 z72 r + II + I rn/ I + II ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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