Solutions_Manual_for_Organic_Chemistry_6th_Ed 406

Solutions_Manual_for - 1(a8-15-hydroxyhexan-3-one ethylj3-hydroxypropyl ketone(bc t3-rapns-2-(or if you named this enantiomer no common name henyl

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Unformatted text preview: 1(a8-15-hydroxyhexan-3-one; ethylj3-hydroxypropyl ketone ((bc))) t3-rapns-2-metuthaoxycyclpohenylbutyraldehyde (or if you named this enantiomer); no common name henyl b nal;j3- hexanecarbaldehyde (d) 6,6-dimethylcyclohexa-2,4-dienone; no common name 18-2 C9HlOO 5 elements of unsaturation (a) IH doublet (very small coupling constant) at 9.7 aldehyde hydrogen, next to CH 5H mUlttiipplleetpeaks3.at6 and.23H 4doublemt onosubstituteCdHCH3 7 -7. at 1 .4 benzene IH mul at -CH- -CH � <� CH3 The splliikteinagquarttheet due to theon carbon-2, nexte tadjacentdCH3. Aisclworthexaminatniog.n of tihtse overallsho\NS that leach peak of ofhe quartet is splisplinittointwg ofrom th tohitshiesaldueehyde,he sploiserngexaminihe aldInehydepeaks The ooks t hydrogen t peaks: aldehydes hydrogenbeand the. metahhydrogen is couplnotd tequifvferent neiigtthboring hydrogensthby yl hydrogens are e o di taloetnt, so iis tofromexpected at efferent be t constainntg constnot s, thequal Ifbe considered separately, just as you would by drawing a split ingcouplfor coupltype wiladjacent hydrogen. tree each of ant ey must CgHgO 5 ele at 28-145 o (b) cluster of 4 peaksments1of unsaturatimnono-or para-substituted benzene ring peak at 21 697 mcetarbonyl carbon (the smalbenzeneheight suggests a ketone rather than an aldehyde) at l peak peak hyl next to carbonyl or < }- C -CH3 or CH3 -o- C- H more likely also possible 18-3 A compound has to to a hydrogen on y has no or other atom) i McLafferty rearrangementhaveoccur. Butan-2-oanecarbon (y-hydrogen.carbonn order for the y position-no CH3-C -CH2 -CH3 t (R,R) =:} CHAPTERl�KETONESANDALDEHYDES 0 0 =:} 0 0 =:} + I + o II =:} sh:lpe, it 0 0 =:} =:} 0 =:} =:} o o o II a a J3 401 ...
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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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