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

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
This is the end of the preview. Sign up to access the rest of the document.

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 tdihhydrogen.ing 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 ...
View Full Document

This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

Ask a homework question - tutors are online