Solutions_Manual_for_Organic_Chemistry_6th_Ed 424

Solutions_Manual_for_Organic_Chemistry_6th_Ed 424 - 1 8-45...

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Unformatted text preview: 1 8-45 continued (c) O} ( 18-46 H3C"""" C II The HNdoes showdias4Hnguiir pslhetthatese.3.1; thmetsihylnal comesappearsthienttwheo NMRylspectr(C-2rulingC-out) adjaTcent to can ti t No is g doublet from meth enes um, and 4 he the carbonyl t by the of hydrogens four nei hbori prot t roughly a qui, nspletitbecausetwosplit ing by on C-3. gThe singgnal forons.he methylene at C-3 appears at 2.0, unknown the Theabsorption ofs cyclcarbonyl at 1790The symmetry inediricsatticedofbysmalelcarbonketNMR rulnegsstoutaistn rstuctengthensThe IcRarbon-oxygeni doubloebutanone,creasincm-ti sIfrequency of vibratiotn.h (SeegSectoiones;12-ri9 in trhe text.r )ure rin n bond, in g is charact 18-48The conjugated diene has a maximum at 235 nm (see ved Problem 15-3) and the ketone has a (a) m about maxiTheumketatone has237nnm, sottrhansittioon around t315n cannotSolbetheusedeneo cannot have.e the compounds. (b) an to e transi io nm that di t differentiat NMR MR 8- 7 A1Tolm4leolnseculstariniodincofemJa zketone. The°a carbonyl (CO) hasculmassA28, sod semi-c28 42, enoughivmass fora negative te The mole70culmeans faiarilsyprobablmole e. (msoli70); witarbazoneementvsatof eunsaturatonlon, we at ar formul small y ass 70 h two el deri and i y m fer the canoreincarbons.presence of a double bond or a ring in addition to the carbonyl. TheIIRregion showsronge absence1790ancm-kene.indiTheationle yofpossiboilneti ieins forsmalsmalnlg.rinNoketpeak icontheain1600-1650 shows a st th peak at of al I, c v a ket a a l ri g one n t ing four cm- are these: carbons 0 0 C4H60 = �O + mJz 114 H2 .Jr-.... CH 'c"""" 'CH3 H CH I . CH3 + . .. [ H3C ..... C" HO XO X 0 mJz 58 0 I -""':CH2 ..... H r • + 0 mass 56 CHCH3 CHCH3 II OH 3 A 4<)' 0 3 & A. � B CH3 B. 8 B. the n* n n* 41 9 ...
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