Solutions_Manual_for_Organic_Chemistry_6th_Ed 268

Solutions_Manual_for_Organic_Chemistry_6th_Ed 268 - 1 2 1 0...

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Unformatted text preview: 1 2 1 0 The molecular wei ht o each isomer is 1 16g/ mole so the molecular io a ea s at rnJz 1 1 6. The left gf , n pp r h a f of eac st ucture is the same loss o a three ca bo radicalg ives a stabili ed catio , each with rnJz 73: l hr ; f rn z n iH2C:O� .. H2C";�t iH2C: �'" H2C,,+�} • .. rnlz73 .. .. .° . · rnlz73 . ° . W here the two st ctures differ is n the alpha-cleavage o h e right side of the ox ge . A lpha-cleavage o ru i nt yn n the le structure loses two carbo s, whereas alpha cleavage o the right structure loses o y o e c ft n n n l n arbon. [ �I o0-/-r CH2CH3 t a lphac leavage loss o f {�.O... �H2 ... �O�CH2} .. C9H200, [ �o*- r I a lphat c leavag e J �..,�, R+ 1 ... loss of . rnJz 87 rnJz 1 0 1 1 2- 1 1 2,6-D imeth lhepta -4 1 , y n -0 h as molecular weight 144. The hi hest mass peak at 1 26 g the molecular io , but rather is the loss of water ( 1 8 from the molecular io . n ) n CH3 �+��,}_ R is not from thef ragme t of rnJz 1 26 . This is called al y lic n l T e peak at rnJz III i s loss of a other 1 5 h n cleavage i t ge erates a 2 all lic, reso a ce-stabili ed carbocatio ; n °, y nn z n. rnJz 1 26 rnJz III The peak at rnlz 87 results fromfra me tatio o o e side of the alcohol : gn nnn 1 2- 1 2 P lease re er to solutio 1 -20,p age 1 2 of thisS olutio s M a ual . f n n n 1 2- 1 3 D ivide then umbers n to 1 0,000 to arrive at the a swer. i n (a 1 603 cm ) -1 1 2- 1 4 (a ) 1 (b 2959 cm ) (c 1 709 cm ) 1 - [�r {JJH )ji + � _ [ � r-i�+- �}+ CH) rnlz 1 44 [�r rnlz 1 44 - H,o+ (CH3) [�r rnlz 1 26 �:����!C mlz 87 reso a ce-stabili ed nn z H} . m ass 57 (f) 3 300 cm -1 (d 1 739 cm ) -1 (e 22 1 2 cm ) -1 H C==C CH2CH3 H t 'H , / / or 1 660 cm -1 stronger absorption-larger 1 7 10 cm 1 - CH2CH3 O==C H t' / d ipole 261 ...
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