Solutions_Manual_for_Organic_Chemistry_6th_Ed 275

Solutions_Manual_for_Organic_Chemistry_6th_Ed 275 - 12-2 3...

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Unformatted text preview: 12-2 3 r r si o ct r r rb r l c ( ) T he on y question is how a e theo the ca ons ar anged. T hem ass spe r um sh ws a p og es o n of s t ( o cr k rm pea s f o themo le ula ion at 1 10 to 95 (l ss of CH3), to 8 1 los so f C2Hs), o 67 (los o f C3H7). The y mo ro rv . lr t r um suggestsi ti s a i nea chain T he ext a e idence that hyd genation of the myster co p und c mass spe il r ri v gi es n-o ctanev e fies that the chain is linea . T he orig na c ompoundm ustb eo ct 1- yne. ( d T he base pea is so st ongb ecause the ion p odu ed iss tabi zedb yr esonan e. ) k r rc li c + � + m ll /z O + � + m 95 /z m/z 8 1 /z 7 m6 m 39 /z '-..... c:::=:::> �_ 12 -2 4 ( a and (b T hem a s spec is consistent with the fo mu a of the alkyne, CSHJ4' m ass 1 1 0 T he IR i sno t ) ) s rl . c onsistent with the a kyne, howe e . O ften, symmet c al y substituted a ynes ha e a m nis ule C=C peak, l vr ri l lk v ic so the fa t that the I R does not sh w this peak does not pro e that the alkyne s a sent. T he m p ant c o v ib i Olt I; thi ab o tion isc ha a te sti of a conjuga e s s rp r c ri c td e iden e in the I R s the signi c ant pea at 1 62 0c m v c i fi k diene. I nstead of the a kyneb eing fo ed, the rea tion must ha eb een a doub e e m ination to the di n . l rm c v l li cc 12 -2 5 (a) �*+ Br b) ( oII '/ c) ( II � Q \ 1 5 80cm-J , -J 12 00 cm OT 0 g - \\ '\ H � I 1 600c m - " k C-C-H I O , ...,... 1 72 0 cm-1 11-- 27 1 0, 2 82 0c m1 - t 17 60cm-I I -CH3 268 ...
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