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Solutions_Manual_for_Organic_Chemistry_6th_Ed 274

Solutions_Manual_for_Organic_Chemistry_6th_Ed 274 - 12-2...

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12 -2 1 (a) D euter iu m h as twic e th e mass of h ydr ogen,bu t s imila r s pr ing c ons tant, k . Compa r e th e fr equenc y of C-D vibr ation to C-H vibr ation b y s etting u p a r atio, ch an ging only th e mass (su bs titu te 2 m for m). = = �lt2 = 0.707 Vo = 0.7 07 vH = 0.7 07 (3000 em-I) '" 2100 cm-1 (b) The func tional gr oup mos t lik ely to be c onfus ed with a C- D str etc h is the alk yne (c ar bon - c ar bon tn ple bond), whic h appears in th e s ame r egion and is of ten ver y weak. 12-22 ( r- m /z 1 14 [+r m/z 1 14 r*r m /z 14 + m /z 57 1 + m /z 57 �. m/z 57 a 1° c ar boc a t ion- not favor able a 2° c ar boc a t ion-r eas onable a 3° c ar boc ation-t he best The most likely f r agment ation of 2 ,2, 3,3- tetr amet hylbu t ane will give a 3°c ar boc a t ion, th e mos t st able of the c ommon alkylc a t ions. The molecu lar ion s hould be s mall or non- exis tent while m/z 57 is lik ely t o be the bas e peak , wher eas t he molecu lar ion peaks will be mor e pr om i nent for n -oc tane and for 3,4- dimethylh exane . 12 -2 3 (a) Th e infor ma t ion t ha t this mys teryc ompound is a h ydr oc ar bon mak es
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