Solutions_Manual_for_Organic_Chemistry_6th_Ed 466

Solutions_Manual_for_Organic_Chemistry_6th_Ed 466 - 19-53...

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Unformatted text preview: 19-53 unknown X (a) -fishy odor � amine -molecular weight Mass spectrum: -fragment at IR spectrum: 10 1 � � odd number of nitrogens if one nitrogen and no oxygen, the remainder is C6H)S 15 = 86 = M - loss of methyl � have this structural piece: CH3 -no OH, no NH NMR spectrum: � � a-cleavage N - the compound is likely to must be a 3° amine -no C=O or C=C or C=N or N02 --only a triplet and quartet, integration about 3 : 2 � ethyl group(s) only assemble the evidence: C6H)SN, 3° amine, only ethyl in the NMR: (b) React the triethylamine with HCI. The pure salt is solid and odorless. (CH3CH2hN + HCI -. (CH3CH2hNH salt + CI - (c) Washing her clothing in dilute acid like vinegar (dilute acetic acid) or dilute HCI would form a water­ soluble salt as shown in (b). Normal washing will remove the water-soluble salt. --- (b) Both answers can be found in the resonance forms of the intermediate, in particular, the resonance form that shows the positive charge on the N. This is the major resonance contributor; what is special about it is that every atom has a full octet, the best of all possible conditions. That does not arise in the benzene intermediate, so it must be easier to form the intermediate from pyrrole than from benzene. Also, acylation at the 3-position puts positive charge at the 2-position and on the N, but never on the other side of the ring, so this substitution has only two resonance forms. The intermediate from acylation at the 3-position is therefore not as stable as the intermediate from acylation at the 2-position. 461 yQ o H H ...
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