Solutions_Manual_for_Organic_Chemistry_6th_Ed 473

Solutions_Manual_for_Organic_Chemistry_6th_Ed 473 - 19-62...

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Unformatted text preview: 19-62 (b) cr continued O:'� H -B .. .� +C q - 0 C-OH •• To this point, everything is the same in the two mechanisms. But now, there is no H on the N to remove to form the imine. The only H that can be removed to form a neutral intermediate is the H onC next to the carbocation. . -H20 . / �H� aD _-' O�:·· + �. �� o�: 0::0 � (X/O C /' o C B- is the conjugate base of the acid HB OH H�B - 11 B: 0 C - - OH I H enamme (c) A secondary amine has only one H to give which it loses in the first half of the mechanism to form the neutral intermediate called an aminal, equivalent to a hemiacetal. In the second half of the mechanism, the H on an adjacent carbon is removed to form the neutral product, the enamine. The type of product depends entirely on whether the amine begins with one or two hydrogen atoms. 468 ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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