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Unformatted text preview: 19-62 (b) cr continued
O:'� H -B
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 B- is the conjugate base of the acid HB OH H�B
- 11 B: 0
- - 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.
- Spring '10