Page 667 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

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p -NO 2 SECTION 7.3
10 Condensation Reactions
of Aldehydes and
Ketones with Nitrogen
m-Br
Nucleophiles
p -Cl
1 H
k obs (min –1 ) 0.1 p -CH 3

p -OCH 3

0.01

2 4 6 8 10 12
pH

Fig. 7.5. pH-Rate profile for the hydrolysis of substituted
benzylidene-1,1-dimethylethylamines. Reproduced from J. Am.
Chem. Soc., 85, 2843 (1963), by permission of the American
Chemical Society.

0

log k ob

–2

0 2 4 6 8 10
pH
Fig. 7.6. pH-Rate profile for hydrolysis of N-methyl-2-
methylpropanimine in water at 35 C. Solid points are from the

hydrolysis reaction and open points are from the formation of the
imine. Reproduced from J. Am. Chem. Soc., 92, 5194 (1970), by
permission of the American Chemical Society.