The formation of an acetal from a ketone or aldehyde has a very similar mechanism to the formation of an imine (review Equations 18-13 and 18-19). Both require acidic conditions to generate a water leaving group. At very acidic pH, however, the rate of imine formation slows down (see the accompanying graph), whereas the rate of acetal formation does not. Explain this pH dependence of imine formation. 1 2 3 4 6 7 pH Rate of imine formation –>

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Chapter1: Chemical Foundations
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The formation of an acetal from a ketone or aldehyde
has a very similar mechanism to the formation of an
imine (review Equations 18-13 and 18-19). Both require
acidic conditions to generate a water leaving group. At
very acidic pH, however, the rate of imine formation
slows down (see the accompanying graph), whereas
the rate of acetal formation does not. Explain this pH
dependence of imine formation.
1
2 3
4
6
7
pH
Rate of imine
formation –>
Transcribed Image Text:The formation of an acetal from a ketone or aldehyde has a very similar mechanism to the formation of an imine (review Equations 18-13 and 18-19). Both require acidic conditions to generate a water leaving group. At very acidic pH, however, the rate of imine formation slows down (see the accompanying graph), whereas the rate of acetal formation does not. Explain this pH dependence of imine formation. 1 2 3 4 6 7 pH Rate of imine formation –>
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