Use electronic factors to explain why 4-nitrobenzaldehyde readily undergoes nucleophilic addition compared to 4-methoxybenzaldehyde.
Propose a mechanism for the reaction of propanone with methylamine at pH=5.6 and explain in detail why the pH of the medium should be controlled.
Propose a detailed mechanism for the reaction of propanone with an excess of methanol in the presence of a mineral acid catalyst.
Propose a mechanism for the acid-catalyzed reaction of propanone with hydroxylamine.
Answer (2)
4-nitrobenzaldehyde undergoes nucleophilic addition more readily than 4-methoxybenzaldehyde due to the electron-withdrawing effects of the nitro group. The mechanism of propanone with methylamine involves nucleophilic attack and requires controlled pH for optimal reaction rates. Similarly, propanone reacts with methanol and hydroxylamine under acidic conditions, with specific mechanisms illustrating the importance of electrophilic activation. ;
4-Nitrobenzaldehyde is more reactive in nucleophilic addition than 4-methoxybenzaldehyde due to the electron-withdrawing effect of the nitro group. The reaction of propanone with methylamine and other nucleophiles involves mechanisms centered around nucleophilic attack and acidity, which affect the electrophilicity of the carbonyl carbon. Controlling pH is essential for optimizing reaction rates in these mechanisms.
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