Imine formation nucleophilic aromatic substitution

CHAPTER 7 CHAPTER 8 CHAPTER 10 CHAPTER 11 CHAPTER 15 CHAPTER 17 CHAPTER 18 Acid-Catalyzed Dehydration of an Alcohol 313 Electrophilic Addition to Alkenes 330 Grignard Reactions 443 The Williamson Ether Synthesis 500 The Diels-Alder Reaction 684 Electrophilic Aromatic Substitution 757 Nucleophilic Additions to Carbonyl Groups 841 Formation of Imines 851 Formation of Acetals 856... 

Aromatic rings are usually not good enough nucleophiles to react with nitriles. If a Brpnsted acid or a Lewis acid is added to improve the electron sink, then electrophilic aromatic substitution can occur. The acidic water workup first protonates the aluminum salt of the addition product to form the imine, which is then hydrolyzed to the ketone by the reverse of imine formation discussed in Sections 8.5.1 and 10.5.2. 

In choosing the Key Mechanisms, I ve used two major criteria. If the mechanism is one of the fundamental mechanisms that make up the longer, more complex mechanisms, then it must be a Key Mechanism. Examples are S l, 5 2, El, E2, nucleophilic acyl substitution, electrophilic aromatic substitution, and so forth. The other criterion is more subjective. If the mechanism is one of the ones I routinely expect students to do on exams, then it is a Key Mechanism. Examples are formation of imines and acetals, aldol and Claisen condensations, and so oa If you feel I have left one out or included one that should not be a Key Mechanism, please let me know. 

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