Transcription of 23.7 ALKYLATION AND ACYLATION REACTIONS …
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23.7 ALKYLATION AND ACYLATION REACTIONS …
ALKYLATION AND ACYLATION REACTIONS OF AND ACYLATION REACTIONS OF AMINESThe previous section showed that amines are Br nsted bases. Amines, like many other Br n-sted bases, are also nucleophiles(Lewis bases). Three REACTIONS of nucleophiles are:1. SN2reactionwithalkylhalides,sulfonateest ers,orepoxides( , , , )2. addition to aldehydes, ketones, and a,b-unsaturated carbonyl compounds (Secs. , , and )3. nucleophilic acyl substitution at the carbonyl groups of carboxylic acid derivatives(Sec. )This section covers or reviews REACTIONS of amines that fit into each of these Direct ALKYLATION of AminesTreatment of ammonia or an amine with an alkyl halide or other alkylating agent results inalkylation of the process is an example of an SN2 reaction in which the amine acts as the product of the reaction shown in Eq. is an alkylammonium ion. If this ammo-nium ion has NLH bonds, further alkylations can take place to give a complex product mix-ture, as in the following example:A mixture of products is formed because the methylammonium ion produced initially is par-tially deprotonated by the ammonia starting material.
23.7 ALKYLATION AND ACYLATION REACTIONS OF AMINES 1133 B. Reductive Amination When primary and secondary amines react with either aldehydes or ketones, they form imines
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