Selected SN Reactions of Heteroatom Nucleophiles at the Carboxyl Carbon

4 Selected SN Reactions of Heteroatom Nucleophiles at the Carboxyl Carbon 

Quite a few substitution reactions of heteroatom nucleophiles at the carboxyl carbon as well as their mechanisms are discussed in introductory organic chemistry courses. The left and the center columns of Table 6.3 summarize these reactions. Accordingly, we will save ourselves a detailed repetition of all these reactions and only consider ester hydrolysis once more. Section 6.4.1 will not only revisit the acidic and basic ester hydrolysis but will go into much more detail. Beyond that, SN reactions of this type will only be discussed using representative examples, namely  

Standard Nu Acylations of this nucleophile you should already be familiar with Acylations of this nucleophile part of which are discussed here as prototypical examples 

H20 or OH Hydrolysis of esters and amides Ester hydrolysis (Section 6.4.1) 

ROH or RO Esterification of carboxylic acids transesterification giving polyethyl-eneterephthalate (Dacron ) Lactonization of hydroxy acids (Section 6.4.2) 

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