Nucleophilic substitution

• The most reactive carboxylic acid derivative (acyl chloride) can be used to create progressively less-reactive derivatives: anhydrides, esters and amides. But the reverse cannot happen.
• Table 51.3 below shows how one can use an acyl chloride to produce a specific product, i.e. anhydrides, esters and amides using the nucleophiles ($RCO_{2}$, $R'OH$ and $R_{2}NH$).

  
  

  Table 51.3: What to react with an acyl chloride to yield a specific product.

  Acyl chlorides
  reacts with$\ldots$	$\ldots$ to yield:
  $RCO_{2}$	Anhydrides
  $R'OH$	Esters
  $R_{2}NH$	Amides