The alcoholysis of acyl halides (the alkoxy-dehalogenation) is believed to proceed via an S2 mechanism (Scheme 10).⁠ However, the mechanism can also be tetrahedral or S1 in highly polar solvents⁠ (while the S2 reaction involves a concerted reaction, the tetrahedral addition-elimination pathway involves a discernible intermediate).
Bases, such as pyridine or N,N-dimethylformamide, catalyze acylations. These reagents activate the acyl chloride via a nucleophilic catalysis mechanism. The amine attacks the carbonyl bond and presumably⁠ first forms a transient tetrahedral intermediate, then forms a quaternary acylammonium salt by the displacement of the leaving group. This quaternary acylammonium salt is more susceptible to attack by alcohols or other nucleophiles.
The use of two phases (aqueous for amine, organic for acyl chloride) is called the Schotten-Baumann reaction. This approach is used in the preparation of nylon via the so-called nylon rope trick.⁠