The Substances Alkylated

Much of the early alkylation work was conducted on nitriles, particularly phenyl-acetonitrile (Eq. 10.4). Numerous nitriles related to phenylacetonitrile have also 

One nitrile which deserves special attention is chloroacetonitrile. Chloro-substitution generally decreases the pKa of a carbon acid by one to two log units. Chloroaceto- 

The carbon acids which are probably most often alkylated under classical conditions are aldehydes, ketones, and esters. The phase transfer alkylation of these systems has also been reported (results presented in Table 10.2) but these compounds deserve special comment. Aldehydes which might readily be alkylated are usually subject to aldol condensation as well (Eq. 10.7). The only aldehydes which have been alkylated 

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