The methylene group in diphenylmethane is mildly acidic with a
pK of 32.2, and so can be deprotonated with
sodium amide. :
Alkylation of various
benzhydryl compounds has been demonstrated using the corresponding alkyl halides, both primary (
benzyl chloride, β-phenylethyl chloride, and n-octyl bromide) and secondary (benzhydryl chloride, α-phenylethyl chloride, and
isopropyl chloride), in yields between 86 and 99%. This is well below the published bond dissociation energies for comparable bonds in
propane, where the BDE of is , and
toluene, where the BDE of is . ==See also==