Abstract
In contrast to previous studies of the Cannizzaro reaction using isotopically labeled reactants, the benzyl alcohol from reaction of 0.60 M benzaldehyde-..cap alpha..-d and 0.25 M NaOH in 74% CH/sub 3/OH to 26% H/sub 2/O solution at 100/sup 0/C includes a substantial percentage of benzyl-..cap alpha..-d/sub 1/ alcohol (21% after half consumption of hydroxide ion) rather than only benzyl-..cap alpha..-d/sub 2/ alcohol. Products from C/sub 6/H/sub 5/CHO in CH/sub 3/OH, CH/sub 3/OH solutions indicate that the side reactions responsible for hydrogen exchanges and adding to the yield of benzyl alcohol are (1) bimolecular hydride transfer to benzaldehyde from methoxide ion, (2) a nearly equal amount of crossed Cannizzaro reaction from the resulting formaldehyde, (3) a smaller amount of hydride transfer to benzaldehyde from the resulting sodium formate leading to sodium carbonate, and (4) a less frequent combination of two benzaldehydes plus methoxide ion leading to benzaldehyde dimethyl acetal. Decreasing the initial concentration of C/sub 6/H/sub 5/CHO to 5 x 10/sup -4/ M decreases the relative contributions of the three termolecular reactions and causes the bimolecular hydride transfer (1) to become the dominant reaction. Its k/sub CH/sub 3/O/sup -///k/sub CD/sub 3/O/sup -// isotope effect is 2.2 +- 0.2. 1 table.
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