1. 2. Oxymercuration. Total of 8 racemates possible. Only 2 are formed. 2. kinetically controlled; high energy TS’s ≠. kinetically controlled; low energy TS’s ≠. 1. 1. 2. Oxymercuration – II; Add a Methyl Group. regiochemistry ; anti addition; Markovnikov.
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If BD4- had been used as the reductant, a mixture of deuterio compounds would form.
Endo and exomercurials give the same radical.
Product distributions the same.
RHgBr + BH4- --------> RHgH
RHgH ---------> R . + .HgH
R . + O2 ---------> ROO .
ROO . + .HgH -------> ROOH + Hg0
ROOH + BH4- --------> ROH
C. L. Hill and G. M. Whitesides,
J. Am. Chem. Soc., 96, 1974, 870.