Solutions to Homework #3
Solutions to problems 10.1 -- 10.10, 10.13, 10.14, 10.16, 10.17 can be
found in your "Study Guide and Solutions Manual"
Answers to WOC problems 7.2, 7.6, 7.7, 7.10 can be discussed with me
during my office hours.
Problem 10.18
Problem 10.19
(a) Hg(OAc)2, H2O, followed by a NaBH4 reduction
(oxymercuration, reduction)
(b) HBr, peroxides (free-radical bromination)
(c) HBr
(d) BH3 followed by H2O2, NaOH (hydroboration-oxidation)
(e) Hg(OAc)2, H2O, followed by a NaBH4 reduction
(oxymercuration, reduction); followed by acid-catalyzed dehydration (elimination to yield
Zaitsev's product); followed by BH3 followed by H2O2,
NaOH (hydroboration-oxidation); and finally a CrO3 oxidation of the alcohol to
the ketone
(f) Hg(OAc)2, H2O, followed by a NaBH4 reduction
(oxymercuration, reduction); followed by acid-catalyzed dehydration (elimination to yield
Zaitsev's product); followed by BH3 followed by H2O2,
NaOH (hydroboration-oxidation)
Problem 10.20
Bromine is involved in the rate-determining step (formation of the bridged intermediate).
Therefore, if we lower the concentration of Br2 in solution we expect
that the rate will decrease as well. Also, if the concentration of Br2 is
lowered then the equilibrium toward the formation of Br3+ lies more
toward the left.
Problem 10.22
