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Fulton- Organic
lecture 5
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Cards (7)
Hydration of alkenes
Alkenes
can be hydrated by
H2O
in the
presence
of
strong acids
Markovnikov's
rule
Reaction
via the most
stable cation
(
OH
at most
substituted carbon
)
Hydration of alkenes with
Hg2+
-alkenes
can be hydrated using
soft lewis acids
such as Hg2+
-1)
Hg(OAc)2
and
H2O
2)
NaBH4
Hydroboration/Oxidation of alkenes
-Alkenes
react with
BH3
to form
Alkyl Boranes
-Then oxidised with
H2O2
and
NaOH
to give alcohols
Hydroboration of alkenes mechanism of reaction
-2
,
2
addition of
B-H
bond and
C=C
bond
-steric
hinderance decided where
BH3
substitutes
-Addition of
BH3
on
least
hindered face of an alkane
-oxidation
of
C-B
bond by
NaOH
/
H2O2
-hydrolysis
of
B-O
bonds in
basic
conditions
RBH2 addition
-Highly
hindered alkenes
-BH3
will on
add
to
one
alkene only
-RBH2 add
to
two
alkenes
-allows
highly regioselective
hydroborations
Highly selective hydroboration
9-BBN
-allows
conversion
of
terminal alkynes
to
aldehydes
