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Our
text
does
not
cover
reaction
8
until
a
later
chapter
Additional
Problems
1. Predict
the
products
for
the
following
reactions:
2. Propose
a
mechanism
for
the
following:
1
Fall
2013
CHEM
210
[CHAPTER
6:
SUBSTITUTION
REACTIONS
OF
ALKYL
HALIDES
3. Draw
a
mechanism
for
the
following:
4. If
an
alcohol
is
used
instead
of
water,
ethers
are
produced.
Draw
a
mechanism
for
the
following:
5. Many
reactions
are
intramolecular.
Here
the
reactants
are
both
in
the
same
molecule.
Draw
a
mechanism
to
explain
the
following:
6. Mercury
is
toxic
and
used
only
when
necessary
for
synthesis.
In
class
we
learned
that
the
oxy-‐
mercuration/demercuration
scheme
could
be
used
to
give
products
of
alkene
hydration
without
rearrangements.
For
each
of
the
following
reactions,
give
the
product
of
each
and
indicate
the
product
you
would
obtain
by
simple
hydration
in
aqueous
acid.
7. Complete
the
following
examples
of
hydroboration/oxidation:
2
Fall
2013
CHEM
210
[CHAPTER
6:
SUBSTITUTION
REACTIONS
OF
ALKYL
HALIDES
8.
Complete
the
following
examples
of
hydroboration/oxidation.
Indicate
proper
stereochemistry
of
products.
9. Predict
the
products
of
the
following
catalytic
hydrogenations.
10. Predict
the
products
of
the
following
halogenation
reactions:
11. Predict
the
products
when
each
alkene
is
treated
with
a
mixture
of
water
and
Br2:
12. Bromonium
ions
can
be
captured
by
nucleophiles
other
than
water.
Predict
the
products
of
the
following:
13. Predict
the
products;
indicate
proper
stereochemistry
where
necessary:
3
Fall
2013
CHEM
210
[CHAPTER
6:
SUBSTITUTION
REACTIONS
OF
ALKYL
HALIDES
14. Predict
the
products
when
each
alkene
is
treated
with
O3
followed
by
Me2S:
15. Predict
the
products:
16. Predict
the
products:
4
Fall
2013
CHEM
210
[CHAPTER
6:
SUBSTITUTION
REACTIONS
OF
ALKYL
HALIDES
KEY
1. Predict
the
products
for
the
following
reactions:
2. Propose
a
mechanism
for
the
following:
3. Draw
a
mechanism
for
the
following:
4.
5
Fall
2013
CHEM
210
[CHAPTER
6:
SUBSTITUTION
REACTIONS
OF
ALKYL
HALIDES
5.
6.
7.
6
Fall
2013
CHEM
210
[CHAPTER
6:
SUBSTITUTION
REACTIONS
OF
ALKYL
HALIDES
8.
9.
7
Fall
2013
CHEM
210
[CHAPTER
6:
SUBSTITUTION
REACTIONS
OF
ALKYL
HALIDES
10.
11.
12.
8
Fall
2013
CHEM
210
[CHAPTER
6:
SUBSTITUTION
REACTIONS
OF
ALKYL
HALIDES
13.
9
Fall
2013
CHEM
210
[CHAPTER
6:
SUBSTITUTION
REACTIONS
OF
ALKYL
HALIDES
14.
15.
10
Fall
2013
CHEM
210
[CHAPTER
6:
SUBSTITUTION
REACTIONS
OF
ALKYL
HALIDES
16.
11
Fall
2013