Chapter 11 Notes

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Unformatted text preview: Chapter
11
 Alcohols
and
Ethers
 Nomenclature
and
Structure
 (1)
Nomenclature
of
Alcohols:
previously
discussed;
see
Sec.
4.3F.
 (2)
Nomenclature
of
Ethers:
 (a)
Common
Names‐
The
groups
attached
to
the
oxygen
are
listed
in
alphabetical
order.










 (b)
IUPAC
Names‐
Ethers
are
named
as
having
an
alkoxyl
substituent
on
the
main
chain.
 Cyclic
ethers
can
be
named
using
the
 prefix
oxa‐.

Three‐membered
ring
 ethers
can
be
called
oxiranes.

Four‐ membered
ring
ethers
can
be
called
 oxetanes.
 Physical
Properties
of
Alcohols
and
Ethers:

Ether
boiling
points
are
roughly
 comparable
to
hydrocarbons
of
the
same
molecular
weight.

Molecules
of
ethers
 cannot
hydrogen
bond
to
each
other.

Alcohols
have
considerably
higher
boiling
points.

 Molecules
of
alcohols
hydrogen
bond
to
each
other.
 Both
alcohols
and
ethers
can
hydrogen
bond
to
water
and
have
similar
solubilities
in
 water.

Diethyl
ether
and
1‐butanol
have
solubilites
of
about
8
g
per
100
mL
in
water.


 Synthesis
of
Alcohols
from
Alkenes
 (1)
Acid‐Catalyzed
Hydration
of
Alkenes:

This
is
a
reversible
reaction
with
Markovnikov
 regioselectivity.
 (2)
Oxymercuration‐demercuration:

This
is
a
Markovnikov
addition
which
occurs
without
 rearrangement.
 (3)
Hydroboration‐Oxidation:

This
addition
reaction
occurs
with
anti‐Markovnikov
 regiochemistry
and
syn
stereochemistry.
 In
Class
Problem:
 Draw
the
structure
of
the
major
product(s)
you
would
expect
when
the
following
 alkene
is
subjected
to
(a)
acid‐catalyzed
hydration,
(b)
hydration
...
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This note was uploaded on 06/19/2009 for the course CHEM 2311 taught by Professor Tyson during the Fall '07 term at Georgia Institute of Technology.

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