Class Notes (838,398)
Canada (510,881)
Chemistry (1,145)
CHEM 222 (112)
Lecture

alcohols.pdf

5 Pages
128 Views
Unlock Document

Department
Chemistry
Course
CHEM 222
Professor
David Harpp
Semester
Fall

Description
ALCOHOLS
 Nomenclature
 When
naming
alcohols,
remember
that
we
want
the
alcohol
at
the
lowest
possible
 carbon
#.

 IUPAC
name:
Z‐hex‐3‐en‐1‐ol
 
 Properties
of
Alcohols
 • Boiling
point
higher
than
corresponding
hydrocarbon
 o H‐bonds
between
OH
groups
 • Alcohols
are
weak
acids
 o pKa(H O)2=
15.5
 o pKa(ROH)
=
16‐17
 • RO‐
and
H+
 o RO‐
is
called
the
alcoholate
 Preparation
of
Alcohols
 A
Markovnikov
addition
is
when
the
C
with
the
most
H
gains
another
H,
and
the
 new
group
(ex:
Br‐)
goes
to
the
C
with
the
least
H.

 • favored
because
less
steric
hindrance
 An
anti­Markovnikov
addition
is
when
the
C
with
the
most
H
gains
a
new
group
 (ex:
Br‐)
and
the
C
with
the
least
H
gains
another
group.

 1. Hydration
of
alkenes
(acid
catalyzed)
 This
reaction
is
a
Markovnikov
addition.

 
 
 Possible
solvents:
H+
in
2 O
 
 
 
 








Hg(OAc 2
in
H 2,
followed
by
NaBH 
 4 2. Hydroboration/oxidation
of
alkene
 This
reaction
is
an
anti‐Markovnikov
addition
to
alkenes,
and
proceeds
in
 two
steps:
1)
BH 
ad3s
to
alkenes;
2)
the
trialkylborane
is
oxidized.

 
 For
ring
compounds,
the
net
effect
is
the
cis
addition
of
H+
and
OH‐.
This
is
 because
of
steric
hindrance.

 
 3. Hydrolysis
of
alkyl
halides
 This
reaction
could
be
complicated
by
elimination
if
there
are
more
than
2
 CH 
2roups.

 
 4. Grignard
reaction
of
aldehydes,
ketones,
esters
and
epoxides
 A
Grignard
reagent
will
react
with
most
carbonyl
functions
to
give
alcohols.

 
 In
planning
syntheses
with
the
Grignard
reagent,
care
must
be
exercised
to
 be
sure
that
other
functional
groups
will
not
interfere.

 Reactions
with
Alcohols
 Reactions
with
alcohols
usually
involve
adding
an
H+
to
the
OH‐
group
so
that
water
 dissociates
and
leaves.
OH‐
is
a
very
bad
leaving
group,
so
it
would
not
leave
on
its
 own.
This
is
why
most
reactions
with
alcohols
are
carried
out
under
acidic
 conditions.

 1. OH
dissociation
(forming
of
alcoholate)
 
 This
reaction
is
often
carried
out
in
NaH,
to
form
RO‐
and
Na+,
with
H 
 2 leaving
as
a
gas.

 pKa
~
16,
which
is
similar
to
water
 2. Displacing
of
OH
with
X
 X
=
I,
Br
or
Cl
 X
≠
F
 
 PROS:
simple,
clean
 CONS:
harsh
acidic
conditions

More Less

Related notes for CHEM 222

Log In


OR

Join OneClass

Access over 10 million pages of study
documents for 1.3 million courses.

Sign up

Join to view


OR

By registering, I agree to the Terms and Privacy Policies
Already have an account?
Just a few more details

So we can recommend you notes for your school.

Reset Password

Please enter below the email address you registered with and we will send you a link to reset your password.

Add your courses

Get notes from the top students in your class.


Submit