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University of California, Berkeley *
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Chemistry
Date
Feb 20, 2024
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Uploaded by CaptainOryxMaster1194
1
Chem 3AL, Fall 2022 Lab H. Pre-lab document for Experiment #9 (What do you take for pain?) (5 pts) 1.Draw the structures of (S)-naproxen as well as (S)-sodium naproxen. Calculate the molecular weight for each of the molecules and write it below each structure. 2. Calculate the maximum number of milligrams of (S)-naproxen that could be isolated from one pill of Aleve (see the annotated lab lecture notes for information). O
HOM
**
-
Na
.
-*
④
O
E
Imos
Na-Naprox
H-Naprox
x
-
X
220mg
Na-Naprox
x
Ig
NaNaP
252
249
Na-Naprox
I
mol
Na-Naprox
230
.
76
g
H-Naprox
-
MoTH-Naprop-x
omg
H-Na
prox
=
200
.
829
my
of
(S)
-
Naproxen
-
19
H-
Naprox
2
5. Here is a start to your flow-chart to put into your lab notebook. Fill in the
boxes and label the different states/phases/conditions (like tablet and
paper towel, or organic and aqueous) following mixing with water and centrifugation.
Tablet
paper
towel
Pulverize, transfer to pre-weighed
test tube
Binder
Blue Coating (OpaDry)
Swirl with 0.5mL EtOH, wipe off tablet
"Na-Naprox"
3. Aleve contains sodium naproxen, a pro-drug. When it hits the stomach,
it is converted to the active compound, naproxen. Draw the structure of
(S) sodium naproxen again ("Na-Naprox" abbreviation), show an arrow
- pushing mechanism where it reacts with H-Cl (stomach acid), to create
naproxen and chloride.
4. Using solubility data found in the lab text, explain why ethanol, and not
water, is used to remove the blue OpaDry coating from the pill.
Add 1 mL H
2
O, heat, centrifuge, separate
Add 0.5 mL H
2
O, heat, centrifuge, separate
1 pill of Aleve
+
+
Add H
2
SO
4
, centrifuge, separate
Supernatent
Solid
Where is H-Naprox?
Add ice-water, centrifuge, separate
Solid
Recrystallize( Co-solvent)
--
S
O-
i
+
H
-
c
**
O
Nag
Na
c
I
O
--
E
-
>
Hom
-
E
you
need
to
use
ethanol
bl
Na-Naproxen
is
not
very
soluble
in
ethanol
and
the
opadry
coating
is
.
Therefore
you
are
able
to
separate
the
2
substances
,
room
temp
Iwarm
Na-Naproxen
is
much
more
soluble
in
water
so
if
you
used
water
while
OpaDry
is
soluble
in
water
you
would
not
be
able
to
separate
the
I
compounds
because
they
world
both
dissolve
.
Na-Naprox
+
binder
blue
coating
Copadry)
Na-Naprox
+
binder
Na-Naprox
binder
Nat
HSOy-
H-Naproxen
H-Naproxen
H-Naproxen
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