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O
NaOH
H3C
CH3
H
C
H
C
H
C
H
C
Materials:
Apparatus
Vacuum Filter
Melting point thermometer
H2O
Chemicals
Benzaldehyde Acetone
C7H6O
C3H6O
Molar
Mass
(g/mol)
BP (C)
MP(C)
Density
(g/ml)
Solubility
Sodium
Ethanol
Hydroxide C2H6O
NaOH
Dibenzalacetone/
Dibenzylideneacetone
C17H14O
106.12
58.08
39.9971
46.07
234.292
178.1
57.12
1.044
57
93
0.791
1,388
318
2.13
78.37
114
0.789
130
112
1.1
In ammonia
In water
Polar
solvents
1.357
Polar solvents
1.361
Soluble in nonpolar
solvents
1.649
Wikipedia
Chemnet.com
Refractive 1.545
Index (nD)
Reference Wikipedia
1.359
Wikipedia Wikipedia
Observations
Procedure:
1. Weigh out 0.265g of benzaldehyde
and a theoretical quantity of
acetone. Calculate the theoretical
quantity of acetone before you
arrive for lab!
2. Add the correct quantities of these
reagents together. (Use the Rainin
pipet to dispense the correct amount
of acetone in microliters.)
3. Dissolve 0.25g of NaOH in 2.5 mL
of water, then add 2.0mL of
ethanol.
4. Cool the hydroxide solution to
room temperature.
5. Add one-half of your
benzaldehyde-acetone mixture to
the hydroxide solution.
6. After about 15min. add the
remainder of this mixture.
7. Rinse the container with a small
amount of ethanol and add this to
the reaction mixture.
8. Swirl occasionally for 30 min.
9. Stir with a stirring rod to allow the
precipitate to break up and
crystallize.
10. Collect the product by.
11. Wash the crystals with 5mL of
water three times to remove any
NaOH.
12. Recrystallize from 95% ethanol
using 2.5mL per gram of product.
13. Check the melting point of the
recrystallized product (110 o to 111o
C).
Moles Acetone__.00136____
gm Acetone:____.07277_______
L Acetone:______________
Theoretical Yield (moles)_____.00136______
Theoretical Yield (grams):___.3186_____
Actual yield of recrystallized product:__.2314.3186100 = 72.6_________
Percent Yield:_____72.6%__________
Melting point of recrystallized product:______111.7____________
Conclusion
We were able to successfully synthesize DNB via an aldol mechanism. We got a high
yield due to the equilibrium being pushed to the right throughout the experiment. This
crossed aldol reaction is considered synthetically useful because the structure of the
reagents permitted only one molecule to exclusively be converted to enolate.
Dibenzalacetone
Acetone
Dibenzalacetone